The Product Market Fit Show: Recent Episodes
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As an early-stage founder you have one goal: find product-market fit. So how do you do it? There's no playbook. There isn't even a definition of what product-market fit is. In The PMF Show, late-stage founders share real stories from their journey to product-market fit. These are not biographies. They aren't promotional narratives about how companies were built. They’re very specific, detailed stories with real examples you can use.
Colin spent eight years building Looker into a $2.7B Google acquisition. Then he left to compete with his own product. He thought traction would take a month—it took nine. A hundred demos got him five verbally-committed customers, and he lost all five. So he spent two months killing bugs, went on one podcast, and won every single trial that came out of it. Omni just raised over $250M.
In this episode, Colin breaks down how to tell the difference between a product that's genuinely better and one the market just doesn't want, why founding with $30M didn't stop them from staying stingy, and the LinkedIn playbook that turned 6,000 connections into a 90% response rate.
Why You Should Listen
- Why losing every deal doesn't mean the idea is wrong—and how to know the difference.
- Why real differentiation shows up as "wow" moments in demos, not signed contracts.
- The LinkedIn social-selling playbook that built Omni's first pipeline.
- Why hiring sellers from your old industry hands you their Rolodex on day one.
Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Omni, Colin Zima, Looker, business intelligence, BI tools, enterprise SaaS, AI analytics, social selling, LinkedIn outbound, founder-led sales, innovator's dilemma
Chapters
- 00:00:00 Intro
- 00:01:58 The Moment of True Product Market Fit
- 00:06:16 Losing All Five Deals and Doubling Down
- 00:10:43 Leaving Looker to Compete With Looker
- 00:17:39 Founding With $30M and Staying Stingy
- 00:22:09 A Hundred Demos Before the Flywheel
- 00:32:15 No Silver Bullet—Just Do More of Everything
- 00:38:32 The LinkedIn Social-Selling Playbook
- 00:46:07 Hiring the Best People You've Worked With
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Rafael launched a crypto insurance product in 47 states, backed by a real carrier. Everyone told him it was genius. Nobody needed it. He shut it down with $2M left in the bank, fired almost everyone, and rebuilt with two engineers on $20K a month. Notch just raised $30M.
In this episode, Rafael breaks down how a POC he entered through the back door turned into a seven-figure contract, why "isn't everyone doing this?" is the feedback you actually want, and how to tell whether an enterprise deal makes you a real company or just their dev shop.
Why You Should Listen
- Why "that idea is genius" is a warning sign, not a compliment.
- How entering a POC last still made them the front runner.
- Why the enterprise deals that scale need zero customization.
- How to stop hiding your idea and go straight to your dream customers.
Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Notch, Rafael Broshi, AI agents, insurance technology, customer experience automation, regulated industries, enterprise sales, POC strategy, pivoting a startup, on-prem deployment
Chapters
- 00:00:00 Intro
- 00:02:00 The Moment of True Product Market Fit
- 00:10:07 One Enterprise Deal or Ten
- 00:15:24 A Genius Idea Nobody Needed
- 00:24:33 Picking the Right Wave to Ride
- 00:34:37 Down to $2M, Firing Almost Everyone
- 00:41:48 Getting Enterprise to Take Your Call
- 00:48:07 The POCs That Aren't Real POCs
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Ben and his co-founder had no product, no law enforcement background, and no pitch—just an offer to help detectives solve cases. One commander took a chance, handed them background checks, and said "let's see what you can do." They worked out of that police department every day for 18 months. Peregrine just raised $250M at a $6.8B valuation.
In this episode, Ben breaks down how researching every police captain in the Bay Area landed their first design partner, why working as free crime analysts for 18 months was "the purest form of method acting," how forward-deployed engineers drove them from $1M to $3M to $10M ARR, and the 120% RFP prep that won a contract written for a billion-dollar competitor.
Why You Should Listen
- Why doing your customer's job is the fastest path to product market fit.
- How two founders with no product convinced a police department to let them in.
- Why over-investing in deployment became a growth engine, not a margin problem.
- How obsessive research wins enterprise deals when you have zero credibility.
Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Peregrine, govtech, public safety technology, forward deployed engineers, selling to government, enterprise sales, data integration, design partners, Ben Rudolph
Chapters
- 00:00:00 Intro
- 00:01:07 The Moment of True Product Market Fit
- 00:11:51 Getting a Police Department to Say Yes
- 00:16:45 Slow Growth and Word of Mouth
- 00:19:49 Forward-Deployed Engineers Before They Were Cool
- 00:27:34 Cracking Government Go-To-Market
- 00:34:08 Winning an RFP Written for Someone Else
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Damien left his job to start a startup solo. Two years later, Nebulock closed a $25M Series A. In between: 90 customer interviews in 90 days, a year of design partners, and a Fortune 500 deal that closed in 6 weeks.
In this episode, Damien breaks down how his 90-in-90 customer discovery sprint killed his original architecture before he wasted money building it, how his design partner program converted 100% into paying customers, and how a POC playbook needing just 2 hours of customer time closed a Fortune 500 in 6 weeks.
Why You Should Listen
- How 90 customer interviews in 90 days saved him from building the wrong product.
- Why every single design partner converted into a paying customer.
- How a 2-hour POC playbook closed a Fortune 500 in just 6 weeks.
- Why procurement—not your champion—decides how fast your deal closes.
Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, cybersecurity startup, solo founder, customer discovery, mom test, design partners, enterprise sales, POC process, AI security, Nebulock, Damien Lewke
Chapters
- 00:00:00 Intro
- 00:01:20 The Moment of True Product Market Fit
- 00:11:33 Going Cold Turkey as a Solo Founder
- 00:23:07 90 Interviews in 90 Days
- 00:36:44 Raising $8.5M Off a Manifesto, Not a Deck
- 00:39:36 Every Design Partner Converted to Paid
- 00:44:00 Building a Repeatable POC Playbook
- 00:48:20 The Procurement Black Hole
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Astro has run X, Alphabet's Moonshot Factory, for 16 years. His teams created Waymo, Wing, and Google Brain—by testing over 1,000 ideas a decade and killing nearly all of them. His whole system rests on one uncomfortable rule: celebrate the people who kill their own projects.
In this episode, Astro breaks down why you should do the hard thing first, how pre-written kill criteria force intellectual honesty, and why X maximizes learning per dollar instead of progress—and never tracks whose idea it was.
Why You Should Listen
- Why working on the riskiest part first is the key to testing new ideas
- How writing kill criteria a year in advance stops you from running a zombie startup.
- Why progress doesn't matter when launching a new startup.
- How to come up with big ideas like Waymo and Wing.
Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Astro Teller, Google X, moonshot factory, Alphabet, Waymo, innovation process, kill criteria, idea validation, deep tech
Chapters
- 00:00:00 Intro
- 00:04:15 Inside Alphabet's Moonshot Factory
- 00:07:22 The Card Counters of Innovation
- 00:14:00 Learning per Dollar, Not Progress
- 00:23:04 Killing Ideas with Testable Hypotheses
- 00:26:34 Train the Monkey First
- 00:35:16 Kill Criteria: A Message to Your Future Self
- 00:41:59 The Moment of True Product Market Fit
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Cos was the CTO of Brex, which he helped scale from 40 people to over 1,000. Before that, he led engineering at Stripe. When he finally left, he had no startup idea—just a co-founder he trusted and one rule: whatever they built had to have massive impact. Six months of brainstorming later, they landed on accounting.
In this episode, Cos breaks down why he capped the company at 21 people after raising $75M, why everyone—engineers and salespeople alike—earns the exact same salary, how he hit a 100% pilot-to-production conversion rate with top accounting firms, and the counterintuitive process he used to pick accounting over every other industry.
Why You Should Listen
- Why the only reason to join an early-stage company should be the equity, never the cash.
- How Accrual hit a 100% pilot-to-production conversion rate selling to the largest accounting firms.
- Why he raised $75M but refuses to grow past 21 people.
- How to tell real product market fit from the "just one more feature" trap.
Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, AI accounting, vertical AI, enterprise sales, pilot to production, Brex, Stripe, Cosmin Nicolaescu, Accrual, lean team
Chapters
- 00:00:00 Intro
- 00:01:56 The Moment of True Product Market Fit
- 00:09:46 Collapsing 6+ Tools Into One Platform
- 00:18:07 Leaving Brex to Start From Scratch
- 00:31:41 Landing H&R Block and Armanino
- 00:34:57 A 100% Pilot-to-Production Playbook
- 00:43:26 A 21-Person Company by Design
- 00:51:38 One Salary for Everyone
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Anurag was employee #8 at Stripe, set for life and free to do anything next. Instead he spent a year and a half hunting for a problem worth decades of his life. He chose to build a product to make it simple for developers to ship apps, going head-to-head with AWS.
In this episode, Anurag breaks down how he hit $10M ARR in 4 years with zero marketing spend, why refusing to launch a free tier was his most expensive mistake, and how putting engineers on customer support rotations quietly shaped the entire product roadmap.
Why You Should Listen
- Why you don't have real product market fit until your users sell the product for you.
- How a sub-2-minute setup turned developers into a word-of-mouth machine.
- Why skipping a free tier for years was his most expensive mistake.
- How engineers doing support on rotation built the roadmap—and 6M+ developers.
Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, developer tools, cloud infrastructure, PaaS, Render, word of mouth growth, product-led growth, AI infrastructure, Stripe
Chapters
- 00:00:00 Intro
- 00:01:44 The Moment of True Product Market Fit
- 00:04:14 The #1 Driver of Word of Mouth
- 00:13:25 Why He Left Stripe to Build Render
- 00:23:48 Why AWS Would Never Build This
- 00:30:33 $10M ARR With No Marketing Spend
- 00:36:43 Engineers as the Support Team
- 00:42:19 Riding the AI Boom
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George had to wind down his last startup and give investors their money back. He went deep into the valley of despair, certain he'd missed his window to build something big. Then he met a co-founder, decided to start over, and started selling.
In this episode, George breaks down how a customer signed a $36K pilot off nothing but a Loom and a one-pager, how cold email took him from zero to $1M ARR with no sales team, and why a "seven out of ten" is the most dangerous hire you can make.
Why You Should Listen
- How a customer signed a $36K pilot after a single Loom and zero calls.
- Why he gave the money back on his last startup—and what "follow your energy" really means.
- How cold outbound email built his first $1M ARR with no sales team.
- Why a "seven out of ten" is the most dangerous hire you can make.
Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, fintech, accounts receivable automation, AI agents, cold outbound email, B2B SaaS, Series A fundraising, services as software
Chapters
- 00:00:00 Intro
- 00:01:39 The Moment of True Product Market Fit
- 00:03:33 Shutting Down a Small-Market Startup
- 00:07:44 Picking Fintech From Five Ideas
- 00:17:12 From Black Box to Full App
- 00:24:47 $1M ARR on Cold Email Alone
- 00:36:11 Why a "Seven" Is the Most Dangerous Hire
- 00:42:15 Compressing a $25M Series A
Send me a message to let me know what you think!
Dan founded and scaled a $50M ARR, SoftBank-backed startup—and could've stayed to make tens of millions. Instead, he handed it to his chief of staff and started from scratch. He wanted something bigger. He took an entry-level paralegal job to learn everything about law hands on. Then he built Manifest, which just raised a $60M Series A.
In this episode, Dan breaks down why he did intake calls for 1,000 legal clients before building anything, how free Slack communities turned Fortune 500 HR managers into buyers without a dollar of ads, and why he refused to sell software to law firms even when investors told him he was crazy.
Why You Should Listen
- How 2 months working as a paralegal beat years of customer discovery.
- How free Slack communities turned Fortune 500 HR managers into clients.
- Why earned media compounds like an asset while paid ads burn like an expense.
- Why impact is the best driver for starting startups.
Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, legal tech, legal AI, AI-native law firm, immigration law, services as software, community-led growth, earned media, customer discovery, Dan Mishin, Manifest
Chapters
- 00:00:00 Intro
- 00:06:34 Walking Away from $50M ARR
- 00:13:12 Why Immigration Law Has AI Leverage
- 00:18:01 The AI-Native Law Firm Model
- 00:21:49 1,000 Intake Calls Before Building Anything
- 00:30:21 Turning Free Communities Into Buyers
- 00:37:20 Earned Media That Compounds
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Ali quit his job a few months after ChatGPT launched, convinced AI would eat labor marketplaces like Upwork. With no co-founder and no code, he collected $12K from real customers—using a faked demo and a cloned voice. Then he pitched 100 VCs in 10 days and got 47 straight 'no's.
In this episode, Ali breaks down how he banked $12K in revenue before writing a single line of code, how a $20/month Slack community drove Amigo's first $1M in ARR, and why he churned every existing customer to go all-in on $100K+ healthcare enterprise deals.
Why You Should Listen
- Why validation only counts when dollars exchange hands.
- How a $20/month paid community turned into $1M in ARR.
- Why he refunded every customer and churned 100% of his revenue.
- Why founders must sell the first $2M themselves before hiring an AE.
Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, AI agents, healthcare AI, enterprise sales, pre-seed fundraising, community-led growth, customer validation, pivot, Amigo AI
Chapters
- 00:00:00 Intro
- 00:08:37 From Upwork to Starting Amigo
- 00:13:30 $12K in Revenue Before Writing Code
- 00:23:24 Pitching 100 VCs in 10 Days
- 00:30:20 47 No's—Then FOMO Took Over
- 00:37:12 The $20/Month Community Behind the First $1M
- 00:45:47 Churning 100% of Revenue on Purpose
- 00:01:49 The Moment of True Product Market Fit
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Mark was running a startup out of a tiny annex office in Dublin with zero product usage. Then one customer turned it on and overnight he saw usage spike to thousands of simulations. He got to $1M ARR 100% through outbound, by sending 500,000 cold emails. A few months ago he closed a $25M Series A.
In this episode, Mark breaks down the pivot from sales roleplay to customer support that unlocked his first real traction, the cold outbound playbook that took him to $1M ARR (500K emails, 250 meetings, 40 customers), and why doorstepping customers in Utah is what drove his net revenue retention to 186%.
Why You Should Listen
- Exactly how to use a cold outbound strategy to hit $1M ARR.
- Why getting on 56 flights last year to visit customers led to 186% NRR.
- How he closed a $25M Series A in just 6 days.
Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, AI startup, customer support, cold outbound, Y Combinator, Series A, enterprise sales, SaaS, Solid Road
Chapters
- 00:00:00 Intro
- 00:06:10 The Pivot From Sales to Customer Support
- 00:12:54 Why Moving to SF Changed Everything
- 00:22:34 Cold Outbound to $1M ARR
- 00:32:47 Doorstepping Customers for 186% NRR
- 00:39:17 Closing a $25M Series A in 6 Days
Send me a message to let me know what you think!
The AI boom is making founders feel like the market is wide open, but the data tells a sharper story: valuations are up, round sizes are bigger, and the bar to “count” in a top-tier fund’s Monday meeting keeps rising. We sit down with Peter to translate Q1 2026 venture capital trends into founder reality, from seed-stage pricing distortions driven by AI infrastructure to the quieter pressure building across the rest of the startup market.
We get specific on early-stage fundraising benchmarks and why Series A now looks riskier than many people assume. Median Series A valuations have climbed close to 2x in a few years, while typical raises jumped from roughly $8M to $10M to $13M to $15M. That changes everything: ownership targets, follow-on costs, and the outcome math that pushes investors (and founders) toward “decacorn-plus” expectations. If you are pitching $100M ARR as the endgame, you may already be behind.
Then we zoom out to the forces shaping who wins: Bay Area gravity, a real valuation gap versus other hubs, and practical tactics like visiting the Bay to capture network effects without uprooting your life. We also dig into defensibility in AI application startups, where building is faster but competition is fiercer, plus the rise of smaller teams and solo founders, and what that means for hiring, equity, and motivation on early teams.
Chapters
- 00:00:00 LLM Hype And Bubble Warning
- 00:02:13 Five Stars Then We Begin
- 00:03:02 Seed Prices Spike In AI Infra
- 00:07:10 2026 Benchmarks For Pre-Seed To A
- 00:09:36 Series A Doubles And Exit Math
- 00:12:54 Bay Area Gravity And Valuation Gap
- 00:18:22 Defensibility Gets Harder In AI Apps
- 00:23:22 Smaller Teams Solo Founders Talent Shifts
- 00:35:20 VC Fund Shakeout And Final Share Ask
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I meet 1,000+ founders every year. Most are bad at fundraising.
I also interview 100+ of the world's best founders on my podcast each year. Most are incredible at fundraising.
One raised $14M in 17 days. another was 3x oversubscribed on a $3M round. another closed a seed in hours from a single X post. All are first-time, unproven founders.
They don't waste time becoming "friends" with VCs. They have a business to build. They treat fundraising for what it is: a process where you manufacture FOMO as fast as possible, take the money, and move on.
This video breaks down the 4 steps the best fundraisers use to raise fast. The same 4 steps taught at YC and 500 Startups (where i went). The same 4 steps you can run on thousands of VCs worldwide to close $2-3M in weeks not months.
Why You Should Listen
- Why you need to reach out to 50 VCs on the same day just to end up with three term sheets.
- How to engineer intro blurbs that make VCs feel like they're already late to the game.
- Why setting fake deadlines is the fastest way to destroy all your credibility with investors.
- How one founder raised $3M in five weeks by starting with a $1.5M target and driving FOMO.
Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, fundraising, raising a seed round, VC pitch, FOMO, startup fundraising playbook, term sheets, investor meetings, Pablo Srugo, venture capital
Chapters
- 00:00:00 Intro
- 00:01:30 Step 1: Build a List of 50 Qualified VCs
- 00:06:00 Step 2: Engineer the Intros
- 00:14:00 Step 3: Compress the Timeline
- 00:20:00 Step 4: Manufacture FOMO
- 00:26:00 Three Rules to Never Break
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Surojit spent 14 years at Google building mobile ads into a $100B+ business and then took Coinbase public as Chief Product Officer in 2021. In early 2023, before "agent" was even a word in AI papers, he started Ema in stealth—betting on a future where teams of AI agents would replace the "human glue" inside Fortune 500s.
In this episode, Surojit breaks down how a Hitachi deployment across 55,000 employees became Ema's true PMF moment, why he spent the first year obsessed with SOC 2, ISO 42001, and air-gapped architecture before chasing revenue, and why one client just cut their HR team from 1,000 people to 550 by automating 65,000 monthly job changes.
Why You Should Listen
- Why true PMF is when your average salesperson can sell the product without you in the room.
- How a single Hitachi deployment unlocked credibility for every Fortune 500 deal that followed.
- Why a cold email—not a warm intro—turned into Ema's largest partner today.
- How partnering with PwC and KPMG became a faster wedge into the C-suite than any conference.
Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, AI agents, enterprise AI, AI employees, Fortune 500 sales, Surojit Chatterjee, Ema, agentic AI, enterprise software
Chapters
- 00:00:00 Intro
- 00:02:00 Hitachi Was the PMF Moment
- 00:04:10 What Ema Actually Does
- 00:11:48 From Coinbase to a Pre-ChatGPT Bet
- 00:28:48 The Cold Email That Won a Top Partner
- 00:30:52 Small Dinners Beat Massive Conferences
- 00:36:11 The Moment of True Product Market Fit
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Sean was spending four days a week inside customer warehouses at Amazon Shipping when he noticed the same thing everywhere: back-office admin staff churning every six months, buried under the same repetitive claims and reshipping tasks. He talked to eighty-five warehouse owners, quit Amazon in July 2024, and cold emailed his way to a pre-seed round within weeks.
In this episode, Sean breaks down why he paused all sales to rebuild BackOps as an enterprise-grade platform, how an SOP recorder that takes eight minutes replaced months of deployment delays, and the scrappy enterprise playbook—from sending donuts to warehouses to building the customer's board deck for them—that wins $300K Fortune 500 deals.
Why You Should Listen
- Why talking to 85 customers before writing a line of code is worth more than anything.
- How an eight-minute screen recording replaced months of SOP-writing delays.
- Why "what are your problems?" fails in enterprise and a pointed use case wins eight out of ten times.
- How to structure pilots that auto-convert so you never end up in post-pilot purgatory.
Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, supply chain, AI automation, enterprise sales, BackOps, first-time founder, warehouse operations, logistics AI, Sean McCarthy, agentic AI
Chapters
- 00:00:00 Intro
- 00:02:24 Beating a Giant on 5% Odds
- 00:09:25 Eighty-Five Warehouse Interviews
- 00:16:33 V1: A Slack Bot for Reshipping
- 00:22:05 Pausing Sales to Rebuild for Enterprise
- 00:34:49 The Scrappy Enterprise Sales Playbook
- 00:48:23 Two Intentional Wow Moments in Every Demo
- 00:53:40 The Moment of True Product Market Fit
Send me a message to let me know what you think!
Alex spent two years building AirOps nights and weekends during the pandemic before raising a single dollar. A chance conversation with Sam Altman—while walking down the street during SF Pride—sent him down the LLM rabbit hole months before ChatGPT existed. He pivoted his product toward AI, picked marketers as his customer, and never looked back.
In this episode, Alex breaks down why he picked marketers over every other AI use case after watching them build 80-step workflows on his platform, the consultative sales motion that converts almost every pilot to annual at $60K–$250K ACVs, and why positioning—not product—was the unlock that took AirOps from $1M to $13M ARR.
Why You Should Listen
- Why picking the highest-taste customer is more important than picking the biggest market.
- How proof-point-driven outbound gets you past the "nobody's heard of you" problem.
- Why the founder-to-seller handoff is a forcing function for focus—and when to make it.
- How a consultative, education-led sale converts almost every pilot to annual contract.
Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, AI marketing, content engineering, SEO, AEO, AI search, enterprise sales, SaaS growth, AirOps, Alex Halliday, Greylock
Chapters
- 00:00:00 Intro
- 00:03:06 Two Years in the Idea Maze
- 00:06:51 Why He Picked Marketers Over Everyone Else
- 00:14:36 What Best-in-Class Content Looks Like Now
- 00:25:42 From $1M to $13M ARR
- 00:28:29 Building a Repeatable Sales Machine
- 00:36:15 Competing in the Hottest AI Category
- 00:38:44 The Moment of True Product Market Fit
Send me a message to let me know what you think!
Isaiah pivoted mid-YC, landed in the bottom 10% of his batch, and watched 180 investors say no—their reason: phone calls won't exist a year from now. Voice AI was not yet a thing. With almost no money left, he and his co-founder bet everything on building AI phone calls from scratch. Bland went from pre-seed to a $40M Series B in a year.
In this episode, Isaiah breaks down how a $60K billboard and a strategic influencer campaign generated close to a billion impressions, why he fired 50% of his customers right after raising a Series A, and the enterprise sales playbook that lands six- and seven-figure contracts with companies most people have never heard of.
Why You Should Listen
- Why 180 VCs saying your market won't exist is actually a bullish signal.
- How two billboards and a wave of micro-influencers generated a billion impressions.
- Why firing half your customers right after raising your Series A can save your roadmap.
- How internal newsletters and org-chart mapping win six-figure enterprise deals.
Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, voice AI, AI phone calls, enterprise sales, Bland AI, YC pivot, billboard marketing, influencer marketing, call center automation, Isaiah Granet
Chapters
- 00:00:00 Intro
- 00:02:34 A Typhoon Replaces an Entire Call Center
- 00:11:52 The YC Pivot and 180 Rejections
- 00:19:05 Betting the Company on In-House AI
- 00:24:11 The Billion-Impression Billboard Campaign
- 00:34:49 Firing 50% of Customers After Raising $20M
- 00:38:43 The Enterprise Sales Playbook
- 00:50:52 The Moment of True Product Market Fit
Send me a message to let me know what you think!
Anada Lakra just raised a $21M Series A for BoldVoice, a $150/year pronunciation app that helps immigrants speak English with confidence. But she started from zero in her Harvard dorm room and a problem most VCs didn't think was big enough. She recruited a Hollywood accent coach, shipped a bare-bones V1, and got into YC.
In this episode, Anada breaks down why she launched a consumer app when every investor was chasing B2B, how a Reddit thread called "Judge My Accent" became an early growth hack, and why switching to annual-default pricing transformed her unit economics overnight.
Why You Should Listen
- Why building a consumer app in the 2020s is not as crazy as VCs think.
- How Reddit threads and guerrilla marketing drove BoldVoice's first thousand users.
- Why defaulting to annual pricing gave her instant CAC payback.
- How she grew from zero to $1M ARR and raised a $21M Series A.
Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, consumer app, B2C startup, pronunciation app, accent coaching, AI app, YC startup, mobile app growth, Anada Lakra, BoldVoice
Chapters
- 00:00:00 Intro
- 00:02:14 The Accent Problem Nobody Was Solving
- 00:11:49 Getting Into YC with No Revenue
- 00:22:48 Shipping V1 from a Dorm Room
- 00:29:31 Guerrilla Growth on Reddit and Facebook
- 00:36:05 Cracking the YouTube Influencer Playbook
- 00:48:09 Why Annual Pricing Changed Everything
- 00:50:47 The Moment of True Product Market Fit
Send me a message to let me know what you think!
Bobby launched Protege in early 2024 to connect data holders with AI model builders. He raised a $10M seed with almost no demand pipeline. A year later, Protege jumped 30x to $30M in GMV and raised $30M from a16z.
In this episode, Bobby breaks down how he built a 250-partner data network by leveraging prior healthcare relationships, why he flies from New York every week to close seven-figure enterprise deals, and why the "texting terms" litmus test tells you if a deal is real.
Why You Should Listen
- Why ignoring a customer's "no" can be the best sales move you make.
- How flying to see buyers weekly became the number one growth driver.
- Why the gap between A and A-plus talent is worth blowing your budget for.
- How Protege went from $1M to $30M GMV in a single year.
Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, AI data, enterprise sales, founder-led sales, data licensing, healthcare AI, a16z, B2B startup, Bobby Samuels, Protege
Chapters
- 00:00:00 Intro
- 00:03:01 Building the First Data Network
- 00:06:12 Why In-Person Sales Changed Everything
- 00:16:08 Going to Market with No Pipeline
- 00:21:07 Ignoring the Lab's No
- 00:27:40 From $1M to $30M in One Year
- 00:34:55 Why A-Plus Talent Is Worth It
- 00:38:28 The Moment of True Product Market Fit
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Maju ran Prime fulfillment technology for all of Amazon — same-day, one-hour shipping, global logistics during the pandemic. He became CEO at Bolt. Then he walked away to start Spangle in a basement with a co-founder, convinced AI could replace e-commerce infrastructure as we know it.
In this episode, Maju breaks down why 40% of e-commerce traffic loses its context the moment it arrives on a brand's site, how Spangle's AI dynamically rebuilds the entire storefront in real time for each visitor, and why he believes the future of commerce will be a battle between AI seller agents and AI buyer agents.
Why You Should Listen
- Why 40% of your marketing traffic is wasted the moment it hits your site.
- Why the future of e-commerce is a showdown between AI seller agents and AI buyer agents.
- How he signed 11 enterprise brands in under a year with a free POC and rev-share pricing.
Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, e-commerce, AI commerce, agentic commerce, personalization, dynamic storefronts, conversion optimization, enterprise SaaS, Series A, Spangle, Maju Kuruvilla
Chapters
- 00:00:00 Intro
- 00:01:25 Amazon VP to Basement Startup
- 00:06:23 Why AI Changes E-Commerce
- 00:09:34 The 40% Traffic Gap
- 00:17:43 AI Merchandising in Real Time
- 00:23:17 Raising $50M for the Seller Agent
- 00:33:12 Signing 11 Enterprise Brands
- 00:37:17 The Moment of True Product Market Fit
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Amanda spent 16 years running a services business for Cisco and Intel. When she tried to productize her business, 22 VCs rejected her. That became 6sense, a $200M ARR company. After stepping aside as CEO and taking five years off, she's back with an AI startup called 1 mind.
In this episode, Amanda breaks down why she always goes enterprise-first when everyone tells her to start small, how she used an AI clone of herself to pitch 60 VCs and raise 1mind's Series A in three days, and why she believes the entire sales process—SDRs, AEs, sales engineers—is about to be collapsed into a single AI "superhuman."
Why You Should Listen
- Why 22 VC partner meetings said no—and how one change fixed it overnight.
- How she used an AI clone of herself to close a Series A in 3 days.
- Why starting enterprise-first beats moving upmarket.
- Why outbound AI email is a race to the bottom and what to build instead.
Keywords startup podcast, startup podcast for founders, product market fit, AI agents, AI sales, enterprise sales, 6sense, 1mind, finding pmf, B2B SaaS, AI enabled services, net dollar retention
Chapters
- 00:00:00 Intro
- 00:05:58 22 VC Rejections—Until She Found the Right Co-Founders
- 00:08:49 Why She Always Starts Enterprise-First
- 00:22:00 Five Years Off—Then the AI Wave Hit
- 00:27:32 Why AISDRs Are a Race to the Bottom
- 00:43:23 Using Her AI Clone to Raise the Series A
- 00:49:52 The Moment of True Product Market Fit
Send me a message to let me know what you think!
Tarek already built a B2B software company to $30M ARR. But when the AI wave hit, he realized he could build a generational business by automating the manual world of accounts receivable. So, he left to start Stuut.
In this episode, Tarek breaks down how he reached $1M ARR in a couple of months and is on track to hit up to $50M this year. He reveals how he pre-sold his first $65k contract with just wireframes, why he forces new customers to introduce him to five peers, and the brutal reality of finding message-market fit through hundreds of cold calls.
Why You Should Listen
- How to pre-sell a $65k enterprise contract before writing code.
- The "Closing Discount" hack to generate 5 referrals from every new customer.
- Why finding "Message Market Fit" is more important than your ICP.
- How to spot and avoid early-stage startup "vultures".
- Why scaling a B2B sales motion requires hiring misfits over pedigree.
00:00:00 Intro
00:01:41 Leaving a $30M Startup to Build with AI
00:08:06 Finding Message Market Fit Through Cold Calling
00:20:07 Pre-Selling a $65k Contract with Wireframes
00:27:51 The Voice AI "Aha" Moment
00:33:07 The Closing Discount Referral Hack
00:37:18 The Brutal Reality of B2B Sales
00:42:19 Hitting $1M ARR and Pacing for $50M
00:45:05 Why Product Market Fit is Never Truly Found
Send me a message to let me know what you think!
Description
Bhaskar was employee #1 at AppDynamics, which was sold to Cisco for $3.7B. He and co-founder Jyoti found a way to change how enterprise monitoring tools worked. From tracking low-level code metrics that ops teams didn't understand to monitoring what the business actually cares about.
In this episode, Bhaskar breaks down how that one insight won them Netflix and Priceline as early customers, why they ran production POCs that no competitor would dare try, and how a free download called AppDynamics Lite generated over 60% of their leads—in an industry where getting started normally took weeks of professional services and six-figure contracts.
Why You Should Listen
- Why selling to developers is operating on hard mode.
- How one-day POCs became the killer enterprise sales weapon.
- Why freemium disrupted an industry that required weeks of professional services to get started.
- How they grew from $2M to $12M in revenue in just one year post launch.
Keywords
startup podcast, startup podcast for founders, product market fit, AppDynamics, application monitoring, enterprise SaaS, B2B sales, finding pmf, freemium strategy, Cisco acquisition, production POC
Chapters
- 00:00:00 Intro
- 00:11:33 Choosing the ICP
- 00:20:37 Landing Netflix with Freemium
- 00:28:44 Growing from $2M to $12M in Year Two
- 00:30:10 The Free Download Strategy That Generated 60% of Leads
- 00:32:04 Days from the NASDAQ Bell—Then Cisco Offered $3.7B
- 00:41:28 The Moment of True Product Market Fit
Send me a message to let me know what you think!
Yogi spent 20 years living the nightmare of enterprise accounting. As a senior finance leader at Rubrik, he watched highly paid professionals spend three weeks every month manually wrangling data into spreadsheets—a problem that caused mass burnout and multi-million dollar stock corrections.
When ChatGPT launched, Yogi knew the technology was finally ready to solve the problem. In this episode, he breaks down how he left his executive track to found Maxima, how he landed massive enterprises like Scale AI and Rippling as early design partners, and why he managed to raise $41M from top-tier VCs like Kleiner Perkins and Redpoint before he even had a pitch deck.
Why You Should Listen
- How a 1st-time founder raised an $11M Seed and a $30M Series A in a year.
- Why replacing accountants with AI is a bigger opportunity than replacing SaaS tools.
- How to use the "Design Partner Playbook" to secure Fortune 500 customers.
- Why charging for an MVP creates the friction you actually need to find true PMF.
- The difference between selling "digital shelves" and selling "folded laundry" in the age of AI.
Keywords
startup podcast, startup podcast for founders, AI in accounting, enterprise SaaS, product market fit, finding pmf, raising seed round, raising series a, B2B sales, design partners
00:00:00 Intro
00:07:37 Leaving a CFO Track to Become a Founder
00:11:52 Raising an $11M Seed Round from Kleiner Perkins
00:20:07 The Design Partner Playbook
00:22:34 Why You Must Charge Your Early Design Partners
00:28:36 The Aha Moment for Product Market Fit
00:33:20 Selling "Folded Laundry" Instead of "Digital Shelves"
00:36:47 Raising a $30M Series A Pre-Emptively
Send me a message to let me know what you think!
Omar already built and sold an AI startup for over $100M. But when the generative AI wave hit, he realized the technology wasn't just the future of software—it was the future of labor. So he started Eudia to completely transform how enterprise legal teams operate.
In this episode, Omar breaks down how he scaled from $2M to $20M ARR in just 12 months. He reveals the exact cold email strategy he used to land C-suite design partners, why he bought an existing legal services company to accelerate his AI platform, and why replacing human labor with AI is the ultimate business model.
Why You Should Listen
- Why selling AI as a service is a much bigger opportunity than selling SaaS.
- How to secure Fortune 500 design partners using cold emails.
- Why playing to win beats playing not to lose.
- How to build a data moat that AI wrappers can't compete with.
- Why ARR shouldn't be your only measure of startup success in the AI era.
Keywords
startup podcast, startup podcast for founders, AI startups, product market fit, AI enabled services, legaltech, B2B SaaS, enterprise sales, finding pmf, generative AI
00:00:00 Intro
00:01:45 Why AI is the Future of Labor
00:04:55 Replacing In-House vs. Outsourced Legal Teams
00:09:35 Selling His First AI Startup for $100M
00:12:11 Why the $1 Trillion Law Firm Industry is at Risk
00:21:59 Landing Fortune 500 Design Partners via Cold Email
00:28:26 Playing to Win vs. Playing Not to Lose
00:33:45 Raising a $6M Seed Round with an 80-Page Transcript
00:38:53 Buying a Legal Services Company to Accelerate Growth
00:44:55 Scaling from $2M to $20M ARR in 12 Months
Send me a message to let me know what you think!
Helen was a software engineer who noticed a massive problem: accounting software for startups was broken, manual, and weeks out of date. Instead of just building a shiny new dashboard on top of legacy platforms, she decided to completely replace the offshore accounting model with AI.
In this episode, Helen breaks down how she raised a $4.7M seed round pre-product as a solo founder and why she chose to build an AI-enabled service instead of pure software. She reveals the exact user research playbook she used across 200 interviews, how to rebuild a monopoly like QuickBooks, why hitting product-market fit actually forced her to stop taking new customers, and how she raised a $15M Series A.
Why You Should Listen
- How to raise a $4.7M seed round as a solo founder with zero revenue.
- Why building an AI-enabled service beats selling pure SaaS.
- Why saying "yes" to too many customers will destroy your growth.
- How to conduct 200 user interviews before writing a single line of code.
- Why rebuilding a legacy monopoly is no longer a crazy idea.
Keywords
startup podcast, startup podcast for founders, product market fit, AI enabled services, fintech startup, user research, solo founder, raising seed round, B2B SaaS, finding pmf
00:00:00 Intro
00:02:13 The Origin Story
00:05:31 Doing 200 User Interviews Before Building
00:11:49 The "Magic Wand" Framework for User Research
00:14:33 Raising a $4.7M Seed as a Solo Founder
00:22:27 Why AI-Enabled Services Beat Pure SaaS
00:28:50 Rebuilding QuickBooks from Scratch
00:39:34 The Public Launch and PR Strategy
00:50:06 Why Saying "Yes" to Customers Hurt Growth
00:53:46 The Moment of True Product Market Fit
Send me a message to let me know what you think!
Mateo had already built a successful food company in Argentina. But he wanted more. So he moved to New York with no network, no credibility, and a dream to build the "Spotify for Food."
The first two years were messy. He nearly ran out of money multiple times, relied on corporate expense accounts to keep the lights on, and failed a major expansion into LA. But then, he noticed a strange behavior: some customers were ordering 10 meals at a time. That single insight led to a massive pivot, a partnership with world-class chefs, and eventually, a $750M run rate.
In this episode, Mateo breaks down the gritty reality of building a marketplace from scratch, how to survive the "messy middle," and why sometimes you have to kill your revenue to save your company.
Why You Should Listen
- Why he shut down a $2M revenue stream to pivot to a model with $0 ARR.
- How identifying the small group of users who would be "very disappointed" unlocked massive scale.
- Why he failed at expanding the first time, but succeeded the second time by changing just one variable.
Keywords
startup podcast, startup podcast for founders, product market fit, food tech, marketplace startups, pivot, founder story, CookUnity, scaling a startup, immigrant founder
00:00:00 Intro
00:02:50 Moving from Argentina to New York
00:07:43 Why Leave a Successful Business?
00:13:37 The "Airbnb for Food" Vision
00:22:44 Faking Traction with Corporate Stipends
00:28:41 The $2M Pivot: Shutting Down On-Demand
00:34:54 Why Unit Economics Mattered More Than Revenue
00:42:14 The COVID Inflection Point & Chef Partnerships
00:48:09 Failing Fast in LA vs. Succeeding Later
00:51:54 The Moment of True Product Market Fit
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Roy is a three-time founder who has cracked the code on enterprise AI. After selling his first company and realizing his second idea was too slow, he pivoted to solving a massive problem: customer service automation.
In this episode, Roy breaks down how GetVocal went from zero to $1M ARR in just five months. He reveals the "Context Graph" technology that allows them to beat LLM wrappers, why he believes purely generative AI is useless for business, and how he turned a single deployment into an enterprise-wide contagion.
Why You Should Listen
- How to hit $1M ARR in 5 months with a single salesperson.
- Why "Context Graphs" are the secret to building AI that doesn't hallucinate.
- How to expand from a single agent to 80 agents across the enterprise.
- The critical difference between Deterministic and Probabilistic AI
- Why starting with a personal passion project failed, but pivoting to enterprise worked.
Keywords
startup podcast, startup podcast for founders, product market fit, enterprise AI, customer service automation, finding pmf, context graphs, AI agents, B2B sales, Roy Moussa
00:00:00 Intro
00:02:29 From Engineer to 3-Time Founder
00:08:11 The Failed Pivot
00:12:49 Solving Sales Efficiency First
00:16:06 The Pivot to Customer Service
00:18:57 Why Chatbots Failed & The Hybrid AI Solution
00:25:43 What is a Context Graph?
00:34:46 The "Contagion" Effect: 80 Agents in 8 Weeks
00:39:34 Competing with Decagon & The Human-Centric Approach
00:41:58 Hitting $1M ARR in 5 Months
Send me a message to let me know what you think!
Ryan was a successful lawyer with a massive problem. He couldn't find a task management tool that worked for his firm, so he built one himself. He thought he'd solved the problem, but for 8 agonizing months, he couldn't sell a single subscription.
In this episode, Ryan breaks down the gritty reality of bootstrapping Filevine into a $3B legal tech startup doing over $200M in revenue. He shares how a random Instagram ad campaign ended his sales drought, how he fought off a Tiger Global-backed competitor built on Salesforce, and how he's completely rewriting his company's architecture to win the AI legal tech war against the likes of Harvey and Legora.
Why You Should Listen
- How 8 months of zero sales almost broke him.
- Why building customizability into your core product is the ultimate defense.
- How to recruit top engineers when you have zero funding.
- Why SMBs often have "beer money but champagne tastes."
- How to pivot from SaaS to AI.
Keywords
startup podcast, startup podcast for founders, legaltech, product market fit, bootstrapping, B2B SaaS, enterprise sales, AI startup, founder story, finding pmf
00:00:00 Intro
00:07:20 Recruiting an Amazon Engineer with No Funding
00:11:52 The First Conference and the "Terrible" MVP
00:15:23 The Dark Months: Zero Sales from Cold Calling
00:19:28 The GTM that Saved the Company
00:27:36 Why In-Person Events Beat Cold Calling
00:36:19 Moving Upmarket to Avoid Demanding SMBs
00:37:32 Beating a $50M Salesforce-Backed Competitor
00:46:45 Rewriting Filevine for the AI Era
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Sam spent years at the Air Force and Palantir before deciding to build Method Security. Instead of launching an MVP and iterating with customers, he did the opposite: he shut out the world and built in the dark for a year based on his own conviction.
In this episode, Sam breaks down his contrarian approach to building a platform for the enterprise and government. He reveals how he raised millions from Andreessen Horowitz with just a prototype, why he refuses to hire a sales team, and how he landed a seven-figure contract right out of the gate.
Why You Should Listen
- Why he ignored the "talk to users" advice and built in the dark for a year.
- How to raise a $5.5M seed round from a16z in just 3 days.
- The "2-Hour Bootcamp" strategy that shortens enterprise sales cycles.
- Why keeping your engineering team dangerously small creates speed.
- How to turn a design partnership into a $1M+ contract.
Keywords
startup podcast, startup podcast for founders, product market fit, cybersecurity, a16z, Palantir, enterprise sales, design partners, government contracting, founder led sales
00:00:00 Intro
00:02:00 From Air Force to Palantir
00:06:28 The "Shared Notion Space" of Ideas
00:10:04 Raising Seed from a16z in 3 Days
00:17:23 The "Dark Period": Building Without Users
00:22:23 Structuring Enterprise Design Partnerships
00:28:48 The "2-Hour Bootcamp" Sales Strategy
00:31:03 Why the Org Chart is Flat (15 Reports to CTO)
00:34:02 Converting Pilots to Commercial Contracts
00:41:07 The Moment of True Product Market Fit
Send me a message to let me know what you think!
Michel raised $185M and achieved a unicorn valuation before he fully cracked monetization. How? By building a community so strong it broke his engineering team.
In this episode, Michel breaks down the chaotic journey from a failed YC marketing idea to becoming the standard for open-source data movement. He reveals why he killed a high-growth fintech product, how he used the "Magic Wand" question to find his true direction, and the specific insight that allowed Airbyte to hit $1M ARR in just 4 months after launching their enterprise product.
Why You Should Listen
- How to hit $1M ARR in 4 months with a bare-bones product.
- The "Magic Wand" framework for validating startup ideas.
- Why you should sometimes optimize for Vanity Metrics.
- How to raise $150M+ by solving the "build vs buy" dilemma.
- The critical difference between Project Market Fit and Product Market Fit.
Keywords
startup podcast, startup podcast for founders, open source business model, data infrastructure, product market fit, Y Combinator, pivoting, fundraising, developer tools, Airbyte
00:00:00 Intro
00:09:37 The Failed Marketing Product & COVID Pivot
00:16:13 The "Magic Wand" Framework for Ideas
00:20:52 Launching Open Source to Solve "Build vs Buy"
00:24:39 Bootstrapping a Community on Reddit & Hacker News
00:30:17 Why Too Many Users Broke the Team
00:34:32 Project Market Fit vs. Product Market Fit
00:36:16 Hitting $1M ARR in 4 Months
00:37:53 Managing a Unicorn Valuation Without Revenue
00:41:20 Advice for Early Stage Founders
Send me a message to let me know what you think!
Didi spent five years building a product that no one really wanted. He raised $10 million, tried endless pivots, and was known as the "black sheep" of his investors' portfolio. Then, with his back against the wall, he made one final bet on a boring, unsexy market: FP&A for Excel users.
In this episode, Didi breaks down how that final pivot turned into a rocket ship. He reveals why he sold cheap monthly contracts to prove demand, how he used his kids to automate LinkedIn outreach, and why targeting the market everyone else ignores (Excel lovers) was the key to unlocking massive growth.
Why You Should Listen
- How to survive 5 years of wandering before finding PMF.
- Why he sold $790/month contracts to validate a pivot.
- How to scale from $0 to $20M ARR with 100% outbound sales.
Keywords
startup podcast, startup podcast for founders, product market fit, finding pmf, pivot, B2B sales, outbound sales strategy, FP&A software, excel automation, Didi Gurfinkel
00:00:00 Intro
00:02:42 The First 5 Years of Wandering
00:11:39 Being the "Black Sheep" of the Portfolio
00:14:12 Identifying the FP&A Opportunity
00:20:55 The Pivot: Selling $790/Month Contracts
00:30:30 Scaling from $1M to $20M with Outbound
00:33:18 Why the Mid-Market is Wide Open
00:34:22 The Moment of True Product Market Fit
Send me a message to let me know what you think!
Russ was running a moderately successful live streaming startup. Then he got a terrifying offer from a tech giant: sell to us for cheap, or we'll crush you. He had no leverage. He was about to fold.
Then he got an email from OpenAI. They had secretly built ChatGPT's voice mode on his infrastructure. Overnight, everything changed.
In this episode, Russ reveals the wild story of how LiveKit became the backbone of multimodal AI, why he almost sold his previous company for parts, and how to survive when the biggest companies in the world are breathing down your neck.
Why You Should Listen
- How to secretly power ChatGPT’s voice mode.
- Why you should build "boring" infrastructure instead of AI apps.
- How to negotiate an acquihire when you have no leverage.
- Why a "sell or die" threat from a tech giant was the best thing to happen.
- How to pivot from a failed consumer app to a unicorn infrastructure play.
Keywords
startup podcast, startup podcast for founders, product market fit, AI infrastructure, multimodal AI, OpenAI, ChatGPT voice mode, founder stories, pivot, LiveKit
00:00:00 Intro
00:02:49 The OG YC Batch Experience
00:07:08 How to Sell a Failing Startup
00:15:51 The "Good Cop, Bad Cop" Investor Negotiation
00:35:56 The First Voice AI Demo That Flopped
00:38:29 The Secret Email from OpenAI
00:43:47 How to Scale Stateful Voice Agents
Send me a message to let me know what you think!
Kevin was building a successful startup in the NFT space. They'd hit $1M ARR. But he looked at the market and realized it wasn't big enough. So he made the terrifying choice to pivot the entire company into cybersecurity.
In this episode, Kevin breaks down how he navigated that transition without killing the business. He reveals how he sold his first $5k/month contract with no product, why he raised a massive seed round he didn't need, and how he convinced Andreessen Horowitz to lead his Series A in the middle of a strategic shift.
Why You Should Listen
- How to pivot from a bad market to a unicorn opportunity.
- Why he sold a $5k/month contract with zero product.
- How to raise a Series A from a16z during a pivot.
- Why you never truly "find" Product Market Fit.
- The danger of building for a niche market (and how to escape).
Keywords
startup podcast, startup podcast for founders, product market fit, finding pmf, pivot, cybersecurity, crypto startup, a16z, raising series a, Kevin Tian
00:00:00 Intro
00:02:17 Meeting at Uber and the "Glass Eating" Phase
00:07:21 The First Idea
00:11:52 Selling the First $5k/Month Contract with No Product
00:16:52 The Decision to Pivot at $1M ARR
00:29:43 Network Selling to Enterprise Cybersecurity
00:32:03 Raising Series A from a16z During a Pivot
00:33:36 Why Product Market Fit is Not a One-Time Event
00:35:10 Action Produces Insights
Send me a message to let me know what you think!
Dileep sold his first company for over $100M. For his second act, he didn't just want another win; he wanted to solve a problem that banks refused to touch: global business banking.
In this episode, Dileep breaks down how Jeeves scaled to $7M ARR in just over a year by doing things that "don't scale"—like physically mailing credit cards to Argentina.
He reveals the counterintuitive strategy of raising from dozens of small investors, how to pivot a fintech when interest rates skyrocket, and why being an outsider was his biggest advantage in building a global banking infrastructure from scratch.
Why You Should Listen
- How to get to $7M ARR in one year through unscalable acts.
- Why a "messy" cap table with 50+ investors is actually a secret weapon.
- The "Beat Down" Framework: A brutal stress test for vetting your idea.
- The offline marketing stunt that actually worked.
Keywords
startup podcast, startup podcast for founders, product market fit, fintech startup, global expansion, second time founder, Y Combinator, fundraising strategy, B2B banking, finding pmf
00:00:00 Intro
00:02:04 Selling His First Company for $100M
00:08:19 The "Beat Down" Framework for New Ideas
00:19:38 The One Metric That Matters for PMF
00:24:44 Why Join YC as a Second-Time Founder?
00:29:15 Shipping Cards to Argentina by Hand
00:39:13 The Pivot to Jeeves Pay When Cards Got Shut Down
00:43:25 The "Messy Cap Table" Fundraising Strategy
00:49:27 The Moment of True Product Market Fit
Send me a message to let me know what you think!
Chaz has founded 3 companies. The first sold for over $40M. The second sold to GoPuff for even more. Now, he’s on his third act with Model ML, having just raised $75M Series A <2 years in.
In this episode, Chaz breaks down the playbook behind his successes. He reveals how he raised his first million by pitching strangers on LinkedIn, why his delivery startup was just a text message system on the backend, and why speed is the only defensive moat left.
Why You Should Listen
- How to pitch strangers on LinkedIn for angel checks.
- Why you should always say you're raising "a bit more" than you actually are.
- Why "Product Market Fit" is no longer static in the age of AI.
- How to launch a massive consumer business.
- Why getting a paid design partner isn't enough.
Keywords
startup podcast, startup podcast for founders, serial entrepreneur, fundraising strategy, product market fit, rapid scaling, AI startup, exit strategy, MVP, fintech
00:00:00 Intro
00:04:46 Pitching Strangers for Angel Checks
00:07:51 The "Fake" Fundraising Strategy
00:23:28 Why MVPs are Dead in the AI Era
00:25:01 Selling to GoPuff While Running Out of Cash
00:32:25 The Origin of ModelML
00:38:30 The Design Partner Playbook
00:46:13 From $5k to $100k MRR in 3 Months
Send me a message to let me know what you think!
Jay was running a respectable AI startup with $3M ARR. But he knew it wasn't a venture-scale rocket ship. So, he decided to fire all his customers, pivot the entire company, and bet everything on a new vertical: legal AI for plaintiff attorneys.
Eve went from zero to unicorn status in under two years, raising $100M at a $1B valuation.
In this episode, Jay breaks down the brutal reality of pivoting a revenue-generating company, how to achieve "demo shock" in an antiquated industry, and why 4-hour user sessions were the first sign that he had struck gold.
Why You Should Listen
- How threatening to shut down your product can reveal PMF.
- Why firing all your existing customers might be the only way to scale.
- How to achieve a 40% conversion rate from cold outreach to demo.
- Why you should target mid market instead of enterprise if you want to deploy AI fast.
Keywordsstartup podcast, startup podcast for founders, product market fit, finding pmf, pivot, legal tech, AI startup, B2B sales, unicorn startup, Jay Madheswaran, Eve
00:00:00 Intro
00:02:27 From VC to Founder
00:08:42 The First Idea: RPA for NLP
00:16:52 The Hard Decision to Pivot at 3M ARR
00:24:26 Product Discovery While Still Supporting Old Customers
00:33:56 40 Percent Conversion from Cold Outreach
00:39:56 Firing Customers to Find True PMF
00:41:06 The 4-Hour User Session Signal
00:46:05 From 1M to 10M ARR in One Year
00:49:11 The Moment of True Product Market Fit
Send me a message to let me know what you think!
Bassem took Briq from a failed data idea to a Series B leader in construction financial automation.But the path wasn't linear.
In this episode, Bassem reveals how he pivoted to RPA bots, why he killed a high-growth fintech product to survive the 2023 cash crunch, and how he uses a relentless "Go-to-Market" strategy. He breaks down his exact ABM playbook, why he hates trade shows, and why he believes AI orchestration is a bigger shift than the cloud.
Why You Should Listen
- How to identify the "Challenger" who will kill your deal.
- Why trade shows are a waste of money (and what to do instead).
- The "1-Person Webinar" hack to close high-value accounts.
- The brutal reality of cutting 50% of staff to survive.
- Why selling "risk reduction" beats selling "time saved."
Keywords
startup podcast, startup podcast for founders, product market fit, account based marketing, construction tech, go to market strategy, enterprise sales, finding pmf, robotic process automation, ai orchestration
00:00:00 Intro
00:06:23 The RPA "Aha" Moment with a Tech Giant
00:11:52 Selling Risk vs. Selling Time Saved
00:13:27 The "New CFO" Signal in Account Based Marketing
00:17:06 Identifying the "Challenger" in Enterprise Sales
00:23:22 The 1-Person Webinar Strategy
00:29:19 Killing the Fintech Product to Survive 2023
00:36:20 Why You Never Truly Have Product Market Fit
Send me a message to let me know what you think!
Max went from a YC rejection to building a $1.8B company in less than two years. His company, Legora, is the fastest YC-backed company to become a unicorn in history.
His path to insane growth was not standard: after raising a massive Series A, Max told his board he was pausing all new sales for six months to rebuild the product infrastructure.
In this episode, Max breaks down the "burn the boats" mentality that drove their growth, the specific demo tactics that convert 55% of prospects, and how to build an engineering culture that ships fast enough to beat incumbents like Thomson Reuters.
Why You Should Listen
- Why he shut down sales for 6 months immediately after raising $35M.
- How a single live demo stunt at a conference generated 150 qualified leads.
- The aggressive pitch strategy that turned a YC rejection into an acceptance.
- How to close a $10M round with Benchmark after a single meeting.
- Why you should encourage your enterprise clients to run bake-offs.
Keywords
startup podcast, startup podcast for founders, product market fit, AI legal tech, Y Combinator, hypergrowth, enterprise sales, Benchmark Capital, fundraising strategy, rapid scaling
00:00:00 Intro
00:06:51 Getting Rejected by Y Combinator
00:15:37 Living on 50k Euros with Design Partners
00:30:19 The Live Demo That Booked 150 Meetings
00:34:06 Raising $10M from Benchmark in 30 Minutes
00:35:13 Shutting Down Sales After Raising Series A
00:46:36 How to Win 85 Percent of Competitive Deals
00:50:05 The Moment of True Product Market Fit
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Russell went from working in private equity to hand-delivering dog food on the NYC subway at 5 a.m. He didn't start with a VC check; he started with a studio apartment kitchen and a belief that dog food was broken.
In this episode, Russell breaks down how he turned a side hustle into Spot & Tango, a direct-to-consumer giant doing over $100M in revenue.
He reveals the gritty reality of early-stage CPG, why he vertically integrated his own factory when everyone else outsourced, and how a simple "fresh dry" product innovation called UnKibble unlocked massive scale.
Why You Should Listen
- How to scale from a studio apartment kitchen to $100M+ revenue.
- How a simple packaging choice created a premium brand identity.
- Why your second product might become your biggest winner.
- Why the best performing ad creative is often the cheapest.
Keywords
startup podcast, startup podcast for founders, product market fit, finding pmf, DTC startup, CPG brand, direct to consumer, scaling a startup, founder stories, Spot and Tango
00:00:00 Intro
00:02:30 From Private Equity to Dog Food
00:07:36 Hand-Delivering to the First Customer
00:11:57 The Dark Ages: Cooking in a Shared Kitchen
00:19:17 Pricing Strategy Without Sales Data
00:22:50 The Pink Butcher Paper Brand Identity
00:26:26 Launching UnKibble: The 9-Figure Product
00:31:52 Why Vertical Integration is a Moat
00:40:54 The Best Ad Creative is a Sticky Note
00:47:09 Selling Out Inventory in 4 Days
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Harman went from cold-calling hotels 100 times a day to building the category-defining guest management platform for the hospitality industry. Canary built a $600M company by first solving one tiny, annoying problem: paper credit card authorization forms.
In this episode, Harman breaks down how a simple digital form became the wedge into thousands of hotels. He reveals why they stuck with outbound sales long after hitting millions in revenue, the terror of collecting physical checks during the first week of COVID, and the exact moment he knew they had hit product-market fit.
Why You Should Listen
- The "Activated Hair on Fire" framework: How to turn a latent problem into a must-have purchase.
- Why outbound sales (and cold calling) is often your top early growth channel.
- How to use a simple, "unscalable" wedge to unlock a massive market.
- Why you should celebrate the lows: A counterintuitive take on managing founder psychology.
- The story of signing 200+ customers in a single day (and finding true PMF).
Keywords
startup podcast, startup podcast for founders, product market fit, finding pmf, vertical saas, outbound sales, cold calling strategies, early stage growth, b2b sales, hospitality tech
00:00:00 Intro
00:02:13 From Management Consulting to Hotel Tech
00:11:32 The Paper Form that Launched a Company
00:17:35 The Activated Hair on Fire Framework
00:24:26 Landing the First Customer via Cold Call
00:28:21 Applying to YC
00:32:35 Making 100 Cold Calls a Day
00:43:42 The COVID Cash Flow Panic
00:48:27 Signing 200 Customers in One Day
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In this episode, Rich breaks down the wild story of Fathom's launch. He reveals how they secured a prime spot on the Zoom Marketplace and generated 100,000 signups in 30 days—only to realize 99.9% of them were useless.
He discusses the pivot to monetization when the market crashed, how to design a product for viral loops, and why staying in private beta for 10 months was the best decision he ever made.
Why You Should Listen
- Why getting 100,000 signups in a single month nearly killed the company.
- How to use the "Iceberg Strategy" to build a defensible moat.
- Why you should attack the "800-pound gorilla" incumbent.
- How to hit $100k ARR by selling a roadmap that doesn't exist yet.
- The "Visible Feature" mechanic that drives zero-cost viral growth in B2B.
Keywords
startup podcast, startup podcast for founders, viral growth, product market fit, AI startup, freemium strategy, Zoom marketplace, PLG, B2B sales, Fathom
00:00:00 Intro
00:03:14 Why Sales Reps Hated Gong
00:07:54 Betting on Transcription Costs Going to Zero
00:11:52 The 10 Month Private Beta Strategy
00:17:46 The Zoom Marketplace Launch
00:19:52 100k Signups and Zero Growth
00:26:39 Selling a Roadmap to Hit 100k ARR
00:33:53 The Viral Loop of Visible Bots
00:36:12 Why Enterprise Sales Was a Trap
00:39:51 The Moment of True Product Market Fit
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Bob is a serial entrepreneur who founded MobileIron, grew it to $150M in revenue, and took it public. Now, he's back with his fourth startup, BlueRock, tackling the next massive wave: agentic AI security.
In this episode, Bob breaks down the distinct difference between finding Product-Market Fit and finding Go-To-Market Fit—and why confusing the two can kill your company.
He shares the exact questions he asked early customers to pivot from a generic mobile idea to a billion-dollar enterprise solution, the painful transition from founder-led sales to a repeatable playbook, and why he believes agentic AI is the "mobile wave" all over again.
Why You Should Listen
- Why asking "what else is bothering you?" can uncover real pain points.
- Why finding Product-Market Fit might actually increase your burn rate.
- Why founder-led sales often fail to scale and what to do about it.
- How to use a "Deal Grind" session to turn anecdotal sales wins into a scientific Go-To-Market machine.
- Why identifying the right tech wave matters more than your initial idea.
Keywords
startup podcast, startup podcast for founders, product market fit, go to market fit, enterprise sales, founder led sales, mobileiron, agentic AI, cybersecurity startup, bob tinker
00:00:00 Intro
00:03:17 Talk to Customers Before Writing Code
00:15:28 Why Finding PMF Can Increase Burn Without Growth
00:17:51 The Founder "Magic Pixie Dust" Trap
00:25:34 The Deal Grind Exercise
00:31:43 From 1M to 80M ARR in 4 Years
00:32:54 Why Agentic AI is the Next Mobile Wave
00:38:30 The Famous Sequoia Tombstone Meeting
00:40:17 The Magic Question: What Else is Bothering You?
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In less than 12 months, Shahar went from an idea to a $30M Series A and a team of 40. He didn't sell another AI tool—he built an AI-first service that replaced expensive human consultants in the massive pen-testing market.
In this episode, Shahar breaks down the "Service-as-Software" playbook that allowed him to hit $1M ARR in just three months. He reveals how to convert design partners into paying customers before the product is finished, why he refuses to sell to service providers, and how to achieve a 40% SQL-to-Close rate in the enterprise.
Why You Should Listen
- How to hit $1M ARR in a single quarter with zero marketing spend.
- Why asking "Would you use this?" is useless and the one question that actually validates demand.
- Why "Service-as-Software" is the single best business model for AI startups
- How to maintain a 100% win rate against competitors in live bake-offs.
- The ultimate litmus test for knowing if you have true Product-Market Fit.
Keywords
startup podcast, startup podcast for founders, product market fit, finding pmf, agentic AI, cybersecurity startup, B2B sales strategy, service as software, rapid scaling, Felicis
00:00:00 Intro
00:04:06 Why Manual Pen Testing is Broken
00:15:42 Ideation and The Wallet Test
00:22:38 How to Convert Design Partners to Paid
00:28:05 40 Percent SQL to Close Rate
00:33:14 The Service as Software Business Model
00:46:06 Hitting 1M ARR in One Quarter
00:48:50 Raising a 30M Series A from Felicis
00:50:01 The Turn It Off PMF Test
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Ashwin built a $1.5B company in two years. He didn't do it with a massive team or a complex 5-year roadmap. He did it by ignoring "strategy" and talking to 100+ buyers until he found a problem so painful they would pay six figures for a solution that didn't fully exist yet.
In this episode, Ashwin breaks down the exact playbook Decagon used to go from zero to unicorn. He reveals why he refused to hire anyone until $1M ARR, how to differentiate in a crowded AI market, and why your customers are the only roadmap you’ll ever need.
Why You Should Listen
- How to hit $1M ARR in 6 months with just two founders and zero employees.
- The "Willingness to Pay" test: How to know if a customer will sign a $150k check.
- Why "over-thinking" your strategy is the fastest way to kill your startup.
- How to close massive enterprise deals before you have a full product.
- Why going vertical is often the wrong move for AI startups.
Keywords
startup podcast, startup podcast for founders, product market fit, finding pmf, B2B sales, enterprise sales, AI startup, customer discovery, pricing strategy, early stage growth
00:00:00 Intro
00:02:56 Selling His First AI Startup to Scale
00:09:11 Why Founders Over Intellectualize Strategy
00:13:48 How to Get 100 Customer Interviews
00:15:10 The 150k Willingness to Pay Test
00:21:05 Hitting 1M ARR with Zero Employees
00:25:09 Ignoring Scalability to Win Early Customers
00:31:43 Defensibility in the Gen AI Era
00:39:42 Mocking APIs to Close Enterprise Deals
00:42:58 The Moment of True Product Market Fit
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Jake founded Serval in April 2024— by Dec 2025 he'd raised a $75M Series B from Sequoia at a $1B valuation.
He didn't look for a "wedge" or a "niche." He looked at ServiceNow—a $160B, 20+ year-old incumbent that everyone IT team relies on—and rebuilt it from the ground up in a YEAR.
In this episode, Jake reveals the audacity behind building a full-platform replacement from Day 1, why he spent months building in the dark with zero revenue, and how he achieved a 50% demo-to-close rate on six-figure enterprise deals.
Why You Should Listen
- How to go from incorporation to a $1B valuation in just 18 months.
- The psychological shift in sales calls that proves PMF.
- How to build a demo so compelling that 50% buy on the spot.
- Why you no longer need to find a small wedge to win post Gen AI.
- The specific question that stops customers from giving you generic feedback.
Keywords
startup podcast, startup podcast for founders, hypergrowth, zero to one, unicorn startup, Sequoia Capital, replacing legacy software, enterprise sales strategy, ServiceNow competitor, Jake Stauch
00:00:00 Intro
00:03:25 Why "Hair on Fire" Problems Matter
00:06:58 Learning What Winning Feels Like at Verkada
00:14:05 100+ Customer Discovery Calls
00:18:12 The One Question That Unlocks Real Pain
00:23:48 Why No-Code Workflows Fail
00:28:45 Taking Risks on AI Model Improvements
00:35:49 From $0 to Six-Figure ACVs in 6 Months
00:39:00 The Strategy to Rip and Replace ServiceNow
00:47:30 The "Rounding Up" Signal of PMF
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Siqi was the CEO of a hot startup doing $20M a year. Then COVID hit. Overnight, revenue went to zero. He had to lay off 95% of his staff. In the chaos of trying to save the company using broken spreadsheets, he found his next big idea: Runway.
But the path wasn't a straight line. Siqi spent four years building the product before fully launching.
In this episode, he breaks down why product taste matters more than A/B testing, and the insane viral launch strategy that overwhelmed his sales team and generated $1M ARR in a single month.
Why You Should Listen
- How a viral marketing campaign added $1M ARR in just 30 days.
- Why "user love" is a trap.
- Why it took 4 years of building in the dark to create the "Figma for Finance."
- How to mentally survive losing 95% of your revenue and staff overnight.
- Why startups are a test of stamina, not intelligence.
Keywords
startup podcast, startup podcast for founders, product market fit, viral marketing, fintech, financial modeling, finding pmf, startup growth, founder stories, Siqi Chen
00:00:00 Intro
00:04:09 The COVID Crash: From $20M to $0 ARR
00:20:36 The V1 Trap: Great UI, Zero Willingness to Pay
00:36:25 The 4 Year Build: Comparing to Figma and Notion
00:46:53 The Viral Time Locked Jacket Launch
00:53:04 Adding 1M ARR in 30 Days
00:53:45 The PMF Moment
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The startup game has completely changed. If you are still building with the 2018-2022 B2B SaaS playbook, you are already behind.
In this episode, we break down exactly how the GenAI shift has altered value creation, competition, and business models forever. This isn’t just about adding AI to your product—it’s about rethinking your entire reason to exist.
If you want to know where the massive, uncrowded opportunities are right now (and why Service-as-Software is the next gold rush), this is your blueprint.
Why You Should Listen
- Why "incremental value" startups are no longer fundable.
- The 3 new threats killing your "time-to-market" moat.
- Why the B2B SaaS playbook is dead and what’s replacing it.
- The massive "Service-as-Software" opportunity most founders are missing.
- Moving beyond "per seat" pricing: The new revenue models winning today.
Keywords
startup podcast, startup podcast for founders, GenAI startups, product market fit, service as software, B2B SaaS, AI business models, startup competition, seed stage, founder advice
00:00:00 Intro
00:01:57 Pre-Gen AI vs Post-Gen AI Eras
00:03:23 The Trap of Incremental Value Props
00:06:58 Gen AI Unlocks Undeniable Value
00:08:50 The New Triple Threat Competition
00:11:50 Why Time in Market Is Dead
00:13:14 Cycle Speed Is the Only Moat Left
00:15:00 Rethinking B2B SaaS Business Models
00:16:45 The Service as Software Opportunity
Send me a message to let me know what you think!
For the holiday break we are resurfacing some of our best episodes so far. Here is the best episode of season 3.
Kyle left his job as a hacker at the NSA to launch Huntress. He bootstrapped for 3 years and burned all his savings. One of his co-founders quit. He got into an accelerator program, but had to sleep in his car for 16 weeks because he couldn't afford a hotel.
Finally, 3 years in he'd hit $1.5M ARR. So he pitched 60 VCs for a Series A—and got 60 'no's. He was forced to raise a small, $1M inside round.
But then things changed:
2018: $1.5M ARR
2019: $5M ARR
2020: $10M ARR
2021: $20M ARR
2022: $40M ARR
2023: $70M ARR
2024: $100M+ ARR
Huntress is valued at $2B.
The investors who backed his $1M bridge are up 140x.
Now every VC wants to invest—and Kyle's the one saying 'no'.
Why you should listen:
How to know whether you should keep going or quit.
What it takes to get through the first few years at a bootstrapped startup.
Why revenue expansion is a huge lever for fast-growth (Huntress has 140% net revenue retention).
How starting a startup can impact your personal life and relationships.
How to work with partners to sell to long tail SMB customers.
Keywords
entrepreneurship, cybersecurity, product market fit, startup journey, military experience, SMB market, funding challenges, automation, human expertise, business growth
Timestamps:
(00:00:00) Intro
(00:2:01) Working at the NSA
(00:6:14) A big win in counter cyber terrorism
(00:10:00) What gave way to Huntress
(00:14:22) Pitching to a startup accelerator
(00:16:29) Adopting curiosity
(00:21:04) Getting ahead of cyber criminals
(00:26:00) Starting to grow
(00:32:50) Cult or conviction
(00:35:00) It takes grit
(00:39:50) Learning from people's lessons
(00:42:20) Cockroaches and underdogs
(00:46:10) Three strikes, I'm out
(00:52:56) Having a military background
(00:56:17) One piece of advice
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They were building a Segment competitor. It was working—customers were paying. But every sales call, prospects kept asking about the backend tech instead of the product.
So they killed the roadmap and pivoted. It took them 18 months to hit $1M ARR. Then they started growing. And so far, they've raised $350M.
Viraj walks through exactly how he validated the pivot, landed the first 10 customers, and why being outside Silicon Valley forced him to show more traction than everyone else.
Why You Should Listen
- How to know when your side feature is actually your real product
- The exact question to ask prospects to validate willingness to pay
- Why getting to $1M ARR slowly can set you up to scale faster
- How to compete when you're not based in Silicon Valley
- What talking to your first customer 4x a day for 2 months teaches you
Keywords
startup podcast, startup podcast for founders, open source startup, B2B SaaS growth, pivot strategy, developer tools startup, finding product market fit, early stage fundraising, design partners, commercial open source
00:00:00 Intro
00:01:46 Getting caught at the Coldplay concert
00:14:29 Deciding to Pivot From a Working Product to Something New
00:17:27 Building a Business Around Open Source Technology
00:19:38 Selling Before You Build
00:27:37 Talking to the First Customer Four Times a Day
00:30:51 Landing the First Ten Customers
00:35:10 Fundraising Without Silicon Valley Pedigree
00:38:48 When He Knew He Had Product Market Fit
Retry
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For the holiday break we are resurfacing some of our best episodes so far. Here is the best episode of season 2.
Here are the key lessons from the past 60 episodes that we've released to date. Each of the 5 steps to Product Market Fit is based on actual case studies with real examples you can use. It's a recap of everything I've learned over the last two years- you don't want to miss it.
Chapters:
(00:00:45) Mistakes Are Unavoidable But Avoidable Mistakes Are Unaffordable
(00:04:41) 1. Before Startup Mode, There's Research Mode
(00:07:16) 2. Only The Insanely Focused Survive
(00:10:49) 3. You Have to be IN the Market to WIN the Market
(00:14:08) 4. Forget Growth. Find Value.
(00:18:05) 5. Pivot Harder & Faster
(00:23:50) Recap
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David had a consumer app with 50,000 users and viral traction—and he shut it down. The retention metrics weren't as good as what he'd seen at Snapchat.
That difficult decision cleared the path for Juicebox, AI for recruiting that grew to $10M ARR in 2 years.
In this episode, David reveals how he pivoted to AI recruiting, generated millions of views with a simple LinkedIn demo, and ground through months of brutal churn to unlock 10x growth. If you want to know how to execute a flawless PLG strategy, run a hyper-lean team, and secure a $30M Series A from Sequoia, this is the blueprint.
Why You Should Listen
- Why you should kill some products even if they're going viral.
- How to launch a B2B product with zero budget.
- The "manual" playbook for fixing high churn.
- Why you should keep your team under 25 people even after raising millions.
- How to land an inbound term sheet from Sequoia.
Keywords
startup podcast, startup podcast for founders, product market fit, finding pmf, PLG strategy, viral marketing, pivoting, AI recruiting, Series A fundraising, Sequoia Capital
00:00:00 Intro
00:03:15 Learning Growth at Snap
00:13:01 Killing a Viral App with 50k Users
00:20:34 The 90 Second LinkedIn Video That Launched Juicebox
00:26:21 Fixing High Churn with Manual Work
00:33:04 Why B2B Products Only Need to be Marginally Better
00:42:27 Scaling to $10M ARR with Founder Led Sales
00:47:40 Raising a $30M Series A from Sequoia
00:50:12 The Moment of True Product Market Fit
Send me a message to let me know what you think!
Jennifer went from VC to founder and immediately broke every rule in the book. When she pivoted Scribe from an automation tool to a documentation platform, her investors told her she had just killed the company. She ignored them.
Instead of polishing her product, she launched a "janky" offline MVP on Product Hunt to test for real market pull. Scribe is now used by 95% of the Fortune 500.
In this episode, Jennifer reveals the brutal truth about ignoring "smart" money, why you should run PLG and Enterprise sales simultaneously from Day 1, and how to tell the difference between pushing a boulder up a hill and chasing one down it.
Why You Should Listen
- Why you sometimes need to ignore your investors to save your startup.
- The "Boulder Test": The definitive gut check for knowing if you have true Product-Market Fit.
- How to validate a massive opportunity with zero marketing budget.
- Why the conventional wisdom about choosing between PLG and Enterprise Sales is wrong.
- How to turn executive hiring interviews into free mentorship sessions.
Keywords
startup podcast, startup podcast for founders, product market fit, PLG strategies, MVP testing, enterprise sales, go to market strategy, early stage growth, finding pmf, founder stories
00:00:00 Intro
00:02:21 1,200 Customer Interviews as a VC
00:22:07 How to Hire for Excellence
00:30:18 The Pivot from Automation to Documentation
00:39:17 Launching a "Janky" MVP on Product Hunt
00:49:09 The Boulder Test for Product-Market Fit
00:52:50 Doing PLG and Enterprise Sales Simultaneously
01:03:12 Ignoring Investors to Save the Company
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Alex built the original Snapchat filters-- and sold his company to Snap for $166M.
Then he left to start Higgsfield. The company just raised a $50M Series A to help brands create AI-generated video ads at scale.
We go deep on why he thinks Adobe is in trouble, how top advertisers are already producing 10,000+ ad creatives a year, and why the companies winning in AI video aren't building foundation models.
Why You Should Listen
- Why consumer AI apps are a trap (and what to build instead)
- How to drive early growth
- The economics of AI-generated video
- How to know when to pivot away from traction that has no long term
Keywords
startup podcast, startup podcast for founders, AI video generation, generative AI startup, social media marketing AI, B2B SaaS growth, founder pivot, AI startup fundraising, creator marketing, product market fit
00:00:00 Intro
00:06:29 Selling to Snap and Working With Evan Spiegel for Four Years
00:08:28 The Origin Story of HiggsField
00:17:47 The Real Use Cases for GenAI Video Today
00:27:26 The First Product and Why They Pivoted Away From Consumer
00:29:08 The $10 Billion Short Form Drama Market Nobody Talks About
00:33:26 Going All In on Social Media Advertising
00:41:16 When He Knew He Had Product Market Fit
Retry
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Eric spent 30 years in cybersecurity. Built and sold an MSSP to private equity for hundreds of millions. Then he started Tenex and hit $43 million in revenue in ONE YEAR.
This isn't theory. This is a founder who's done it multiple times breaking down exactly how AI-native companies are about to eat every services industry alive. If you're building anything that touches AI, services, or enterprise sales, this is the episode.
Why You Should Listen
- Why selling outcomes beats selling products every time
- How to close enterprise deals in 60 days instead of 12 months
- The difference between AI-native and AI-bolted-on companies
- Why founder-led sales is non-negotiable in the early days
- How to build for IPO from day one without slowing down
Keywords
startup podcast, startup podcast for founders, AI startup growth, founder-led sales, zero to one startup, enterprise sales strategy, AI native company, managed services startup, cybersecurity startup, product market fit
00:00:00 Intro
00:10:29 Selling His Last Company for $100Ms
00:15:10 The Origin Story of TENEX
00:36:47 How They Hit $43M ARR in Year One
00:43:27 The 30 Second Demo That Closes Enterprise Deals
00:47:10 Why Selling Outcomes Beats Selling Products
00:51:29 The Mechanics of Going From Zero to $40M ARR
01:01:09 Go to Market and Founder Led Sales
01:05:32 When He Knew He Had Product Market Fit
Retry
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Carta's Peter Walker is back with the freshest data on what's actually happening at the early stage—and it's not what you're reading on X. While headlines scream about record-breaking rounds, the reality on the ground tells a different story.
Seed deals are down. Time between rounds is stretching. And there's a brutal divide between the companies getting all the attention and everyone else.
We dig into the exact valuations, graduation rates, team sizes and revenue you need for Seed and Series A... plus why the lowest-quartile seed rounds are failing at twice the rate. If you're raising or planning to raise, this is the episode.
Why You Should Listen
- The round size that cuts your Series A odds in half
- Why smaller teams are winning (and what that means for your hiring plan)
- The real median valuations at pre-seed, seed, and Series A right now
- How long it actually takes to get from seed to Series A in 2024
- When taking secondary as a founder makes sense (and when it doesn't)
Keywords
startup podcast, startup podcast for founders, seed round valuation, Series A fundraising, startup fundraising data, venture capital trends, pre-seed funding, startup metrics, founder secondary, seed to Series A
Chapters:
00:00:00 Intro
00:02:46 Seed Valuations and Who Actually Graduates to Series A
00:06:58 What Founders Outside the Hot Cohort Should Do
00:11:44 Team Sizes Are Shrinking and Employees Are Getting Less
00:17:40 Crowded Categories and Competing with Foundation Models
00:24:47 Founders Starting Companies for the Wrong Reasons
00:33:32 When Founder Secondaries Make Sense
00:39:55 The Actual Median Valuations at Pre-Seed Seed and Series A
Send me a message to let me know what you think!
Alex and his co-founders spent 2018 pitching parking lot owners on computer vision tech. Every meeting ended the same way: "Cute startup, come back in 30 years."
So they did something else—they bought the parking operators and implemented the AI themselves. VCs called them delusional. But today, Metropolis has 20 million members and adds 1 million new members every month. Every 1-2 seconds someone signs up.
Alex's biggest lesson? When enterprise customers won't adopt your tech, don't convince them—buy them. Sometimes the only way to disrupt an industry is to become the industry.
Why You Should Listen:
- The "growth buyout" playbook—buy old companies to force your tech
- Why adding friction made their product better
- The counter-intuitive metric: success = less time users spend in your product
- Why VCs said "absolutely not" to their best strategic move
Keywords:
startup podcast, startup podcast for founders, Metropolis, Alex Israel, computer vision, growth buyout, parking technology, M&A strategy, enterprise sales, B2B SaaS
00:00:00 Intro
00:03:05 Seeing the parking opportunity
00:06:37 The original vision
00:12:33 Raising $7.5M and leasing the first two parking lots
00:16:04 First customer transaction
00:22:58 The growth buyout strategy
00:27:54 Acquiring SP Plus with 23,000 employees
00:34:32 Building beyond parking
Send me a message to let me know what you think!
Amit walked away from being President of 1-800-Flowers after scaling it from $500M to $2B because he saw smart people trapped in dumb systems. His insight: half of global GDP is 90% manual work—salespeople entering data instead of selling, technicians reading manuals instead of fixing.
He started Instalily in Spring 2023 when everyone said AI agents were impossible. Instead of replacing workers, he built AI that finds signals in noise—telling each salesperson exactly which deal to focus on right now. The results are insane: $1M ARR within months, tripling revenue year two, delivering $150M+ value to single customers.
His secret? While competitors pitched flashy demos, Amit's team attended 100+ trade shows to understand actual operator pain. They hired fresh AI grads who "shipped fearlessly" instead of senior talent stuck in old paradigms.
Why You Should Listen:
- How "operator market fit" beats product market fit for enterprise sales
- The GTM playbook that hit $1M ARR in months by attending 100+ trade shows
- Why hiring AI-native grads crushed hiring senior talent for AI products
- How focusing on time-to-value unlocked enterprise deals
- The counterintuitive approach: augment the best parts of jobs, not the worst
Keywords:
startup podcast, startup podcast for founders, Instalily, Amit Shah, AI agents, enterprise sales, operator market fit, B2B SaaS, AI automation, vertical SaaS
00:00:00 Intro
00:04:42 Leaving 1-800-Flowers
00:09:55 Starting when everyone said AI agents were impossible
00:11:51 The vision—amplify the best parts of work, not replace the worst
00:16:59 Operator market fit over product market fit
00:20:48 Landing first $2B enterprise customers
00:29:00 The 100+ trade show GTM strategy that actually worked
00:33:02 Why they hired AI-native grads instead of senior talent
00:34:51 Hitting $1M ARR in months
Retry
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Wayne tested flight insurance over a single weekend with a WordPress site and Google ads. When people tried to pay, he showed a fake error message. The result: 15.9% conversion. That validation led to Sure, now powering insurance for Tesla, Toyota, and MasterCard.
But the journey was brutal. Wayne worked solo for a year, burning through savings in San Francisco. Flew to South Africa for 7 weeks to land his first insurance partner.
The real breakthrough came 4 years later, in 2019, when Elon tweeted about Tesla insurance—instant rocket ship growth. Today Sure is the rails for embedded insurance, like Visa for credit cards.
They raised $120M but haven't needed money since 2021 because they've been profitable since their Series B.
Why You Should Listen:
- How to validate an entire business in a weekend.
- Why he worked solo for a year before raising money or hiring anyone.
- The exact playbook for pivoting while keeping your old product alive.
- How one Elon Musk tweet created instant product-market fit.
Keywords:
startup podcast, startup podcast for founders, Sure, Wayne Slavin, embedded insurance, InsurTech, product validation, bootstrap to profitable, Tesla insurance, B2B pivot
00:00:00 Intro
00:01:48 The flight to Vegas that sparked a $120M insurance company
00:03:03 Building a fake insurance product in one weekend to test demand
00:11:00 Working solo for a year while burning through savings
00:14:43 Flying to South Africa for 7 weeks to land first insurance partner
00:19:58 Convincing 5 friends to quit their jobs
00:27:56 Pivoting from mobile app to embedded insurance
00:46:03 Elon's tweet creates rocket ship growth overnight
Send me a message to let me know what you think!
Matt sold his first company at 19 and made $100K. He sold his second at 21 and made $800K. A couple years later, he launched Clover and grew it to $8M ARR in 6 months.
His secret? Insane distribution. His formula is to ignore quality—and engineer quantity instead. While everyone obsesses over viral content, Matt posts 1,000 videos across 333 accounts daily, guaranteeing a million views through pure math. No luck required.
He applies the same "volume negates luck" philosophy to everything: 15,000 cold emails daily, thousands of Reddit posts to dominate SEO rankings.
Matt reveals the exact Reddit hack to guarantee #1 Google rankings, how AI agents automate everything from account creation to content generation, and why he purposely changes video metadata to trick algorithms at scale. At 23, he's cracked distribution so thoroughly that he can now incubate any business and guarantee its growth.
Why You Should Listen:
- How posting 1,000 videos daily GUARANTEES 1M views
- The Reddit hack that guarantees #1 Google rankings in 7 days
- Why referral revenue is the only true sign of product-market fit
- The "volume negates luck" framework that beats any growth strategy
Keywords:
startup podcast, startup podcast for founders, Matt Everett, Clover, growth hacking, viral marketing, SEO hacking, distribution strategy, AI automation, bootstrapping
Chapters:
00:00:00 Intro
00:01:31 Selling first company at 20
00:03:54 Selling second company for $800K in 3 months
00:06:37 The 1000 videos per day distribution hack
00:24:39 How to guarantee #1 on Google with Reddit posts
00:30:52 15,000 cold emails daily—the outbound machine
00:47:27 Why 30% referral revenue is true product-market fit
Send me a message to let me know what you think!
Russ has started and sold multiple companies over 30 years, but his Dynamic Signal journey will change how you think about product-market fit. They had $5M ARR selling influencer marketing software.
Then Russ told investors to pretend the $5M didn't exist and bet on a $200K pipeline instead. That pivot led to 600 Fortune 2000 customers and an exit at $50M ARR.
Now building his AI measurement startup Larridin, Russ shares why being a repeat founder creates a different problem—everyone tells you your idea is great even when it's not. His solution? Don't believe anything until someone writes a check.
Why You Should Listen:
- Why he walked away from $5M ARR to pursue a $200K pipeline.
- How emergent user behavior revealed a $50M business.
- Why "everyone loving your idea" means nothing.
- Why finding product-market fit is only step 1.
Keywords:
startup podcast, startup podcast for founders, Dynamic Signal, Russ Glass, product-market fit, enterprise sales, employee advocacy, pivot strategy, B2B SaaS, influencer marketing
00:00:00 Intro
00:01:36 30 years of Silicon Valley startups
00:03:05 Dynamic Signal's original idea
00:07:29 The emergent behavior that changed everything
00:15:38 Walking away from $5M ARR to pursue a $200K opportunity
00:18:23 Why product-market fit is never final
00:22:14 Selling Dynamic Signal
00:24:30 Starting Laridin
00:36:34 Raising $17M as a repeat founder—why everyone says yes
Send me a message to let me know what you think!
Harish spent 9 months building Deliver and could barely get 10 customers. The product worked. Merchants liked the fast delivery promise. But nobody was signing up.
Then he made two changes—and scaled to $100M in revenue in 2 years. Shopify acquired them for over $2B.
Harish says it wasn't about finding product-market fit. It was about finding product-PRICE-market fit. The product was fine. The pricing model was killing them.
This episode breaks down why pricing often isn't just a business decision—it's part of your product, how to build self-serve systems that scale to thousands of customers without talking to anyone, and why you must obsess about end users AND economic buyers if you actually want adoption.
Harish is now building Augment, an AI company for logistics that just raised an $85M Series A. He shares what he learned shadow-sitting operators for 60 days and why demos mean nothing in the AI era.
Why You Should Listen:
- Why PMF is often not enough—you need product-price-market fit
- Why subtle changes can have huge results
- Why you need both users AND buyers to love your product
- How to master self-serve
Keywords:
startup podcast, startup podcast for founders, product market fit, pricing strategy, $2B exit, Shopify acquisition, product-price fit, logistics startup, self-serve systems, Amazon fulfillment
00:00:00 Intro
00:07:06 Starting Deliver in 2017
00:14:24 Struggling with only 10 customers after 9 months
00:19:53 The two changes that changed everything
00:23:43 Zero to $100M in 2 years and product-price-market fit
00:29:32 How the $2B+ Shopify acquisition happened
00:32:07 Starting Augment AI for logistics
00:47:35 PMF moments and top advice
Send me a message to let me know what you think!
Dheeraj built Nutanix into a $20B public company—then walked away to start DevRev. He just raised a $100M Series A.
This episode breaks down why most founders "sell and run" (chase new logos instead of delivering value), why that strategy fails, and how Dheeraj thinks about building platforms with use cases instead of just features. He explains why the biggest opportunities come from bundling and why you need to hit 130%+ NRR to scale in B2B.
Dheeraj also shares the two near-death experiences at Nutanix in the first 5 years, how they survived, and what he's building differently at DevRev in the AI-native world.
If you're wondering whether you have real PMF, how to think about platforms vs features, or why your existing customers matter more than new ones—this is mandatory listening from someone who's done it twice at massive scale.
Why You Should Listen:
- Learn why PMF at $1M doesn't mean PMF at $10M—and why you have to find it again at every milestone
- Why "sell and run" kills startups—the real work starts after you close the deal
- See how platform thinking (not feature thinking) took Nutanix to $1B ARR
- Understand why 30-40% of revenue from existing customers is real PMF
Keywords:
startup podcast, startup podcast for founders, product market fit, platform thinking, Nutanix founder, enterprise SaaS, net dollar retention, PMF milestones, fastest to $1B, second-time founder
00:00:00 Intro
00:01:58 Starting Nutanix
00:14:24 Why he left a $20B company
00:18:53 The DevRev thesis
00:27:39 Pre-AI vs post-AI product strategy and the agent shift
00:40:57 Platform vs features
00:46:25 PMF is not a destination
00:48:10 #1 Advice
Send me a message to let me know what you think!
Simon spent 10 years at Shopify scaling databases to millions of requests per second. Then he discovered vector databases were so expensive that companies couldn't launch AI features. So he solved it.
When Cursor emailed about their crushing costs, Simon flew to San Francisco unannounced. They migrated their entire workload within a week, cutting their bill by 95%. Then came Notion. Justin pulled 24-hour coding marathons during their POC, fixing 300 milliseconds of latency in three hours. They signed on July 25th—the same day Simon's daughter was born.
Now TurboPuffer powers Cursor, Notion, and Linear while staying profitable with just 17 people. Simon shares why he turned down easy Series A money and his framework of exactly 6 legitimate reasons to ever raise capital.
Why You Should Listen:
- The power of making something 10-100x cheaper
- Why you need to be willing to fly to early customers (how that landed Cursor)
- The 6 reasons to raise money (and why you often shouldn't)
- How working 24-hour sprints during POCs converted enterprise customers
- Why staying profitable with 17 people beats raising $30M you don't need
Keywords:
startup podcast, startup podcast for founders, TurboPuffer, Simon Eskildsen, vector database, Cursor, Notion, bootstrapping, database startup, AI infrastructure
00:00:00 Intro
00:07:52 Finding the problem
00:12:25 Building alone
00:22:27 Going viral on X
00:26:18 Closing Cursor
00:40:17 Closing Notion
00:45:26 Why he didn't raise $30M when everyone expected him to
Send me a message to let me know what you think!
Guy spent 2 years and $4M building Snyk to $100K ARR. Thousands of developers loved the product. They just wouldn't pay.
Then he figured out the problem: he had product-user fit, but not product-buyer fit. Developers loved Snyk. Security teams (the actual buyers) didn't care about it. The distance between user and buyer was killing him.
So Guy spent a year building governance features, reporting, and enterprise capabilities—all the stuff developers didn't care about but security teams needed to write checks.
Four months later, Snyk hit $650K ARR.
A year after that, $4.5M.
Then $19M.
Today it's over $300M ARR.
This episode breaks down the brutal reality of PLG when your user isn't your buyer, why Guy thinks the worst outcome for a founder is getting stuck (not failing), and how he's now raising $125M for his next company Tessl.
If you're building PLG, selling to enterprise, or wondering why your users love you but won't pay—this is required listening.
Why You Should Listen:
- Learn why thousands of users loving your product means nothing if they won't pay
- Discover the difference between product-user fit and product-buyer fit
- Understand why the worst outcome isn't failure—it's getting stuck in the grey zone
- Master the art of anchoring in the future instead of just filling today's gaps
Keywords:
startup podcast, startup podcast for founders, product market fit, PLG strategy, product-user fit vs product-buyer fit, developer tools, security startup, enterprise sales, bottoms-up GTM, Snyk founder
Chapters:
(00:00:00) Intro
(00:01:37) The first start up :Blaze.io"
(00:06:16) The Beginning & Concept of Skyk
(00:15:27) Why use Snyk
(00:23:41) The Product Led Growth for Snyk
(00:33:08) Raising for Snyk
(00:38:58) The Beginning & Concept of TESL
(00:46:39) Raising for TESL
(00:48:52) Finding PMF
(00:49:26) One Piece of Advice
Send me a message to let me know what you think!
Amar is a 5x founder who helped birth Tinder (it was the 10th project—after the first 9 failed), then sold his next company to Ford for putting a platform in every single vehicle they make.
But the wildest part? He got Ford to commit in under a year by doing something most founders would never do: he asked for SO MUCH money that only the CEO could approve it. That one move made him "part of the transformational change" instead of a vendor they could ignore.
In this episode, Amar breaks down the exact pricing strategy he used to land an 8-figure deal, why founders who sell discounted pricing are sabotaging themselves, and what it actually takes to compete against billion-dollar incumbents like Carta (his current company, Mantle, is doing exactly that).
If you're trying to sell to enterprise, wondering if you should bootstrap or raise, or questioning whether your market even exists—this episode will reset how you think about all of it. Amar's built companies in mobile, vehicles, security, and fintech. He knows what works.
Why You Should Listen:
- Learn the pricing trick that got a CEO to sign off to an 8-figure deal.
- Discover why asking for MORE money (not less) is how you win enterprise deals
- Why getting told "you're nuts" might mean you're dead right
- Master the one metric that matters more than ARR in the early days
Keywords:
startup podcast, startup podcast for founders, enterprise sales, 5x founder, product market fit, pricing strategy, Tinder origin story, competing with incumbents, bootstrapping vs raising, SaaS pricing
Chapters:(00:00:00) Intro(00:03:56) The Start & Finding PMF for Tinder
(00:09:04) Xtreme Labs
(00:12:18) Autonomic
(00:17:03) The Contract Turned Acquisition
(00:22:04) The origin of Mantle
(00:28:56) Going into a Dominated Category
(00:32:39) Raising & Pitching for Mantle
(00:40:01) One Piece of Advice
Send me a message to let me know what you think!
Ben Alarie spent 8 years building Blue J with "partial product market fit"—real customers, real revenue, but no real market pull. Then he made a bet that would either kill the company or 10x it: he put the existing product in maintenance mode and gave his team 6 months to rebuild everything from scratch using a technology that barely worked.
Two years later, Blue J went from $2M to $25M in ARR. They're adding 10 new customers every single day. NPS went from 20 to 84.
This isn't a story about getting lucky. It's about a founder who knew—with absolute conviction—that the market would eventually arrive, and made sure he was ready when it did. But it's also about the danger of fooling yourself into thinking you have PMF when you only "kind of have PMF."
Why You Should Listen:
- Learn the brutal difference between fake and real PMF
- Discover when to abandon millions in existing ARR to go all-in on something else
- Why "time to value" might be the single most important metric for word-of-mouth.
- See what it takes to survive until the market is ready.
Keywords:
startup podcast, startup podcast for founders, product market fit, founder journey, early stage startup, startup pivot, AI startup, SaaS growth, founder advice, hypergrowth startup
Chapters:
(00:02:00) Starting BlueJ
(00:9:26) Introducing AI to Tax Research
(00:12:44) Starting to Build
(00:17:03) Not Having True PMF
(00:19:44) Believing in Retrieval Augmented Generation
(00:25:34) Updating to V2 of BlueJ
(00:30:58) The Necessity of Time to Value
(00:33:47) When You Knew You Have PMF
(00:38:19) One Piece of Advice
Send me a message to let me know what you think!
Dean thought he'd have to bootstrap Axonius because no investor would fund a solution to a problem that had existed for 20 years. He was wrong—they've raised $500M.
The breakthrough came when a Fortune 500 company was actively being hacked by Chinese state actors. Their first customer almost said no—they had 20 bugs during the POC. But Dean's team fixed each one within 48 hours while their competitors took quarters to respond. That speed changed everything.
They went from zero to $100M ARR in under 5 years, created an entirely new category (cyber asset management), and achieved an NPS score in the 80s—unheard of in cybersecurity.
His framework for the three types of enterprise journeys will change how you think about positioning.
Why You Should Listen:
- Why responding to customer issues in hours changes everything.
- How to turn a "dormant pain everyone accepts" into a $500M+ company.
- Why speed beats everything.
- The 3 types of enterprise software journeys and which one VCs won't fund.
Keywords:
startup podcast, startup podcast for founders, Axonius, Dean Sysman, cybersecurity startup, enterprise sales, Unit 8200, cyber asset management, B2B SaaS, YC alumni
00:00:00 Intro
00:02:25 From Hacker to CyberSecurity
00:14:46 The three types of enterprise software journeys
00:18:41 Why time to value beats everything
00:29:33 Thought they'd bootstrap but VCs validated the problem
00:35:14 Failed POCs and landing first customer with 20 bugs
00:40:10 Zero to $100M ARR in under 5 years
00:45:24 When to know you have product-market fit
Send me a message to let me know what you think!
Casey turned hackers into a marketplace and built Bugcrowd to $180M+ raised. But the real story isn't about cybersecurity—it's about how he validated a two-sided marketplace with almost no product, refined his pitch by literally testing it on Uber drivers until it clicked, and cracked the code on category creation when everyone thought hackers were the enemy.
You'll learn about the exact moment he knew he had product-market fit, why he blew every pitch to top VCs until he reframed his vision, and how giving away 500 t-shirts did more for growth than any paid marketing.
If you're building a marketplace, creating a category, or just trying to figure out how to explain what you do—this is required listening.
Why You Should Listen:
- Master the 30-second Uber pitch test—Casey's framework for refining your message until anyone gets it.
- Learn why problem-solution fit without product-market fit is worthless
- Validate your marketplace with $500 and no code
- Why your network is your only real asset pre-Series A
- The surprising ROI of early brand marketing
Keywords: startup podcast, startup podcast for founders, marketplace startup, go-to-market strategy, product-market fit, category creation, B2B sales, early-stage fundraising, founder pitch, cybersecurity startup
00:00:00 Intro
00:01:36 From white label pen testing to the Bugcrowd idea
00:18:58 Testing with MailChimp and 5000 hackers signed up
00:21:46 Landing Google as customer in month four
00:24:24 Blowing every pitch meeting in Silicon Valley
00:33:21 The Uber pitch technique for simplifying the message
00:36:57 Early go-to-market tactics and hitting $1M
00:43:37 Open heart surgery and stepping back as CEO
Send me a message to let me know what you think!
Zach spent 8 years at Google leading engineering for Google Docs, then left to build a photo sharing app with zero go-to-market plan.
Reality hit hard: "At Google, anything you launch gets millions of users. At a startup, the challenge isn't building—it's getting anyone to care." After writing a brutal postmortem documenting everything that went wrong, he started Warp with strict principles: only hire product-obsessed people, document every process, build pure software not services.
For three years, Warp had hundreds of thousands of free users but no revenue. Then they pivoted to AI-powered development in 2024. Here's how they went from taking 300 days to hit their $1M to now adding $1M ARR every 10 days.
Why You Should Listen:
- Why working at Google can set you up to fail as a founder
- How to know when to quit your own startup
- Why you should write down every operating principle before starting
- The shift he made to grow insanely fast
- Why competing directly with fast-growing startups is actually smart
Keywords:
startup podcast, startup podcast for founders, Warp, Zach Lloyd, Google alumni, developer tools, AI coding, product-market fit, startup pivot, Series B
00:00:00 Intro
00:01:48 From law school to Google via Craigslist
00:05:01 Why Google makes you a terrible startup founder
00:10:36 Joining SelfMade as technical co-founder
00:19:00 Writing a brutal post-mortem of the startup experience
00:27:15 Building Warp and getting 10,000 signups day one
00:38:08 Raising $50M Series B with zero revenue
00:41:50 Pivoting to Agent Mode and AI development
00:46:27 From 300 days to $1M to adding $1M every 10 days
Retry
Send me a message to let me know what you think!
Alex had $2,000 in his checking account when Microsoft acquired his last company. For years, he paid himself $30K while his friends made six figures at corporate jobs. He had only 2 months of runway for 18 straight months.
Then retail media exploded and everything changed—he went from grinding against the current to riding a wave.
After selling to Microsoft, he took 6 months off, got bored, and started Bluefish AI with the same team. This time they called Fortune 500 CMOs before building anything.
His #1 advice for early-stage founders: Get on the plane. And go meet your customers. You'll be shocked by how big a difference that makes.
Why You Should Listen:
- How to survive on 2 months of runway indefinitely
- How to validate your next startup before writing any code
- Why second-time founders often have more blind spots than first-timers
Keywords:
startup podcast, startup podcast for founders, PromoteIQ, Microsoft acquisition, Alex Bluefish, retail media, product-market fit, MarTech, enterprise sales, second-time founder
00:00:00 Intro
00:01:58 From management consulting dreams to startup world
00:04:44 Trying to return $200K to investors after 30 days
00:07:19 Pivoting through iterations to find retail media
00:12:13 Finding product-market fit like a river reversing
00:21:28 Microsoft acquisition with $2,000 in the bank
00:24:30 Post-exit sabbatical and starting Bluefish
00:35:08 Building for AI marketing with Fortune 500 design partners
00:43:12 Always get on the plane
Send me a message to let me know what you think!
Brett had a drug dealer's car for 13 days. By day 11, the death threats started coming. This is the reality of building ServiceUp, the "DoorDash for auto repair."
Brett literally stole DoorDash's entire playbook—city launches, three-sided marketplace, everything—but discovered even if he got 90% right, 10% of B2C customers can end you.
He raised from Tiger just as the firm exploded. The DoorDash partnership that seemed like salvation turned into their worst nightmare. But then they pivoted to B2B and saw their average order value grow 5x overnight.
"Work-life balance is BS. If you can work seven days a week, you'll fail faster, fix faster, and find product-market fit faster."
Why You Should Listen:
- Why just 10% of your customers can destroy your business
- How to close funding in the middle of a macro crisis
- Why work-life balance is BS if you want to build something big
- How stealing another startup's playbook can lead to 5000% growth
- Why your worst customers might actually show you your best pivot
Keywords:
startup podcast, startup podcast for founders, ServiceUp, Brett Carlson, marketplace startup, B2B pivot, Tiger Global, auto repair tech, fleet management, startup growth
00:00:00 Intro
00:01:40 Failed auto shop becomes ServiceUp idea
00:03:27 Pulling co-founder out of retirement
00:09:30 Raising $2M seed from angels
00:13:23 Building the MVP in Puerto Rico
00:15:01 Early Bay Area operations and getting shops
00:17:50 The drug dealer death threat incident
00:21:17 Tiger Global loses $8B during Series A
00:26:57 DoorDash partnership disaster
00:28:36 Pivoting from B2C to B2B fleets
00:30:00 Finding product-market fit
Send me a message to let me know what you think!
Doug Scott and the Ethic team spent years building technology before landing real customers. While other startups were growing fast, Ethic was focused on building, and after two years had only a modest amount of AUM. Until he and his team found a way to help his customers help them WIN new clients they couldn't land before.
That shift took them to ~$250M AUM in one year. He reveals why he left investment banking in Australia, sold everything, and moved to the Bay Area within three weeks with no idea what company to start.
He pitched over 100 investors to raise early rounds, survived years of building with no traction, and discovered the enterprise sales playbook that unlocked distribution in wealth management. Today Ethic manages $7 Billion and has raised over $160 Million in funding.
"If I knew how difficult it would be, maybe I wouldn't have done it." This is the reality of building a decade-long overnight success.
Why You Should Listen:
- Why helping customers win new business is the killer ROI
- How to survive a 3-year build phase when everyone else is growing fast
- Why you should pitch 100+ investors even if only 5 will say yes
- How to figure out distribution and go-to-market
- Why the best value-add investors never pitch their value-add
Keywords:
startup podcast, startup podcast for founders, Ethic, Douglas Scott, wealth management, ESG investing, fintech, B2B2C, Series A, distribution strategy
00:00:00 Intro
00:01:47 What Ethic does
00:08:15 Leaving Australia for Bay Area with no plan
00:17:06 The breakthrough for 5x YoY growth
00:29:42 Three years building with no traction
00:38:36 Distribution partnerships unlock growth
00:42:44 Finding product-market fit
Send me a message to let me know what you think!
Arnold Schwarzenegger mastered three completely different fields—bodybuilding, acting, and politics—with one simple philosophy: reps, reps, reps. This solo episode reveals why speed of execution is the only real moat for early-stage founders.
One founder takes an idea from conception to signed customers in three weeks. Another takes six months. They both had equally good ideas, but one got 100 reps in a year while the other got 10. Even Twitter, an established app, became top 5 in the App Store not through one or two big changes but 300 small iterations.
Teams naturally slow down over time. You used to ship in days, now it takes months. You have more engineers but move slower. This episode breaks down why this happens and how to maintain that day-one velocity even at $10M ARR.
Why You Should Listen:
- Why speed is the only moat early-stage founders actually have
- How to get 100 reps while your competitor gets 10
- Why MVPs shouldn't stop after you have a product in market
- How Twitter went top 5 in the App Store with 300 tiny changes
- Why teams naturally slow down and how to fight it
Keywords:
startup podcast, startup podcast for founders, startup speed, MVP strategy, iteration cycles, product development, founder mode, execution velocity, startup growth, early-stage strategy
00:00:00 Intro
00:00:32 Arnold Schwarzenegger and reps, reps, reps
00:02:18 Speed as the only moat for early-stage founders
00:03:48 Why founders lose MVP mentality after launch
00:09:22 How to stay in Jeff Bezos' day one
Retry
Send me a message to let me know what you think!
Aviv spent months walking construction sites carrying tools for managers just to understand their problems—speaking to customers is "bullsh*t"—you need to work beside them to see reality.
His company Buildots had a working AI product that tracked construction progress perfectly, but 90% of users got zero value from it. Until he made one key change that took them from barely surviving to 3-4X yearly growth.
He reveals why his first customers had negative margins, how he accidentally underpriced by 10X, and why you should never build a feature until you've proven the value manually in Excel first. After nearly dying, today Buildots does tens of millions in revenue.
Why You Should Listen:
- Why you need to stop talking to customers and start working alongside them.
- Why one simple change can transform usage and value creation.
- Why you should prove value without product before writing a single line of code.
- How to price when you have no idea.
Keywords:
startup podcast, startup podcast for founders, Buildots, Aviv Leibovici, construction tech, customer development, product-market fit, B2B SaaS, computer vision,
00:00:00 Intro
00:01:41 From Israeli intelligence to construction tech
00:05:03 Working alongside construction managers
00:10:20 Understanding the problem
00:21:41 First customer deployment disaster
00:30:29 COVID and nearly failing
00:39:04 The pivot that changed everything
00:45:16 Finding product-market fit
Send me a message to let me know what you think!
Shensi cold messaged 50,000 engineers to build Merge. She worked 9am-9pm every day, gave her first customers two months free to prove herself, and refused to hire anyone remote—even during peak COVID.
She purposefully didn't collect a single dollar of revenue until she knew she could hit $1M in a months. "Startups are all about momentum."
She lost their biggest deal to a competitor who copied them, then won that customer back years later. She outbounded her way from zero to $10M through sheer force of will, doing demos all day until her calendar was completely booked. Today Merge has raised $75M and powers integrations for hundreds of B2B companies.
This is raw, unfiltered founder advice from someone who believes you just have to "man up" and outbound your way to success.
Why You Should Listen:
- Why you should wait to collect revenue until you see a clear path to $1M ARR.
- Why you need to outbound thousands of people to build your team.
- You can will your way to $10M—but you'll need something else to hit $100M.
- Why they are an in-office company, even for remote rockstar devs.
Keywords:
Startup podcast, Startup podcast for founders, Merge, Shensi Ding, integrations, B2B SaaS, outbound sales, seed funding, product-market fit, API, developer tools, startup growth
00:00:00 Intro
00:02:55 From coding in middle school to investment banking
00:06:45 How she found the problem
00:09:09 100 customer conversations
00:13:51 Quitting during COVID
00:16:16 Raising $4.5M seed in 3 weeks
00:21:01 Outbounding 50,000 engineers
00:25:32 Landing first customers through cold LinkedIn
00:31:37 Not collecting revenue on purpose
00:37:47 When product-market fit actually hit
Send me a message to let me know what you think!
Eldon put a $150K line of credit on his house to start eSentire in 2001. No VCs would touch him—they didn't understand services businesses. He worked 12-hour days, 7 days a week for 7 years to hit $1M in revenue. His co-founder coded while he flew to New York on $99 JetBlue flights from Buffalo to save money.
Then something clicked: they brought in an experienced CEO who transformed their scrappy cybersecurity consulting into a managed service.
Revenue grew from $1M to $10M in just 3 years. They won 95% of competitive deals against Dell-backed SecureWorks by comparing themselves to a local burger joint versus McDonald's.
Today eSentire is worth over a billion dollars. This is the raw, unfiltered story of building a massive B2B company without following any of the Silicon Valley playbook—no YC, no venture capital for years, just pure survival mode.
Why You Should Listen:
- How to win head-to-head sales battles against bigger competitors with no marketing budget.
- Why taking a long time to hit $1M ARR doesn't mean failure.
- How bringing in an experienced CEO after 8 years saved the company.
Keywords (comma-separated):
Startup podcast, Startup podcast for founders, eSentire, Eldon Sprickerhoff, cybersecurity, bootstrapping, managed services, B2B sales, Canadian startup, MSSP, founder-led sales, pivot
00:00:00 Intro
00:01:00 Starting eSentire after 9/11
00:03:26 The dot-com crash reality
00:05:23 $150K home equity line to start
00:08:32 Landing first customer at ING
00:14:03 Making up the rules as they went
00:19:09 Bringing in an experienced CEO
00:22:44 The hamburger pitch that beat Dell
00:28:36 From $1M to $10M in 3 years
00:34:39 Common founder mistakes
00:40:39 Chief survival officer mindset
Send me a message to let me know what you think!
Soham spent 6 months building AI that would auto-generate integrations between any software. He locked down Glean as an early customer because he had friends there. And it failed completely.
So he pivoted. This time, he refused to work with friendly customers who knew him. Instead, he did 10-20 calls per day with strangers who would tell him his product sucked. He posted on Discord communities at 3am, wrote technical blogs that went viral on Reddit, and created fake landing pages to see what integrations people actually wanted.
In one year, Composio grew to 100,000 developers and raised $30M from Lightspeed in just 3 weeks.
His contrarian take: in AI, asking users what they want will just get you faster horses. Built it instead, and watch their eyes light up.
Why You Should Listen:
- Why friendly customers will kill your startup.
- The 20 calls per day strategy that scaled Composio to 100,000 users.
- Why you can't validate AI products by asking.
- The exact Discord and SEO tactics that got their first thousand users without spending on ads
Keywords (comma-separated):
The PMF Show is a startup podcast. The Product Market Fit Show is a startup podcast. Startup Podcast, Composio, Soham Ganatra, AI agents, developer tools, pivot, Series A, Lightspeed, integrations, API, tool calling
00:00:00 Intro
00:06:44 Playing with GPT-2 before ChatGPT
00:12:37 Leaving his job to start Composio
00:21:16 Pivoting to integrations for AI agents
00:28:42 Why friendly customers are dangerous
00:31:01 Getting first users through viral content
00:36:01 Taking 10-20 customer calls per day
00:40:58 Scaling from 1,000 to 100,000 developers
00:43:58 MCP and the explosion of growth
00:48:59 Raising $30M from Lightspeed in 3 weeks
Send me a message to let me know what you think!
Sahil was 18 when TechCrunch published a hit piece calling him a copycat. His co-founder Aaron was 16. They'd just raised $6 million from YC and top VCs for their crypto startup, then got subpoenaed by a state government and watched their business implode.
So they fired everyone, moved back to their parents' homes, and spent months cold-calling dentists and lawn care companies to find a real problem. What they discovered: 80% of SMBs still use community banks from 1995. Now Affiniti has 2,000 customers, $10M ARR run rate, and just raised $17M by partnering with trade associations to acquire customers at 25% the cost of traditional fintech.
This is the raw story of teenage founders who got punched in the face by Silicon Valley and came back swinging.
Why You Should Listen:
- How getting destroyed on TechCrunch at 18 and subpoenaed by the government led to a $3M revenue pivot in 12 months
- Why going back to square 0 is often the best move
- The trade association go-to-market strategy that worked for SMB.
- Why 200 VC rejections and raising $6M in peak 2021 couldn't save their first startup—but taught them everything they needed to know.
- Get comfortable with bad days—stoicism is the only way to survive.
Keywords:
Affiniti, Sahil Phadnis, SMB fintech, startup pivot, Y Combinator, teenage founders, Series A, B2B payments, startup failure, trade associations
00:00:00 Intro
00:01:50 COVID existential crisis at 16
00:08:36 Building websites for restaurants
00:11:11 Meeting Aaron on Instagram
00:15:17 200 VC rejections then raising $6M
00:23:03 Getting called a fraud on TechCrunch
00:29:15 Firing everyone and moving home
00:31:16 Faking toothaches to research SMBs
00:40:50 Launching Affiniti
00:47:00 The trade association growth hack
00:55:03 Raising Series A in 3 weeks
00:58:30 Stoicism and bad days
Send me a message to let me know what you think!
Jon spent 3 years building Gamma with barely any traction—just a few hundred users after burning millions. Then ChatGPT dropped. In desperation, he pivoted to AI-powered presentations in March 2023 with one year of runway left. What happened next was insane: Paul Graham publicly mocked their launch tweet calling it worthless—then it went viral.
They went from 2,000 signups a day to 60,000. Their servers crashed for three days, but when they came back online, panicked users threw $50K at them thinking they needed to pay to make it work. Within two months of launching payments, they hit $1M ARR and became cashflow positive.
This is the raw story of how a dying startup caught the AI lightning and never looked back.
Why You Should Listen:
- How to survive 3 years with no traction.
- Why 80% hype and 20% value can still build a real business
- The exact onboarding flow that turned 5% activation into viral growth
- How negative viral engagement can still drive massive revenue
- The difference between 10x better and 50% better
Keywords:
Gamma, Jon Noronha, AI presentations, product market fit, pivot to AI, viral growth, Paul Graham, ChatGPT, cashflow positive, productivity startup
00:00:00 Intro
00:02:15 Why presentations haven't changed in 40 years
00:11:55 User research reveals the real problem
00:26:26 The market crashes and runway shrinks
00:34:32 ChatGPT drops and everything changes
00:43:19 Paul Graham trashes the launch tweet
00:48:59 Going viral by accident
00:51:33 60,000 signups a day breaks everything
00:55:07 Hitting $1M ARR in 2 months
00:58:47 Endurance is everything
Send me a message to let me know what you think!
Soham co-founded Rubrik by taking what he learned from building Google's data center tech to enterprises desperate for cloud migration. Two quarters later, he hit $1M ARR. And a few years later, a $16B IPO.
Soham breaks down why paid pilots beat free trials, how to sell enterprise hardware before it works, and why early customers become your biggest champions when you solve real pain.
Now building WisdomAI after watching the ChatGPT moment unfold, he shares what's different about competing in AI's gold rush versus owning an ignored category.
Why You Should Listen:
- Why early customers endure broken products
- How he hit $1M ARR in 2 quarters selling enterprise hardware
- Why you should always charge for pilots
- Customer feedback is the only PMF signal that matters
Keywords:
Rubrik, Soham Mazumdar, enterprise sales, data backup, IPO, product market fit, B2B SaaS, cloud migration, WisdomAI, data centers
00:00:00 Intro
00:04:26 Leaving Google to start a company
00:11:00 Building the founding team
00:14:27 Landing the first customer in Australia
00:22:30 Hitting $1M ARR in two quarters
00:25:42 Go-to-market strategy and the DeLorean stunt
00:30:30 When Arvind left to start Glean
00:34:10 Starting WisdomAI after the ChatGPT moment
00:51:22 Advice for early stage founders
Retry
Claude can make mistakes.
Please double-check responses.
Send me a message to let me know what you think!
Stéphan bootstrapped AODocs to $55M in revenue and 250 employees without taking a dime of VC money—while competing directly with venture-backed competitors. Starting as a services company in 2012, he spotted the cloud migration wave early and built document management for enterprises moving to Google Workspace.
In this episode, Stéphan breaks down why doubling every two years beats hypergrowth, how to win enterprise deals with zero funding, and why touching business-critical documents means year-long sales cycles but 10-year retention. This is the anti-Silicon Valley playbook that actually works.
Why You Should Listen:
- Why the founder must personally close every single deal in 0 to 1
- How doubling every 2 years (not every year) creates a more stable business
- The brutal reality of enterprise POCs: doing it for free before getting paid
- Why you can't have both fast customer acquisition and high retention
- How being French/European became an advantage against US competitors
Keywords
AODocs, bootstrapping, Stéphan Donzé, enterprise sales, document management, SaaS, Google Workspace, cloud migration, product market fit, B2B
00:00:00 Intro
00:01:12 Bootstrapping vs VC backed
00:03:44 From services to SaaS
00:19:08 Landing the first customer
00:20:47 Why they turned down VC money
00:25:32 The 997 grind—four days on-site with customers every week
00:35:21 Why you can't have fast sales and high retention
00:40:33 Product-market fit
Send me a message to let me know what you think!
Andrew bootstrapped Wrike and grew it from 0 to a $2.2B exit by doing the exact opposite of what every startup book tells you. No pivots. No talking to customers before launch. No narrow niche. Just 17 years of relentless focus on one problem while everyone else was pivoting every 18 months.
In this episode, he breaks down exactly why bootstrapping saved his company (and why VC would have killed it), why he ignored customer development and just built in a bunker, and how manning the support phones himself became his secret product development weapon.
Now building Zencoder (AI coding agents), he shares why the future isn't about replacing developers but making every human "superhuman" at their job. This is mandatory listening for any founder questioning conventional startup wisdom.
Why You Should Listen:
- Grew to $2.2B with no pivots for 17 years while competitors kept "failing fast"
- How he doubled revenue every year from $0 to $100M+ ARR
- Why manning support phones himself was better than any customer development process
- Why copycats helped Wrike grow faster
- The future of AI agents
Keywords:
Wrike, Andrew Filev, bootstrapping, 2 billion exit, product market fit, SaaS, Zencoder, AI coding agents, no pivot strategy, collaboration software
00:00:00 Intro
00:03:30 Moving to Silicon Valley from Russia to build for millions
00:10:06 Going all-in after previous side projects failed
00:11:27 Why he never pivoted once in 17 years
00:18:47 Launching without talking to customers first
00:24:12 Manning support phones and discovering the real roadmap
00:29:01 When Microsoft Project, Basecamp, and Jira were the competition
00:34:31 The only job definition—double the business every year
00:54:16 Why Developers won't be replaced, and become superhuman
01:01:57 The $2.2B exit and making employees' dreams come true
01:04:36 Finding product-market fit at Zencoder vs Wrike
01:06:55 Focus on people—everything traces back to them
Send me a message to let me know what you think!
Peter Walker from Carta drops the hard data every founder needs. Based on actual cap table data from 1000s of startups, this Q2 update reveals the brutal new reality.
It takes 2+ years to go from seed to A (up from 1.6), you need 3X the revenue you used to, and if you're not AI, you're getting half the attention.
But there's good news too—teams are finally getting leaner, exits are picking back up, and the worst of the funding winter might be behind us.
If you're raising in 2025, this is your reality check.
Why You Should Listen:
- $3M ARR is the new Series A bar—& it takes 1 in 4 founders 3.5+ years to get there
- Half as many seed deals are getting done but at 20% higher valuations—you're either in the AI club or you're out
- Founders own just 56% after their first priced round and only 10% by Series D—every round costs more than you think
Keywords:
Carta data, Series A requirements, startup fundraising 2025, seed to Series A timeline, ARR benchmarks, AI startup valuations, bridge rounds, founder dilution, startup team size, venture capital trends
Send me a message to let me know what you think!
Hedra CEO Michael Lingelbach breaks down how his generative video app went from zero to millions of users and an eight-figure run rate in months — then deliberately slowed down to rebuild a V2 that enterprises would pay for. We dig into the prosumer-to-pro upsell, why free users are a false signal, and how a creator-seeded launch can outpull ad spend.
Michael shares the GTM that signs enterprise contracts every few days with no outbound, the exact moment he killed feature churn to ship a real workflow, and what to hire (and fire) in the first 10 people. If you’re building AI or any early product, this is a must-listen blueprint on getting from hype to revenue.
Why You Should Listen* How Hedra hit an 8-figure run rate in months — with a prosumer → enterprise wedge * The “free user” trap: why signups ≠ demand and how to price for pain * When to pause growth to build V2 that actually sells (workflow > tech demo) * A creator-led launch playbook that drives virality without paid influencers * Hiring early: bring in a talent lead fast, staff for speed, survive co-founder changes
KeywordsAI video, generative AI, product market fit, Hedra, Michael Lingelbach, creator tools, PLG, enterprise SaaS, go to market, startup growth
00:00:00 Intro
00:02:25 Why he built his own proprietary models
00:10:19 Target use cases faceless channels marketers podcasts
00:15:31 Early hiring lessons
00:38:00 Free vs paid
00:51:03 V2 launch and shift to enterprise
00:53:46 Hitting eight figure run rate and scaling GTM
Send me a message to let me know what you think!
Ross went from lawyer to self-taught engineer to CTO at a 1,600-person unicorn—then quit to build Wordsmith AI.
In 18 months, he's raised $30M and grown to mid-single-digit millions in ARR by doing everything differently. He tested co-founders by starting fights. Built in Slack for 10 months before adding a web interface. Kept his team at 8 people while competitors hired dozens.
This episode breaks down his exact playbook: how to test co-founders before committing, why attacking someone's core job kills your sales cycle, and how he accidentally created the hottest seed round by ghosting every VC. Plus the reality of building a rocket ship with a newborn at home.
Why You Should Listen:
- Why starting fights with co-founders can be a great way to test conflict.
- Why keeping your team at 8 people until PMF lets you move faster
- The accidental fundraising playbook that made VCs go crazy
- How having a baby forces you to be 10x more productive as a founder
Keywords:
Wordsmith AI, Ross McNairn, AI legal tech, product market fit, co-founder selection, Series A, Index Ventures, Slack integration, startup pivots, legal AI
00:00:00 - Intro
00:01:31 - From Lawyer to CTO
00:03:45 - Starting Wordsmith AI
00:06:41 - Testing Co-Founder Relationships
00:14:42 - Building the MVP
00:20:44 - First Product Iterations
00:26:39 - Finding Product Market Fit Through Slack
00:37:42 - Go-to-Market Using Webinars and Influencers
00:47:00 - Balancing Startup Life with a 10-Month-Old Baby
Send me a message to let me know what you think!
Rick built Persona into a $100M+ ARR unicorn, but he never thought it would work. In fact, Rick started Persona believing it would probably fail, and that mindset might be exactly why it succeeded.
In this episode, Rick reveals how a casual project with zero expectations turned into a billion-dollar business, why early-stage startups should avoid hyper-optimization, and the secrets he learned at Square about identity fraud that became his breakthrough.
If you want to challenge the typical startup narrative, this one’s a must-listen.
Why You Should Listen
- How Rick Song took Persona from $0 to $100M ARR without believing in product-market fit.
- Why obsessing over optimization might be killing your startup.
- How to think differently about fundraising—Rick raised $2.4M without even trying.
- The real truth about what decisions actually matter in your early days.
Keywords
product market fit, startup advice, early-stage founders, fundraising, hyper-optimization, identity fraud, Persona, Rick Song, Square, founder mindset
00:00:00 Intro
00:08:07 Finding Persona’s First Customer
00:17:56 How to Quit a Successful Job for a Risky Startup
00:26:54 Early Product Strategy
00:37:40 Hiring the First Employees Without Selling the Dream
00:47:54 Fundraising Without Even Trying
00:56:55 Hyper-Optimization is Hurting Your Startup Decisions
Send me a message to let me know what you think!
Neil Patel just flipped everything you know about startups upside down. He says product-market fit is overrated, giving away your software for free can make you rich, and the real secret to scaling isn’t charging customers—it’s monetizing the leads your free product generates.
Neil breaks down his playbook on how startups can leverage free products to grow exponentially, why your churn doesn’t matter if you monetize correctly, and the reality about brand building that most founders completely miss. This episode challenges conventional startup wisdom and reveals a totally different way to think about building billion-dollar businesses.
Why You Should Listen
- Why Neil Patel thinks chasing product-market fit is a waste of your time.
- How offering your software for free can create a viral growth engine.
- How to monetize without charging for your product.
- Why branding matters, but why you’ll have to wait 10 years to feel it.
Keywords
Neil Patel, product market fit, SaaS growth, freemium model, lead generation, churn reduction, monetization strategy, startup branding, digital marketing, SaaS startups
00:00:00 Intro
00:07:05 The Secret Math Behind Giving Software Away for Free
00:21:32 How Free Software Can Disrupt Billion-Dollar Industries
00:26:26 The Truth About Branding (and Why It Takes 10 Years)
00:29:59 Neil’s Final Advice to Early-Stage Founders
Send me a message to let me know what you think!
Roy Lee went from getting kicked out of Harvard and Columbia to building Cluely, one of the fastest-growing AI startups ever—going from 0 to $5 million ARR in just 3 months.
We go deep on Roy’s playbook for using controversy, virality, and content to get millions of views—and millions in ARR. You’ll learn why Roy intentionally designs content to spark outrage, how he leveraged Twitter to raise millions from top VCs within 24 hours, and his tactical advice for mastering the short-form algorithms that dominate attention today.
If you want an unfair advantage to scale your startup, this is a must-listen.
Why You Should Listen
- How Roy Lee mastered viral marketing to scale from 0 to $5M ARR in 3 months.
- Why controversy and shock value are the ultimate distribution hacks.
- Exactly how Roy raised $5M in 24 hours by leveraging Twitter virality.
- Why short-form content is the most underrated growth channel for startups today.
- The secret to X/Twitter's algorithm.
Keywords
Roy Lee, Cluely, viral marketing, startup growth, product market fit, AI startup, raising venture capital, short-form content, going viral, Twitter strategy
00:00:00 Intro
00:02:20 Getting Kicked Out of Harvard and Columbia
00:10:31 How Roy Engineered His Viral Moment
00:17:23 Launching Cluely and Hitting $5M ARR in 3 Months
00:20:49 Secrets to Mastering the Twitter Algorithm
00:28:21 The Formula Behind Virality
00:38:31 Leveraging TikTok, Instagram, and an Army of Creators
00:44:06 Retention Challenges and Future Product Vision
00:50:50 Roy’s Advice for Early-Stage Founders
Send me a message to let me know what you think!
Mary Beth Snodgrass shares the raw and real story behind Healthiby—an innovative healthcare startup that succeeded in delivering measurable health outcomes but ultimately didn't take off. Hear firsthand what went wrong, from unclear payer dynamics and sales friction, to macroeconomic shifts and storytelling gaps. This episode pulls back the curtain on why having a working product isn’t enough and why mastering the market dynamics is crucial to your startup’s survival.
Why You Should Listen
- Learn why even successful products don't always take off.
- Understand the hidden hurdles in long sales cycles.
- Discover why storytelling and personal founder journeys are key.
- See how market timing and macro changes can dramatically impact your startup’s trajectory.
- Avoid the pitfalls of focusing solely on solving problems without a robust go-to-market strategy.
Keywords
product market fit, healthcare startups, go-to-market strategy, founder advice, chronic conditions, startup storytelling, B2B sales, health tech, behavior change
00:00:00 Intro
00:03:04 Pivoting Fast
00:06:16 Finding Initial Users
00:08:53 Building a Behavior Change Product
00:17:48 Navigating Complex Sales Models
00:19:56 Key Lessons
00:22:45 Final Advice for Early Stage Founders
Send me a message to let me know what you think!
Tanay started coding at 10, built a product with millions of users by 11, and never stopped. In this episode, he shares how he created Wispr Flow—one of the fastest growing AI startups today. He's built the world's best voice to text app. I use it myself every single day. And he just raised a $30M Series A from Menlo Ventures
This is a must-listen for any founder obsessed with building something users can’t live without.
Why You Should Listen
- How Tanay built one of the world’s first voice assistants at 11—and what it taught him about startups.
- Why most founders get product-market fit wrong
- The critical mistake that almost killed Wispr AI
- The one thing Tanay wishes he’d known about building a startup team five years ago.
Keywords
product market fit, AI startup, Wispr Flow, Tanay Kothari, founder stories, startup pivot, voice interface, building teams, hyper-growth startup, deep tech startup
00:00:00 Intro
00:07:22 Learning to Code in Secret
00:13:27 From New Delhi to Stanford and Silicon Valley
00:17:34 Feather X—Tanay’s First Big Startup Exit
00:24:33 The Original Moonshot Vision of Wispr AI
00:31:19 Why Wispr AI Had to Pivot
00:38:32 The Power of Incremental Change Over Radical Shifts
00:43:00 Achieving Explosive Growth and True Product-Market Fit
00:49:01 The Most Important Lesson—Building the Right Team
Send me a message to let me know what you think!
We go through some lessons I learned from my own startup journey. I also go through why almost every business challenge beyond product-market fit is actually a people issue—and how to quickly spot and fix these hidden problems. You’ll learn why staying in direct contact with your customers accelerates your path to true product-market fit, and hear a powerful story of how making something radically different—even free—can disrupt entire industries and create massive competitive moats.
Why You Should Listen
- Discover the #1 reason your startup’s growth might be stalling
- Learn why staying hands-on with sales longer accelerates finding PMF
- Find out how to instantly identify if your team members are truly A-players.
- Uncover the hidden power of making your product free—even when competitors think you’re crazy.
- Understand why radically different strategies beat incremental improvements every time.
Keywords
product market fit, startup hiring, startup growth, founder lessons, free business model, early stage sales, team building, radical differentiation, founder mistakes, scaling startups
00:00:00 Intro
00:04:21 Every Startup Problem is Actually a People Problem
00:05:56 How to Identify Great Talent Without Hiring
00:07:10 Why Founders Should Stay in Sales Longer
00:09:35 Subtle Details are The Key to True Product Market Fit
00:12:24 Zeffy and the Hidden Power of Being Radically Different
00:17:00 The ROI of Being Uniquely Different
Send me a message to let me know what you think!
Immad grew Mercury to $500M in annualized revenue and profitable. Mercury is one of the fastest-growing fintech startups ever. No wonder they just raised $300M from Sequoia at $3.5B.
Immad breaks down exactly how he structured a viral launch, why fundraising is easier with zero customers than you think, and how he unlocked massive word-of-mouth growth. If you’re building a startup, especially in fintech, you can’t miss this episode.
Why You Should Listen
- How Mercury went from $0 to $1M ARR in just 5 months
- How Mercury leveraged Twitter to explode user growth at launch
- Why building with zero users might be your secret advantage
- Why Immad believes defining company culture at employee #4 was critical to hitting $500M in revenue
Keywords
Mercury, Sequoia, Immad Akhund, startup fundraising, fintech startup, product market fit, neobank, early-stage growth, Y Combinator, banking as a service, startup culture
00:00:00 Intro
00:09:23 How Immad Validated the Idea for Mercury
00:17:53 Why Immad Turned Down VC to Start Another Company
00:28:11 How Immad Raised a $6M Seed Round Before Writing Any Code
00:36:08 Launching Mercury and Going Viral on Twitter
00:47:08 Knowing You Have Product Market Fit
00:51:48 Raising a $20M Series A Just 3 Weeks After Launch
00:53:10 The Importance of Defining Your Culture Early
Send me a message to let me know what you think!
Ever wonder why some startups follow every “right” rule and still fail, while others break every norm and dominate? Mike Maples (Floodgate, author of Pattern Breakers) reveals how true breakthrough startups aren’t built by checking boxes—they’re created by founders bold enough to reject consensus, ignore conventional wisdom, and rewrite the rules entirely.
This episode explains why your biggest risk isn’t failure, it’s wasting years on the wrong idea. If you want to build something people are desperate for, not just mildly interested in, Mike’s insights will change how you think about startup success.
Why You Should Listen
- How to know if your startup idea is worth years of your life—or if it’s secretly wasting your time.
- Why “non-consensus and right” ideas create billion-dollar breakthroughs.
- How raising too much money too soon can sabotage product-market fit.
- The difference between playing by market rules and inventing your own.
- Why the best startup ideas polarize rather than please everyone.
Keywords
product market fit, startup ideas, breakthrough startups, seed funding, Mike Maples, lean startup, inflection points, AI startups, zero to one, startup growth
00:00:00 Intro
00:04:12 The Real Reason “Pattern Breakers” Win
00:12:00 Stop Finding Problems Start Living in the Future
00:21:23 Why Most Founders Play the Wrong Game
00:31:01 How to Know You’re Actually in the Future
00:36:38 The Hidden Cost of Raising Too Much Money
00:46:20 The True Purpose of Your First Million in ARR
00:50:58 Three Tests to Know You’ve Found Product Market Fit
Send me a message to let me know what you think!
Zuben turned his personal experience with crippling overdraft fees into Brigit, a fintech he sold for $460 million after hitting $100M ARR. This episode gives early-stage founders the unfiltered truth: how Zuben discovered massive market pain hidden in plain sight, validated the idea with real customers, built bulletproof unit economics early, and navigated brutal early-stage fundraising. It’s a real story about solving problems banks deliberately ignore—and getting rewarded big time.
You don’t want to miss this.
Why You Should Listen
- How Zuben turned a personal $1000 overdraft nightmare into a $460M exit.
- Why solving your customer’s deepest pain point is the only way to unlock real growth.
- How to validate product-market fit fast (and what most founders miss).
- The surprising reason Zuben says unit economics matter way earlier than you think.
Keywords
fintech, overdraft fees, product market fit, earned wage access, early stage startups, customer validation, fundraising, founder stories, lending, unit economics
00:00:00 Intro
00:08:47 Inside the Hidden Overdraft Market
00:16:34 Validating Your Idea the Right Way
00:27:37 How Brigit Cracked Customer Acquisition
00:33:38 Why Unit Economics Saved Us
00:37:08 Navigating a Crisis and Coming Out Stronger
00:45:14 Behind the Scenes of a $460 Million Acquisition
00:48:57 The Moment of True Product Market Fit
00:50:22 Advice Every Early-Stage Founder Needs
Send me a message to let me know what you think!
Joseph built Freshline to $3.5 million in revenue and nearly $2 million raised. It looked like a marketplace success story—until it wasn’t. In this episode, Joe shares the hidden reasons marketplaces fail, critical lessons on how to spot the right market, and why traction alone doesn’t guarantee success. It’s a raw, real look at what happens when hype meets reality.
Why You Should Listen
- How a $3.5M startup stalled despite traction
- Hard lessons on finding the right market
- The hidden traps of marketplaces
- Why staying gritty isn’t always enough
- Painkillers vs. Vitamins Rethinking Startup Advice
Keywords
marketplace, product market fit, startup failure, raising capital, entrepreneurship, founder advice, traction, B2B SaaS, early-stage startup, growth challenges
00:00:00 Intro
00:04:10 Crashing the Boston Seafood Expo
00:08:25 From Shopify to Marketplace
00:12:40 Door-to-Door Fish Sales
00:17:55 Hidden Risks of Marketplace Models
00:23:05 Cracks Emerge at $3.5M Revenue
00:26:45 COVID Hits and the Pivot Begins
00:30:50 Why Market Matters More Than Grit
00:32:55 Rethinking Painkillers vs Vitamins
00:35:30 Staying Alive Long Enough to Win
Send me a message to let me know what you think!
Forget what you thought about early-stage growth. In this must-listen episode, you’ll hear firsthand how startup success truly happens—and spoiler alert, there’s no playbook. From companies like Carbon6 using roll-up strategies to Graphite pivoting multiple times before exploding, we unpack real founder journeys that prove getting to $1M ARR fast isn’t what matters. You’ll see why the real winners chase true product-market fit, why copying competitors is a trap, and why patience in the early stage might be your biggest competitive advantage. If you’re building a startup, stop what you’re doing and listen now.
Why You Should Listen
- Discover why getting to $1M ARR fast is NOT the goal (and what really matters instead).
- Learn how randomness and serendipity shape startup success—straight from real founder stories.
- Understand why chasing product-market fit beats obsessing over short-term revenue milestones.
- Hear why copying existing playbooks can sabotage your startup’s long-term growth.
- Find out how radically different paths—roll-ups, pivots, or total serendipity—can all lead to success.
Keywords
product market fit, startup growth, early-stage startups, founder stories, zero to one, ARR milestones, startup pivots, product differentiation, scaling startups, startup playbook
00:00:00 Intro
00:02:47 Carbon6’s $210M Exit—Roll-ups and Serendipity
00:04:27 Lightspeed’s Unplanned Journey to $1B
00:06:04 Graphite’s Pivots—How a Failed Idea Led to Success
00:07:27 Vapi’s Rapid Rise After Three Years of Flat Growth
00:08:55 Why There’s No Single Path to Product Market Fit
00:11:19 The Million-Dollar ARR Myth
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Andrew Rubin raised $40M in 6 months before writing a single line of code—and another $100M before seeing his first dollar of revenue. Today, Illumio is valued at billions and counts Morgan Stanley among its earliest customers. But Andrew’s journey wasn’t smooth or easy. Listen in to learn how he navigated the fine line between being early and being too early, how he raised venture capital at unprecedented speed, and why he believes an entrepreneur’s conviction—backed by customer insights—is the real key to startup survival.
Why You Should Listen
- How to raise $40M in 6 months with no product or revenue
- Why “too early” often means bankrupt—and how to avoid it
- Why activity ≠ funding (and what to do instead)
- The hard truth about selling enterprise early
- Why market timing matters more than product genius
Keywords
product market fit, fundraising, early-stage startups, startup fundraising, venture capital, enterprise sales, market timing, Andrew Rubin, Illumio, cybersecurity
00:00:00 Intro
00:08:15 Why Being Early Can Bankrupt You
00:16:09 Creating a Market That Doesn’t Exist
00:27:55 Activity Does Not Equal Funding
00:38:06 Landing the First Enterprise Customer
00:49:57 Surviving Enterprise Sales Cycles
00:54:56 Navigating the Emotional Rollercoaster
01:00:46 The Truth About Product Market Fit
01:01:55 Andrew Rubin’s Best Advice for Early Founders
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Rob Woollen, founder of Sigma Computing, shares the unfiltered reality of going from 0 to $100M ARR. After spending seven years grinding without product-market fit, Sigma finally hit an inflection point—tripling revenue year over year. Rob dives deep into the pivots, setbacks, and critical decisions that turned early failure into a massive success. If you’re an early-stage founder feeling stuck, this episode will show you how patience, resilience, and radical product decisions can transform your startup.
Why You Should Listen
- How Sigma went from $0 to $100M ARR—but spent 7 years figuring it out.
- The pivot that turned years of failure into explosive growth.
- Why obsessing over speed to product-market fit is the wrong game.
- How to handle the psychological toll of startup uncertainty.
- The hidden power of building features your customers never ask for.
Keywords
product-market fit, Sigma Computing, pivot, startup growth, business intelligence, Snowflake, early-stage startup, SaaS growth, cloud analytics, founder stories
00:00:00 Intro
00:02:49 Debating speed to product–market fit
00:10:14 Quitting Salesforce and the EIR leap
00:23:12 Two years of prototypes that went nowhere
00:36:53 The Snowflake meeting and spreadsheet pivot
00:45:41 Dealing with Investors
00:52:30 Tripling three years straight to $100M ARR
00:54:46 Why most people shouldn’t start a company
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This is the brutally honest startup story every founder needs to hear. Benedetta shares how she built a fintech app to half a million users and raised $10M—yet still failed.
You’ll learn why chasing big partnerships can backfire spectacularly, how a seemingly successful startup can quietly fall apart, and how to set yourself up to avoid common but deadly fundraising mistakes.
This isn’t just another success story; it’s a real guide on how not to fail.
Why You Should Listen
- Discover why even rapid growth and millions raised might not save you.
- Find out the hidden dangers of relying on corporate VCs.
- Learn why equal founder equity splits might not be a good idea.
- Hear the biggest fundraising mistakes early-stage founders make (and how to avoid them).
- Get practical advice on how to truly validate your startup before building tech.
Keywords
startup failure, fundraising mistakes, fintech startup, founder lessons, corporate VC, startup partnerships, product validation, founder equity split, early-stage fundraising, startup growth challenges
00:00:00 Early Days at Uber and Moving into Fintech
00:07:00 Launching a Consumer Fintech App in Europe
00:13:37 Validating Without Tech Building an MVP by Hand
00:19:22 Why US Startup Models Don’t Work in Europe
00:23:07 Raising Money Quickly—and the Hidden Costs
00:28:56 Running Out of Cash When COVID Hit
00:32:15 Tough Decisions Layoffs, Sales, and Shutdown
00:37:53 How Big Partnerships Can Sink Your Startup
00:43:41 Staying Optimistic Even When Everything Falls Apart
00:46:38 Crucial Fundraising Advice for Early-Stage Founders
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How do you build a $100B business without hypergrowth or endless funding rounds? Hernan Kazah co-founded Mercado Libre, the Latin American ecommerce giant, at the peak of the dot-com bubble. But when the market crashed, funding disappeared, and competitors doubled down on spending, Mercado Libre focused relentlessly on building a rock-solid, profitable core product—ignoring pressure to chase faster growth. Hernan shares how they turned extreme constraints into a secret weapon, why getting profitable early was a game-changer, and why the biggest businesses are built by doing fewer things, better.
Why You Should Listen
- How Mercado Libre survived going bankrupt by pivoting overnight.
- Why most startups die chasing growth—and what to do instead.
- How to build unstoppable momentum by nailing one thing first.
- The simple test to know if your startup has real product-market fit.
- The one thing all $100B companies do differently.
Keywords
Mercado Libre, product market fit, Hernan Kazah, startup advice, ecommerce growth, marketplace strategy, profitability, venture capital, early-stage startups, Latin America startups
00:00:00 Intro
00:04:07 Why We Chose the eBay Model
00:08:56 The Early Hack That Got Us Our First Users
00:14:23 Raising Money at the Worst Possible Time
00:21:37 Becoming Profitable and Going Public
00:26:34 How Mercado Libre Stayed Patient While Competitors Chased Growth
00:34:05 Why We Expanded Across Latin America From Day One
00:45:11 Our Secret to Winning Against Better-Funded Competitors
00:50:04 The Most Important Advice for Early-Stage Founders
00:52:16 Why AI is Different From the Internet and Mobile Revolutions
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Four founders prove you don’t need Silicon Valley, a technical degree, or a massive seed round to build a massive company. We go through the key observations from the last 4 episodes: How Skip created a $200M business in a third tier city, Polarsteps’ NPS‑obsessed rise, Jobber’s decade‑long compounding engine, and why a small decision was key to Public.com’s huge success.
You’ll learn when to ignore best practices, how to choose one north‑star metric, and why slow, relentless improvement beats silver‑bullet fantasies. Perfect fuel for scrappy founders hunting product–market fit.
Why You Should Listen
- The single‑metric focus that took a travel app to $10M ARR through Covid
- Turning six months of “no’s” into $100M ARR: the slow‑burn playbook
- Why mastering your craft first can unlock your next billion‑dollar idea
- Picking the rules to break: using “unconventional” as an unfair advantage
00:00:00 Intro
00:01:30 Why location odds matter less than you think
00:02:50 Skip the Dishes proves huge wins can start in tiny markets
00:05:30 Polarsteps shows what happens when one metric rules them all
00:09:00 Jobber’s decade‑long slow burn to compounding growth
00:14:40 Public.com and the power of diving deep into your craft
00:21:40 The real skill: knowing when to ignore conventional wisdom
00:24:30 Key takeaways and next steps for your own playbook
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Jordan Dearsley spent 3 years building a startup stuck at $500K in revenue—then he burned it all down and moved to San Francisco. A year later, he was at $10M ARR. This episode walks through Jordan’s decision to abandon a profitable business, why solving a painful customer problem was the key to explosive growth, and how finding product-market fit is as simple—and as brutally difficult—as discovering a 10/10 burning pain.
If you’re a founder struggling to find breakout growth, this episode is your blueprint.
Why You Should Listen
- How to pivot from a dead-end idea to $10M ARR in one year.
- The power of solving a 10/10 burning pain.
- When customer anger becomes your biggest growth signal.
- Why chasing local maxima can trap your startup.
- How true conviction unlocks explosive growth.
Keywords
product-market fit, startup pivot, explosive growth, voice AI, founder stories, SaaS startups, early-stage startups, customer pain points, San Francisco startups, developer tools
00:00:00 Intro
00:02:35 Stuck at $500K ARR & Burning the Boats
00:07:15 Knowing When It’s Time to Quit
00:08:49 The Side Project that Became Vapi
00:16:28 Early Growth and Finding First Customers
00:23:32 The Product Hunt Launch that 3X’d Growth
00:27:57 Surviving Explosive Growth
00:35:17 Competing Against OpenAI and Big Tech
00:41:26 How to Identify a True 10/10 Pain
00:48:53 The Moment of Real Product-Market Fit
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Two founders, two wildly different paths to $100M ARR: Arvind Jain, founder of Glean, walked away from a unicorn to start over—raising $15M without revenue and ignoring lean startup rules. Kyle Hanslovan, founder of Huntress, faced brutal rejection, slept in his car, maxed out credit cards, and still crushed it. This episode is packed with raw lessons on fundraising, product-market fit, and why relentless hustle alone won’t save you. If you’re a founder chasing growth, stop everything and listen.
Why You Should Listen
- Learn exactly what top founders did to get from zero to $100M ARR
- Why chasing perfection won't work (and how to stop)
- The secret to surviving brutal fundraising rejections (over 60 VCs said no to Kyle)
- Why hustle culture isn’t enough—here’s what matters more
Keywords
product-market fit, startup fundraising, unicorn startups, founder hustle, lean startup method, scaling startups, early-stage growth, AI startups, SaaS growth, venture capital advice
Chapters
(00:00:00) Intro
(00:02:05) Quitting a Unicorn to Start Again
(00:05:09) From NSA Hacker to Startup Founder
(00:09:18) Ignoring the Lean Startup
(00:12:59) Knowing When to Launch
(00:16:32) Finding Product Market Fit
(00:18:01) Final Advice for Founders
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Avery Pennarun raised $160M for Tailscale—without even meaning to. What started as a small, simple project exploded into an unstoppable force in network connectivity and security. This episode reveals exactly how Avery turned a tiny seed round into millions of dollars in ARR, powered by nothing more than word-of-mouth and an obsession with solving everyday developer headaches. Learn why your startup idea is probably wrong (and why that’s okay), how Tailscale found explosive product-market fit, and why the biggest opportunities are hiding in the “smallest” problems. If you’re an early-stage founder looking for practical insights, game-changing growth hacks, and lessons from someone who’s been through it all, this is the episode you can’t miss.
Why You Should Listen
- Learn how Avery grew Tailscale from zero to millions in revenue purely through word-of-mouth.
- Discover why chasing enterprise deals too early might actually slow you down.
- Find out why solving “small, simple” problems can lead to billion-dollar outcomes.
- Hear the counterintuitive reason why your product failing early users is actually a huge advantage.
- Understand how Tailscale turned COVID lockdown into an explosive growth opportunity.
Podcast Keywords
product market fit, startup growth, product-led growth, Tailscale, word-of-mouth growth, startup fundraising, developer tools, network security, B2B SaaS, early-stage founder advice
(00:00:00) How Tailscale Raised $160M Without Chasing Investors
(00:01:48) Building a Billion-Dollar Idea From Scratch
(00:05:18) How to Find Real Problems Worth Solving
(00:13:14) Landing the Critical First Customer
(00:22:25) Why Great Founders Start Small, Not Big
(00:28:33) Turning Bottom-Up Adoption into Enterprise Deals
(00:36:55) Growing from Zero to $1M+ ARR Through Word-of-Mouth
(00:46:16) When Avery Knew Tailscale Had Product Market Fit
(00:48:27) Avery’s Most Important Advice for Early-Stage Founders
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Description:Jack Kuveke returns to unpack the wildest startup news this month: from billion-dollar frauds and crypto scams, to OpenAI’s secretive $6.5 billion gadget project with Apple’s design legend Jony Ive. We dig into why big-name investors keep missing red flags, and why AI might be crushing entry-level tech jobs faster than anyone expected.
Keywords
startup scams, OpenAI Johnny Ive, Elizabeth Holmes, Builder AI scandal, tech IPO crash, AI job loss, crypto meme coin fraud, venture capital news, tech layoffs, Theranos lessons
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After two pivots and nearly running out of runway, Merrill Lutsky found insane growth—scaling Graphite to tens of thousands of daily users and millions in ARR. He reveals exactly how Graphite landed its first massive enterprise customer, doubled revenue overnight by changing pricing, and turned user feedback into momentum.
Merrill shares hard-earned lessons on recognizing true product-market fit, leveraging internal tools as a market wedge, and surviving the chaos every early-stage founder faces. If you’re building, pivoting, or scaling your startup, this is a must-listen episode.
Why You Should Listen
- How to Know When It’s Time to Pivot—or Keep Going
- Landing Your First Enterprise Deal (and Getting to $1M ARR in 10 Months)
- Why Daily User Feedback is a Secret Weapon
- Finding the Real “Must-Have” Product
- Why Your First Pricing Model Probably Won’t Work (and How to Fix It)
Keywords
product market fit, developer tools, pivot, enterprise sales, startup growth, code review, pricing strategy, software startups, founder lessons, Graphite dev tool
00:00:00 Raising a seed round on Airbnb Wi‑Fi
00:10:40 Lessons from the first failed DevTool
00:16:00 Why daily‑use products win
00:24:30 Pivoting from mobile rollbacks to code review
00:31:00 Ex‑Meta engineers spark a viral wait‑list
00:40:00 Switching on pricing and racing to $1 M ARR
00:48:30 The pricing tweak that doubled revenue
00:50:00 Surviving outages, bank collapses and chaos
00:52:30 Co‑founder trust makes or breaks startups
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Most early-stage founders get trapped in the chaos of endless tasks, there's always too much to do and not enough time. We go through the last 4 episodes to see what how the best founders prioritize. We also see why you can raise millions without real traction but can’t fake product-market fit, how positioning yourself for luck is as important as having a plan, why slow initial growth might be your secret weapon, and how true passion gives you staying power.
Why You Should Listen
- How to prioritize ruthlessly—focus is about saying no.
- Why you can't game product-market fit.
- Turning random luck into edge.
- When slow growth still wins
- Why true founder-market fit keeps you in the game longer.
Keywords
product-market fit, founder-market fit, startup prioritization, fundraising strategies, early-stage startups, growth strategies, startup pivot, founder lessons, bootstrapping startups, AI startups
00:00 Intro
02:58 Why Founders Need to Drop Some Balls
05:04 You Can Fake Fundraising but Not Product Market Fit
09:22 Positioning Yourself for Luck
13:33 Why Slow Initial Growth Might be OK
17:28 Why True Passion Buys Staying Power
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Dax built Lightspeed into a $1B ARR public company—even though he bootstrapped for the first 7 years. In this episode, he reveals exactly how he used a 4x pricing shift to create a global reseller machine that grew him to $10M ARR. He also breaks down why obsessing over design and deep customer empathy built the foundation for success.—and how stepping away from his comfort zone as an introverted developer was the key to scale. If you’re an early-stage founder trying to nail pricing, distribution, and long-term strategic decisions, this story is your playbook.
Why You Should Listen
- Learn how to price your product to build a distribution machine.
- Why early profitability can make your startup unstoppable.
- How bootstrapping forces clarity—and can unlock massive scale.
- Why the hardest move for founders is often letting go of what they’re best at.
- Why giving away titles and equity too soon is a trap.
Keywords
product market fit, pricing strategy, bootstrapping, reseller partnerships, early-stage startups, go-to-market strategy, startup scaling, founder lessons, Lightspeed POS, profitability
00:00:00 Intro
00:07:56 Landing the First Customers Without a Product
00:11:28 The Pricing Strategy that Changed Everything
00:19:20 Growth Through Partnerships
00:26:18 Why a Business Plan Can Actually Help
00:34:33 Profitable from Day One
00:42:15 From On-Premise to the Cloud
00:46:59 Finding Product-Market Fit
00:49:15 The Truth About Early Employees and Equity
00:53:18 Reinventing Your Role as Founder Every Year
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Carta just released their report for Q1 2025. Peter is Head of Insights at Carta, and the person who owns their data practice. We sit down to talk about the largest trends he saw across fundraising, industries, graduation rates and even hiring practices.
Carta data shows that graduation rates from Seed to A are as low as they've ever been. Bridge rounds make you even less likely to raise an A. And why seed-strapping might be an answer for many founders.
VCs read and understand all this data. If you want to operate on equal footing— you should too.
Why you should listen:
- What the Series A gap is and what do about it.
- Learn what the latest data says on valuations for seed and early-stage companies, round sizes etc.
- Why bridges and extensions have become so popular.
- Why bridge rounds have lower graduation rates to Series A.
- Why you might not need to move to the Bay Area to raise large rounds.
Keywords
venture capital, AI, fundraising, market trends, valuations, startup ecosystem, early stage, late stage, investment, venture capital, bridge rounds, seed extensions, startup growth, hiring practices, AI impact, early stage funding, market trends, valuations, exits
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Kazi Ahmed took a small insight—seeing friends cash out from Amazon brands—and built Carbon6, a software roll-up startup, selling it for $210M just three years later.
But behind the quick success was a frantic scramble to survive. Aggressive acquisitions nearly ran them out of cash, forcing a brutal pivot from burning $1M per month to profitability and explosive organic growth.
This episode dives deep into Kazi’s playbook: when to ignore customer interviews, how to pivot on a dime, and why getting started immediately beats perfect planning every time.
Why You Should Listen:
- How Kazi Ahmed built a startup from $0 to a $210M exit in just 3 years.
- Why chasing perfect ideas kills startups (and what to do instead).
- How aggressive acquisitions almost destroyed the company—and the tough pivot that saved it.
- Why customer interviews are overrated and sales beats surveys every time.
- How to identify when a roll-up strategy makes sense (and when it doesn’t).
Keywords:
startup growth, Amazon FBA, acquisition strategy, profitable pivot, roll-up startups, founder stories, SaaS growth, startup exits, e-commerce software, early-stage advice
00:00:00 Intro
00:02:35 How COVID Unlocked an Amazon Gold Rush
00:06:51 From Aggregating Brands to Aggregating Software
00:12:04 Funding Acquisitions with Friends and Family
00:16:18 The Art of Structuring Deals
00:21:50 Pivoting from Acquisition Spree to Profitability
00:26:35 Aggressive Cost Cutting and Cultural Reset
00:29:43 Scaling Upmarket with a Sales-Driven Approach
00:36:51 The $210 Million Acquisition by SPS Commerce
00:40:26 Reflections and Realities of a Big Exit
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I break down my top insights from recent conversations with four founders who won in unconventional ways. You’ll hear how Noah turned LinkedIn posts into his primary sales channel (without ever going viral), why Dan’s startup survived a brutal 95% downround but ended up at $400M ARR two years later, how Adam turned a stagnant $3M ARR business into a $25M cash cow by solving one overlooked customer pain point. Plus, and how Cleerly used a 17 day-from- bankruptcy moment as its turning point.
Why You Should Listen
• How to turn LinkedIn into your best sales channel without going viral
• Why a 95% downround doesn’t mean your startup is over
• How near-failure experiences can lead to breakthrough growth
• The power of uncovering overlooked customer problems to drive massive profits
• Why constraints and limited resources can become your biggest advantage
Keywords
product market fit, startup growth, LinkedIn lead generation, fundraising, downround, bootstrapping, founder lessons, pivoting, scaling startups, entrepreneurship
00:00:00 Intro
00:01:01 How Stacker Leveraged LinkedIn for Explosive Growth
00:04:43 Clutch’s Wild Ride from Unicorn to Nearly Bankrupt and Back
00:07:38 Navigating Market Cycles as a Founder
00:08:32 Retention.com’s Pivot from Stagnation to Massive Profits
00:13:33 Cleerly’s Near-Death Moment with Only 17 Days of Runway
00:16:21 Why Constraints Are a Secret Weapon
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Public co-founder Jannick Malling shares exactly how he grew his startup from a tiny beta to millions of users—and hundreds of millions raised. He reveals why fractional shares changed the game for user acquisition, how the company cleverly seized on the GameStop moment to explode growth, and why relentless product focus was critical to scaling quickly.
He explains the mindset shift needed to nail product-market fit multiple times and why you should only tackle timeless problems if you want your startup to last.
Why You Should Listen
• Learn how Public went from 1K beta users to millions in just 18 months by flipping the playbook.
• Discover how to capture viral growth moments like GameStop and turning them into sustained growth.
• Understand how intense product focus can drive massive results even with limited resources.
• Hear why you need to solve timeless problems, not trendy ones.
Keywords
startup growth, product market fit, fractional shares, viral growth, Public investing app, fintech startup, user acquisition, scaling startups, startup advice, founder interview
(00:00:00) How Public Went from 1K Users to Millions
(00:09:41) Jannick’s Path from Teen Designer to Fintech Founder
(00:19:03) Fractional Shares Unlock Explosive Growth
(00:26:31) Why Community was Key (and How it Actually Worked)
(00:31:36) Launch Day Metrics Go Off the Charts
(00:35:38) Unusual Strategy Behind Public’s Word-of-Mouth Success
(00:42:38) How Public Increased Average Deposits by 30x
(00:49:12) How GameStop Doubled Public’s User Base in 48 Hours
(00:53:00) Jannick’s Real Advice on Picking Problems That Matter
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Corporate spies stealing Slack messages. Adam Neumann raising another $100M (for WeWork 2.0?). AI startups hitting $34B valuations with zero revenue and ordering Ben & Jerry's ice cream over 15 payments with Klarna on DoorDash.
April was wild, and Jack Kuveke joins the show to unpack the chaos, controversy, and insanity behind the biggest startup headlines.
This is different than our normal episodes— definitely a much lighter twist, to be taken with a grain of salt. Let us know what you think!
Why You Should Listen
- Why Adam Neumann can raise billions—but you can’t raise your seed round
- How a $40B valuation for AI startups might not be as insane as it sounds
- Why espionage is moving from Wall St to Silicon Valley
- What Klarna and DoorDash teaming up says about consumer debt culture
- Why A16Z thinks VCs will be the last job standing when AI takes over
Keywords
Adam Neumann, AI startups, Silicon Valley espionage, A16Z, Klarna DoorDash, startup news, corporate spies, consumer debt, tech valuations, VC funding
00:00 Intro
01:45 Neumann’s new $500 M raise and the WeWork déjà‑vu
08:20 Deel‑vs‑Rippling spy saga uncovered
13:00 11x growth scandal and TechCrunch backlash
18:25 Marc Andreessen says only VCs are irreplaceable
20:38 ChatGPT’s $10 M “please & thank‑you” GPU bill
26:10 Safe Super‑Intelligence and the $34 B pre‑revenue club
30:00 Klarna × DoorDash lets you finance ice cream
37:40 How consumer debt became America’s default setting
41:55 Quick survival guide for founders (and a few rants)
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Forrest Zeisler spent 6 months hearing “no” from every potential customer he spoke to. One year in, Jobber had just three customers—paying $29/month. Today, Jobber generates over $100M ARR, has raised $180M in VC, and employs nearly 1,000 people.
In this episode, Forrest shares the brutally honest story behind Jobber’s early days: months of rejection, maxing out credit cards, and nearly quitting. You’ll learn why there are rarely any “silver bullets”, how he handled relentless investor skepticism, and how incremental daily improvements—not crazy inflection points—led to exponential growth.
If you’ve ever wondered whether your startup can make it through the grind, this is a must-listen.
Why You Should Listen
• Learn how to persist through brutal rejection—Jobber took 6 months to land their first customer.
• Understand why chasing “silver bullet” features or channels rarely works.
• Find out when it makes sense to keep going despite extremely slow traction.
• Hear why your first investors can shape or destroy your startup journey.
• Discover why “compound growth” beats chasing short-term inflection points.
Keywords
product market fit, startup growth, founder stories, fundraising, bootstrapping, Jobber, vertical SaaS, early stage startups, scaling startups, startup rejection
(00:00:00) Intro
(00:01:55) From Freelance Devs to Startup Founders
(00:07:23) Six Months of Rejection
(00:15:09) Landing the First Customer and Almost Losing Hope
(00:25:39) Brutal Investor Feedback and the $250K Seed Round
(00:35:13) Early Growth and Near-Death Experiences
(00:44:15) Hitting Customer Milestones and Finding True Product Market Fit
(00:48:41) Crossing $100M ARR and Key Lessons Learned
(00:51:11) When to Quit and When to Persist
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He turned a personal travel tracker into an app with 10 million users and $10 million in revenue, with almost no funding. He reveals how ignoring conventional startup advice—like launching early, chasing revenue, or partnering for growth—was key to their viral success.
He realized everything growth was about word-of-mouth. So the key to success was obsessing over a single metric: NPS.
If you’re an early-stage founder deciding where to focus, this is your must-listen episode.
___
Why You Should Listen
• From losing 90% of users overnight to over $10M in revenue.
• Why obsessing over Net Promoter Score (NPS) instead of revenue can drive explosive organic growth.
• How to stay hyper-focused on one metric—and avoid distractions.
• The truth about partnerships and why most startups shouldn’t chase them.
• The counterintuitive decision to build for quality first, even if it delays your launch.
____
Keywords
product market fit, startup growth, net promoter score, organic growth, consumer apps, app monetization, viral growth, user retention, travel app, early-stage startup
_____
(00:00:00) Losing 90% of Users Overnight
(00:01:10) Turning a Personal Project Into a Travel App
(00:09:36) Raising $50K and Building Before Launch
(00:24:09) Launch Day and First 2000 Users
(00:30:35) Why Chasing Partnerships Can Hurt Growth
(00:36:40) How Polarsteps Reached $10M Revenue
(00:41:00) Surviving COVID as a Travel Startup
(00:42:20) Finding True Product Market Fit
(00:43:26) The Moment Polarsteps Almost Failed
(00:45:03) One Metric Every Founder Should Track
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Jordan Boesch started 7shifts as a teenager helping his dad manage restaurant shifts. Today, his software runs scheduling for 50,000 restaurants. This episode dives into how Jordan bootstrapped early growth, why relentless focus on solving real customer pain mattered more than funding, and how tight partnerships supercharged his expansion.
Jordan also shares hard-won lessons on managing burnout, dealing with near-failure, and creating a company culture that lasts. It’s packed with practical insights every founder needs.
___
Why You Should Listen:
• From side project to being used by 1 in 10 restaurant workers in the U.S.
• How to use SEO and partnership strategies that drove early growth
• Why customer complaints are often a good sign.
• What to do when you're about to run out of cash.
• See why defining clear core values early was key to building a resilient team.
_____
(00:00:00) Building for Passion Not Profit
(00:01:32) Solving Dad’s Restaurant Problems
(00:06:01) Getting the First Real Customer
(00:10:47) Taking the Leap to Full-Time Founder
(00:13:07) Moving to Silicon Valley and Finding Focus
(00:16:51) Growth Hacking with SEO and Partnerships
(00:24:59) How to Actually Make Partnerships Work
(00:27:08) Building a Big Company Outside the Bay Area
(00:30:29) Raising Money and Surviving Near-Failure
(00:35:49) Defining Culture to Scale
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Wesley turned a simple AI headshot generator into a $10M ARR, profitable company—in just two years.
He was fired from his job, broke in San Francisco, and, after getting rejected by 30 VCs, down to his last few thousand bucks. But Wesley saw a moment: generative AI was taking off, and no one was tackling AI headshots.
Fast-forward two years, and he’s doing $10M in revenue, profitable, with just 10 employees. He shares every bold tactic—bundling random AI packs, hacking Google rankings, landing affiliates, and manually doing customer support until there was no time left. Wes shares insights that every founder should know, including how he navigated intense competition, handled burnout, and maintained growth without a sales team. You’ll walk away with clear, actionable strategies you can apply immediately.
If you want a raw, practical take on zero-to-10M product-market fit in the AI era, this one’s unmissable.
Why You Should Listen:
• How Wes grew Aragon to $10M ARR—without burning any money.
• The guerrilla marketing tactics Wes used to turn a $30 idea into millions of revenue.
• Why starting early let him outrun lookalike competitors.
• How one affiliate blog post drove more than 50% of early sales.
• How he managed high early churn in the early days until the product improved.
Keywords:
AI startups, early-stage growth, product-market fit, AI headshots, founder stories, affiliate marketing, startup tactics, SEO for startups, guerrilla marketing, startup growth strategies
(00:01:54) Zero to $10M in Two Years
(00:02:34) Exploring Ideas Before AI
(00:05:25) Discovering the AI Headshot Opportunity
(00:07:37) How Getting Fired Led to a Startup
(00:18:31) Doubling Down on Professional Headshots
(00:24:11) Early Guerrilla Marketing and Traction
(00:27:59) From $2K to $200K a Month
(00:32:13) Affiliate Marketing as a Growth Lever
(00:43:18) The Moment of True Product Market Fit
(00:47:18) Surviving Near-Failure and Burnout
Send me a message to let me know what you think!
Mike first raised $30M for a marketplace that never truly had product-market fit. Then he bet only $10K on ButcherBox. A few years later, he's doing $550M in revenue and he's profitable.
The difference is in his first startup he was just catering to investors— in his second one only to customers. If you’re an early founder chasing growth, listen to how Mike ditched vanity metrics, found sustainable traction, and grew ButcherBox past $500M in revenue—with no outside funding.
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Why You Should Listen
-
Why not raising can often be a powerful forcing function.
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Why what VCs want is often not the same as what customers want.
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How to differentiate in what seems like a commoditized market.
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Why there is no stronger force in startups than true product-market fit.
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Keywords
product market fit, bootstrapping, butcherbox, direct to consumer, CPG subscription, grass fed beef, founder lessons, Kickstarter, food startup, early stage founder
_____
(00:00:00) Mastering the VC Game
(00:01:45) How I Raised $30M Without Product Market Fit
(00:08:21) Why my VC-backed Startup Failed
(00:15:34) Growing Revenue but Losing Money
(00:28:07) Early Signals of Real Product Market Fit
(00:34:59) Solving Supply Chain to Scale ButcherBox
(00:39:43) Bootstrapping to $550M (The Power of Constraints)
(00:51:18) Product Market Fit from Day One
(00:52:42) Why Founders Need a Lifestyle Plan
Send me a message to let me know what you think!
Gopi Rangan has invested in 29 early-stage startups from scratch. He shares a simple but powerful approach to picking the right VCs, structuring your pitch (long-term vision + short-term plan + fuzzy mid-term path), and proving you are the sort of founder every pre-seed investor craves.
If you’re raising a pre-seed or seed, Gopi’s tips will make your process faster, more targeted, and a lot less painful.
___
Why You Should Listen
-
The 2-minute test for "real" pre-seed investors – Spot VCs who truly lead early rounds vs. those who waste your time.
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His 3-step framework for finding your perfect lead – Forget the 100 investor pipeline. Zero in on 10 prospects who’ll actually write a check.
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How to balance short-term execution with a massive mission – Win over pre-seed VCs by knowing your next 6 months and your 10-year ambition.
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Why "business acumen" beats everything – Gopi explains how it trumps domain expertise or brand-name credentials.
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When to be fuzzy, when to be precise – The counterintuitive approach that shows you’re open to customer feedback while still having big vision.
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Keywords
Pre-seed Funding, Early-Stage VC, Business Acumen, Go-to-Market Strategy, Founder–Investor Fit, Strategic Networking, Seed Round Pitch, Warm Introductions, Mission-Driven Startups, Conviction Investing
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(00:00:00) Why Ruthless Prioritization Wins
(00:03:29) Why Investing at Pre-seed is Personal
(00:08:36) Investing When There Are Still Typos in the Pitch Deck
(00:12:23) Spotting Founders with Exceptional Business Acumen
(00:17:21) Great Ideas in the Hands of the Right Founder
(00:26:29) The Practical Guide to Raising Your Seed Round
Send me a message to let me know what you think!
Cardiologist Jim Min watched too many 50-year-olds die with no heart-attack warning. He co-founded Cleerly to automate detailed coronary scans—no invasive procedures, no endless manual work.
Yet healthcare’s glacial pace, payers, and federal approvals all stand in his way.
Hear how he’s testing AI across thousands of patients, fighting for universal insurance coverage, and coping with near-burnouts. If you’re a founder navigating hyper-regulated markets, Jim’s journey is the blueprint.
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Why You Should Listen
-
Heart Disease Kills More Than All Cancers Combined – The staggering truth behind silent heart attacks (and why most diagnoses come too late).
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Jim’s Big Bet on Early Detection – He’s using advanced AI to spot “dangerous plaque” long before a patient gets chest pain or drops dead.
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A 10–15 Year Fight to Save Lives – The brutal reality of building a medtech startup in a system that moves slower than any other.
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Surviving a 17-Day Runway – How his mission-focus (and supportive backers) pulled Jim’s startup back from the brink.
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Why repeated failure drives game-changing breakthroughs
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Keywords
Heart Disease Detection, Medtech Startup, Coronary CT Angiogram, AI in Healthcare, Early Heart Attack Prevention, FDA Approval Process, CPT Code Reimbursement, Plaque Imaging, Cardiovascular Innovation, Clinical Trials
____
(00:00:00) Embracing Failure & Surviving Dark Days
(00:01:56) From Cardiologist to Startup Founder
(00:03:07) What Most People Don’t Know About Heart Attacks
(00:06:39) Using AI & Imaging to Predict Heart Attacks
(00:09:19) Why Cleerly Needed to Exist
(00:16:34) The Reality of Healthtech
(00:20:41) How Cleerly Built its First Product—and Why it Wasn’t an MVP
(00:28:33) Raising $225M to Prove a Radical Idea
(00:33:57) Finding Product-Market Fit & the Fight Worth Having
Send me a message to let me know what you think!
Adam Robinson once struggled with a stagnant email SaaS stuck at $3M ARR, but he kept experimenting until he found how to solve a problem no one else was tackling—and everything changed. Suddenly, buyers were begging for his identity-based marketing tool—so he spun out Retention.com and grew it to $14M+ in annual profit with no outside funding.
In this episode, Adam reveals why he ignored “scalable hacks” until his product proved undeniable, the two keys that finally unleashed product-market fit, and how he uses no-friction brand marketing on LinkedIn to sign up thousands of new leads.
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Why You Should Listen
-
He chose profit over fundraising – Adam shows how ignoring “growth-hack hype” and focusing on real word-of-mouth built a wildly profitable SaaS.
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Shocking pivot to product-market fit – A failed email tool spun out a game-changing identity product that users demanded.
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The #1 trap killing early-stage founders – Why “growth hacking” tactics fail without genuine pull, and what to do instead.
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Bootstrapping to $14M profit – His surprising path from 3M stalled ARR to unstoppable momentum (with a team of only six).
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LinkedIn brand building done right – How to attract thousands of perfect-fit leads—no spammy sequences required.
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Keywords
Bootstrapped SaaS, Product Market Fit, Email Marketing Growth, Founder Lessons, B2B LinkedIn Strategy, High Profit Margins, Startup Pivot, Word-of-Mouth Marketing, Early-Stage Experimentation
Timestamps(00:00:00) Intro
(00:01:57) A Bootstrap Story
(00:06:33) Why Bootstrapping Often Means You Can't Lose
(00:10:36) The downside of raising VC
(00:19:53) A Case Study: Constant Contact
(00:22:45) Find an Unsolved Porblem
(00:32:06) PMF and Word of Mouth
(00:46:45) Piece of Advice
Send me a message to let me know what you think!
Dan Park joined Clutch when it was selling 20 cars a month. Then he grew it from $20M in 2019 to $200M in sales by 2022. He was one of Canada's fastest growing companies. Just as he was going to close a $100M round, the macro changed completely. Suddenly, he was left with only six weeks of cash. He was forced to go through a 97% down round at a $15M valuation.
Just two years later, he not only grew right back to a $575M valuation, he also doubled revenue from its previous peak to $400M.
This episode unpacks every near-disaster move, including turning off test-drives (and why it worked), re-engineering unit economics in real time, and renegotiating debt so Clutch could keep buying cars.
Dan’s hard-won lessons will change the way you think about speed, iteration, and survival.
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Why You Should Listen
-
He had just six weeks of runway – Find out exactly how Dan rescued Clutch from the brink.
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Taking a car startup to $400M in sales – The surprising moves that made consumers buy cars online, sight unseen.
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Cutting 75% of staff—then doubling revenue – The inside story of Clutch’s brutal pivot and swift rebound.
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How to survive capital-intensive nightmares – Lessons on debt, term sheets, and crisis-mode fundraising.
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Why fast iteration trumps everything – Dan’s secret to making big bets—then yanking them back if needed.
________
Keywords
Used Car Marketplace, Capital-Intensive Startup, Near-Bankruptcy Turnaround, Automotive E-Commerce, Cash Flow Management, Startup Layoffs, Rapid Iteration, Debt Restructuring, Growth vs. Profitability, Founding Team Dynamics
Timestamp
(00:00:00) Intro
(00:02:23) The Birth of Clutch
(00:04:37) The Chicken and Egg Problem
(00:08:31) How Do We Scale This?
(00:14:21) Baby Steps and Achievable Milestones
(00:22:45) Becoming Profitable
(00:34:45) Do Whatever Makes Sense for The Business
(00:37:29) Finding Product Market Fit
(00:42:23) Piece of Advice
Send me a message to let me know what you think!
Noah Greenberg grew a content-distribution product from zero to $1M ARR in just one year (and to $4M in 2 years) by focusing on a single channel most founders underrate: LinkedIn. He posted insights daily, highlighted key players in his industry, and made it impossible for prospects not to notice him.
In this episode, Noah reveals the exact step-by-step playbook, including how to structure 3-month pilots for fast feedback, craft DMs that actually get replies, and pick the right content “watering holes” so your future customers come to you eager to sign.
If you're a founder trying to figure out your go-to-market approach, you need to see what Noah did.
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Why You Should Listen
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Turning LinkedIn into a Free PR Engine – Noah shows how daily micro-posts drive high-value leads without needing to go viral.
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Finding Your First 10 Customers with 3-Month Pilots – Short trials = instant feedback on who’ll stay and who’ll churn.
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Never Stop Triangulating – How 50 customer conversations per month reveal the right product, price, and packaging.
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Selling without Selling – The “this isn’t a pitch” call that makes prospects lean in and ask, “Wait, how do we buy?”
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Earning Credibility at Scale – Noah’s “watering hole” posts spark real engagement from decision-makers (and reel in 5-figure deals).
_______
Keywords
B2B Sales, LinkedIn Strategy, Early-Stage Growth, Founders’ Playbook, Bootstrapped Startup, Content Distribution, Sales Prospecting, Pilot Contracts, Outbound Leads, Product-Market Fit
Timestamps(00:00:00) Intro(00:02:35) Stacker's Origin Story
(00:06:00) How to generate warm leads
(00:15:53) How to use LinkedIn for lead gen
(00:21:42) No One Wants To Be Pitched
(00:26:06) How to get feedback on pricing
(00:38:08) LinkedIn Go-To-Market Strategy
(00:42:20) Breaking Above The Noise
Send me a message to let me know what you think!
We break down the real startup playbook: fake users, fake traction, real secondaries. From starting a company with zero customers, to raising millions and launching a VC fund that's built to lose money, Jack shares the blueprint for getting rich (without working hard).
Forget chasing product-market fit.
Start chasing growth, money, and, most of all, hype.
Why You Should Listen
- Why you need to spend most of your time fundraising.
- Learn exactly how to fake traction, drive FOMO and raise millions-- even with a terrible product.
- Get Jack's ultimate playbook for quitting early and winning big (without working hard)
- How secondaries can make you rich BEFORE your startup fails.
- Why League of Legends is the key to startup success
Keywords
startup fundraising, pivot strategy, early stage VC, founder mistakes, product market fit, startup advice, venture capital, startup growth, entrepreneur mindset, founder stories
(00:00:00) Intro: Why Quitters Win and Fundraising Beats Traction
(00:02:54) Ex-Googlers Can’t Hack It as Founders
(00:03:12) Raising Money is Your Only Job
(00:10:49) How to Fake User Growth & Create FOMO
(00:14:18) Quit Fast, Pivot Faster
(00:15:28) Jabroni Capital: The World’s Worst VC Fund
(00:26:26) Hiring Hacks: How to Convince People to Join Your Startup
(00:28:27) Adam Neumann: Hero or Villain?
(00:38:16) The Real Jack Kuveke: Satire, Startups, and Why VC is Broken
Send me a message to let me know what you think!
Wes Bush wrote the original bestseller on Product-Led Growth—and then watched everyone try to copy Dropbox and Slack without truly getting it. Now, he’s here to break down exactly what goes wrong when early-stage founders jump into PLG, how to spot your product’s “million-dollar free problem,” and how to fix the three biggest onboarding gaps that sabotage new users.
He’ll show you why some sales-led companies die when they try freemium, how to carve out a simpler “first strike” moment, and the reason you need bumpers (like an onboarding checklist) to guide people to success. If you’re still using the “Request a Demo” button, this episode could totally transform your approach and give you a self-serve funnel that scales faster than any sales deck ever could.
Why You Should Listen
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Make Users “Smell the Cologne” – Learn Wes’s approach for letting users experience the core value before they buy.
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Turning Complex Setups into a No-Brainer – How to map out product, skill, and knowledge gaps so anyone can get started.
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Bowling Alley Onboarding – A framework to slash unnecessary steps, guide users to that “aha” moment, and cut churn.
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Freemium vs. Free Trial vs. Reverse Trial – How to pick the perfect model for your startup.
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Sales-Led to Product-Led – Why some founders fight this shift, and how to pull it off without blowing up your funnel.
Keywords
Product-Led Growth, PLG Strategies, SaaS Onboarding, Freemium Model, Free Trial Optimization, User Adoption, Customer Success, B2B SaaS Growth, Onboarding Framework, Go-to-Market Tactics
Timestamp
(00:00:00) Intro
(00:01:27) What is Product Led Growth
(00:04:37) When to use PLG
(00:18:20) Why Simplicity is the key
(00:20:15) Wes's Favorite Case Study
(00:25:42) The Bowling Alley Framework for Onboarding
(00:31:02) Free Trials Must Have Progression
(00:36:28) Finding Those Ideal Limits on your Trials
Send me a message to let me know what you think!
Jeff Adamson co-founded SkipTheDishes, scaled it to 80% market share, and sold it for $200M—all before Uber Eats and DoorDash even got serious about Canada. He started with zero tech experience, got doors slammed in his face by restaurant owners, and had to personally place orders just to keep early partners engaged. Then, when Uber Eats launched in Toronto, backed by billions in funding, he thought it was over.
Instead, Skip became Canada’s dominant food delivery platform and got acquired for $200M.
Then Jeff did something even crazier—he decided to take on the banks.
With Neo Financial, he’s tackling Canada’s most entrenched industry, building a modern, full-stack digital bank from scratch. He's raised $100s of millions at a $1B valuation.
Why you should listen:
- How bootstrapped SkipTheDishes took on $10B UberEats
- How to build a three-sided marketplace.
- Why building trust with customers is key to long-term success.
- Why beginnings are always messy and more about grit than perfection.
- Why Jeff didn't stop after exiting for $200M.
Keywords
SkiptheDishes, Neo Financial, entrepreneurship, delivery service, startup journey, market competition, founding team, restaurant industry, business growth, feedback loop, three-sided marketplace, startup journey, Canadian startups, entrepreneurship, financial services, exit strategy, partnerships, growth strategies, advice for founders
Timestamps
(00:00:00) Intro
(00:02:00) Gotta Have Thick Skin
(00:03:54) Skip's Origin Story
(00:07:18) Competing with Uber
(00:16:09) The First Few Restaurants
(00:22:45) Initial Demand
(00:26:28) Three-Sided Marketplace
(00:38:38) The Original Mission
(00:52:10) The First Year at Neo
(00:58:40) Product Market Fit
(00:59:55) A Piece of Advice
Send me a message to let me know what you think!
One of the most common questions I get is 'How do I know if I have product market fit?" Especially when you're in that gray zone where things are kind of working but they're not really taking off yet, how do you know if you have product-market fit or not?
That's exactly what we dive into here.
Why you should listen:
- Why demo to close is an excellent leading indicator of PMF.
- Why NPS is not as good as Sean Ellis test to measure product-market fit.
- Why retention is the best long-term metric, but takes long.
- What qualitative signals you'll feel when you have true PMF.
- What to do if you realize you don't have real product-market fit.
This podcast originally aired on Matt's podcast called Product Driven, because the topics were so relevant, I figured I'd post it here too.
Timestamps
(00:00:00) Intro
(00:00:55) How do you know if you have PMF
(00:06:33) Why some problems are good
(00:11:24) Solve a True Top of Mind Pain
(00:15:54) Why timing matters
(00:21:30) How to Know When to Pivot
(00:25:00) Asking the Right Questions to Customers
Send me a message to let me know what you think!
Edo Liberty left a high-paying job at AWS—where he was building AI at the highest level—to start Pinecone, a company no one understood. He pitched 40+ VCs, got rejected by every single one, and nearly ran out of money. Then, he flipped the pitch, raised $10M, and built one of the most important infrastructure companies in AI.
Then ChatGPT dropped.
Suddenly, Pinecone was the must-have database for AI apps, with thousands of developers signing up daily. The company exploded, leading to a $100M round led by Andreessen Horowitz and a 10x revenue surge.
If you’re an early-stage founder, this episode is a must-listen.
Why you should listen:
•How he went from from 40 VC Rejections to a $10M Seed Round
• Why he quit a High-Paying Job at AWS to start a Startup
• The game-changing shift that made VCs finally “get it”
•What really happened inside Pinecone when AI took off
•Why most founders misunderstand market timing and what to do about it
Keywords
AI, Machine Learning, Startups, Entrepreneurship, Vector Databases, Fundraising, SageMaker, AWS, Technology, Innovation, Pinecone, vector database, seed funding, ChatGPT, startup growth, business model, AI, infrastructure, early stage founders
Timestamps(00:00:00) Intro
(00:07:50) Edo's Story
(00:12:27) The Early Days of Machine Learning
(00:32:23) Seed Funding
(00:42:09) Unsustainable Scaling
(00:53:41) Told You So
(00:59:24) A Piece of Advice
Send me a message to let me know what you think!
Jon Yoo’s startup wasn’t working. He pivoted mid-YC, spent five brutal weeks without signing a single customer, and then—right after raising his seed round—his co-founder left.
Most startups die right there.
Instead, Jon figured out how to land massive customers like FiveTran and Snowflake. He grew from $500K to $2M ARR in 6 months.
Why you should listen:
•Navigating a founder breakup – What happens when co-founders split and how to handle it.
•The real YC experience – What worked, what didn’t, and how they pivoted mid-program.
•Landing major customers – How they got big logos like Snowflake.
•Fundraising insights – What really matters to investors at the seed and Series A stages.
•Why startups need forcing functions – The tactics that drove fast product development.
•How to know if you have product-market fit – The signals John saw at Sugar.
•Burn rate discipline – Why they raised millions but barely spent it.
Keywords
entrepreneurship, startups, investment banking, Salesforce, Y Combinator, founder dynamics, product market fit, scaling, cloud marketplaces, business strategy, fundraising, startup, YC demo day, customer acquisition, product-market fit, founder dynamics, early stage startup, team building, scaling, challenges
Timestamps(00:00:00) Intro
(00:07:55) The Origin of Suger
(00:13:30) Going All In
(00:19:08) The first 10 customers
(00:24:20) The Hardest Pain Point
(00:30:29) Becoming Profitable
(00:37:05) Celebrate The Small Wins
(00:39:56) Finding Product Market Fit
(00:42:27) A Piece of Advice
Send me a message to let me know what you think!
This is one of the wildest founder journeys you’ll ever hear. Dmitry Gurski went from growing potatoes and picking mushrooms on a farm in Belarus to building Flo—a billion-dollar company with 75M monthly users that dominates the health and fitness category worldwide. He started Flo in a market already controlled by PayPal co-founder Max Levchin’s startup, which had $30M in funding from a16z. Today, Flo is 100x bigger than its once-dominant rival.
Dmitry shares raw, unfiltered startup truths—like why he got rejected by 200+ VCs, why 90% of startup failures are team-related, and why most founders are delusional about product-market fit. He breaks down how simplicity beats complexity in product, why retention is everything, and how deleting features can actually boost revenue.
If you’re a founder, this episode will fundamentally change how you think about perseverance, pivots, and building something that lasts. Listen now—you’ll be referencing this one for years.
Why you should listen:
- Why big market beats niche – How Flo won because it targeted all women’s health while competitors focused only on fertility.
- How Retention is the real test – A product with natural recurring use cases (like periods) has built-in retention, unlike fitness or productivity apps.
- Why simple wins – The first version of Flo was less complex than competitors but had far better predictions—accuracy mattered more than features.
- Fundraising is brutal – Flo got 300+ investor rejections before raising $300M. Many VCs just didn’t “get” the space.
Keywords
startup, entrepreneurship, product design, user retention, Flow app, health and fitness, early stage founders, product market fit, simplicity, user engagement, retention, user case, app development, entrepreneurship, product market fit, mobile apps, business strategy, team dynamics, failure, success, risk, uncertainty, decision making, market demand, competition, product-market fit, fundraising, entrepreneurship, startup success, female health
Timestamps(00:00:00) Intro
(00:09:10) Why you Need to Keep it Simple
(00:13:10) Why B2C is All About Retention
(00:19:05) Why you Need to Delete Features
(00:24:14) PMF is about the Shape of the Curve
(00:39:17) When to Persevere, When to Pivot, and When to Quit
(00:42:22) More attempts = more success
(00:51:34) The Idea for Flo
(00:59:05) Finding Product Market Fit
(01:02:07) Advice for An Early Stage Founder
(01:10:22) A Potato Story
Send me a message to let me know what you think!
Saurav started a Groupon-like offering for SMBs in 2011. He quickly learned it wasn't going to work. He and his team pivoted and started driving leads to suppliers using Facebook ads. It worked and they generated revenue—but they were becoming a digital advertising agency. It wasn't at all what they wanted to build.
So they pivoted again. They used the cash from that business and built Perkbox. The idea was a subscription-based offering that that gave perks to SMB customers. Telcos started buying it and attaching it to their products to drive sales. Then, they pivoted again, this time moving away from customer perks and to employee perks.
This time, it worked. They grew from $2M in ARR to $14M in just 2 years. They kept growing and hit $36M in ARR. Then he sold the business to PE for $170M.
It took longer than expected. There were more pivots than expected. But it was a huge success.
Here's how it happened.
Why you should listen:
- How to use new social media channels to drive growth.
- How to leverage partnerships to get end user adoption.
- Why having a profitable agency can be a great way to get started.
- Why capital efficiency can be a huge edge.
- Rebranding can help clarify market positioning.
- What it feels like to make $10s of millions in one day.
Keywords
PerkBox, Groupon, startup journey, business model, SMB market, marketing strategies, recurring revenue, partnerships, entrepreneurship, exit strategy, venture capital, entrepreneurship, startups, employee benefits, social media marketing, capital efficiency, business growth, acquisition, rebranding, emotional marketing, lessons learned
Timestamps(00:00:00) Intro
(00:01:48) The origin of Perkbox
(00:04:52) Going after SMBs
(00:12:16) The Pivot
(00:26:35) Creating Viral Ads
(00:32:28) Demo to Close Rate
(00:40:12) Selling to PE Firms
(00:49:38) A Piece of Advice
Send me a message to let me know what you think!
In 2005 most people didn't even have cellphones yet. Those who did used flip phones. That's when Noah started Olo, a webapp to let people pre-order coffee from nearby shops. Users had to login on web, add a credit card, create pre-made orders and then send a text to a preset number when they wanted to pre-order. It was way, way ahead of its time.
Noah and his team 7 years to hit $1M in ARR. In the meantime, they raised a round with 50% dilution the week before the financial crisis, went on live TV to an audience on 6M viewers and had to pivot from a marketplace to B2B SaaS.
But overtime smartphone penetration increased, on-demand ordering became a trend, and then, one day, Starbucks launched their app. All of a sudden, every single restaurant in the world wanted a way to let their users pre-order.
And there was Noah and his team at Olo.
Today, Olo is a public company worth over $1B and generating nearly $300M in sales. Here's the story of how it happened.
Why you should listen:
- How to use guerrilla marketing tactics to get early growth.
- Why PR can move the needle but not in ways you expect.
- How to pivot from a marketplace to B2B SaaS.
- Why it often takes much longer than you might hope to hit an inflection point.
- Why fundraising was so hard, even though Olo became a $1B+ public company.
- Why Noah thinks founders should embrace challenges and adversity.
Keywords
Olo, Noah Glass, entrepreneurship, product-market fit, restaurant technology, mobile ordering, startup journey, business challenges, marketing strategies, innovation
Timestamps:
(00:00:00) Intro
(00:02:20) Building an app in 2005
(00:13:20) The Burn the Boats Moment
(00:16:31) Building A Network Business
(00:26:08) The Cold Start Problem
(00:30:33) A Happy Accident
(00:36:55) Going through the 2008 Financial Crisis
(00:51:20) Finding Product Market Fit
(00:57:20) Blueprint of Values
(01:05:11) Best Piece of Advice
(01:06:08) A Big Milestone
Send me a message to let me know what you think!
Frankie lost $10K in a crypto transaction—so he started Staging Labs to find a way to help others prevent crypto scams. He was head of an incubator called Entrepreneurship First and had seen dozens and dozens of founders build startups. He knew exactly what to do—and he did everything right. He found a co-founder, built an MVP, did customer discovery, checked willingness to pay—but he still failed.
The world changed when crypto crashed in late 2022. The people who were originally interseted in paying for crypto insurance nolonger were. And by the time Frankie realized it, it was too late.
Here's how it happened—and how he was able to sell his startup even though the product wasn't working out.
Why you should listen:
- How to sell your startup even when it's not working out.
- Why sometimes the best ideas come from personal struggles.
- Why you need to constantly validate willingness to pay.
- Why you can't treat lean startup as a series of checklists.
- The last 10% of execution is often what determines success or failure.
- Partnerships can be a double-edged sword in startup strategy.
- How aligning personal values with customer needs is essential for founders.
Keywords
entrepreneurship, startups, crypto scams, fundraising, product launch, market timing, personal experience, validation, community building, business challenges, willingness to pay, user experience, scams, customer alignment, market cycles, acquisition, strategic partnerships, investor relations, startup lessons
Timestamps:
(00:00:00) Intro
(00:02:25) The Idea & The Origin of Staging Labs
(00:08:07) Next Steps & Pre-Seed Fundraising
(00:13:27) Why you should never depend on partnerships
(00:18:28) How to create urgency
(00:24:55) Pivoting
(00:28:43) Trying to sell the business
(00:35:55) Biggest Lessons Learned
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Hussein's travel startup was doing $10s of millions when COVID hit. His revenue didn't just go to zero, it went negative. There were more customers asking for refunds than new sales. He was 4 months from running out of money.
He ended up making a complete pivot, he changed the company's name from SnapTravel to Super.com. He went from travel to fintech and launched a banking card. It seems like a strange pivot —but through deep research he'd realized what his customers truly needed. They needed more money—not for travel or vacations—but for every day life.
The new card helped customers earn points and rewards, it helped them save on everyday expenses. The pain was so acute and the solution so perfect, that just 3 years later, Super.com is doing $150M in ARR.
Like Hussein said, he got 50 'no's from VCs for every 'yes' he got. He saw his business grow and then crumble over night. He was literally going to zero.
But he turned it all around. Now he's not just growing, he's profitable now.
And here's how it went down.
Why you should listen:
- How to think from first principles to figure out the right product expansion.
- Why cross-selling is much harder than you think, and how to make it work.
- Why finding an unfair advantage is key to scaling a startup.
- How to use actual customer behavior to understand what customers truly want.
- Why testing and validating ideas through smoke tests is essential.
Keywords
Super.com, SnapTravel, COVID-19, travel industry, pricing strategies, customer needs, market fit, entrepreneurship, AI, business growth, COVID-19, resilience, travel industry, financial innovation, membership model, customer insights, entrepreneurship, investor relations, business strategy, cross-selling
Timestamps:
(00:00:00) Intro
(00:02:39) The original startup: Snap Travel
(00:08:40) Why a great user interface is a big edge
(00:11:26) How to acquire customers
(00:13:30) When your entire hypothesis is wrong
(00:22:52) Meeting Steph Curry
(00:29:03) Nearly crashing to zero-- and going bankrupt
(00:33:51) Starting over and rebranding
(00:42:42) Creating the Fastest Growing Membership Program
(00:52:17) Finding Product Market Fit
(01:00:00) One Piece of Advice
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When Amplitude launched Mixpanel was the big game in town. They were first to market, had raised more money, and had a well-known brand. VCs passed on Amplitude because it seemed like just another Mixpanel.
Today, Amplitude is a $1.5B public company—they're about 2x bigger than Mixpanel. Mixpanel's marketing spend helped educate the market. But before buying an analytics solution most businesses do market research. That's when they'd find out that Amplitude had several features Mixpanel lacked—and they were much, MUCH cheaper.
It's not cool to win on price, but it works. It worked for WalMart, CostCo, Shein, and it worked for Ampltiude.
Here's the story of how it all happened.
Why you should listen:
- How to use cheaper prices to win in a crowded market.
- Why you often need 12 hour days to win in Startupland.
- Why even massive $1B+ successes often have trouble raising early rounds.
- How pivoting can often be the key to finding real market pull.
- Why big competitors can often be a huge tailwind.
- How to use storytelling to raising bigger rounds.
Keywords
startups, entrepreneurship, analytics, Amplitude, pricing strategy, market positioning, data processing, voice recognition, technology pivot, competitive advantage, market dynamics, differentiation, product-market fit, storytelling, fundraising, startup challenges, customer relationships, analytics tools, business strategy, entrepreneurship
Timestamps:
(00:00:00) Intro
(00:06:13) A cool demo-- but a bad business
(00:18:36) Why funding was so hard
(00:25:43) Why lower prices are a big differentiator
(00:40:50) Working 24/7
(00:50:35) Product Market Fit
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This first time founder just raised a $38 million Series A. The crazy part is that for all of 2021, 2022, 2023, he had almost no revenue. He spent all that time building and pivoting. Finally he launched in 2024—and it blew up.
I saw his LinkedIn post and his revenue chart doesn't look like a hockey stick... it looks like straight a vertical line. He built a health benefits platform—it doesn't get less sexy than that. And yet, it absolutely exploded to millions in ARR in less than a year.
All because he figured out how to make something that every single company in the U.S. needs, exceptionally simple.
Here's the story.
Why you should listen:
- Why choosing the right co-founder is the most important thing.
- Why having a mission is crucial to make it through the ups and downs.
- How to listen to and understand customer pain points.
- Why pivots are not a bad thing, and can actually be the key to crazy traction.
- How to use external deadlines to drive urgency and focus .
Keywords
Thatch, startup journey, co-founders, healthcare innovation, product market fit, venture capital, entrepreneurship, health benefits, business challenges, pivoting, healthcare, startups, product development, market demand, customer needs, external deadlines, product market fit, scaling, company culture, founder intuition
Timestamps:
(00:00:00) Intro
(00:02:27) Finding the Right Co-Founder
(00:10:23) Why You Need to Go All In
(00:16:20) The Seed Round & Pivoting From the Original Idea of Thatch
(00:30:08) How to use external deadlines to drive focus
(00:37:55) The Growth in 2024 & The Business Model
(00:42:16) The Benefits of Forcing Functions
(00:45:58) How Many Customers are Using Thatch Today?
(00:47:50) Finding True Product Market Fit
(00:52:10) People Didn't Believe in Thatch
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Carta just released their report for Q4 2024. Peter is Head of Insights at Carta, and the person who owns their data practice. We sit down to talk about the largest trends he saw across fundraising, industries, graduation rates and even hiring practices.
Carta data shows that graduation rates from Seed to A are much lower for companies that have raised a bridge round. We analyze why that might be and what that could mean for early-stage founders.
VCs read and understand all this data. If you want to operate on equal footing— you should too.
Why you should listen:
- The role of AI in the venture capital landscape.
- Why there are a trend of larger funding rounds going to fewer companies.
- Why so much capital is being allocated to AI companies.
- Valuations for seed and early-stage companies are on the rise.
- Why bridges and extensions have become so popular.
- Why bridge rounds have lower graduation rates to Series A.
- What the data shows about how hiring practices are changing.
Keywords
venture capital, AI, fundraising, market trends, valuations, startup ecosystem, early stage, late stage, investment, venture capital, bridge rounds, seed extensions, startup growth, hiring practices, AI impact, early stage funding, market trends, valuations, exits
Send me a message to let me know what you think!
Alon was a hacker for the Israeli Defence Forces' cyber department. There he saw the most advanced methods used in cyber warfare. So when he left, he started IntSights-- a company that helped enterprises defend themselves from cyber attacks.
He was a first-time founder who didn't even know the word 'unicorn'. He made all the mistakes you could make. But he had real, undeniable pull. He grew to $1M ARR in a year and to $4M a year later. By the end of it, he was doing $30M in revenue and exited for $335M.
But when I asked him what it felt like to sell for hundreds of millions, he said it 'felt like emptiness'. Alon is a builder—that's all he wants to do. So he quit post-acqusition and left millions of dollars on the table. Money he was guaranteed to make if he just stayed in his role.
Instead, he started PointFive to help enterprises reduce wasted spend on cloud infrastructure. He know nothing about the space. One year in, he's raised $36M and grown to millions in ARR— even faster than IntSights.
Here's the story.
Why you should listen
- Why Alon felt empty after exiting for $335M.
- Why he left millions of dollars on the table to start a new startup.
- Why the mistakes he made in his first startup helped his second one grow way faster.
- Why he raised $36M in under a year.
- Why true customer pull comes from solving top of mind problems.
Keywords
LinkedIn, video content, cloud cost optimization, engineering responsibilities, startup funding, second-time founders, product market fit, customer traction, entrepreneurship
Send me a message to let me know what you think!
Ned had a chance to run Robinhood Asia but he turned it down. Instead, he launched a competitive product. He decided to go B2B and sell to banks and other financial institutions. He locked down a $400K revenue sale before writing a line of code. It seemed easy at first. Overtime, he grew to $3.5M in revenue, billions in assets under management and hundreds of thousands of users. He raised $20M in venture capital.
But then the problems started. Enterprises that paid for large contracts didn't push the product—many had no marketing budgets. In some cases, they shelved the product altogether. The one-time revenue never turned into ARR. Running out of money, he was forced to raise a small bridge and lay off more than half his staff.
He came close—but ultimately, he just wasn't able to recover. He sold off the company for parts and went through a wind down.
This is his story—and the lessons he learned.
Why you should listen:
- Why the difference between success and failure can be minimal.
- How to balance custom contracts with building scalable product.
- Why enterprises might not push the product they've paid $100K+ for.
- How to build a strong company culture.
- Why layoffs are the hardest thing a founder will go through.
- When things go south, "the days are long, but the months are short".
Keywords
startup, FinTech, B2B2C, customization, revenue models, marketing, client engagement, leadership, company culture, lessons learned, B2B sales, startup challenges, emotional toll, liquidation, lessons learned
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Jason built a data center company in the 2013. When he exited in 2019, it was the third-largest exit in Canada that year. He'd sold his previous startup and invested 100% of his capital into ROOT. He grew to 10s of millions and exited for 100s of millions.
Now he's invested in over 20 angel-stage startups. He shares the story of ROOT and what he looks for in the startups and founders he backs.
Why you should listen:
- Why seeing inefficiencies can lead to huge advantages vs competitors.
- How customer concentration can actually lead to a huge success.
- Why the 'Why Now' slide is so important.
- Why Jason values startups can get to free cash flow within 1-2 years.
- How to use the lead to conversation ratio as a leading indicator of PMF.
Keywords
data centers, investment, entrepreneurship, product market fit, angel investing, business growth, technology, risk management, funding strategies, customer relationships, investment, startup, venture capital, product-market fit, founder advice, business model, cash flow, total addressable market, team dynamics, entrepreneurial hunger
Send me a message to let me know what you think!
Pablo is the first guest that has the same name as me-- so you KNOW this episode will be great. Pablo hustled for months just to get to $70K in ARR. He got rejected from YC, re-applied, and finally got in.
But after months in YC, he realized his first product was not going to work. He had some traction, but not nearly enough customer pull. So he shut it down. He went back to square one. He did customer discovery in a totally different space and leveraged the latest in Gen AI. He then built AI agents that automate calls in the logistics space.
Just a year after shutting down his first product, he'd grown to $2.2M in ARR. In December, he raised $15.6M from a16z.
Here's how it happened.
Why you should listen:
- Why you should be careful of "free" money from grants.
- Why YC changed the trajectory of Pablo's startup.
- How a big pivot is often necessary-- even when you have customer traction.
- Why the key is to find a true, no-brainer pain point.
- Meeting customers where they are can lead to smoother adoption of new technologies.
- How to build a product that provides clear ROI is essential for customer buy-in.
- Continuous exploration and adaptation are key to finding the right market fit.
Keywords
Happy Robot, startup journey, product market fit, early stage funding, co-founders, computer vision, YC, venture capital, entrepreneurship, business development, funding, European founders, Y Combinator, customer acquisition, pivoting, logistics, AI agents, startup growth, Series A, market research
Send me a message to let me know what you think!
Alex sold his last IoT startup for over $200M to Samsung. He felt the needed to build something much bigger, so he started BrightAI. The goal was to use AI and IoT to solve big problems for enterprises.
A few years later, he bootstrapped to $100M in revenue across just 7 customers. Last quarter, he raised $15M in venture funding. He shares how he closed million-dollar enterprise projects before building a product, why he refuses to go after just one vertical, and some of the biggest lessons he's learned after years building startups.
Why you should listen:
- Why impact is the biggest driver for starting startups.
- How to find champions and get enterprise design partners.
- How AI and IoT can combine to solve real-world issues.
- How to make sure you don't get stuck in a niche forever.
- How to tell if you're on to something in less than 18 months since launching.
Keywords
SmartThings, Bright, IoT, critical infrastructure, pest control, AI, technology, innovation, entrepreneurship, product development, AI, pest control, multimodal AI, revenue streams, platform scaling, product-market fit, early-stage founders, entrepreneurship, sustainability, critical infrastructure
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Nathan has interviewed 100s of founders on how they raised their first few rounds. In this interview, we go through some of the most compelling stories he's heard. We go through step-by-step what you should do to raise a round, how to get meetings, how to tell stories, and every other piece of the fundraising puzzle.
If you're planning to raise a round anytime this year-- check this episode out.
Why you should listen:
- Why you need to look for believers in the early days.
- Why you need to meet way more investors than you might want to.
- How to create momentum for your round.
- Why spending more time planning will mean spending less time raising.
Keywords
fundraising, startup, venture capital, investor relations, fundraising process, founder stories, capital raising, startup funding, investor introductions, fundraising strategies
Send me a message to let me know what you think!
A few years into building Flashfood, Josh was $35K in debt with no money in his account. Just a few months earlier, he'd lost both the pilot customers he'd worked so hard to lock in. He'd worked for months to land them and had delivered what he promised.
But both retailers told him the problem he was solving was not important enough.
And then, he met Loblaws-- one of Canada's largest retailers. They loved the case studies he had. They tested it out and quickly launched it across 100% of their locations.
"I was going to shut down the company." That's how close it came to failing completely. Instead, a year after meeting Loblaws he was doing $1.5M ARR and had raised a $3M seed round. Now, he does 10s of millions in revenue and will soon be profitable.
Here's the story.
Why you should listen:
- Why startups often drive founder to near bankruptcy.
- Why you need to keep testing your startup until you hear 'no'.
- Why sometimes large customers might be easier to close than small ones.
- How to get champions to close enterprise deals.
- Why you might be a top priority for some customer sets and not others.
Keywords
food waste, grocery stores, app development, early stage founders, product market fit, sustainability, entrepreneurship, discount food, consumer behavior, environmental impact, enterprise sales, customer priorities, stakeholder buy-in, corporate culture, product-market fit, revenue growth, grocery industry, startup challenges, business strategy, environmental impact
Send me a message to let me know what you think!
Darius started an EdTech startup to help users of online courses collaborate with each other. It blew up during COVID when everyone felt isolated. It gained thousands of users. They were engaged. They came back to use the platform. And, most importantly, they dramatically improved completion rates for online courses.
Darius thought he had it. But it turned out universities didn't want to pay. What users cared about was not what universities (the buyers) cared about.
His biggest lessons is that he should've pivoted much sooner. Here's why.
Why you should listen:
- Why success and failure are often not that far apart.
- Why engagement and usage don't always lead to revenue.
- How to figure out the KPI that matters for your buyer.
- Why users and buyers are not one and the same.
- Why you need to pivot much sooner than you might think-- or like.
Keywords
startup challenges, entrepreneurship, online learning, EdTech, market dynamics, product development, business strategy, lessons learned, networking, pivoting
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Zach was burned out after a decade of working at top roles in Coinbase, Square and Brex. He quit with no startup idea-- and then, he went right back in. Given their background, Zach and his co-founder quickly raised an $8M seed round to build an NFT-related product in Web3.
One month later, they completely abandoned their idea. They realized it was never going to work. Then, the floor fell from underneath them. FTX went bankrupt. SVB fell apart. They took punches to the face for the first 6 months straight.
But, when everyone was paying attention to Gen AI in late 2022, Zach kept going deep in Web3. He noticed stablecoins were growing but there was no platform for developers to build with. So he built Bridge, a Stripe-like API for stablecoins.
The first months post-launch were underwhelming-- until they landed a fast-growing customer. From then on, the next year was exceptional 10x+ growth. Then Stripe noticed them.
In Oct 2024, they were acquired for $1.1B. Just 2.5 years after he started.
Here's the story of how it all happened.
Why you should listen:
- Why even $1B+ exits still feel like rollercoasters from the inside.
- How to quickly abandon ideas and pivot to what truly matters.
- How they found a massive opportunity where no one else was looking.
- Why starting outside of the Bay Area was critical to their success.
Keywords
startup, billion-dollar exit, stablecoins, investor relations, crypto, fintech, market dynamics, entrepreneurship, pivot, challenges, stable coins, startup journey, acquisition, fintech, market resilience, product market fit, Pablo Srugo, Bridge, Stripe, entrepreneurship
Timestamps(00:00:00) Intro
(00:2:46) Starting at the Worst Time
(00:8:56) The Emotions on Pivoting a Month After Raising
(00:11:44) Pivoting
(00:18:24) Leaving Brex
(00:20:36) Working on Something Out of Trend
(00:28:34) The Core Beliefs of Bridge
(00:32:56) Launching & First Customer
(00:38:57) Sometimes you Can't Think Too Much
(00:42:29) Series A
(00:44:24) The Acquisition
(00:49:05) The Feeling of Exiting for a Billion
(00:52:24) One Piece of Advice
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We took examples from the last 100 episodes and built a clear, 5 step path to finding product market fit:
1.Before Startup Mode, There’s Research Mode —> Become an expert to find problems worth solving.
2.Only the Insanely Focused Survive —> Focus all your resources to do more with less.
3.You have to be in the market to win the market —> Use niche markets to discover unique insights.
4.Forget Growth. Find Value. —> Optimize for value delivery and growth will follow.
5.Pivot Harder, Faster —> As soon as you realize you’re not solving a #1 problem, pivot.
Why you should listen:
- Why creating value by solving problems is the core of startups.
- Startups must avoid perfectionism and embrace learning.
- Research mode involves deeply understanding customer needs.
- Insane focus and hustle are essential for early-stage success.
- Validation comes from engaging with the market directly.
- Why growth should be a byproduct of delivering value.
Keywords
startups, product market fit, entrepreneurship, research mode, focus, hustle, validation, customer experience, growth, business strategy, Wattpad, user-generated content, agility, iteration, product market fit, startup growth, pivots, entrepreneurship, value creation, founder stories
Timestamps:
(00:00:00) Intro
(00:01:47) Who is Chris Saad?
(00:02:30) Pablo's Story
(00:05:53) The Core to Early Stage is PMF
(00:09:07) Step 1: Research Mode
(00:16:44) Step 2: Only the Insanely Focused Survive
(00:23:46) Step 3: Be in the Market to Win the Market
(00:32:57) Step 4: Forget Growth, Find Value
(00:37:59) Step 5: Pivot Harder and Faster
(00:45:45) Recap
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Gusto is a $9.5B startup that does $500M ARR. Josh built an absolute monster of a company-- and it all started with payroll software for SMBs. Not just that, he started by servicing only new tech startups that were based in California. It was exceptionally niche, and it worked.
After YC, he raised a $6M seed round from tier 1 angels, back when large seed rounds were not at all common. But, unlike others, he didn't spend the money. He kept his team small as they iterated on the product. By the time they raised their $20M Series A, they were only 10-15 people.
Gusto is now a $9.5B startup doing $500M ARR. Here's the story of how they got started, gained initial traction, and took off.
Why you should listen:
- Why starting super small can lead to massive outcomes.
- Why you need a huge, no-brainer pain point to succeed.
- How to use early customer interviews to deeply understand your ICP.
- Why small teams allow for faster decision-making and execution.
- Why deep passion about the problem set is so important.
Keywords
Gusto, Josh Reeves, entrepreneurship, startup, payroll, small business, Y Combinator, business model, innovation, technology, fundraising, startup, product-market fit, team building, customer satisfaction, growth strategy, small business, Gusto, entrepreneurship, SaaS
Send me a message to let me know what you think!
We go through the top 5 product-market fit lessons I've learned from speaking to well over 100+ founders on this show over the last 3 years.
These are the top 5 things you should keep top of mind going into 2025.
Why you should listen:
- Small teams outperform larger ones in early stages.
- Paying employees well is needed to build A+ teams.
- Go all-in on fundraising to do it faster.
- Mind your burn rate to maintain flexibility.
- Creating undeniable value is essential for growth.
Keywords
product market fit, startup strategies, fundraising, small teams, value creation, entrepreneurship, founder insights, business growth, early stage startups, team dynamics
Send me a message to let me know what you think!
Tolga stumbled upon a problem in the security monitoring space. Motion cameras generated way too many false alerts. So he decided to solve it using AI. He raised over a million dollars and got several customers.
But he always felt he was pushing a boulder up a hill. At one point, one of his large customers churned and went with a competitor. Tolga pivoted, but it was too late.
Now, thinking back, he realizes that one of the main issues is he may never have been solving an important-enough problem. And in my experience that's the reason that 95%+ of startups fail.
You learn a lot from the massive successes— but you can only really know what drives success if you pay attention to the failures as well. So here it is, back by popular demand.
Why you should listen:
- Why learning from failures is as important as celebrating successes.
- Why you need to deeply validate the problem with customers before building.
- How to tell if your product isn't a top priority based on sales cycles.
- Why you probably need to pivot sooner than you think.
Keywords
startup failure, founder stories, learning from mistakes, customer validation, market dynamics, business pivot, entrepreneurship, PromiseQ, AI technology, security solutions
Timestamps:(00:00:00) Intro
(00:02:50) What is PromiseQ
(00:11:06) Working on a Non-Priority Pain Point
(00:16:10) Realizing the Different Costumer Profiles too Late
(00:18:23) The Business Model
(00:20:52) Why you need to pivot fast
(00:28:32) If Things Went Differently
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There are a few things harder when building startups than getting your first few customers. When you're on a standstill, getting momentum is incredibly hard. Going from zero to one takes an incredible amount of effort—you have absolutely no credibility, no proof points.
So to help you out I went through 24 ways of getting your first customers using 24 different examples from this show.
Why you should listen:
- Figure out how to land your first few customers. You are guaranteed to find at least one example that works for you.
Keywords
customer acquisition, startup strategies, community building, persistence, experimentation, free services
Timestamps(00:00:00) Intro
(00:01:35) Stay22 - Pay your Customers
(00:02:25) Reddit - Creating your Community
(00:02:58) Rappi - Seeding Supply
(00:04:04) Wattpad - Seeding Demand
(00:05:05) Cameo - Finding Someone With an Audience
(00:05:43) Noibu - Showcasing the Value of the Platform
(00:06:41) Bridgit - Showing up in Person
(00:07:24) Rewind - Attaching to an Ecosystem
(00:08:36) Clio - Adding Friction to the Funnel
(00:09:06) Wealthsimple - Lunch & Learn
(00:09:29) Athennian - Classic Customer Discovery
(00:10:00) Carbon Robotics - Presales from Customer Discovery
(00:10:34) StackAdapt - Creating Custom Software
(00:11:21) ApplyBoard - Identifying Power Users
(00:12:27) Forma AI - Sheer Force of Will
(00:15:01) Blockthrough - Starting with an Obvious Problem
(00:16:25) GoBolt - Finding Problems Close to You
(00:17:08) Shopify - Building a Waitlist & Showcasing the Product
(00:17:43) Fullscript - Cold Emailing
(00:18:30) Spellbook - Running Experiments Exceptionally Quickly
(00:19:27) Legion - Finding a Design Partner
(00:20:18) Knak - Consulting
(00:20:54) Dabble - Building Distrobution
(00:21:55) Zeffy - Making the Product Free
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Ankit left his job as a VC to launch a Voice AI platform—back in 2018! It wasn't the voice AI of today. The first demo sounded like a robot. But still, he convinced large enterprise customers in the healthcare space to try it out. He found a highly manual, call intensive workflow in the back office and autoamted it using AI.
Years later, he's raised $102M and has dozens of large $1M+ enterprise customers using the product. He talks about how he started it, how he saw the AI opportunity so early on, and how he found a way to lock in champions that pushed his product inside large enterprises.
Why you should listen:
- Why the search for product-market fit never stops.
- How to build trust with enterprise customers.
- How to get champions to fight battles for you and win enterprise deals.
- Why even successful startups are never straight lines up and to the right.
Keywords
product-market fit, AI in healthcare, automation, conversational AI, startup challenges, scaling, founder advice, technology evolution, compliance, trust in AI
Timestamps
(00:00:00) Intro
(00:02:01) How it all started
(00:06:29) Automating Insurance Calls
(00:16:37) Landing the first customers
(00:22:02) Giving your persona phone number to early users
(00:27:43) Landing large enterprise customers
(00:33:45) Getting Early Adopters to Believe
(00:36:34) Finding Product Market Fit
(00:38:04) One Piece of Advice
Send me a message to let me know what you think!
Marty and his co-founders lived full-time in their office for several months. They worked on their startup 24/7. To come up with the idea, they messaged 120 potential customers every day for 3 months.
Originally, when they pitched YC they were told their idea would never work. YC said they'd seen it several times and it was destined to fail. So in 2 weeks Marty landed a customer and built a product-- and YC let him in. He went on to raise a $3M seed round from General Catalyst in 6 days and later a $17M Series A from a16z in 14 days.
We go deep into how to come up with massive ideas, how to get to product-market fit, and how to quickly fundraise from tier 1 VCs.
Why you should listen
- Why all 3 founders living in the office was the best decision they ever made.
- How to raise a seed round in 6 days and a Series A in 14-- all from tier 1 VCs.
- How to leverage LinkedIn to get exposure and lots of leads.
- How to get more mindshare from your employees.
- Why Pylon has almost no meetings.
- How to come up with an idea using both top-down and bottoms-up processes.
Keywords
founders, startup, customer support, Pylon, co-founders, omnichannel, B2B, venture capital, product market fit, entrepreneurship, startup, Y Combinator, fundraising, product development, market trends, customer support, AI integration, team dynamics, venture capital, entrepreneurship
Timestamps
(00:00:00) Intro
(00:01:35) Why he chose to sleep in the office
(00:07:11) Project Management instead of People Management
(00:11:24) How it all started
(00:23:33) Cold Messaging Potential customers
(00:28:02) Finding the Trend
(00:35:49) Building V1
(00:38:32) Getting into YC as ChatGPT Comes Out
(00:42:37) Why fundraising is a "social game"
(01:01:21) Raising Series A from A16
Send me a message to let me know what you think!
I interviewed Martin on the keynote stage at the SaaS North conference. Here is the audio version. Martin built Applyboard into a $4B unicorn doing $100M+ in ARR. He left and started a new startup called Passage— and raised a $40M seed round.
He talks about 100-hour weeks, hiring exceptional talent, why smaller teams can outperform—and why he decided to start all over again.
Why you should listen:
- Why great founders thrive in high-stress situations-- on "the edge of failure" as Martin calls it.
- How to make your first hire.
- Why you need to go all-in and work crazy hours to build a unicorn.
- Why Martin thinks it's key to never give up, even in tough times, as cliche as it might sound.
- The importance of creating a positive environment to attract good people.
Keywords
entrepreneurship, education, immigration, impact, startup, Passage, ApplyBoard, perseverance, business model, founder journey
Timestamps
(00:00:00) Intro
(00:03:54) Getting Into Coding
(00:06:48) Accidentally Making Applyboard
(00:10:41) Starting startup #2
(00:17:19) Raising the Biggest Seed in Canada with Only 20 Employees
(00:20:07) If You Can't Outsmart Them, Outwork Them
(00:23:21) Getting the First Software Developer
(00:25:48) One Piece of Advice
Send me a message to let me know what you think!
Jon started a sports betting app 4 years ago-- now he does $150M in revenue and $1B in betting volume. AND he's profitable. In his first year alone , he did $10 million in revenue.
He took a year to build the app and as soon as he launched it, it took off. He did $10M in revenue in his first year.
Honestly, it sounds too easy. But the reason it worked is because, as he shares on the episode, he'd spent 7 years in research mode. He'd spent years building a marketing agency in the sports betting space. He not only understand the market, the customers and the product, he'd also built a distribution machine and knew exactly how to get in front of users.
Here's how it happened.
Why you should listen
- Why distribution is the difference between success and failure
- How spending a long time in research mode can make go-to-market much faster
- Why simple product difference can lead to huge differences in outcomes
Keywords
sports betting, Dabble, entrepreneurship, product-market fit, startup journey, social betting, technology, marketing, revenue growth, challenges
Timestamps
(00:00:00) Intro
(00:01:49) Getting Into Sports Betting
(00:04:22) Before Dabble
(00:08:08) Starting Dabble & First Steps
(00:10:55) The Initial Vision
(00:17:55) How Sports Betting Works
(00:24:26) Nearly Going Bankrupt
(00:27:53) Building the App
(00:31:23) Launching
(00:35:47) Revenue Timeline
(00:38:28) Finding Product Market Fit
(00:41:48) One Piece of Advice
Send me a message to let me know what you think!
Yanni started building in crypto back in 2013, when you could buy one Bitcoin for $20. At one point, he was playing poker games and betting 1 bitcoin each round!
He built an extension that let people use bitcoin to buy anything, anywhere on the internet. Then he pivoted to building the first on ramp for bitcoin. And finally, pivoted into Wyre, which was like Stripe for Crypto, a platform to let developers build Web3 apps.
In a couple of years he scaled it from nothing to a $90M run rate. In late 2021, he started working on an exit with Bolt. By mid 2022 the deal was signed. The company was to be sold for $1.5B.
Yanni would make hundreds of millions of dollars himself.
And then, at the absolute last minute, the world changed. Stocks fell, crypto plummeted— and the deal fell apart.
Startups are often one call, one customer or, in this case, one day away from complete success—or total failure. That’s the game you’re playing.
And there are few stories better than the one you’re about to hear.
Why you should listen
- Why if you want to be a founder you can't avoid taking punches to the face
-
How Yanni found Bitcoin just a couple of years after it was started
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Why it often takes multiple twists and pivots to find real PMF
-
How acquisitions tend to happen and why they can always fall apart
Keywords
startup, acquisition, Bitcoin, Web3, entrepreneurship, crypto, payment processing, innovation, technology, business, crypto, infrastructure, product-market fit, Web3, acquisition, startup challenges, fintech, business growth, developer support, market downturn
Timestamps(00:00:00) Intro
(00:01:50) Buying Bitcoin in 2013
(00:04:48) Creating a Hacker House in San Francisco
(00:19:08) Creating Crypto Wallets
(00:26:41) Becoming Wyre
(00:33:56) Making the Decision to Go All In on Crypto
(00:41:18) The Acquisition that Didn't Happen
(00:47:33) Learning from All the Mistakes
(00:52:03) Some People are Builders
Send me a message to let me know what you think!
Aaron was Director of Product at Amazon, VP Product at Twilio, PM at Facebook and Twitter. Now he’s head of product at Deel where he reports directly to the CEO. Deel was founded in 2019— now, just 5 years later, it’s worth $12B and raised over $650M.
We go deep on what it takes to build world-class products, how early-stage founders can balance customer feedback, vision and data, and how the best product leaders are leveraging AI today.
Keywords
productivity, AI, product development, user experience, product management, customer feedback, product market fit, technology, innovation, startups
Why you should listen
- Why you’re better off trying to enhance than replace with AI— at least today.
- Why you need to deeply understand your users to build products they truly love.
- How to avoid the customer feedback trap and only build features that move the needle.
- How and when to hire your first product manager.
- What makes a product truly great
Timestamps:
(00:00:00) Intro
(00:10:25) AI Solves the Informational Retrieval Problem
(00:14:54) AI Agents Aren't Real Yet
(00:18:12) Signals that Could Lead Towards to PMF
(00:23:04) Finding the Customers Need
(00:25:17) Hiring Product Managers
(00:28:00) Difference Between an excellent Product vs an Okay One
(00:34:17) Prioritizing Bug Fixing vs Feature Requests from Existing Users
Send me a message to let me know what you think!
Description
Tate started doing commercial fishing at 16. He took that money and started lending it— on Craigslist! By 23 years old, he’d lent out $250,000. Then he found out about cash advances, and decided to start ZayZoon, a platform to help employers pay their employees faster.
Tate was one of the early pioneers of the entire Earned Wage Access space. By partnering with payroll companies and employers, ZayZoon lets employees access their earned wages faster.
It took Tate and his co-founders 4 years to get to their first million of ARR. And as soon as they felt they had it, revenue crashed 60% in a quarter. The team got things back on track and since then has grown from 20 to 200 employees— revenue is now closer to $100M than $10M.
Here’s the story.
Why you should listen:
- Why you need to be all-in at the early stages
- How to arm channel patterns to sell your product
- How to re-position your product so it’s clear you solve customer problems
- Why it can take years for a new category to take off
Keywords
entrepreneurship, lending, FinTech, earned wage access, startup journey, mentorship, risk management, payroll integration, business challenges, market challenges, growth strategies, employer empowerment, product-market fit, exponential growth, timing, customer engagement
Timestamps:
(00:00:00) Intro
(00:01:25) Lending Money on Craigslist in Highschool
(00:13:06) The Origin of Zayzoon
(00:19:18) The Next Step After the Aha Moment
(00:24:44) Problems Starting Off
(00:29:08) Launching First Payroll
(00:30:58) Fundraising
(00:34:11) Making the Product Easy to use
(00:45:32) Hitting a Million Dollars
(00:48:53) Why timing matters
(00:53:34) Finding Product Market Fit
(00:54:27) One Piece of Advice
(00:56:29) How all in were you?
Send me a message to let me know what you think!
Zeffy is one of my biggest misses so far. I met Francois 3 years ago when he was raising his $3M seed round. But I passed.
They were at ~$500K in revenue at that point. In the last 3 years, they've grown 30x. Clearly, I missed out.
But it's been a long road for Francois. Before he got to the current idea, he had to make 3 pivots, including building a marketplace and selling to schools.
Finally he landed on what Zeffy is today, a fundraising platform for nonprofits. The crazy thing is that it's absolutely free to use. They make all of their money, which is now in the tens of millions in revenue a year, from tips. Voluntary tips that are given by donors while they donate to the nonprofits who use Zeffy's platform.
It's not an easy model to wrap your head around, but it's working in a big way.
Takeaways
- How to use new revenue models as differentiators.
- When to use sales-led vs marketing-led growth.
- Why the one and done funding model can work so well
- Why getting to profitability gives founders so much power.
Keywords
fundraising platform, nonprofits, product market fit, startup growth, profitability, marketing strategy, trust building, talent density, donation model
Timestamps
(00:00:00) Intro
(00:02:49) The Origin of Zeffy
(00:05:56) Gaining the Trust & Cold Calling
(00:08:52) Having a Sales Team Not Trying to Get Money
(00:13:21) Zeffy's Growth Timeline & Raising
(00:15:35) Google Ads Changed the Game
(00:18:54) The Mindset After Raising the Seed
(00:21:50) Staying Conservative When Recruiting
(00:24:05) What Makes Zeffy Unique
(00:27:38) Finding True Product Market Fit
(00:28:37) One Piece of Advice
Send me a message to let me know what you think!
In 2014, Ian launched a simple product: it let social media marketers buffer Instagram posts. It was originally a hackathon project. But it quickly gained users. So he and his co-founders went all in.
They raised just one small seed round. His main competitor, HootSuite, raised over $300M. In spite of that, he built a $40M ARR business that sold for well over $100M.
Here's the story of how it all happened. And why there's an option besides bootstrapping and raising round after round: it's called the one & done.
Why you should listen:
- Why you won't know if people love your product until you charge them.
- How to use content marketing to drive inbound traffic.
- How user experience can be a big differentiator even in a competitive market.
- What the acquisition process is like and why it often drags on.
Keywords
startup, product market fit, user feedback, monetization, content marketing, growth strategies, social media management, entrepreneurship, user acquisition, pricing strategy, startup, growth, competition, user experience, influencer marketing, acquisition, exit process, founder advice
Timestamps:
(00:00:00) Intro
(00:03:05) "Ian's dumb ideas"
(00:07:27) Hackathons
(00:10:41) Finding a market
(00:13:30) Early feedback
(00:17:50) The growth curve
(00:21:08) Turning on pricing
(00:26:35) A seed strapper
(00:31:58) Focusing on small and medium businesses
(00:38:24) Being well positioned
(00:43:19) Bough by private equity
(00:47:50) Relief
(00:50:59) A new project and a piece of advice
Send me a message to let me know what you think!
David's startup failed. But he had everything going for him: a solid thesis, $16M in funding across 3 rounds, $1.5M in ARR. At a high-level it seemed like everything was going the right way. And yet, it didn't work out.
This is what happens to 95% of startups. On thhis show, we mainly speak with the top 5%-- the ones where things went right and everything worked out. But you tend to learn more from failures than successes.
On this episode, we go deep with David to see what building Tandym was like, why it ultimately didn't work, and what he would do differently the second time around.
Why you should listen:
- Why you should always start with the model that requires the least capital
- Why you need to be a number one priority for your customers
- Why even hitting $1M ARR doesn't mean you will succeed.
- Why you need to pivot quickly as soon as things are clearly not working. i
Keywords
product-market fit, startup journey, fundraising, fintech, brand partnerships, business model, sales challenges, urgency in sales, Tandem, lessons learned, startup, fundraising, product strategy, compliance, revenue growth, entrepreneurship, lessons learned, business pivot, mid-market brands, capital management
Timestamps(00:00:00) Intro
(00:03:30) The Origin of Tandym
(00:09:26) Taking the Leap
(00:11:37) The Business Model
(00:17:22) Developing the Product
(00:21:05) Struggling to Create Urgency
(00:26:50) Raising Rounds & Shifting
(00:35:11) First Signs of Problems
(00:39:01) The Product that we should've launched
(00:42:12) How it All Ended
(00:49:56) Final Thoughts & Advice
Send me a message to let me know what you think!
Justin sold his first bootstrapped startup for over $10M. He raised $2M out of the gate for his second and then grew from $250K to $3M ARR in one year. He raised $40M in total, including a Series B from Bessemer.
And yet, just a week before recording the episode, he shared a post on LinkedIn about a recent panic attack that left him frozen for 15 minutes. It turns out, the sheer pressure of running a startup gets to him-- like it does to most founders-- and shows up in the forms of panic attacks. Fortunately, he's getting better, but like all of us, mental health is something he has to grapple with, despite all the success he's had.
We discuss mental health in startups, what it takes to be successful, the difference between bootstrapping and the VC-backed route, and how he grew his startup from nothing to 8 figures in just 4 years.
Why you should listen
- Mental health issues among founders are common but rarely discussed.
- Startup life often requires sacrificing work-life balance for success.
- How seemingly simple problems can lead to tremendous value and growth.
- Why starting a startup isn't for everyone.
Keywords
startup stress, mental health, entrepreneurship, product-market fit, venture capital, startup journey, growth, leadership, team dynamics
Timestamps(00:00:00) Intro(00:01:07) The Stress of Being a Startup Founder
(00:05:42) The Responsibility for your Workers as a Founder
(00:07:27) Work Life Balance Can't Exist
(00:15:39) The Origin of Aiwyn
(00:20:30) The First Product
(00:27:46) The Main ROI and Business Model of Aiwyn
(00:30:52) Starting During the Pandemic
(00:32:14) The Seed Round & Growth
(00:37:01) Series A
(00:41:41) Reputation Matters
(00:43:42) Finding True Product Market Fit
(00:44:13) One Piece of Advice
Send me a message to let me know what you think!
Rob founded Outpoint in 2020 to help marketers optimize their ad spend. He was a growth marketer and his founder a data scientist. He had team-market fit, a solid thesis, and paying customers. But when the recession hit and ad spend dropped, growth ground to a halt. Nothing he did could revitalize growth. Ultimately, he decreased expenses and exited. He was able to return some cash to investors, find a home for his team and keep the product going.
You tend to hear about what happens to the best 1% of startups. Here’s what tends to happen to the other 99%.
Keywords
Outpoint, product market fit, startup journey, acquisition, growth marketing, venture capital, business strategy, lessons learned, entrepreneurship, market dynamics
Why you should listen
- Why a great team and thesis won’t always lead to success
- How things out of your control can completely change your trajectory
- Why you should build something that works in both up and down markets
- How to find an acquisition when things aren’t going well.
Timestamps:
(00:00:00) Intro
(00:01:13) The origin of Outpoint
(00:14:49) Outpoint's Runway in 2022
(00:19:21) Trying to sell your company
(00:26:07) Lessons Learned
(00:28:53) Almost Finding Product Market Fit
(00:30:23) Planning a Startup vs starting one organically
(00:34:30) Closing Thoughts
Send me a message to let me know what you think!
Cameo is one of the best-known recent consumer startups. You've either used it or know someone who's used it to get famous people to create personalized videos. And, for a while, they were a total rocket ship.
Year 1: $300K GMV
Year 2: $4M
Year 3: $20M
Year 4: $100M
They were backed by Jeremy Liew, the VC who seeded Snapchat in 2012. Cameo became a unicorn in 2021. But as the markets turned, revenue decreased, investor interest waned, and their valuation dropped from $1B to $100M. After the restructuring and the layoffs, Steven found a way to turn things around.
Now the company is profitable again. And growing.
Here's how he did it.
Why you should listen:
- Why you don't need liquidity to launch a marketplace.
- How to hack your way to a successful marketplace launch.
- Why organic growth is the way to grow a marketplace.
- How to turn things around after your valuation crashes by 90%.
Keywords
Cameo, startup, entrepreneurship, product-market fit, celebrity endorsements, marketplace growth, business strategy, VC funding, early-stage startups, innovation, Cameo, gifting, unicorn status, Chicago startup, engagement, COVID-19 impact, business diversification, down rounds, product-market fit
Timestamps:
(00:00:00) Intro
(00:02:46) Where The Idea for Cameo Came From
(00:11:54) The Client Interface of Cameo in the Early Days
(00:14:12) The Failed launch that Could've Ended it All
(00:21:23) Gaining Momentum
(00:25:37) The Math Behind Cameo
(00:31:27) Becoming a Unicorn
(00:34:34) Meeting Jeremy Liew (the VC who backed Snapchat)
(00:40:47) Engagement on the Platform
(00:43:00) The Impact of Covid
(00:56:06) Finding Product Market Fit
(00:56:30) One Piece of Advice
Send me a message to let me know what you think!
Q3 startup data just dropped. We chat with Peter Walker, Head of Insights at Carta about valuations at pre-seed, seed and Series A. Why the current fundraising environment is the new normal and not about to get much better. We also talk about trends in founder vesting, and why some founders are choosing to vest for longer.
Finally, we go through what to do if you’re stuck with some product-market fit but mediocre growth, and why more exits are happening now than anytime in the fast couple of years.
Why you should listen
- Founders should not expect a return to the fundraising conditions of 2021.
- Competition among founders has increased, raising the bar for fundraising.
- Many startups are still alive despite challenging conditions, adapting to survive.
- Why the professionalization of the startup ecosystem offers more options for founders.
- Startup ecosystems are growing in tier two and three cities.
- What the one-and-done funding model is and how to use it.
Keywords
State of private markets, early stage funding, SAFEs, startup trends, liquidity, valuations, venture capital, market analysis, fundraising, AI, AI startups, vesting schedules, funding models, startup ecosystems, venture capital
Timestamps
(00:00:00) Intro
(00:01:33) Top Highlights from Q3 Report
(00:04:45) The market won't get any easier
(00:06:13) Two Reasons why the SAFE Boom Could Change Things
(00:12:34) Professionalization of the Industry is a Double Edged Sword
(00:17:44) Rounds that are Leading the Market are as Competitive as Ever
(00:22:36) Vesting Schedules
(00:30:05) Best Location to Raise & the One and Done Method
Send me a message to let me know what you think!
Lior is the Elon Musk of VC. In just 8 years, his venture fund went from 0 to $4B under management. And while doing that, he founded Bright Machines, which to date has raised over $400M. He's both the CEO of Bright Machines and the Managing Director of Eclipse Ventures.
And he's not building "easy" software startups either. Bright Machines is looking to automate the entire manufacturing process with robots. He launched it with a $179M round and a 100-person team.
Lior is not normal. His story isn't either. You won't want to miss this one.
Keywords
venture capital, startup journey, Bright Machines, manufacturing innovation, fundraising challenges, robotics, automation, customer relationships, product market fit, entrepreneurship, Eclipse Ventures
Timestamps:
(00:00:00) Intro
(00:08:31) Starting Eclipse & Becoming a VC
(00:13:58) How he started Bright Machines
(00:18:43) The First enterprise deal with Flextonics
(00:24:49) The Process of Automation and Assembly
(00:30:25) Making a Machine as Reliable as a Human
(00:34:44) Bright Machine's Struggles
(00:36:56) The Business Model of Robotics
(00:39:49) Finding Product Market Fit
(00:40:37) One Piece of Advice
Send me a message to let me know what you think!
Parker quit his job as VP Finance at a late-stage startup in mid 2021. He raised $4M out of the gate because, well, it was 2021. But he didn't ramp up sales, he didn't hire 15 developers. He kept the team to 5 people for the first year.
He worked with a dozen design partners until the value prop was perfect. He even refused to let customers pay upfront in annual contracts. He wanted monthly payments to light a fire for him and his team.
This month, just 3 years after quitting his job, he closed a $28M Series A.
Here's exactly how he did it.
Why you should listen:
- Why the early stages are all about customer value and delight.
- Why you need to focus on product-market fit before growth.
- Why you need to solve a top-of-mind problem and deliver clear ROI to take off.
- How to transition from build mode to sales mode.
- Why monthly contracts can provide valuable feedback loops for early-stage startups.
Keywords
Numeric, startup, product-market fit, funding, accounting, customer engagement, sales strategy, ROI, growth, Series A
Timestamps(00:00:00) Intro(00:01:07) Coming Up with the Idea
(00:06:13) Research, Taking the Leap & Pre-Seed Funding
(00:11:48) Keeping the Team Small
(00:16:55) Why Annual Payments Don't Work Early On
(00:22:10) The Challenges in Going into Market
(00:26:53) Measuring ROI
(00:33:26) Series A
(00:35:05) Finding Product Market Fit
(00:36:11) One Piece of Advice
Send me a message to let me know what you think!
Mike started selling SaaS before SaaS was a thing. PointClickCare is the Salesforce of healthcare. For the first 7 years, they raised just $600K from friends and family. With that funding, they grew to $50M in ARR.
Through that time, they went through the 2000 Dotcom crash and nearly went bankrupt in 2004 as they chased too many markets too soon.
Since then, the company has continued to grow at over 20% compounded rate and hit $500M in ARR in 2024 and a $5B valuation.
Mike shares how they started the company, the go-to-market strategy they used to go from 0 to $10M ARR and some of the most common mistakes he sees in the founders he works with today.
Why you should listen:
- Why you might need to live with your customers to really understand them.
- Why the first 10% market share is the hardest to achieve.
- How chasing the wrong sales opportunities can lead to customer disappointment.
- Why you need to focus on delighting customers before chasing revenue.
- Why TAM isn't nearly as important as founders are made to think.
Keywords
product market fit, startup growth, healthcare technology, customer delight, market entry, capital efficiency, company culture, founder advice
Timestamps:(00:00:00) Intro (00:01:43) Target Market is as Important as PMF
(00:06:42) The Origin of PointClickCare
(00:10:23) Being a Pioneer in SaaS
(00:20:18) Measuring Customer Delight
(00:28:40) Common Mistakes when Trying to Find PMF
(00:34:32) Entering the US Market
(00:37:57) Surviving Payroll to Payroll
(00:40:13) Losing the Original Ethos of your Company
(00:52:08) Finding Product Market Fit
(00:53:48) One Piece of Advice
Send me a message to let me know what you think!
Apple sold only 370,000 VisionPro headsets-- much fewer than it expected. Meanwhile, Meta Ray-Bans are the top-selling product in 60% of Ray-Ban stores. The outcome of their AR/VR products couldn't be more different, even though they both have as much awareness as you could possible buy.
There are 3 reasons:
- Price.
- Killer feature vs cool product.
- Destination vs always-on.
Check this episode out if you want to understand the where mixed reality is going and what you need to do to make sure your product takes off.
Send me a message to let me know what you think!
Piotr met his co-founders at a party in Coachella. He built them an app for influencers to post online. That simple idea evolved into one of the world's first influencer marketplaces.
While so many other tried and failed, Piotr and his team targeted marketing agencies with big budgets. They grew to $150M in revenue over a 10 year period. This summer, they were acquired by Publicis Groupe for $500M.
This is the story of how it all started, where the idea came from and how partnering with IBM of all companies drastically changed Influential's trajectory. Piotr also goes through in depth what it feels like to actually sell your company, and to go from living like a salaried employee to having tens of millions of dollars.
Why you should listen:
- Why the right go-to-market channel is the difference between failure and a $500M exit.
- How to shift from a manual process to a tech-enabled marketplace
- How to know which partnerships are key— and which are totally useless.
- What it feels like to go from a regular person to having $10s of millions in the bank.
Keywords
Influencer marketing, startup journey, product-market fit, technology, partnerships, exit strategy, ad agencies, growth strategies, entrepreneurship, venture capital
Timestamps:
(00:00:00) Intro
(00:01:27) The Start of Influential
(00:11:49) Raising the Seed Round
(00:14:41) How to leverage a partnership with a large incumbent
(00:21:26) Series A and Superbowl Campaign
(00:30:02) Winning because of go-to-market
(00:35:43) The Acquisition
(00:38:56) One Piece of Advice
Send me a message to let me know what you think!
New Carta data shows that 30% of seed-stage startups used to raise a Series A within 2 years of their seed. Now, only 15% do. The bar for Series As is as high as it's ever been. And the number of seed extensions that I see is going up as a result.
But for founders, this is NOT a bad thing. I remember as a seed-stage founder I was obsessed with raising a Series A. But now I've seen startup after startup that raised $8-12M Series A when they didn't truly have product-market fit. Most of those startups ended up hiring too many people, burning too much money, and not growing any faster. They are now money-losing startups with no growth.
The VCs aren't happy, but they're okay. But the founders aren't. They are at the bottom of the stack. They can't sell their business and can't grow it either. They're stuck between a rock and a hard place.
The solution? If you're not performing at top quartile levels, if you don't have clear undeniable product-market fit, then raise a smaller round.
Seed extensions might not be what you wanted—but in many cases, it's what you need.
Send me a message to let me know what you think!
Liran quit a cozy job at IBM to launch Fusic, a TikTok-like app back in 2011. He raised over $10M, acquired tens of thousands of users, and failed.
So he went back to what he knew: deep tech and enterprise. He launched WEKA in 2013 to improve the efficiency of GPUs. He was operating on hard mode: building deep tech and selling to large enterprise customers. It took him 5 years to build a commercially-ready product. In that time, he raised over $35M from strategic investors, since VCs didn't get it.
Once they launched, they more than doubled every year. And this year, they crossed $100M in ARR.
Here's how Liran built WEKA and got it off the ground.
Why you should listen:
- Why deep tech is much harder than normal software startups and always takes much longer.
- How to get enterprise customers to commit well before your product is ready.
- How to leverage strategic investors to get you through the early days when you have no revenue.
- How Liran was able to get customers to pay 6-figure deals when competitors offered 'similar' products for free.
KeywordsWeka, deep tech, large enterprises, GPUs, OS, product-market fit, funding, strategic investors, POCs, POVs, AI, GPU use case, performance, cost reduction, rapid growth
Timestamps:
(00:00:00) Intro
(00:02:12) Why my first startup failed
(00:08:35) Starting WEKA
(00:15:04) WEKA's First Customer
(00:17:43) The Operating System of CPUs
(00:21:19) The Issues with Deep Tech Companies
(00:26:19) Competing with a Free Product
(00:32:57) Reaching a Couple Million in ARR
(00:36:26) Fundraising
(00:43:19) Finding Product Market Fit
(00:44:08) One Piece of Advice
Send me a message to let me know what you think!
This episode is going to piss you off. Most founders struggle to raise their first few million. Many have to bootstrap for years. Even once there's revenue, many get rejected because they're "too early".
Dan had dozens of VCs asking to invest before he even quit his job. He raised his first $5M with no deck, no story, and no product idea. All it took was two founders who wanted to build something in the security space. To add fuel to the fire, 6 months after he incorporated, he raised a $50M round from Sequoia... with no revenue!
He didn't pitch dozens of VCs. He didn't create a deck. He just spoke to a partner at Sequoia and had a term sheet in 3 days. The reasons are part macro, part team, part market... and part just the insanity that sometimes happens in Startup Land.
It's hard to beleive and makes little sense from the outside. But it often works. Chainguard just closed $140M Series C, has 100s of customers and does 8 figures in ARR.
Here's how it happened.
Why you should listen:
- Why launching multiple products at once worked for Dan.
- How to raise from a position of strength to get favourable terms.
- Why identifying the right markets can be such an important step.
- Why time to value and leads to fast growth and high close rates.
Keywords
startup, fundraising, product market fit, Sequoia, security, open source, venture capital, entrepreneurship, growth strategies, technology, innovation
Send me a message to let me know what you think!
It was “really slow in the first couple of years...really, really slow.” GoHenry was an app and debit card for kids to help parents teach their kids about money. Dean started over a decade ago in 2012, when mobile was just truly taking off.
And yet, it took multiple years to get off the ground. Once he found the right channels and repeatable growth, he and his team started pouring fuel on the fire. In total, they raised over $100M.
He ultimately grew to 2 million paying customers. Earlier this year, they were acquired for an undisclosed sum in what is one of the bigger fintech M&A deals of the last few years.
Here's how it happened.
Why you should listen:
- Why even with millions of paying users, Dean speaks with a handful of customers one-on-one every week.
- Why timing is so important and how to spot trends early-on based on small things happening around you.
- How finding the right channels is key for consumer startups.
- Why Focus and clarity are key to maintaining a successful business.
KeywordsGoHenry, startup, acquisition, product market fit, customer feedback, financial education, kids debit card, scaling, marketing strategy, entrepreneurship
Timestamps:
(00:00:00) Intro
(00:1:34) The Beginning of GoHenry
(00:5:57) Why I talk to users every week
(00:11:22) You Grow by Learning Faster than Your Competitors
(00:26:50) V1 of GoHenry
(00:35:26) Getting to 10,000 Customers
(00:38:33) Conversion Rates from Social Media
(00:41:51) Getting Acquired
(00:50:59) Finding Product Market Fit
(00:51:33) One Piece of Advice
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Jaspar graduated YC & closed a $11.5M seed round this week. He launched Artisan just 8 months ago. And this is the first venture-backed startup he's ever ran.
He started with product-led-growth but struggled. In May, he moved to a sales-first go-to-market & scaled from $200K ARR to $1.3M ARR by September.
We go deep and tactical to figure out exactly what he did to grow so fast: from hiring a Chief of Staff as one of his first hires, to living in the same house as his employees, to meeting 50-100 Account Executives for each AE he hires. He shares specific numbers, specific tactics, and specific mistakes he made along the way.
Why you should listen- How solving a #1 priority problem is the single biggest reason for fast growth.
- How to use LinkedIn, Reddit, and SEO to generate so many leads your AE's are drowning. (Jaspar's AEs do 20 demo calls per day).
- How to close yourself by hiring a Chief of Staff early on.
- How to find 10/10 Account Executives that closes $300K ARR in their first month.
Keywordsstartup growth, sales strategy, marketing tactics, customer success, hiring AEs, product-led growth, sales-led growth, founder insights, business scaling, ARR, product-market fit
Timestamps(00:00:00) Intro
(00:02:10) What is Artisan
(00:03:44) Rage Baiting on Reddit
(00:06:00) Launching an Imperfect Product
(00:10:17) Replacing BDRs
(00:12:28) Blogging SEO
(00:15:33) LinkedIn SEO
(00:17:10) Getting a Chief of Staff Early
(00:19:39) Reddit SEO
(00:21:30) Hiring Good AEs
(00:24:46) Getting a Million
(00:26:10) Making Customers Successful
(00:29:43) One Piece of Advice
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Cody started a ride-share business in 2017 with no capital. He focused exclusively on small towns (<100K) where Uber/Lyft weren't available. I would 100% have passed if he pitched me years ago—and I would've been dead wrong.
So far he's raised only $2.1M, compared to Uber's $30B+ raised. And yet, he build a business doing $20M+ in annual revenue that is live in a dozen markets and multiple countries.
Besides competing with massive companies, he was also weeks away from bankruptcy when ride-share froze during the early days of COVID. He goes through exactly what he did to survive—and to grow well beyond where he was pre-COVID just a year after.
If you're bootstrapping or competing with better funded players, check this episode out.
Why you should listen:
- Why even massive competitors often don't mean you can't build a business.
- How to hack your way to millions in revenue with no budget.
- Why customer service and success are the keys to unlock word-of-mouth.
- How to survive 3 weeks of cash and near-bankruptcy.
KeywordsUride, rideshare, entrepreneurship, bankruptcy, business growth, startup challenges, market expansion
Timestamps:
(00:00:00) Intro
(00:01:48) Thunder Bay Ridesharing
(00:03:49) A Problem that Shouldn't Exist
(00:06:44) The Launch
(00:08:15) Growing and Outgrowing
(00:10:50) A Bylaw Loophole
(00:13:27) Expanding to Other Communities
(00:17:05) Three Phases
(00:21:54) Surviving
(00:29:18) The Demand Curse of Ride Sharing
(00:34:09) Unride Focus
(00:39:46) Long Ways to Go
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I tried to pay my employees as little as possible. I thought I was being resourceful—& it seemed to work. Until it totally backfired. I learned my lesson the hard way.
No founder wants to hire B-level or C-level talent. Everyone is looking for A-players. But most founders don't put in the work. And they end up with B-level teams.
If you're serious about getting and keeping A-players there's only one way to do it. You need to have a coherent strategy, you need to be intentional, and you need to make it priority number one. Here's how.
Takeaways
- Why paying employees less than they're worth incentivizes the wrong behaviour
- Why you need to have a system for regular performance reviews and salary adjustments.
- How to attract and retain A players
- How great junior talent can outperform B-level experienced talent.
Keywordsfounders, compensation, hiring, A players, salary strategy, employee retention, startup culture, leadership, team building, performance reviews
Send me a message to let me know what you think!
Kyle left his job as a hacker at the NSA to launch Huntress. He bootstrapped for 3 years and burned all his savings. One of his co-founders quit. He got into an accelerator program, but had to sleep in his car for 16 weeks because he couldn't afford a hotel.
Finally, 3 years in he'd hit $1.5M ARR. So he pitched 60 VCs for a Series A—and got 60 'no's. He was forced to raise a small, $1M inside round.
But then things changed:
2018: $1.5M ARR
2019: $5M ARR
2020: $10M ARR
2021: $20M ARR
2022: $40M ARR
2023: $70M ARR
2024: $100M+ ARR
Huntress is valued at $2B.
The investors who backed his $1M bridge are up 140x.
Now every VC wants to invest—and Kyle's the one saying 'no'.
Why you should listen:
- How to know whether you should keep going or quit.
- What it takes to get through the first few years at a bootstrapped startup.
- Why revenue expansion is a huge lever for fast-growth (Huntress has 140% net revenue retention).
- How starting a startup can impact your personal life and relationships.
- How to work with partners to sell to long tail SMB customers.
Keywordsentrepreneurship, cybersecurity, product market fit, startup journey, military experience, SMB market, funding challenges, automation, human expertise, business growth
Timestamps:
(00:00:00) Intro
(00:2:01) Working at the NSA
(00:6:14) A big win in counter cyber terrorism
(00:10:00) What gave way to Huntress
(00:14:22) Pitching to a startup accelerator
(00:16:29) Adopting curiosity
(00:21:04) Getting ahead of cyber criminals
(00:26:00) Starting to grow
(00:32:50) Cult or conviction
(00:35:00) It takes grit
(00:39:50) Learning from people's lessons
(00:42:20) Cockroaches and underdogs
(00:46:10) Three strikes, I'm out
(00:52:56) Having a military background
(00:56:17) One piece of advice
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MrBeast's 36-page framework leaked this week. It's how he built a $1B+ company and became the #1 YouTuber in the world. His channel is worth over $1B. For the first time ever, we get to see how MrBeast operates.
We go through the 7 most important things that startup founders can learn from MrBeast. From what maniacal obsession looks like, what it means to be an "A player", to how to teach employees to never take 'no' for an answer. In the leaked document called "How to Succeed at MrBeast Productions, he goes into specific details and share clear examples of what you should do.
MrBeast Mode puts Founder Mode to shame.
Keywords
MrBeast, onboarding, clear mission, hiring A players, obsession, extreme ownership, consultants, persistence, documentation
Why you should listen
- Have a clear mission that everyone understands.
- Hire A players who are obsessive and coachable.
- Obsession is crucial for success in content creation.
- Extreme ownership leads to better accountability.
- Consultants can save time and provide valuable insights.
- Persistence is key; never take no for an answer.
- Every employee should know the company's expectations.
- A strong culture is built on shared values and principles.
Timestamps(00:00:00) Intro
(00:00:42) 1. Have a clear mission
(00:02:05) 2. Hire A players
(00:03:49) 3. Be Obsessed
(00:05:22) 4. Extreme Ownership
(00:07:19) 5. Copy & Steal
(00:09:29) 6. Never take 'no' for an answer
(00:010:49) 7. Write a doc!
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Andres Bilboa is one of the co-founders of Rappi, the highest-valued app of LATAM ($5B valuation). Now he runs an incubator called Makers and has invested in dozens of startups.
In this episode, he shares how Rappi started with no funding and no network. They added restaurants into their platform without permission and gave cash to couriers to buy meals. Demand was through the roof. But just as they started closing funding and scaling, Uber and UberEats came to compete.
Here's the story of how Rappi found product market fit, and what Andres learned about founder psychology and mental health.
Why you should listen
- How to launch an MVP even if that means giving cash to couriers.
- How to fight off massive competitors like Uber and UberEats.
- Why founders with insane ambition and a relentless drive are more likely to achieve outsized returns.
- How the psychological aspects of entrepreneurship, such as fear of failure and the need for constant achievement, can impact a founder's well-being.
KeywordsRappi, on-demand delivery, competition, growth, fundraising, founders, ambition, drive, entrepreneurship, fear of failure, achievement, therapy, fundraising
Timestamps:
(00:00:00) Intro
(00:02:53) The Origin of Rappi
(00:06:58) How Rappi Works
(00:13:37) RappiCash
(00:15:55) Colombia's World Class Convenience
(00:18:05) It's a Winner Takes All Market
(00:20:44) Andres' Roles at Rappi
(00:22:27) Competing with Uber
(00:26:00) Crazy Doesn't Cut It
(00:29:51) The Problem is You are What You Achieve but Nothing Is Ever Enough
(00:40:44) Fear is Unproductive
(00:45:25) What is Makers
(00:50:30) One Piece of Advice
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Douglas has been in media and PR for over two decades. He’s the founder of Betakit Inc and has been running Betakit, Canada’s TechCrunch, for nearly 10 years. He understands what startups need to do to leverage PR, and how PR can help startups hire, fundraise and sell.
On this episode, we get tactical and go deep on exactly when it makes sense to use PR and how founders can get the most from it.
Why you should listen
- Why you should treat PR like a subset of inbound marketing
- PR is all about telling the right stories to the right audiences
- How to conduct media profiling to find the right journalists in the right channels so you can get other people to write about you
Keywords
PR, media strategies, startups, business goals, target audiences, media storytelling, marketing initiatives, traction, leads, stories, funding announcements, product launches, media profiling, channels, audiences, founder, pitch, media, framing, storytelling, target audience, channels, journalists, PR, origin story, company values, thought leadership, customer stories, employee stories
Timestamps:
(00:00:00) Intro
(00:05:19) The 101 of Media PR
(00:06:04) Three Questions
(00:08:40) An Operational Lens for Media Engagement
(00:12:16) Understanding the Target Audience
(00:19:55) Inbound Marketing
(00:25:20) A Super Important Caveat
(00:29:08) Roam Auto as an Example
(00:34:00) The Right Channel
(00:36:40) Treating Media Pitching Like Investor Pitching
(00:43:04) Be Professionally Interested
(00:44:49) Putting a Human Face on Your Company
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In this episode, I sit down with Nick Frosst, Co-Founder of Cohere, the $5.5B AI startup that’s targeting the enterprise landscape.
We go through the origin story of Cohere, the challenges of building foundational models, and why he believes large language models (LLMs) won’t lead to artificial general intelligence (AGI). We also explore the fierce competition in AI, what sets Cohere apart, and Nick’s advice for founders building in AI today.
Why you should listen
- LLMs are powerful but have clear limitations and won't lead to AGI.
- Why AI startups need to start with real problems vs leveraging AI for its own sake
- Why ChatGPT was as much of a UI/UX revolution than a technological one
- What tech founders need to do to win in AI
Timestamps:
(00:00:00) Intro
(00:03:21) AI Expectations
(00:06:05) A Unique and New Moment
(00:09:38) Resource Intensive Industry
(00:12:03) Zero to One
(00:15:07) Base Language Model to Chat Model
(00:17:15) Carving Out a Niche
(00:21:03) Open Source
(00:24:00) The Limits of LLMs
(00:26:18) Agents
(00:29:30) AGI
(00:34:04) A Little Bit of Data
(00:39:05) Speed of Development
(00:40:47) Finding True Product Market Fit
(00:43:37) One Piece of Advice
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We talk about product-market fit constantly in this podcast. Hopefully, we learn from what others did and improve our chances of finding PMF. But, even if we do everything right, we may still fail to find PMF. That's why even repeat founders have only 1.5% chance of building a unicorn.
But there is one way to guarantee that one day you will find product market fit. We explore that in this episode.
Got sick this week so re-releasing one of the best short episodes from last season that was originally published exactly a year ago today.
Send me a message to let me know what you think!
Don founded Vena and was CEO for the first 8 years. Last month, Vena became a Centaur and crossed $100M in ARR. Don built it from nothing to $50M in revenue.
When he started, the market was crowded, but everyone else was trying to replace excel. He built a budgeting and planning (FP&A) solution that leveraged excel at the core and as he says "disrupted the disruptors".
He knew the problem, he knew the space, he knew the customers and he leveraged it to build the right solution and grow from 0 to $1M in ARR in 18 months.
Here's how he did it.
Why you should listen
- How to close the first few customers
- How to close 6-figure deals without any proof points
- Having knowledge and a network in the industry you're entering makes it easier to find success as a founder.
- In crowded markets, a differentiated approach and the ability to solve pain points for customers are key to standing out.
- Why there's no feeling like the satisfaction of taking an idea and product to market, working with great people, and seeing others succeed.
Keywords
startup, scaling, Vena Solutions, network, crowded markets, budgeting and planning, differentiation, pain points, revenue intelligence, SaaS, founders, startups, entrepreneurship, entrepreneur, venture capital
Timestamps:
(00:00:00) Intro
(00:02:36) The Beginning of Vena Solutions
(00:06:06) Step 1 of Vena
(00:09:35) First Conversations
(00:11:09)The Market in Planning
(00:17:50) The Market in Workflow
(00:20:02) Wealth Fargo
(00:22:23) Getting to a Million
(00:26:05) The Biggest ROI
(00:29:03) Una
(00:34:33) Not Retiring
(00:35:55) Finding Product Market Fit
(00:38:29)One Piece of Advice
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It's the first time I see a candidate BS his way through interviews with multiple people, impress each one of them, and ultimately end up being a complete fraud. But the biggest learning wasn't that you should watch out for fraud-- it was that you shouldn't trust interviews nearly as much as you'd think.
While fake candidates are rare, candidates who are 10x better at interviewing than they are at the job are quite common. In fact, the only thing you know about candidates with great logos is that they know how to interview. Otherwise, they wouldn't have worked at Google in the first place.
What you don't know is if they're truly great. Here's how to find out.
Takeaways
- Don't rely solely on interviews when hiring
- Hire based on referrals and conduct thorough reference checks
- Former founders are often the best hires
- Logos and impressive resumes don't mean as much as you think
Keywordsfounder, hiring, fraud, interview skills, backdoor reference checks, referrals, former founders
Send me a message to let me know what you think!
Ashutosh is one of those rare founders who founded not just one, but two unicorns. He worked at Google for 4 years, left and started Bloomreach, which was last valued at $2.2B.
Halfway through that journey, he left to do it all over again. He started Eightfold AI which is the one we're talking about today. In 2021, he raised $220M from Softbank at a $2.1B valuation.
When he left Bloomreach, he didn't even have a clear idea of what he was going to build. He just knew he wanted to have more impact and go from 0 to 1 again.
It took him about 2 years to figure it out— then he grew from $1M ARR to $3M ARR in a year & to $12M ARR the year after that.
Why you should listen
- Why founders need to validate ideas with an open mind to not have tunnel vision.
- Why even unicorn founders don't get it right and often need to pivot to success.
- How to address problems that are not just today problems, but likely to be problems for a long time.
Keywords
unicorn founder, Bloomreach, Eightfold, product-market fit, pivot, HR space, digital marketers, talent, hiring, market need, scaling
Timestamps:
(00:00:00) Intro
(00:01:41) His first unicorn - Bloomreach
(00:05:22) Starting Eightfold AI
(00:08:50) Not Marrying Yourself to One Idea
(00:11:55) Finding real customer problems
(00:14:46) Solving Today's Problems vs Future Problems
(00:16:47) Hiring From Already Rejected Candidates
(00:22:50) Fundraising
(00:24:40) Building a V1
(00:27:00) Pivoting and then Reverting Back
(00:30:43) First Customers
(00:32:59) Finding Product Market Fit
(00:35:04) One Piece of Advice
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Carta is the backbone of most venture-backed startups. They have access to specific information about every single round, not just what's reported in TechCrunch.
Today, Peter Walker, Carta's Head of Insights joins us to share the findings from Carta's Q2 reports. We go deep into data from pre-seed, seed and Series A rounds. We cover median valuations, time between rounds, graduation rates between rounds, the AI and repeat-founder premiums, and much more.
VCs know most of this data. Founders need to be equally well-informed. You won't want to miss this episode.
Why you should listen:
- What are the typical pre-seed, seed and Series A rounds.
- Why stacking SAFEs is very dangerous.
- How to minimize dilution in the early-stages
- What is standard founder ownership, founder equity splits and ESOP sizes.
- Why the graduation from Seed to Series A is so low and the bar for Series A so high.
- Many more data points for pre-seed to Series A Venture Capital and Startup data.
Keywords
startup ecosystem, fundraising trends, total fundraising, down rounds, bridge rounds, company shutdowns, pre-seed funding, seed funding, series A funding, valuations, round sizes, dilution, founder equity, early employees, equity compensation, seed round size, series A
Timestamps:
(00:00:00) Intro
(00:01:35)Findings from the Q2 Report
(00:06:12)Typical Pre-Seed Round
(00:07:29) Post Money Safe vs Pre-Money Safe
(00:11:54) AI and Repeat Founder Premiums
(00:15:03) Typical Seed Round
(00:17:07) Time & Graduation Rates Between Rounds
(00:22:08) Typical Series A
(00:28:14) Equity Splits
(00:35:02) Founder Ownership
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Last quarter, Sanish raised a $50M Series D. His company has raised over $130M. They have enterprise customers across 14 countries including Dollar General, Aldo, and CircleK.
And it all started because Sanish was working out of coffee shops. He wasn't looking for a startup idea--he was just having casual conversations with retail workers. After a few of those, he noticed the problems retail workers and managers were facing, and he decided to build Legion to help solve them.
He partnered with one local coffee chain, worked as a barrista for a week, and developed the product with them for a year. He didn't try to sell to other customers, he stayed heads down until the local chain adopted the product across their entire organization. By the time they went to sell to other enterprises, they knew the product worked.
Why you should listen
- Why listening with an open mind is a common way to identify customer problems.
- Why providing clear and immediate ROI is a must-have for enterprise customers
- How to perfect your product with design partners that are heavily invested
- How to raise a Series A without meaningful revenue.
Keywords
Legion, workforce management, enterprise software, problem validation, value proposition, scaling, pricing model, ROI
Timestamps:
(00:00:00) Intro
(00:01:35) The Origin Story of Legion
(00:04:53) The Mindset of Most Frontline Workers
(00:11:05) Gathering Data
(00:20:00) Building an MVP
(00:24:30) Insights from Customers Using V1 Products
(00:30:15) Series A
(00:32:13) Legions Core ROI
(00:36:15) Scaling Legion
(00:39:47) Finding Product Market Fit
(00:41:19) One Piece of Advice
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Sean Ellis created THE test for PMF. He led growth teams at Dropbox, Eventbrite and LogMeIn, which sold for $4.3B. He coined the term Growth Hacking and wrote the best-selling book Hacking Growth.
Today we go deep and tactical with him. He takes us through how to use the Sean Ellis test to perfectly measure and understand product market fit.
He takes us to case studies of things that he did at LogMeIn and Dropbox to dramatically increase growth. And he shares exactly what you can do to drive more referrals for your startup.
Why you should listen:
- Why the Sean Ellis test is THE product-market fit test every founder should use. How to implement it today and use it to get closer to PMF.
- Why a great first-time user experience is the key for growth and referrals.
- How to optimize each growth levers, such as acquisition, activation, engagement, retention, and referrals.
- How to build a data-driven culture that is focused on measuring and improving PMF.
Keywordsproduct-market fit, Sean Ellis test, growth hacking, referrals, first-time user experience, optimization
Timestamps:
(00:00:00) Intro
(00:1:55) The Origin of the Sean Ellis Test
(00:13:13) Finding Product Market Fit Using the Test
(00:18:21) Focus on "Must Have" Users
(00:21:38) Growth Vs Marketing
(00:25:38) Old School vs New School Marketing
(00:30:17) 4 steps to growth
(00:36:24) Improving Sign ups to Usage
(00:41:37) The impact of Referrals
(0045:31) One Piece of Advice
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Daniel's been building robots for 20 years. He's sold 100s of AI robots-as-a-service to Walmart, FedEx, & DHL amongst others. Last month, he raised a $40M round.
6 years ago, he realized why robots weren't getting massively adopted. Builders like him were trying to build perfect robots that always worked. But every situation has edge cases. What if you designed robots to work only 80% of the time and use humans for the other 20%?
That one unique insight changed everything and was the reason he started Vecna. His robots can tell when they need help and ask humans to assist in real-time.
Like most capital-intensive startups, Daniel played on hard-mode. Here's how he built hardware, robotics and AI, sold enterprise contracts, and grew to $10s of millions in revenue.
Takeaways
- Why as a founder you need to trust your gut and stick to your convictions.
- How to be objective and create an accurate model of the world to predict the future and make informed decisions.
- How to bootstrap even a capital intensive company in robotics
Keywords
Vecna Robotics, robotics, warehouse industry, automated forklifts, reliability, safety, customer adoption
(00:00:00) Intro
(00:02:05) The Beginning of Early Robotics
(00:06:00) Edge Cases in Robotics
(00:08:15) Robots Shouldn't be Perfect and AI Isn't Intelligent
(00:14:05) Technology Empowers Humans
(00:18:19) When Robots Need Help
(00:21:29) The First Pilot and Customers
(00:29:49) Covid Slowed Everything
(00:33:52) Finding Product Market Fit
(00:34:45)One Piece of Advice
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Early-stage founders are bombarded with advice. A lot of it from investors who have never operated a business, never ran marketing, never led sales.
And yet, many founders take VCs' advice as sacrosanct. And many VCs feel like they can and should opine on everything. If many people treat you like an expert, you must be one... right?
VCs have a lot to offer founders. But, like everyone, they have circles of competence.
Be careful who you listen to.
Why you should listen
- Why power dynamics between VCs and founders can distort decision-making and advice-seeking.
- Why you should be skeptical of advice that is outside of a VC's circle of competence.
Keywordscustomer needs, business problems, power dynamics, VCs, founders, advice
Send me a message to let me know what you think!
Alex quit the company he'd been working at for 9 years. He gave himself 6 months to launch a startup.
Even though he got the co-founder of a public company to join him and raised $6M out of the gate—it took him 3 years to make his first sale.
But after he shifted from selling to SMBs to selling to MSPs (Managed Service Providers i.e., outsourced IT), things took off:
April 2015 - $1K MRR
August 2015 - $10K MRR
June 2016 - $100K MRR
Nov 2018 - $1M MRR ($12M ARR)
And growth never stopped—soon, he'll cross $100M ARR.
Alex and his co-founder did many things differently. They came up with an idea by starting with markets, not customer problems. They raised a lot of money upfront and built a sophisticated product instead of an MVP. And they deliberated cultural values before making their first hire.
Clearly—it worked.
Why you should listen
* Learn why you should define culture before making your first hire.
* How to find market trends and customer problems top-down instead of bottoms-up.
* Why keeping your product unchanged but targeting a different market can have a massive impact and lead to product-market fit.
* Why you should be willing to be bold and not hedge.
* Why you should only focus on one thing at a time.
* How to use constraints to do more things faster.
Keywords
Auvik, software company, networking, SMBs, mid-market, decoupling, control plane, hardware, software solution, automate, configuration, user research, product design, team, company values, SaaS, IT management, product-market fit, pivot, managed service provider, MSP, boldness, discipline, advice
Timestamps(00:00:00) Intro
(00:01:47) The Origin of Auvik
(00:07:20) Getting a partner
(00:12:35) It's People Who Build Companies
(00:14:10) Finding the Concept for Auvik
(00:18:12) Explaining Decupling Networks
(00:20:07) Making the Product
(00:25:25) Two Great Timing Moments for Auvik
(00:30:30) First Customer Experiences
(00:34:40) Feedback Loops
(00:36:30 ) MSPs in the early 2010s
(00:39:08) Getting to a Million
(00:41:33) Finding Product Market Fit
(00:42:54) One Piece of Advice
Send me a message to let me know what you think!
When an employee unexpectedly quits, an investor backs out, or a big customer churns— fear of failure takes over. When you close a new round, land a big customer, or make a big hire— you feel pure excitement.
Every founder is on a fear-excitement spectrum. There's no way to prevent yourself from feeling the two extremes. But I've seen great founders use several tactics to help themselves operate out of excitement more often than out of fear.
Those founders also feel fear— but they use these tactics to spend more time closer to excitement. Because operating out of failure is playing not to lose—whereas operating out of excitement is playing to win.
Here are 3 ways to do just that.
Why you should listen
- How to use multiple plans to operate more freely and objectively
- Why runway and low burn are the keys to lower founder stress
- Why working with the right investors is more important than raising big rounds
- What Tobi Lutke (founder of Shopify) did to change his employees' mindsets
Keywordsfounders, fear, fear of failure, excitement, validation, runway, partners, mindset, expectations
Send me a message to let me know what you think!
Why you should listen
- How to transition from a consulting/services business to a scalable tech startup-- and why it might be more painful than you think.
- What you need to do to shift from SMB to midmarket and from midmarket to enterprise.
- How to use enterprise customers to scale to $10M+ without needing thousands of customers
- How to balance urgency and patience to build a successful startup
Keywordspatience, learning, building a company, failures, product-market fit, consulting business, marketing automation platforms, template product, creation platform, raising funding, urgency
Time Stamps:
(00:00:00) Intro
(00:08:50) The Story of Knak
(00:11:04) Going from Zero to a Million
(00:16:16) Pivoting from SMB to midmarket
(00:19:42) Adding "obvious" features to get closer to PMF
(00:24:07) How to position against incumbents
(00:27:35) Turning Into a Enterprise Platform
(00:30:30) Finding True Product Market Fit
(00:33:34) Bootstrapping to Series A
(00:40:02) One Piece of Advice
Send me a message to let me know what you think!
There is no better storyteller in the world than Matthew Dicks. He tells stories for a living. He gets paid by the world's biggest brands to create stories for them. He's won Moth StorySLAM (a storytelling competition in NYC) a record 59 times.
Every founder knows storytelling is a critical skill. But 99% of founders I meet are terrible storytellers. They overcomplicate, they include too much information, they try to convince with data.
Like Matthew says, "Most of what people say in business is forgettable".
Whether you want to close customers, investors or employees, you need to stand out and be remembered. And the best way to do that is to tell compelling stories that resonate.
Here's how to do it.
Why you should listen
* Why the key being remembered is being different
* How to use stories to stand out and resonate with customers, investors and employees
* Learn how to tell an effective story that is relatable, creates suspense, and includes personal connections.
* How to use personal stories to sell more product.
* Why you often shouldn't start a story at the beginning.
Keywords
storytelling, business, relatability, suspense, personal connection, Slack, Salesforce, communication, connection, simplicity, contrast, value proposition, trust
Timestamps(00:00:00) Intro(00:02:52) A Story About Why Storytelling is Important
(00:11:18) Deconstructing the Story
(00:15:07) Keeping a Story in Present Tense
(00:16:58) Start With Location and Action
(00:20:41) When to Tell a Story Chronologically
(00:28:13) The Story for Slack
(00:35:33) Making a Pitch with No Data
(00:41:51) It's not B2B or B2C-- it's H2H
(00:47:57) The Goal is to be Remembered
(00:52:23) Use Truth in Your Story for Relatability
(00:55:11) Making up stories on the fly for portfolio companies
Send me a message to let me know what you think!
5 years ago, Shubham had just graduated college and had no network. He bootstrapped to $3M in ARR, then raised $200M & grew to $85M ARR.
But he started trying to sell AI for marketing to enterprises with no network.
So for 2 months, he'd go to the lobby of a bank and sit there for an hour. He'd wait for the CMO to walk by, just so he could say hi. He'd tell receptionists he was waiting for an interview.
Finally, one day the CMO had enough and asked him who he was. Shubham got his 15-minute moment. That turned into a free pilot.
That free pilot turned to $1.2M ARR.
2 years after he'd started the company, he bootstrapped to $3M ARR and was profitable— since then, the growth never stopped.
Why you should listen
* How to start a startup top-down from a market vs bottoms-up from customer problems.
* Why doing insane things in the early days can lead to insane results.
* How Founder-led sales and tight feedback loops are the key for product development and customer success.
Keywords
AI startup, product market fit, challenges, marketing, scaling, fundraising
Timestamps(00:00:00) Intro
(00:01:52) Origin Story of Pixis
(00:07:05) Getting the First Customers
(00:09:14) What is Pixis
(00:11:26) Video Generation
(00:14:54) Finding the Problem Going Top-Down
(00:19:55) The Pitch
(00:24:30) The First Pilot
(00:27:08) Scaling the Team
(00:31:57) Raising the First Round
(00:33:59) The AI Market
(00:35:54) Finding True PMF
(00:37:13) One Piece of Advice
Send me a message to let me know what you think!
Google is in talks to buy cybersecurity startup Wiz for $23B (a 40x revenue multiple). Wiz is the company that in 2021 announced it grew from $0 to $100M ARR in just 18 months.
How did this cybersecurity company grow so fast in a crowded space?
How does it get a 40x revenue multiple when FAANG stocks trade at 5-15x?
Who are the exceptional founders that were able to create the largest venture-backed exit in history in just 4 years?
In this episode, we dive into the 3 ingredients that made Wiz into such a success: insane growth, insane team, and insane discipline.
Why you should listen
- Why addressing a full 'Job to be Done' is key to fast growth
- Why having an A+ team is irreplaceable
- Why you need several factors to come together to have exceptional, outlier results
KeywordsGoogle, Wiz, acquisition, cybersecurity, growth, team, discipline, end-to-end risks, cloud infrastructure, COVID
Timestamps:
(00:00:00) Intro
(00:01:00) Wiz's 3 Ingredients to Success
(00:01:09) 1. Insane Growth
(00:02:30) Jobs to be Done Framework
(00:03:30) What does Wiz do?
(00:05:36) 2. Insane Team
(00:07:54) 3. Insane Discipline
Send me a message to let me know what you think!
Paul built a startup that was acquired for $2.2B. He worked on AI at Uber and Oculus. But when a farmer told him about some of the problems he was facing, he quit and went all-in on farming.
He built a robot that attaches to the back of tractors, uses computer vision to identify weeds and lasers to shoot and kill them. He sells each robot for $1.5M. He's sold nearly 100 so far— & generated nearly $150M in revenue.
Whether you're working on a hardware startup or not, you'll want to listen to this episode to see how to do proper customer discovery, how to raise pre-product, and how to get millions of dollars in pre-sales without having to ship.
Why you should listen
- Why hardware is hard-- but easier than it's ever been.
- How to tell a story to raise $10M pre-revenue
- How to set up milestones for fundraising
- How to generate $10M in pre-orders before shipping product
- How to get a sense of product market fit even before the product is fully developed
Keywords
Carbon Robotics, deep tech, AI neural nets, deep learning, weed control, farming, manual labor, lasers, research and development, funding, seed round, prototype, Series A, pre-orders, manufacturing challenges, revenue
Timestamps:
(00:00:00) Intro
(00:02:09) A Background in Deep Tech
(00:05:50) Problem and Solution Interest
(00:07:35) Find the Passion
(00:07:37) Get Behind the Mission
(00:09:39) Back to Seattle
(00:11:40) The Epiphany
(00:16:50) A Human Affair
(00:18:00) The Money Flows to the Best Storyteller
(00:21:45) A Farmer's Weed Control Dilemma
(00:25:56) Weed-Shooting Lasers
(00:28:11) Funding the Prototype
(00:30:13) Hardware is Hard But Rewarding
(00:36:46) Why Laser Weeding Works
(00:41:19) Series A
(00:42:51) Robot Autonomy
(00:45:42) Pricing
(00:48:12) Telling the Story After It Happened
(00:51:44) Fighting Through Disaster
(00:54:50) Finding True PMF
(00:55:41) One Piece of Advice
Send me a message to let me know what you think!
Elon Musk single-handedly took on the entire automotive industry. No one, including me, thought he would succeed. But he's built an $800B company. Whether sales are slowing down misses the mark: the punchline is it took well capitalized, professional automakers 15 years to catch up to a single founder.
Sure, Elon Musk is special. But this goes beyond just Elon Musk. It shows that founders today have more business power than founders have ever had. They can take on the most established industries.
The reason is that the pace of innovation is faster than ever. No business model is safe.
And founders are the only ones who can react.
KeywordsTesla, EV market, car manufacturers, Elon Musk, disruptive innovation, business models, founders, rate of change
Send me a message to let me know what you think!
Last month, Ashby raised a $30M Series C. Ashby is used by customers like Notion, Ramp and Sequoia. Benji built Ashby as an end-to-end Applicant Tracking System (ATS) that would replace several point solutions. In meant he had to build heads down for a while and couldn't launch a simple MVP.
Surprisingly, even though he raised $3.5M at seed, he didn't grow his team. He built the product with just 3 people. "We could spend time recruiting or we could spend time building"-- he decided to build.
When they launched, they grew to $200K in ARR within a year and then 10x'd a year after that. Here's the story of how they found product-market fit.
Why you should listen
- Why keeping your team small helps you go faster.
- How to displace point solutions with an end-to-end platform
- How to validate pain points.
- How to move up market from startups to enterprise companies.
KeywordsAshby, all-in-one platform, recruiting, reporting, pain points, product market fit, Series A
Timestamps:
(00:00:00) Intro
(00:01:29) No Website, No Problem
(00:03:08) A Viral Loop
(00:04:40) Origin Story of Ashby
(00:05:39) The Biggest Pain Point
(00:07:50) De-Risking
(00:09:26) A Sticky Product and Market Evolution
(00:10:50) A Hundred Conversations
(00:13:09) The Main Feedback and Key Learnings
(00:16:16) The Pitch
(00:17:20) Bundling and Unbundling
(00:20:50) Building a Great Engineering Organization
(00:22:26) Letter of Intent Stage
(00:24:45) Validation and Feeling Ready
(00:28:18) A Little Bit of Luck
(00:31:51) Finding True PMF
(00:32:44) One Piece of Advice
Send me a message to let me know what you think!
AI startups don’t necessarily have to beat incumbents. Some will start entirely new markets instead.
Like Canva to Photoshop, Shopify to Amazon or Pickleball to Tennis, many of these won’t even have to compete. They create 10x easier to use products and through that open up an entirely new space. They solve problems people didn’t even know they had. In many cases they expand the market for incumbents too— pickleball didn’t steal tennis players, it became a gateway and created even more.
We discuss the 3 factors a startup needs to be able to create a new market and why there is plenty of opportunity left in the AI space.
Send me a message to let me know what you think!
"I was technically homeless at the time. I was sleeping on my buddy's couch. I had declined $250,000/ year at McKinsey... I had no idea what I was doing." Now, Blake has $150M in ARR, growing 30% per year, with 80% gross margins. He's raised $400M and his startup ID.me is worth over $1B.
This is the story of how pivoted for a Groupon-like model to an identity verification platform. Blake talks about how he raised the initial round, closed the first few enterprise contracts, and why he thinks finding product-market fit is more of a science than most founders think.
After his pivot, ID.me doubled its user base every year. Now, over 40% of Americans have an ID.me account.
Why you should listen
- Learn how even successful founders are often much closer to failure than you'd expect
- How to get credibility as a founder and close enterprise deals.
- Why fear of failure can be a powerful motivator if used constructively.
- How to use a niche market to quickly find product-market fit
- Why staying close to customers is the best way to pivot into the right problem/solution set.
KeywordsID.me, military, tech founder, product-market fit, startup, business model, capital raising, mentorship, scientific approach, user base, revenue growth
Timestamps:
(00:00:00) Intro
(00:01:56) The Origin of ID.me
(00:04:44) The Two Parts of Credibility
(00:11:16) In Order to Win you Have to Focus Small
(00:14:53) Fear of Failure Can Be Positive
(00:20:54) Paypal for Identity
(00:23:59) Moving to DC and Raising 500k
(00:27:53) Belief in the Person Over the Business Model
(00:30:55) Pivoting to Identity Wallets
(00:41:07) Under Armour
(00:48:06) Getting to a Million
(00:49:39) One Piece of Advice
Send me a message to let me know what you think!
Every startup needs to compete with incumbents. But it's different with AI.
AI startups need to create websites or apps from scratch and drive traffic. Incumbents can just add AI as a feature. They have distribution built in.
AI is not like previous tech revolutions. Unlike mobile, the internet, or the PC revolution, AI is not a new distribution channel. Startups are at a much bigger disadvantage than they've ever been.
In this episode, we discuss the 3 key elements you need to consider to answer the most important question:
Will you get distribution faster than incumbents get product?
KeywordsAI, startups, incumbents, distribution channels, technological shift, mobile, internet, PCs, sustaining innovation, disruptive innovation, product versus distribution, founders
Why you should listen
- This time it's different. AI is easier for incumbents and harder for startups than previous tech revolutions.
- Startups need to consider the incumbents they are up against, the power dynamics in the market, and the primary use case they are targeting.
- Understand how to think through the race and what elements are most important
Send me a message to let me know what you think!
Andrew spoke with 120+ VCs to raise a $1.5M pre-seed round. He closed $2.7M and had demand for many millions more. He devoted 90% of his time to fundraising, but only took weeks from the first meetings to close.
99% of founders I meet do not fundraise at this level. It takes them longer to close, they have fewer choices and raise less.
This is a specific, detailed and tactical guide to closing a round. If you're ever going to raise, you need to listen.
Why you should listen
- Why talking to more investors will help you raise 10x faster.
- How to use an investment memo to articulate your thoughts and as a base to build a pitch deck
- How to get warm introductions to VCs
- How to take control of investor meetings and put VCs on their heels
Keywordsfundraising, seed round, investors, memo, deck, pitch, negotiating terms, trust, conviction, dilution
Timestamps:
(00:00:00) Intro
(00:02:02)How Taxwire Thought About Fundraising
(00:04:02) The Start of Taxwire
(00:06:32) Making a Memo Before a Deck
(00:09:50) Reaching Out
(00:16:10) Wanting to Oversubscribe
(00:21:32) Keeping Control and Qualifying Investors
(00:31:10) The Basic Structure of the Pitch
(00:34:24) Target Close Day
(00:39:01) The Timeline for Fundraising and Meetings
(00:44:41) Deciding Who to Accept Funds From
(00:50:18) One Piece of Advice
Send me a message to let me know what you think!
Zoom was THE work-from-home stock. It's down 90% from peak. The same hype that fuelled work-from-home stocks is now fuelling AI. What happened to Zoom will happen to many AI companies.
AI startups today need to carefully position against foundational models and incumbents. Here's how to think through it.
Why you should listen:
- Learn why what happened to Zoom will happen to many AI companies
- How to position yourself against the two AI giants: Foundational models & incumbents.
- How to think through the product vs distribution race all AI startups face.
KeywordsZoom, AI, positioning, foundational models, incumbents, use cases
Send me a message to let me know what you think!
Chris is the founder of Refine Labs & Passetto. He bootstrapped Refine Labs to $22M in revenue. He's also a LinkedIn Top Voice with 150K followers.
On this episode, Chris shares the story of how he got Refine Labs off the ground, what he did to grow so fast, and also why he regrets spending so much on growth instead of focusing on profitability.
He goes exceptionally deep on sales and marketing and provides tactical advice you can steal.
Why you should listen:
- Learn when to switch away from founder-driven sales
- Why sales velocity is the key metric you need to track
- How to use customer feedback to drive a consistent marketing campaign and drive organic inbound.
- How to know if you have product-market fit based on customer satisfaction and retention.
- Why Chris regrets not focusing more on cash flow profitability vs growth.
Keywords:
entrepreneurship, founder sales, marketing, customer insights, zero-to-one growth, go-to-market strategy, product management, growth strategy, product-market fit
Timestamps:
(00:00:00) Intro
(00:01:21) Starting e-commerce companies on the side
(00:04:56) Going all in
(00:11:30) Balancing sales and marketing
(00:18:05) Focusing on Customer FeedbackLanding the first customers
(00:27:19) Why you should not spend on advertising
(00:37:55) His most viral marketing campaign
(00:41:04) Finding Product Market Fit
ChatGPT just crossed $3B in ARR. Sam Altman is getting access to 1.5B users through Apple. Hate him or love him, he's a strategic genius.
You'll recognize a pattern: Sam has an idea, positions correctly, lets the bets play out, and goes all-in on what works.
Rinse, repeat, rinse, repeat, rinse, repeat.
In under 2 years, he has over 10M paying subscribers.
A brand name the average 60-year-old recognizes.
And, of course, $3.4B in ARR.
KeywordsOpenAI, revenue growth, strategic decision-making, positioning, Sam Altman, Microsoft, Apple, AI technology, ChatGPT
Reddit. You know the name, you've used the site. It's a ~$10B company, with nearly $1B in revenue. Their 1B+ monthly active users are so powerful they can move markets. This is the story of how it all began.
On this episode, we interview Chris Slowe, Reddit's current CTO and Founding Engineer. Chris was in YC's first-ever batch with Steve and Alexis. He was their roommate. When Chris's own startup failed, he moved over and joined them to build Reddit. This was almost 20 years ago, in 2005.
It only took them a year to hit 1 million monthly active users. But it took them well over 5 years to hit $1M in revenue. Here's the story of how they hit product-market fit and built the world's most powerful online community.
Why you should listen:- Learn how Reddit got started in 2005 and why it took them many years to monetize
- See how word of mouth & organic growth are the key to building a community like Reddit
- Hear Chris's perspective on scaling teams and organizations, preserving culture, and signs of clear product-market fit
- Why applying lessons from your first startup to your second one is not as easy as you think it might be
Keywords
Reddit, Y Combinator, growth, startups, founders, acquisition, Conde Nast, community-driven platform, culture, word of mouth, Google, organic growth, Hipmunk, monetization, product-market fit, scaling, startup advice
Timestamps:
(00:00:00) Intro
(00:01:55) The Start of Reddit
(00:07:13) Joining Reddit
(00:12:56) Building Communities
(00:20:37) The First Year of Reddit
(00:22:56) The Acquisition
(00:26:50) Staying Lean
(00:28:58) Leaving Reddit to do Hipmunk
(00:37:14) Hiring for Hipmunk
(00:41:08) Coming Back to Reddit
(00:45:05) Making the Mobile App
(00:47:13) Monetization
(00:50:05) Finding True Product Market Fit
(00:50:41) One Piece of Advice
Wardah was a PhD graduate working at a biomedical imaging startup. But all it took was two different dentists giving her two totally different diagnoses for her to quit her full-time job.
She was unemployed with no idea what to build.
All she knew was that something was broken—and she had to fix it. Her startup Overjet is now the #1 dental AI platform, valued at $550M.
Why you should listen:- Why founder obsession is a key trait
- Why learning speed is the main KPI early on
- Why staying close to customers is how you build the right product.
- How to get customers to share data with you and let you spend time in their office, watching how they work.
Timestamps:
(00:00:00) Intro
(00:00:52) The Start of Overjet
(00:05:05) Obsession Increases your Chances
(00:08:15)A Bad Dentist Appointment
(00:11:35) Surpassing Dentist's Analysis Using AI
(00:15:52) Finding a Co-Founder and Fundraising
(00:24:22)Finding True Product Market Fit
(00:27:33) One Piece of Advice
Dane was the CEO of Squarespace from 2007 to 2011. He grew the company from ~$2M in revenue to ~$15M. He's a multi-time founder with multiple exits. His current startup, Odeko, raised $227M.
He takes us through his long journey as a founder of multiple companies and shares the key startup lessons he's learned.
Why you should listen:- Why 7-day trials led to higher conversion than 30-day trials at Squarespace
- Why you should talk to customers every single day.
- Why SMB usage doesn't always translate into revenue.
- Why you need to follow customer problems over business models and TAM.
Timestamps:
(00:00:00) Intro
(0:00:0:37) Before Odeko
(00:06:54) Leaving Squarespace
(00:07:31) SumAll
(00:13:01) Conversion Rates with Free Trials
(00:16:10) The Start of Odeko
(00:20:05) Staying Close to Clients
(00:26:36) Realizing the New Model was Working
(00:31:47) Landing the First Few Customers
(00:37:00) Overhiring
(00:39:17) Finding Product Market Fit
(00:41:32) One Piece of Advice
"Find a better mouse trap. Build a product that's just a better version of a product that already exists. It's a lot easier to sell."
His first startup was a cool idea: Uber for Valet Parking. Investors loved it. But the unit economics didn't work out. So he had to pivot. He ended up selling it, but decided to do things differently the second time around.
With Argyle, he didn't start with a cool idea. He replaced a product customers already paid for. His pitch went from "Wouldn't it be cool if?" to "I'll do what they do but twice as well and for half the cost".
Why you should listen:- How to work with design partners to build the first version of your product
- How to use those partners to get credibility and make your first enterprise sale
- Keeping your sales teams small and staying close to the customer for as long as possible
Timestamps:
(00:00:00) Intro
(00:01:04) The Origins of Argyle
(00:04:03) The Aha Moment
(00:15:06) When to Charge for the Product
(00:19:31)Landing the First Customer
(00:21:38) Staying Close to Customers
(00:25:16) From Seed to Series A
(00:32:06) Delivering clear ROI
(00:35:58) Finding Product Market Fit
(00:36:38) One Piece of Advice
His travel startup crashed 90% overnight. Here’s how he used AI to grow past $2M/year—to $2M a month:
For a while, Andrew was crushing it. Accelerator -> $750K pre-seed -> $2M ARR -> $2.5M seed round. Then COVID hit.
He was selling to events like CES, SXSW, etc. Revenue dropped from $160K/month to under $10K... overnight.
After nearly going bankrupt, he finds a way to pivot. A year later, his business takes off.
2020 - $0
2021 - $1M
2022 - $5M
2023 - $15M
Now - $24M.
Why you should listen:
- Andrew shares a technique to land early customers. He offered to PAY his customers to use the product.
- Learn how to deal with massive swings in revenue and unpredicted events. Early-stage founders are always one deal, one employee, one fundraise away from success... or failure.
- Learn why you "can never celebrate until the money is in the bank"
Timestamps:
(00:00:00) Intro
(00:01:16) The Start of Stay22
(00:07:15) The Seed Round
(00:11:53) Pivoting the go to Market
(00:19:38) Investors Pulling out Due to Covid
(00:26:56) Finding the Opportunity in the Pandemic
(00:31:31) Tapping into the Blogger Market
(00:37:31) Growing Back from Zero
(00:38:49) Finding True Product Market Fit
(00:39:35) One Piece of Advice
Poojan is a multi-time successful founder. He raised $60M for his first startup and exited. He raised $11M for his current startup off just a deck. But it wasn't always easy.
- In his first startup, he had to hover beside conference booths for hours to land his first customer.
- He gave his product away for free to the first several customers.
- It took him 6 years to cross $10M in ARR
This year, he raised a $75M Series D and grew 4x to well over 8-figures in ARR.
Why you should listen:
-
Learn exactly how a successful repeat founder thinks about team structure in the early days. Though he raised $11M, he spent only a third of it.
-
Understand why sometimes giving your product away for free is the best way to get off the ground.
-
Hear about specific sales tactics you may want to use to get your first customers.
Timestamps:
(1:30) Before Clumio
(5:53) Raising 7 Million Dollars off a Power Point
(9:35) Starting Clumio
(16:41) Starting Conversations with Customers
(20:08) Finding and Solving the Real Pain Points
(24:18) The Stage Between Series A and B
(26:02) Keep your Team Lean
(27:47) Finding True Product Market Fit
(29:06) One Piece of Advice
Arvind Jain was a Distinguished Engineer at Google, where he’s credited with making Google “faster than the blink of an eye”. He quit that job and founded Rubrik, a company that does $500M in revenue and will go public later this year. But that wasn’t enough.
He left Rubrik in 2019 and founded Glean, an AI-powered work assistant. That company raised a $200M Series D at a $2.2B valuation just two months ago.
Arvind didn’t follow lean startup principles. He didn’t quickly build an MVP and iterate. He ignored early market feedback.
And it worked.
Check out this episode if you want to learn why sometimes doing things differently can produce massive outcomes.
Snapchat got 0 downloads the day it launched. 6 months in, it had only 127 users. Today Snapchat is an $18B company with 400 million daily active users. Evan Spiegel noticed what even Zuck missed: daily communication is meant to be ephemeral, not recorded for all time.
In this episode, we dive deep into how Snapchat went from idea to product-market fit.
Our guest is Jeremy Liew, a Partner at Lightspeed and the first investor in Snapchat. He led Lightspeed's seed round in 2012 at a $5M valuation (!!).
He shares his four-part B2C framework that helped him understand why Evan and Snap were special before anyone else.
If you want to understand why Snapchat took off when so many other consumer startups fail to do so, check this episode out.
If you feel like the ‘unicorn or bust’ playbook isn’t for you, then this episode definitely will be. Rand Fishkin is a multi-time founder and published author of Lost and Founder. He founded Moz, raised $29M in VC, grew to $50M in revenue and exited for $70M.
But he ultimately realized that the VC-backed life wasn’t for him.
So he went on to start SparkToro, a profitable 3-person startup that does $2M in revenue and takes only 30 hours a week of work. For those of us in the VC-backed startup world, it’s a totally different way to play the game. It won’t make you a billionaire. But it very well may make you $10M— with less stress, less work, and less risk.
If you want a transparent account of the pros/cons of a venture-backed vs a bootstrapped startup, check this episode out.
While Voice AI is all the rage now, it wasn't a hot sector in 2017. After Dylan graduated from YC, VCs rejected him. He couldn't raise a round. They all assumed Google would do it. So he raised what he could from angels and made it work for the next 3 years.
He's now built the world's most accurate Speech AI model. He's grown to 5,000 customers and raised $115M in venture capital. Last quarter, he raised a $50M Series C from Accel.
Just this week, Assembly launched Universal-1, their most powerful speech recognition model to date. Trained on over 12.5 million hours of multilingual audio data, Universal-1 is 22% more accurate than APIs from Azure/AWS/Google and has 30% fewer hallucinations than competing models.
In this episode, we go through how Dylan came up with the idea, how he saw Gen AI coming long before others, and what he did in the early days to grow to $1M in ARR.
Andrew is the founder/CEO of Enable. And he is riding a rocket ship:
2020: $17M Series A
2021: $45M Series B
2022: $94M Series C
A few months ago he raised $120M at a $1B valuation.
But it took him five years from the time he started Enable in 2015 until he was able to raise his first round in 2020.
Andrew was running a profitable development shop as he built the first version of Enable. He often had to chase down customers so he could make the next payroll. He had to balance serving existing customers while building an entirely new startup. Ultimately, he had to move to SF to raise a round and accelerate growth.
We go through the details of how Andrew turned a 'boring' enterprise software company from the UK into one of America's hottest new unicorns.
Alex started Apt2B in 2010. He sold couches online before IKEA did. It took him over 3 years to make as much money as he used to as a furniture salesperson. But it paid off. After growing the business to $6M in revenue, he sold the company.
Post-acquisition he grew the company to $40M in sales. In this episode, we dive deep into what Alex did to get started, how he closed his first few customers and what he did to grow to $1M in revenue.
From landing a Super Bowl ad to selling couches at Costco, this episode is full of sales and marketing anecdotes you can steal. You don't want to miss it.
Following the sale, Alex is now back at it as the founder and CEO of couch.com, a platform to help people find great furniture.
Every founder wants to build the next $1B+ company. So it’s normal to get inspired by what companies like Apple, Shopify and Microsoft do. But it’s also a huge mistake.
In this episode, we look at what Shopfiy, Fullscript and Spellbook did to find product-market fit. In many ways, it’s the opposite of what they do now, as big succesful companies.
Big companies are operating in a post-product-market fit world. Pre-product-market fit startups are in a different world entirely.
The same rules don’t apply.
Spellbook is ChatGPT for lawyers. They've raised $30M in the last 6 months. They now have over 2,000 law firms as customers. But it wasn't a straight line-- it took Scott 6 years to get here.
For the first 5 years, Scott worked on a legal tech platform called Rally. During that time, Scott along with his co-founders and their small team ran hundreds of experiments, pushed dozens of landing pages and built a process to test feature after feature.
In this episode, Scott goes through his process to test product-market fit. It was because of this process that he was able to jump on the AI-enabled opportunity and grow 12x in one year.
Kyle Braatz is the founder of Fullscript, a $900M revenue company that started by helping health practitioners recommend supplements to their patients. It's like the Shopify for doctors, nurses and nutritionists
Even though he captured 50% of the Canadian market in one year, early-stage VCs didn't see the opportunity. So he bootstrapped his way to success. He cracked open the US market and quickly scaled from $0 in 2012 to $25M in revenue by 2016.
Today, Fullscript has grown to a profitable company that makes it easy for health practitioners to prescribe and manage treatment plans for whole person health, through their market-leading tech platform.
If you're struggling to raise but know you have a huge opportunity ahead of you, you won't want to miss this episode.
Aydin Senkut is the Founder and Managing Partner at Felicis. He invested in Shopify's Series A in 2010 at a $25M valuation. He joins us to tell the story of how Shopify found product market fit.
Shopify is now a $100B company. But as Founder & CEO Tobi Lutke said, in the early days, his goal was "to build a 20-person company". Shopify is not a story of explosive, 10x growth and massive funding rounds. Shopify is a story of consistent growth. Of doubling year after year, from 0 to over $7B in revenue and a $100B valuation.
If your goal is to build a generational company, you won't want to miss this episode.
If you've been struggling to raise—you're not alone. Seed funding has been falling every quarter for the last 2 years. Rounds are smaller and take longer to raise.
So we decided to record an episode to help you. Here are all the mistakes, tips and tricks we’ve seen first-hand that actually work. We touch on things like
- What the perfect raise looks like
- Why Post-Money SAFEs are TERRIBLE for founders
- The greatest power move that any founder can use when fundraising
If you’re raising or planning to raise anytime this year, in a macro environment that is not friendly, don’t miss this episode.
The Super Bowl is the best place to get in front of customers—if you have $10M to spend. Which means for virtually all startups, it’s 100% useless. So I decided to look into some of the best campaigns early-stage startups used to drive millions of leads.
Shopify used a $100K Build A Business Competition in 2010 when it was a bootstrapped business. The campaign drove 1350 new businesses and was paid back in under a month.
https://shawngraham.me/blog/shopifys-kickass-build-a-business-contest
DollarShaveClub launched with a YouTube video about its $1/mo razors. The video was everything a GIlette ad was not. The company was ultimately acquired for $1B.
https://www.youtube.com/watch?v=ZUG9qYTJMsI&t=1s
Purple had the famous Raw Egg Goldilocks video that compared its mattress to others by seeing which one broke raw eggs. For less than $10K it got 200M views, more than the Super Bowl itself.
https://www.youtube.com/watch?v=4BvwpjaGZCQ
This isn’t a unicorn fairytale. It’s a story about what it really takes to build a company and get to an exit.
Nazim takes us through how he nearly went bankrupt, took years to turn things around, and ultimately sold his business for $30M all cash.
4K likes, 365 re-shares and over 1M views, without any marketing spend. For an ad promoting your product, that sounds too good to be true-- and yet that's exactly what Yoav did. He leveraged it to get tons of press, more customers than he could manage, and raise a $15M Series A in under a year after incorporating.
Here's the story of how Yoav got started with Walnut and how he ultimately found product-market fit. Yoav goes deep on tactics you can use to drive inbound traffic, generate leads and fundraise.
Viral video: https://www.linkedin.com/posts/yoav-vilner_weareprospects-weareprospects-activity-6960959679111778304-nOrW?utm_source=share&utm_medium=member_ios
Viral video 2: https://www.linkedin.com/posts/yoav-vilner_weareprospects-weareprospects-activity-7006660780150427648-P4vD?utm_source=share&utm_medium=member_ios
$1B startups get all the hype. But for 99% of founders, it’s the wrong goal. You’re better off building a sustainable business with consistent growth.
Raising big rounds won’t make your company big and staying lean won’t make your company small. That's just VC Myth 1.
Raising round after round does not equal success. That's just VC Myth 2.
Just because you raise more money, doesn’t mean you make more money. That's just VC Myth 3.
Over 10 years of hard work, Ilya has helped over 2000 individuals change their lives. In the meantime, he built a profitable, cash-flowing business with no outside funding. While the billion-dollar outcomes get all the hype, this is what success looks like for most founders.
In this episode, we dive into how Ilya turned a resume-editing business into a multi-million dollar recruitment platform, how he landed his first customers, and exactly when he knew he had product-market fit.
We released The Five Steps to Product Market Fit a few weeks ago and received lots of questions on how to apply the steps. In this episode, Rob and I share more colour and more stories on each step to help you understand how to apply them, and also, when these steps might need to be broken.
I know most founders today are planning for the new year, so sharing the top 3 mistakes I've seen early-stage founders make when forecasting. If you're forecasting for 2024, you don't want to miss this.
Here are the key lessons from the past 60 episodes that we've released to date. Each of the 5 steps to Product Market Fit is based on actual case studies with real examples you can use. It's a recap of everything I've learned over the last two years- you don't want to miss it.
As they say, "Experience is the teacher of all things"... and my last startup was a ruthless teacher. Today, my co-founder Lee Silverstone and ex-CEO Rob Woodbridge join me to go through some of the insane stories from Gymtrack, our last startup.
From strapping a whiteboard to the roof of Lee's Civic, to going to conferences with a 3D printed "smart" pin, to getting PR at the worst possible time, the stories are funny, engaging, and clear examples of what NOT to do.
This is the story of the emotional rollercoaster that was my last startup, Gymtrack. Hope you find it helpful as you navigate your own startup journey.
You can read the article here as well: https://entrepreneurshandbook.co/i-was-supposed-to-be-a-millionaire-at-25-instead-i-went-bankrupt-ef525370e353
Phil Knight, Nike's founder, might hold the all-time record for taking punches to the face. From giving up 49% of his company to a part-time advisor; to having Prefontaine, a famous runner and Nike's main ambassador, die unexpectedly; to getting blindsided with a $25M import tax when he could not afford it. Anything that could go wrong, did.
In this episode, multi-time founder Rob Woodbridge and Pablo Srugo go over Phil Knight's (founder/CEO Nike) road to product-market fit and why we believe he is the CEO all founders should imitate.
Nike was built backwards. Instead of building a product and taking it to market, Phil Knight first built a distribution machine for running shoes. Eight years later, he finally launched his own product (the Nike shoe) and did $3M in sales in the first year. This is not the full story of Nike. It's the story of how Phil Knight got to product-market fit.
Mark (CEO GoBolt) didn't set out to build a billion-dollar company. He just solved a problem other university students were facing. And then he constantly "made the best decision possible at each moment in time". To be honest, that's how most unicorns are made.
Everyone tells you that you need to start with a niche, a beachhead market, and then grow from there. But how does that actually work? What does that really look like? It looks like Mark's story starting and growing GoBolt.
Mark started off storing items for students over the summer. He expanded to storing all things for all people. He now provides logistics for enterprises. He's raised over $150M and has over 1,000 employees. But it wasn't pre-destined, it was 100% organic.
What really matters is finding a problem that you're acutely positioned to solve and then solving that problem. If you have real demand, and you stay close to your customers, things tend to take care of themselves.
Think of Product Market Fit as a pyramid. At the bottom you have vision, then value prop, then product and at the top is go-to-market.
As you go from 0 to Product Market Fit your job is to tweak the pieces of that pyramid, from top to bottom, until things click.
Founders are told to pivot when things aren't working. They're also told to never give up. So how do you know when to push through and when to completely change course?
Like most things in 0 to 1, it's more art than science. And unfortunately, most founders can't figure it out until after they experience it themselves. That's why on this episode we spoke with Andrew Tai, the founder and CEO of MotoInsight.
MotoInsight was acquired by Autotrader after it grew to tens of millions in revenue. But Motoinsight is the result of a major pivot. It took Andrew 3 years to realize that his initial marketplace solution was not going to work. We dive deep into the signs he saw that drove him to pivot to enterprise software and how doing so helped him go from 0 to $10M+ in just a few years
Weak customer discovery is the number one reason why most idea-stage startups fail. It usually leads to founders wasting months solving fake problems.
In my case, bad customer discovery cost me even more-- I ditched a startup idea that other founders built into several companies worth $10B+.
Here's a step-by-step account of how to do proper customer discovery. From how to source potential customers, conduct proper interviews and test your early product -- Ron has done it all. He shares each step with lots of details, so you can easily copy (i.e., steal) his ideas.
Rushing through customer discovery is the most common mistake founders make. Check out this episode to learn how to do it right.
Being capital efficient is the #1 power move you can make as a founder. It gives you time, control, and a huge edge with investors. Check out this episode to understand why it matters and what you can do to get there.
Michael Hyatt founded BlueCat, which was sold for over $700M. Since then he’s shifted to the investor side and has invested in dozens of startups.
Through it all, Michael has seen three financial crashes: the Dotcom boom and bust, the financial crash of 2008 and the recession we are facing today. He shares several insights on what it’s like to be a founder and investor through these storms.
Founders should pay attention.
95% of idea-stage startups fail because they don't solve an important enough problem in the first place. The most important part of customer discovery is to make sure you are solving real problems. But almost all founders do customer discovery wrong the first few times. Check out this episode to learn which mistakes you should avoid at all costs.
We've had plenty of episodes showing you what you should do. So here's an episode on what NOT to do.
Myles is an exceptional founder, thoughtful and charismatic. But he's made plenty of mistakes: whether it's coming up with an idea the wrong way, doing fake customer discovery, or simply hiring too many employees.
These are all mistakes I've made in my startup days. Mistakes you've also either already made or are about to make. Unless, of course, you learn how to avoid them.
We talk about product-market fit constantly in this podcast. Hopefully, we learn from what others did and improve our chances of finding PMF. But, even if we do everything right, we may still fail to find PMF. That's why even repeat founders have only 1.5% chance of building a unicorn.
But there is one way to guarantee that one day you will find product market fit. We explore that in this episode.
Never give up.
Three words every founder has heard many times-- and probably has said themselves. While true, those three words couldn't be more overhyped. Because, frankly, sometimes you need to give up.
You might need to give up on a product, an idea, or even a startup. Because not all will work. However, if you want to guarantee that you'll one day find Product Market Fit, what you can't give up on is the game itself.
If you want to understand what that looks like, listen to this episode.
Every startup has the same competitor: Status Quo. Your customers have done things a certain way for many years. Status Quo might seem awful to you, but it's worked for them. It's entrenched. It's accepted. In many cases, it's loved.
Classically, your product needs to be 10x better to beat Status Quo. But what does that really mean? What is 10x better? And 10x better for who? In this episode, we deep dive into the two ways to win vs. Status Quo: (1) finding the weak spot, and (2) if you can't beat them, join them.
"Wouldn't it be cool if..."
Usually, those words are uttered by first-time founders. And unfortunately, they usually lead to terrible ideas.
It was no different for Plooto. Their first idea sounded cool, but it didn't provide real customer value. Fortunately, Hamed noticed it and pivoted. Not once, but twice.
This is the story of how Hamed pivoted from a Bitcoin-based payment service to an Accounts Receivable and Accounts Payable platform for small businesses. If you think you might need to pivot, this is the episode for you.
Most bad ideas are born the same way. A founder says to themselves: "Wouldn't it be cool if...". I know because I did it. "Wouldn't it be cool if your workouts were automatically tracked" was the genesis for Gymtrack, my failed startup.
When you do this, you are starting from the solution, not the problem. Great startup ideas come from uncovering real problems. That's why we always say that before Startup Mode, there's Research Mode.
Finding Product Market Fit is often a long journey, especially if you're a first-time founder who jumps in with two feet and no upfront research.
It took Rodolphe FIVE pivots to get from where he started to the $10M+ ARR startup he has today. This is the story of each one of those pivots. How and why he decided to make big changes each time, and how each pivot brought him closer to product-market fit.
If you're looking for product market fit, you need to check this story out.
It's easy to pay lip service to focus. Just about every founder and VC I've met says that focus is important.
And yet, few understand what it really means to be focused.
Those that are truly focused often will do things that look insane. That's why we say that before the product market fit, "Only the Insanely Focused Survive".
They say the best founders can walk through walls. Well, nothing can stop Nabeil.
For the first two years, Nabeil and his team worked out of his house. His entire house, except for his bedroom, was an office. He would nap while changes were loaded to production only to wake up 2 hours later to test again. He got in a car crash a week before launch and didn't even set aside time to deal with it. Maniacal focus meant there was only one thing that mattered: launching on time.
A year later, Nabeil had an important meeting with a customer in Ohio. But, last minute, his flight got cancelled because of a snowstorm. So they book another flight: Toronto to Vegas and back through the redeye to Ohio. They get on the flight... but it's delayed. Somehow, Nabeil manages to convince the pilot to let him off the plane. They get off the plane and fly the next day at 6am. They were late but made the meeting. And guess what?
They closed the customer.
If you want to see how deals get closed in Startupland, check this episode out.
Many founders start companies because they want to get rich. Honestly, that’s what I did. Unfortunately, only caring about making money often leads to bad startup ideas. Focus on value instead.
Seed stage VCs are called “investors”, just like hedgefund managers or stock pickers. It’s a poor choice of words. Finding seed VCs to back you is less about finding “investors” and more about finding “believers”.
The key to product-market fit is delivering clear and exceptional customer value.
The story of Applyboard shows you exactly what that looks like. Martin changed the lives of thousands of students who he helped study abroad. He impacted not just them but their entire families. In the meantime, he delivered 10x ROI to schools: for every $1 they paid Applyboard they made $10+ on tuition.
It’s nearly impossible to push yourself to unicorn status. The market needs to pull you there. And it’ll only do it if you provide incredible customer value. If you want to understand what that looks like, check this episode out.
Starting your second startup should be much easier, right? Well, yes and no.
Jafar was the founder and Chief Revenue Officer of Loopio, which went on to raise $200M+ and land thousands of customers. He left to start Barley. This is the story of how he decided to leave, and what it was like to start over a second time.
On the one hand, some things, like fundraising, are much easier. On the other hand, the 0 to 1 journey is just as hard. Delivering value in a big market is no easy task, even if you've learnt from prior mistakes.
In this episode, he shares what skills transfer over and which ones don't. If you're a repeat founder, or a prior founder thinking of starting a new one, check this episode out.
Before the pandemic, there were 24 employees at Certn (Or Certonians, as they're called). After the pandemic, there were 500. That's 20x growth in just two years. That only happens for one reason... insane product-market fit.
This is the story of how Certn got there. Andrew (CEO) walks us through his five-step process to find product-market fit. He used that in the early days of Certn to veto his initial idea and quickly shift to tenant verification. Through continuous PMF-ing, he uncovered employee verification as well. When COVID hit, he was in the right place, at the right time, with the right product.
The rest is history.
If you're on the road to product-market fit, you need to check this episode out.
Bootstrapping isn't sexy. At least not at first. As they say, it's not greed that runs the world but envy. And when your founder friend raises $10M, it's hard not to want it too.
But 10 years later, when you're running a $100M+ per year bootstrapped business, all of a sudden things aren't looking too bad. No runway to worry about. No pressure to sell. When you bootstrap a business past product-market-fit, the ones that raised $10M+ start to envy you.
In this episode, Vitaly shares exactly how they did it. From humble beginnings building a minimum viable product for one client, to making a $500/mo salary and raising minimal VC funding, to one of Canada's largest startups today.
Raising money in 2022 isn't easy. Even if it was, it's not clear raising it is optimal. It's always good to do more with less.
If you're bootstrapping or thinking of it, this is the episode for you.
What's the most important asset of any startup? It's easy. The talent. The software you build is not defensible. It can be replicated. The team you build is what's special. And the culture you develop is what's unique.
In this episode, Rob shares some incredible advice from his days at Uber and as the CEO of Float on how to build a high-performing team. He talks about hiring A+ talent by spending 80% of his time on recruiting and paying 90th percentile. He shares his hiring philosophy about hiring with high conviction (appropriately called "F--K Yes and F--K No"). And he talks at length about what culture is and how to make it work for your startup.
If you're running a team of any size, you have to check this out. Guaranteed at least three tips you can copy or your money back!
Wealthsimple is arguably the hottest private startup in Canada, with over 3M users and a valuation of over US$4B.
In this episode, Mike (CEO) shares stories he’s never shared before. He goes deep into how he came up with the original idea, launched the product, and got early traction.
From getting rejected by YC, to running around Toronto hosting Lunch & Learns, and calling every single one of his first customers personally, this episode is filled with stories you wouldn’t expect given where Wealthsimple is today.
But all start-ups have humble beginnings. Wealthsimple is no exception. If you want to learn how one of the biggest successes coming out of Canada got started, check this episode out.
When you launch a product and no one buys it, the decision is rather simple. You kill the product. At the very least, you make some serious changes to it.
What happens when you do real customer discovery, launch a product that solves a pain point, and get some traction, but can't really seem to take off? What happens when your product is generating revenue, but true product-market-fit still seems unattainable?
Michael, the CEO of LumiQ, shares the story of two products. The Luminari recruiting marketplace, which generated close to $1M in sales but couldn't scale. And LumiQ, his current product and the result of a major pivot, which is on a path to 8 figures in ARR.
If you want to understand how to identify the need to pivot, how to conduct proper research to find the right pain points, and how to execute the change, this is the episode for you.
There's nothing quite like going from 0 to an 8-figure+ acquisition, especially on your first startup. And 100% bootstrapped!
Aydin, the founder of Fluidware and now founder of Fellow, shares the story of his humble beginnings as a Jr Engineer, to launching a startup that would compete with SurveyMonkey and ultimately join their ranks.
Notably, Aydin never raised money at Fluidware. While it had its downside, it enabled him and his team to solve customer problems without worrying about the market size or the big picture. Each step helped them discover new insights and led them closer to product-market fit.
Want to get a feel for what it takes to bootstrap to PMF? Check this episode out.
Customer discovery is easy, right? You just call up a dozen or so potential customers, ask them a bunch of questions, and you're done. It seems absurd but that's what a lot of founders do. No one becomes a founder because they like to research; they become founders because they like to build. But building too early often comes at the cost of building the wrong thing.
Phil and his team at Paper did real customer discovery. They moved to a different country and rented a house right next to their customers. They visited their customers every day for months. Countless hours later, they understood exactly what was needed and built the right thing.
They took Research Mode seriously. And it paid off. In 2022, they raised $300M and became a unicorn. Clearly, their product struck a chord. If you want to learn how exactly they did it, check this episode out.
You've built a startup from nothing. You've set up a corporation, built a product, had customers, raised some funding, and maybe even had an exit. The entire time you're thinking to yourself, "Wow, next time it'll be so much easier!".
That's what Mike thought. He built TopHat from nothing to 500 FTEs. In early 2020, he raised US$130M and exited the company. He had a huge success and decided to do it all over again.
In this episode, Mike shares what it's like to start over. Which parts of the process are easier and which parts are not. If you're a repeat founder about to start over, this is the episode for you.
Finding product market fit is rarely a straight line. Many founders zig and zag through different iterations of their product, different target markets and competitive positioning until they find true product market fit.
It was no different for Hongwei, the CEO and Founder of MappedIn. He went from building indoor maps for malls, to getting an investment on Dragon's Den, to finally building an 8-figure ARR startup.
In this episode, he shares the main milestones and pivots that took him from a student at Waterloo to the CEO of a company with almost 100 employees. The main lesson? You might start off with a niche, non-scalable idea. But by working with customers you find unique insights you would otherwise never have uncovered.
To win, you have to first be in the game.
Every founder knows before you launch, you have to build an MVP. They also know that to build an MVP, you should do customer discovery. But few understand how to properly do customer discovery.
Before startup mode, there's research mode. And most founders don't do it right. Failure to do so is why most founders end up solving fake problems. If you want to avoid the fake problem trap, you need to spend a lot more time than you might think on research and customer discovery.
Before launching the product, Adrian spoke to hundreds of paralegals. He hosted in-person focus groups in multiple cities. It was critical to his success and it's how he learned exactly what the problems were and exactly what to build.
If you want to learn how he did it, check out the episode.
If you're selling to businesses, you already know... before you publicly launch your product, you'll have to go through a private beta.
But beta programs are not all made equal. Many founders go through the motion but get very little out of it. Others, like Jack (the founder/CEO of Clio, a $1.5B start-up) leverage it to get the right customers, helpful feedback, and a successful launch.
Who should you let in and how do you get them? How early should you let customers in? When do you know you're ready to launch? Those are a few of the questions Jack answers on the show. If you're going through a beta, this is the episode for you.
Raising money seems really easy when you're reading Techcrunch. Then you go out and try to do it and all of a sudden it seems impossible. Especially when you're new to the startup world and know no one.
That's exactly what it was like when Aman, the founder/CEO of Procurify, raised his first round. He describes in vivid details how he flew to San Francisco, slept on the floor of a shared house, cold emailed Mark Cuban and got him to invest. The series of events in this episode are extremely unlikely. They are hard to believe. But they are real.
The reality is that early rounds raised by first-time founders often look like pure luck or serendipity. But you'll notice the hustle, the networking, and the determination that creates these "happy accidents". If you're about to try to raise a pre-seed or seed round, you'll want to check this out.
Before startup mode, there’s research mode.
Many startup stories sound like happy accidents, where founders stumble upon an amazing idea more by chance than by strategy. The reality is the best founders have a deep understanding of the problem they’re solving. They are experts in their industries. They make sure not to invest time and resources into solving fake problems. And they achieve that through customer discovery.
Prior to writing a single line of code, Hanif spoke with 100s of industry experts, employees and potential customers in his industry. He broke down his research into multiple phases. And he didn’t commit to building Symend until he was sure there was a problem worth solving.
If you want to understand how to do customer discovery right, check out this episode.
There are two types of startups: those that sell into existing markets and those that create new markets.
There are ups and downs to both. Selling into an existing market means you have a clear idea of customer needs and market size. It also means you have lots of competition. Creating a new market tends to cost a lot of money and the upside is uncertain. But you get to define the market and potentially capture a strong position in your customer's minds, like Uber or Airbnb.
When Dialogue started, telemedicine wasn't really a thing. At least, it wasn't a thing companies paid for in Canada. Cherif built Dialogue into a public company in just a few years by creating a new market.
In this episode, he shares details of how we crafted the story and sold the product to his first few customers. If you want to learn how to create a new market, check this episode out.
The standard advice is you need to first generate your own demand, and only then look for partnerships to accelerate your business. Another piece of standard advice is you should probably raise a small round early on to hire key employees. The last piece of advice is that if you're a business founder, you probably should get a technical co-founder.
Laura chose to do exactly the opposite. And it worked.
She decided not to bring on a technical co-founder, and it's "the best decision she ever made". She decided to bootstrap the company for as long as possible, and it helped her focus on what really mattered. And she decided to start with partnerships and it worked.
If you want to learn how she did it, check out this episode.
You've launched a startup. Your excitement turns to anxiety as it becomes clear things aren't working out. Some customers are buying but not nearly enough. They like your product, but they don't love it.
You realize you don't have product-market fit and are unlikely to get it. You'll need to change things up. You'll need to pivot.
It's a painful process, but pivots are more common than you think. The right pivot can take you from nothing to billion-dollar status. Many unicorns, including Slack, Twitter and Ada, started off as completely different businesses.
The key, of course, is to do it right. Mike and his co-founder spent a full year as customer service agents to feel their customers' pains. They solved those problems over time and a few years later raised at a $1.2B valuation.
If you want to hear exactly how they did it, have a listen.
You have a startup idea. You tell 10 friends and they all tell you it's awesome. What have you proven?
Unfortunately, not much.
Validating your idea requires you to go outside your building and talk to real customers. Not only that, real validation means having customers pay for your product. But how do you do that without having to build something first?
Find out from Eran, the CEO of Thriver on this episode. Eran and his co-founders generated thousands of dollars in sales before writing a single line of code. By the time they started building, they knew for sure there'd be demand... because they'd already closed real customers.
Getting started with a consumer product is HARD.
Unlike selling to businesses, you can't just grind it out with cold calling. You'll need to figure out how to get noticed and drive traffic to your site.
And getting media attention is one of the best ways to do it. Andrew is the founder of Borrowell, a startup with millions of users. When he launched he was featured in dozens of publications across the country. For the first time, he describes in clear, step-by-step detail, exactly how he did it.
If you want to maximize media attention, you won't want to miss this episode.
You want to become an entrepreneur. But you're stuck at level 1.
How do I come up with an idea? It's not easy. And there's no silver bullet.
Matt, the founder of Assent. has built three successful startups: NoNotes, Assent Compliance, and Millions. In this episode, he shares the stories of how he came up with each one.
There's no playbook for how to come up with a billion-dollar idea. But there is a mindset that will help. Check this episode out - maybe you'll get inspired.
Building a product is the easy part. With the right resources, you can build just about anything.
But once you've done that, how do you launch it? How do you get people to know your product even exists? And how do you do it on a tight budget?
Jay, the founder of Bold Commerce, has launched dozens of succesful e-commerce products. In this episode, he shares the detailed story of how he launched Kickbooster, an affiliate management program for kickstarter campaigns.
If you're planning to launch a product for SMBs, you don't want to miss this one.
Once you have clear traction, once revenue is up and to the right and growing quickly, investors come to you.
But what about early on? How do you get people to invest millions of dollars when all you have is an idea?
Stephany, the founder of Tealbook, has raised over $70M. She got her first cheque from an angel investor she met during her kid's soccer game. In this episode, she dives into how she raised her first few rounds. Angels investors invest in people- and Stephany shares details into how to build relationships that may catalyze your round.
Check this episode out to learn how to raise your first round.
How do you launch a marketplace? How do you get beyond the chicken-and-egg problem? Derrick's answer: Fake it Till you Make it.
When launching Drop (a rewards app with millions of downloads), Derrick needed both consumers and brands to join. Instead of going after both at once, he found a way to seed supply and added brands' logos to his website, whether they had joined or not. It may have led to some Cease and Desist letters (or Conversation and Discussion letters, as he called them), but it also led to considerable growth.
If you're about to launch a marketplace or are struggling to get it off the ground, listen to this episode and see how Derrick did it.
When you're selling to consumers or small businesses, you can put up an MVP, generate traffic, and watch the money roll in. Not so for enterprise. Enterprise means long sales cycles, procurement departments, security audits, pilots, and many more hurdles.
How do you get your first enterprise sale? How do you convince a company 1000x your size to take a risk and work with you? Corey, the founder of Sensibill, had to sell to one of the most complicated and heavily regulated enterprises of them all: banks. And he got it done, securing multiple pilots prior to getting funded.
If you're working on an enterprise product and are starting to speak with customers, this is the episode for you.
Most startup founders recognize they need advisors. The question is who do you get, how do you get them, and how do you structure it all? In this episode, Darryl shares his framework for how to set up the perfect board of advisors.
It starts by imagining that you're five years in the future once your startup is a huge success
and asking yourself- what are all the key pieces that are required? From there, Darryl methodically targets advisors that will help with each of the key pieces. He discusses how to get in front of them, how to convince them to join, and how to structure the advisory board.
As a startup founder you will need advisors to help on your journey. Listen to this episode to learn how to do it right.
Running a startup is hard. Doing it alone, especially when it's your first time, can be downright tortuous.
Lindsey started off on her own, without much of a network in the startup scene in Toronto. Not only that, as a business type she didn't have the skills needed to build a prototype, let alone the full product. On this episode, she discusses how she methodically set out to find her co-founder through three steps: networking, networking, networking.
If you're a solo founder looking for your second half, you'll want to give this a listen.
For even the most successful startups, finding product-market fit is often a long journey and Klipfolio was no exception.
Founders often feel that one more feature, one more UI change will get them to product-market fit. The reality is that the path to PMF is more of a step function. If your first product doesn't quite get you there, a small change is unlikely to get you the results you're hoping for. You made need to dramatically change your product or even your market.
In this episode, Allan shares the story of how Klipfolio went from consumer to enterprise and back to SMB before finally finding real product-market fit. He shares lots of clear details on what true product-market fit feels like.
If you're a founder of a company that hasn't quite made it beyond PMF, you'll want to check this out.
It’s one thing to work hard. It’s another to work hard with a well-researched destination in sight.
In this episode of The Product Market Fit Show, Rob Boukine gets real about the mistakes he made in his early days as cofounder of Noibu and dives deep on how he pivoted his business. He discusses the importance of using customer discovery to ensure your products are “need to have” rather than “nice to have”.
If you’re working hard but nothing is working out as expected, perhaps his advice on tracking down the right pain point will hit home.
Launching is often thought of as a huge event. Lots of noise, lots of PR. One big bang. For Ray, it's just a series of many small experiments.
Ray realized that the number one value prop for a consumer was coverage: when a user opened the app, the majority of merchants that were walking distance needed to show up. So, he set up an experiment. He targeted a handful of office buildings and a dozen merchants, all located on the same block. He didn't need to onboard all the merchants in Toronto, just all the merchants on this one block.
If you're about to launch a consumer product or a marketplace, check out what Ray has to say.
"Ideas are a dime a dozen". Maybe. But executing on a mediocre idea won't get you very far.
In this episode, Ray, a multi-time founder who sold his first company to Google, discusses how he came up with the idea for Ritual. It was not your typical aha-moment. Many ideas came together over a long time until the idea for a pick-up order app was born. Since then, Ritual has gone on to launch in over 40 cities and raise over $100M.
If you feel you want to be a founder but are struggling to come up with a great idea, maybe Ray's story will help you out.
If you want to validate an idea, the conventional wisdom is to build an MVP. But even an MVP takes time to build. What if you could validate not only your idea but your entire funnel, without writing a single line of code?
That's what Moe did. He built a landing page, found ways to advertise and generate traffic, and went so far as to convert traffic to paying members- before having any product to sell! (Of course, he immediately refunded those early customers and added them to a waiting list.)
If you have an idea and want to know if there is real demand - this is the episode for you.
After you've had an idea and validated the problem, it's probably time to build. But how exactly do you decide what to build, how to build it, and how to get end users to actually adopt the solution?
Carol is a multi-time founder and she has this process down to a science. On this episode, she shares how she built the first version of Axonify (now acquired for over US$350M). She explains how to find a champion, how to stay close to them throughout the build phase, and how to get end users to adopt the product.
If you're starting to build out a product, especially in a b2b or b2b2c context, check out this episode.
To launch a startup you have to leave your job and spend considerable capital, with no guarantee of success. It involves considerable risk, right?
Not for Mike.
Mike started Rewind- a company now approaching unicorn status- fully on the side. It started off as a project, and neither Mike nor his co-founders took any salary cuts to get Rewind off the ground. Instead, they worked nights and weekends, steadily growing MRR and joined one at a time as the startup became self-sufficient.
If you have an idea but aren't ready to go all in, check out this episode and learn how to start it on the side.
Why do professional athletes have coaches, but professional entrepreneurs don't?
Dan thought this was odd. So many years ago, a long time before starting Koho - a company now worth over $250M- Dan started working with performance coaches. In this episode, he walks us through how to pick a coach, what exactly a coach is (hint: it's not an advisor), and how a coach can help your startup grow. In fact, Dan is such a believer in coaching that Koho offers coaching to all of their 200+ employees.
If you're interested in performance coaching, or are looking for an edge, listen to what Dan has to say.
Ask most early-stage founders what they need with and you'll likely get the same answer: money.
Especially early on, before you have much traction, raising money can be daunting. If you don't have much of a network, it's hard to even know where to start. Who are these angel investors and how do you find them? How do you get them to take a meeting? And how do you get interested investors to actually close?
Marc walks us through his first fundraise at Unito. How he leveraged an accelerator to build a network, got other founders to get him investor introductions and used various tactics to build momentum and FOMO.
If you're looking to raise one of your first rounds of funding, check out how Marc got it done.
Many people say that hype leads nowhere, that instead you should keep your head down and focus on building. But hype- or raising the profile of your company, as Solon calls it- brings many benefits. It means more potential hires, more investors, and even more customers.
As you'll see, Solon is the master of creating hype.
Find out how Solon raised the profile of MindBridge to get a multi-time founder to join as CEO, to poach key technical talent and to raise money well ahead of building product.
Launching a marketplace is hard. The chicken-and-egg problem often seems insurmountable.
In 2021, Wattpad was acquired for over $600M. But it wasn't easy. Early on, Wattpad cofounder and CEO Allen Lau almost gave up. He discusses the virtues of starting with a small niche and allowing growth to come with time. He explains the ASSET framework he’s developed to help you launch and scale a marketplace.
If you’re about to launch a marketplace or just launched one and are not seeing the traction you were hoping for, you might want to give this a listen.
Building a successful startup starts well before the first prototype is created or the first investor goes all in.
It starts with customer discovery, and Mallorie Brodie has some unique insight into what that looks like. Now the cofounder and CEO of Bridgit, she started out as a college student eagerly chasing down construction cranes and listening to complaints. Today, she tells The Product Market Fit Show the secret to finding great startup ideas.
If you think you already know your market’s pain points, you’re probably doing it wrong.