Paradigm Shift: Recent Episodes
Ashish Kundra and Zane Salim
Candid conversations with people building the future. We discuss breakthrough moments and hard-earned insights that shaped people, products and technologies. Hosted by Ashish Kundra and Zane Salim.
In this episode we talk with Ali Partovi about lessons learned identifying, evaluating and accelerating talent across a long and storied career in Silicon Valley. We talk about his founder experience, great investments he's made, and his new accelerator Neo (which is something like YC 2.0).
You can learn more about Neo here, and follow Ali to on Twitter to connect with him.
Michael Martocci is the Founder and CEO of SwagUp, a platform that makes it easy to create, automate and distribute swag globally.
In this episode we talk about:
- Lessons learned bootstrapping SwagUp to over $100M in revenue
- Advice on managing cash flow and how Michael approached forecasting
- Michael's vision and SwagUp's unique position to reimagine the entire end to end workflow from the customer experience to the complex supply chain.
This was a really fun conversation. We hope you enjoy it as much as we did!
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- Follow Michael on Twitter
- Follow Ashish and Zane on Twitter
Michael Stoppelman is the former SVP of Engineering at Yelp and profilic angel investor in 300+ startups. In early 2007, he left Google to join Yelp, and helped scale Yelp Engineering from 6 to 600 engineers.
In this conversation we talked about Michael's lessons learnt building and scaling a world class engineering team- from hiring to motivating to leading world class teams. We also talk about lessons learned from early days at Google, and his approach to angel investing where he has an extremely impressive portfolio and track record.
This was a really fun conversation. We hope you enjoy it as much as we did!
Links
- Follow Michael on Yelp
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- Click here to share feedback — it only takes a minute
Cameron Peake is a Partner at Restive Ventures, an early stage fintech focused VC fund. Previously Cameron was co-founder and CEO of Azlo, a company that provided online banking services for small businesses, entrepreneurs, and freelancers, and quickly grew to almost $1B in deposits.
Cameron understands fintech from multiple vantage points: building for international markets, building one of the first neobanks in the US, and now funding early stage companies. In this conversation we discuss what it takes to build an enduring fintech, drawing from Cameron's experiences as both a builder/operator and investor.
- Path to building fintech products
- Founding, building and scaling Azlo
- Experiences and advice on managing fraud
- Fintech landscape and building enduring companies
- Closeout questions
This was a fun conversation. We learnt a ton, and hope you enjoy it as much as we did!
Links
- Follow Cameron on Twitter
- Avoiding common fraud traps
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- Click here to share feedback — it only takes a minute
Semil is the founder and GP at Haystack, an early-stage VC firm with $450M+ AUM. He’s an investor in 200+ companies including DoorDash, Instacart, Hashicorp, Figma and more.
In this conversation we discuss the current funding environment, Semil's approach to venture capital and making early investments, and his advice for founders starting a company and fundraising in today's market.
This was a really fun discussion and we hope you enjoy it as much as we did!
Links
- Follow Semil on Twitter
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- Click here to share feedback — it only takes a minute
Beerud Sheth in a rare founder who’s started not one, but two unicorns — UpWork and Gupshup. He’s seen a lot of pivotal moments in SV history — having started Upwork in 1998 before the dot com bubble, and Gupshup in 2005, three years before the GFC.
Today, Upwork is a publicly traded company valued at $1.5B and Gupshup is a unicorn, last valued at $1.4B+ as of April 2021.
In this conversation, we talk with Beerud about his experiences building UpWork and Gupshup across almost 25 years.
Links
- Learn more about Gupshup and try Upwork
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- Click here to share feedback — it only takes a minute
Wei is the founder of Clipboard Health. Clipboard Health makes it really easy for nurses to search for jobs based on what they're qualified for and what they care about, and apply with one click.
Over the last few years, Clipboard has have experienced rapid growth and become the leading marketplace for healthcare profesional to find on-demand shifts at healthcare institutions. Clipboard has raised $94M from top VCs that include YC, Initialized, Caffeinated Capaital, and Sequoia, most recently at a $1.3B valuation.
In this conversation we talk about Wei's path to founding Clipboard Health, how we iterated through multiple ideas and products to find PMF, and her approach to blitz-scaling 25x in 18 months during Covid.
Wei is one of the most formidable founders we have ever met and we were so blown away by this conversation. Hope you enjoy it and learn as much from it as we did.
Links
- Follow Clipboard Health on Twitter
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- Follow Ashish and Zane on Twitter for summaries
- Click here to share feedback — it only takes a minute
In this conversation, we speak with James McGillicuddy. James was previously Head of Strategy at Carta ($7.4B valuation) where he brought products like CartaX to market, and before that was the COO and early team member of SourceGraph — a universal code search tool company valued at $2.6B. He was also early at RelateIQ (acquired by Salesforce for $390M) and played college football for Stanford under Jim Harbaugh.
Some highlights: how James approached decisions on which early stage companies and founders to work with, lesson learned from building and scaling GTM at the zero to one stage from earliest days to unicorn-level for multiple companies, approach to building teams and why he loves it, and some really fun stories and lessons from playing college football with legendary coach Jim Harbaugh. We hope you enjoy this episode as much as we did.
Links
- Follow James on Twitter
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- Click here to share feedback — it only takes a minute
Bryan is the founder of LayerZero Labs, which is an omnichain interoperability protocol that unites decentralized applications across disparate blockchains, enabling cross-chain applications.
LayerZero Labs is building foundational crypto infrastructure. Since being founded in 2021, the company has raised over $140M from top investors including Sequoia Capital, a16z, Tiger Global, Coinbase, Cristies, Paypal, Polygon and Dapper Labs.
In this conversation, we discuss the LayerZero founding story, how Bryan approached building complex decentralized infrastructure, their explosive launch and seemingly immediate product-market fit, and the cross-chain opportunity space.
This was an incredibly fun conversation and we learnt a ton from Bryan about the "behind the scenes" of building and launching widely used crypto infrastructure.
Links
- Follow Bryan and Layer Zero on Twitter
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- Click here to share feedback — it only takes a minute
Kunal Shah is a serial entrepreneur and founder of two iconic Indian companies -- CRED and Freecharge. CRED is an Indian consumer fintech that is valued at over $6.4B, and Freecharge was one of the earliest Indian fintechs that sold to Snapdeal in 2015 for $450M.
Kunal has an unmatched track record not just as a founder, but also as an investor and thinker. He’s a prolific angel investor in over 200+ Indian startups and shares insightful, bite-sized philosophical wisdom on Twitter with over 700K followers.
In this conversation we explore frameworks and insights that have guided Kunal's approach to building consumer internet products, the "delta-4" framework he uses to evaluate the potential for a breakout product, how consumer behavior changes in trust vs trust-less societies, and his approach to angel investing.
In the closeout, we ask Kunal about the most difficult/challenging feedback he has received and how he processed it, and superpowers he has identified in himself that he leans on day to day.
Links
- Follow Kunal and CRED on Twitter
Hit subscribe to keep up with new episodes!
- Follow Ashish and Zane on Twitter for summaries
- Click here to share feedback — it only takes a minute
Andrew is the founder of Skiff, which is a privacy-first, end-to-end encrypted, wallet native workspace with email, file sharing, and collaboration.
Skiff has hundreds of thousands of users and is part of a broader trend towards privacy-first and decentralization. Skiff is backed by Sequoia Capital who led their seed and Series A.
In this conversation we discuss Andrew’s path to building privacy-first products, approach to finding Product-Market Fit with Skiff, and the various tarde-offs and opportunities when building privacy-forward and web3/decentralized products.
This was a really fun conversation and we learnt so much about what why privacy products matter, their path to increasing mainstream adoption, the business models that are working, and how companies like Skiff are taking us into an exciting future where technology continues to democratize and protect privacy and digital freedom.
Topics discussed:
- How did you end up working on privacy-first products?
- What is your vision for Skiff and what does the product to today?
- How did you approach integrating crypto login with meta-mask and decentralization?
- How did you approach being privacy-first from the ground up? How does that affect the user experience and user journey?
- How did you approach the trade-offs between building on centralized and decentralized APIs/components for the best user experience? Eg: onboarding, account recovery, etc.
- How did you approach e2e encryption and interoperability when building a privacy-first Skiff email product?
- How did you get started building the initial Skiff MVP and who was your first user?
- What are your thoughts on competing with very mature incumbent products like GMail, Drive, Notion and Evernote? How have you approached it?
- How did you build conviction in the opportunity around Skiff and the market opportunity?
- What have you noticed are some triggers that make people switch to a privacy-first email or collaboration product like Skiff? What are some archetypes of people who seek out these products and switch?
- Since you don’t track your users, how do you figure out who they are, what they want and figure out how to improve the product?
- How do you think about the global opportunity and internationalization?
- How do you cross the user adoption chasm to mainstream adoption from where we are today to privacy-first networked products like email?
- How do you think about business models for Skiff and privacy products?
- What made you decide to be consumer first vs enterprise and b2b focused?
- Who should use Skiff and how should they use it?
- Zooming out what are some areas in the privacy space that you’re most excited about?
- Closeout questions: what is the most challenging or difficult feedback you’ve received and how have you processed it? What are some superpowers you’ve identified in yourself that you like to lean on?
Links
- Follow Andrew and Skiff on Twitter
- Signup for Skiff for end to end encrypted web3 email, drive and docs
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- Click here to share feedback — it only takes a minute
Keith is a Silicon Valley legend— an accomplished operator, founder, and investor. He started his career as an early executive at PayPal, LinkedIn and Square, before going on to co-found companies like OpenDoor (which IPO’d in 2020) and OpenStore.
He’s currently a General Partner at Founders Fund and Co-Founder/CEO of OpenStore. Along the way, he’s made incredible investments as an angel and VC in companies like DoorDash, Affirm, Stripe, YouTube, Palantir, Airbnb, Ramp, Faire, and many more.
In this conversation we ask questions that span three broad areas: how to grow through a downturn, how to develop good judgement, and how to build an iconic company.
This episode is packed with incredible insights and actionable advice from Keith. We hope you enjoy this conversation, and learn as much from it as we did.
In this episode we discuss:
- Growing through a downturn
- Given the current market correction underway, what do you think happens next?
- What advice do you have for founders starting companies in this market context?
- You’ve said you believe the best companies are built in the public markets. What do you think needs to happen for more companies to go public within 4-6 years vs 10-15 years?
- What do you think is the right time (or maturity level) for a company to go public?
- Developing good judgement
- You have been extremely successfully at investing super early. What has been your approach to making investments when it’s just a team and a keynote deck?
- You’ve talked about how you look for a “spark” when making early-stage investments. Could you describe a time you’ve seen that? What has it looked like?
- Could you share some examples where things have not gone well and how you’ve approached those situations?
- How have you honed your skill in evaluating people and opportunities, and what advice do you have for someone trying to improve their own judgement?
- How much overlap do you think there is between the skills used to hire and the skills used to evaluate a founder? How do you approach assessing people in both those contexts?
- Building an iconic company
- You’ve seen a lot of companies navigate the path to product-market fit. What approaches you’ve seen work particularly well? What has been your own approach to getting to PMF?
- Post PMF, how do you think about the trade-off between growth and efficiency? Do you think the current market context changes the traditional blitz-scaling strategy?
- When evaluating investment opportunities, to what extent are you thematically driven vs opportunistically driven?
- You’ve talked about how people often don’t map their time to their priorities well. As a VC and an operator, how do you approach setting priorities and what does that look like on a week-to-week basis?
- How have you approached coaching/helping founders and new managers/executives better prioritize their time towards the highest leverage activities?
- Closeout questions
- What is the most challenging/difficult feedback you’ve received — how have you processed it and incorporated it going forward?
- What are your superpowers that you find yourself leaning on often?
- Anything you’re reading right now that you’d recommend?
Links
- Follow Keith, Founders Fund and OpenStore on Twitter
Hit subscribe to keep up with new episodes!
- Follow Ashish and Zane on Twitter for summaries
- Click here to share feedback — it only takes a minute
Abhishek is the co-founder and CEO of AppSmith, which is a low-code tool that helps developers build dashboards and admin panels very quickly. AppSmith has raised over $50M from investors like Accel, Bessemer, Insight and Prasanna Sankar (previously on the pod!).
In this conversation we primarily explore how Abhishek is building AppSmith with the open source community as a core part of the product, business model and long term strategy. We also talk about Abhishek’s incredible journey (and lessons) as a serial entrepreneur, how the Indian startup ecosystem has evolved over the last 10+ years, and the key drivers behind the trend of Indian startups building for the world.
In this episode we discuss:
- Lessons from serial entrepreneurship and journey to founding AppSmith
- How did you get into building things?
- What were the most impactful learnings from your early startups?
- What is AppSmith and what led you to founding the company?
- AppSmith and building an open source powered company
- How did you evaluate whether to build an open source company? And whether open source could be both an advantage and a viable strategy for AppSmith?
- What are some of AppSmith’s biggest differentiators vs other no-code internal tool products in market today?
- How did you approach getting your first customer? How did you evaluate early product market fit for the open source product/project?
- What were the biggest risks you were focused on mitigating early on and how did you approach it?
- What have you experienced as being the biggest advantages of building an open source product/company?
- What is your current scale and traction about 20 mos after launch?
- Growth and monetization for an open source project
- What does the open source flywheel look like and which levers are you most focused on to drive adoption and keep improving the product?
- Where do you focus your marketing and growth efforts for an open source company?
- Why do people choose you over alternatives? How do customers and buyers evaluate the pros/cons of the open source nature of your product?
- In the context of your open source approach, what is your business model and how do you think about your monetization strategy?
- What’s your long term vision for AppSmith and what’s your approach to getting there?
- What has been the big differentiator between open source projects that have had great monetization vs ones that have struggled with monetization?
- Indian startup ecosystem
- From your vantage point, what have been some big inflection points from the last 10+ years that have led to the thriving Indian startup ecosystem?
- What do you think is driving the trend of Indian startups building for the rest of the world?
- What are some of the advantages you see to building world class products in India?
- Closeout questions
- What is the most challenging or difficult feedback you’ve received and how have you incorporated it going forward?
- What are your superpowers that you find yourself leaning on often?
- What’s something you believe that would surprise most people?
Links
- Learn more about AppSmith
- Follow Abhishek and AppSmith on Twitter
Hit subscribe to keep up with new episodes!
- Follow Ashish and Zane on Twitter for summaries
- Click here to give feedback — it only takes a minute
Andy is a serial entrepreneur and CEO of Eco a new kind of wallet to spend, send and save money. It combines traditional banking rails with crypto rails to deliver a new kind of experience that creates more value for customers in an easy to access way. Before Eco Andy was a co-founder at CoinList which is another very successful crypto project.
In this conversation we talk about the founding stories behind both CoinList and Eco. We discuss Andy’s lessons from navigating the last crypto winter. And we discuss Andy’s approach to building Eco into a mainstream crypto-based product that competes with traditional retail banking.
In this episode we discuss:
- Early career building things
- How did you get stated building things?
- What are some memorable lessons from the Stanford Bitcoin Group?
- CoinList and the early ICO token sales wave
- What was the founding story for CoinList?
- How did you approach the decision on whether to spinout CoinList from AngelList?
- Who was the first customer (Filecoin) for CoinList and how did you scale from there (Eg: Blockstack)?
- What were the biggest challenges running an early crypto company?
- How did you approach operating the company during the last crypto winter?
- What advice do you have for founders grappling with the current crypto winter/pullback?
- What was the strategy behind the large $100M Series A fundraise?
- What were the new services/business lines you added and how did you approach that?
- How did you nurture the marketplace and network effect dynamic at CoinList?
- Founding and leading Eco
- What was the founding story behind Eco and what led you joining the team?
- How did you build conviction on the idea and opportunity behind Eco?
- What were the early services and features that really resonated with consumers?
- How did you approach building for mainstream consumers / normies?
- How have you gotten people to switch from traditional banks to Eco?
- What is the biggest growth bottleneck (potential unlock) for Eco’s next phase of growth?
- What is our approach to building during the current downturn?
- Why should someone sign up for Eco today?
- What is your vision for the product and company?
- How do the economics for rewards and yield work in the current market context?
- How do you think about CAC and lifetime value of a customer?
- Closeout questions
- What is the most challenging/difficult feedback you’ve received — how have you processed it and incorporated it going forward?
- What are your superpowers that you find yourself leaning on often?
Links
- Learn more about Eco
- Follow Andy and Eco on Twitter
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- Click here to give feedback — it only takes a minute
Adrian is a serial entrepreneur and currently Founder/CEO of Forward. Forward is a healthcare startup that provides a membership-based healthcare system. Forward is redesigning the way healthcare is delivered using cutting edge technology that has long been neglected such as sensors, mobile, and AI.
Before Forward Adrian founded AI startup Wavii which was acquired by Google, where he subsequently led Special Projects for the entire company. In this episode we dive into Adrian’s entrepreneurial journey and how Forward is redefining healthcare from first principles.
In this episode we discuss:
- Wavii and early journey as an entrepreneur
- What led you into an entrepreneurial path?
- What was Wavii and how did it apply AI?
- How did you end up getting acquired by Google?
- How did you approach AI at Google post acquisition?
- Leading Special Projects at Google
- How did you end up working with Larry Page on Special Projects at Google?
- How did you approach structuring and creating the various Alphabet companies?
- How did you approach problems, prioritize opportunities and measure impact?
- What was working with Larry Page like and what were his greatest strengths?
- How did you apply first principles thinking when starting new projects at Google?
- Why is Forward not an Alphabet company?
- Reimagining healthcare with Forward
- What is forwards goal and what led you to founding the company?
- What were some of the principles that gave you conviction in building D2C healthcare?
- What is your perspective on competing with incumbent business models?
- What is your vision for Forward and shifting healthcare from inflationary to deflationary?
- Path to Product Market Fit and Scaling Forward
- What was your path to Product Market Fit and proving out the D2C business model?
- How did you maintain conviction and push back on calls to pivot in the early days?
- How did you figure out how to tell your story and start driving growth?
- What does your current scale look like and what have been the hardest parts to scale?
- From a consumer’s perspective, why should someone sign up for Forward?
- What do the economics look and how do you make them work without taking insurance?
- How do you supercharge doctors and build tools to turn healthcare into a product?
- What are the segments where you’re seeing the best fit today and expanding from?
- Closeout questions
- What are your superpowers that you find yourself leaning on often?
- What is the most challenging/difficult feedback you’ve received — how have you processed it and incorporated it going forward?
- Who’s the most talented person you’ve worked with & what do you respect most about them?
Links
- Learn more about Forward
- Follow Adrian and Forward on Twitter
Hit subscribe to keep up with new episodes!
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- Click here to give feedback — it only takes a minute
Dhruv is the Co-Founder/CEO of ShipBob, the leading global omni-fulfillment platform designed to provide small and medium-sized businesses access to best-in-class supply chain and fulfillment capabilities.
Dhruv started ShipBob in his Chicago apartment in 2014, and has scaled it today to over 7,000 e-commerce brands, with fulfillment centers around the world. They’ve raised $300m+ and have achieved a $1B valuation.
In this episode we discuss:
- Going from an Electrical Engineering PhD to building things
- How did you end up building things?
- What were some early ideas and products you tested?
- What led you to the problem you’re solving with ShipBob?
- How did you build conviction to quit your job and start ShipBob?
- Founding ShipBob and finding Product Market Fit
- What was the problem you were trying to solve?
- What was your initial solution?
- How does third party logistics work and what was new about ShipBob?
- How did you solution evolve over time?
- How important was timing with e-commerce wave and how did you approach competition?
- What were some of the biggest inflection points that drive growth?
- When did you know you had strong product market fit?
- Approach to blitz-scaling
- How did you approach scaling an operations heavy business?
- What was your approach to getting the unit economics right before scaling?
- How did you approach fundraising and finding the right partners for your business?
- How did you approach blitz-scaling and how did you evolve your role as a leader?
- What advice do you have for founders making the transition from pre to post PMF mode?
- Logistics market and recent disruptions
- What are some of the challenges you and your customers are facing?
- What have been some of the recent headwinds and tailwinds for e-commerce brands?
- Closeout questions
- What is the most challenging/difficult feedback you’ve received — how have you processed it and incorporated it going forward?
- What are you optimizing for at this point in your career and how has that evolved over time?
- What are your superpowers that you find yourself leaning on often?
Links
- Learn more about ShipBob
- Follow ShipBob on Twitter
Hit subscribe to keep up with new episodes!
- Follow Ashish and Zane on Twitter for summaries
- Click here to give feedback — it only takes a minute
Nikhil is a managing director at Insight Partners, where he invests in software, fintech, and crypto companies. In this conversation we talk about the recent market corrections, investment landscape in the Indian startup ecosystem, and some of the opportunity areas Nikhil is most excited about across software/SaaS, fintech and crypto.
In this episode we discuss:
- Market context and Insight Partners as a fund
- What’s your perspective on the current market backdrop?
- What are the areas Insight Partners is most focused on?
- What are you seeing behind the scenes in terms of fundraising activity?
- How has your advice/guidance for companies changed vs 3mos ago?
- What are some asymmetric opportunities for founders when fundraising gets harder?
- What are some efficiency metrics that you find yourself focusing more on?
- Opportunities areas and trends in the Indian market, fintech, and crypto
- What’s your “why now” for the Indian startup market?
- What are some recent investments you’ve made and what was most exciting to you?
- What does the earliest stage of funding look like in the Indian startup market?
- How do you think about exit scenarios and exit valuations in the Indian market?
- What’s your take on Indian fintech and opportunity areas?
- What are your thoughts on long term monetization in the Indian market?
- What types of crypto opportunities have you been focused on?
- Closeout questions
- What are some of your superpowers that you’ve learnt to rely on often?
- What is something you believe that might surprise most people?
- What content have you consumed recently that has made an impact?
Links
- Follow Nikhil on Twitter
- Learn more about Insight Partners
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- Follow Ashish and Zane on Twitter for summaries
- Click here to give feedback — it only takes a minute
Paul Yacoubian is the founder/CEO of Copy.AI. CopyAI is building AI-powered tools that help users automatically generate marketing copy in seconds, and has over 1M registered users.
Paul is an extremely positive and inspiring presence on twitter and has mastered the art of building in public. In this conversation we talk about Copy.AI, Paul’s approach to building in public, and the future of AI powered tools.
In this episode we discuss:
- Building in public
- How did you get started building in public?
- What principles guide your online content?
- What have been the benefits of building online?
- How has it helped you get early adopters and investors?
- How do you approach how much time to spend on twitter?
- What advice do you have for someone getting started building in public?
- Copy.AI and future of AI powered tools
- What is copy AI and what is the long term vision?
- How do people use Copy AI to generate copy and ideas?
- How do you make AI better at writing copy?
- What are some really popular use cases?
- How much of the AI is off-the-shelf vs your own models?
- How unique and defensible is the AI in workflow tools?
- How do users make the product better in workflow tools?
- What channels have worked best to acquire your 1M registered users?
- What has engagement, retention and monetization looked like?
- What do you think the future of AI powered creative tools looks like?
- Closeout questions
- Who is the most talented person you have worked with and why?
- What are some superpowers you have identified in yourself and like to lean on?
Links
- Follow Paul on Twitter
- Check out Copy.AI
Hit subscribe to keep up with new episodes!
- Follow Ashish and Zane on Twitter for summaries
- Click here to give feedback — it only takes a minute
Nolan is one of the best HR leaders in the world for high growth startups. He’s currently the Founder/CEO at Continuum, which is a talent marketplace that helps startups hire the best people for key functional needs, and helps executives work with multiple companies at once.
Before that he was the Chief People Officer at Carta helping it grow to a $10b valuation, Head of Talent at DoorDash from early days of 50 employees to 800+ employees, and a recruiter at Google helping scale a new org from zero to 80 engineers.
Thanks to Ashley Davis and Jessica Stolbach for contributing some great questions.
In this episode we discuss:
- Early career and landing at Google
- How did you go from being a collegiate baseball player to working at Google?
- What did you learn at Google based on how they approached recruiting?
- How did Google approach Hiring Committee and what did you learn from it?
- What did the recruiting funnel look like at Google vs startups later in your career?
- What did speed of hiring look like at Google vs Facebook, startups, etc?
- Leading recruiting for DoorDash during hyper growth from 50 to 800+
- How did you end up at DoorDash and what was the scale like? h/t Kym Lee!
- You’ve said Tony is the best recruiter in the world. What makes him so great?
- What were you optimizing for when you moved to DoorDash and why did you pick them?
- What were the challenges recruiting and how did you approach it?
- How did you maintain and raise the hiring bar while scaling quickly?
- How did you get hiring managers to own sourcing and recruiting outcomes?
- What KPIs and funnel metrics were you focused on each month/quarter?
- How did you hire people better than you? How did you help people grow?
- Leading the HR function at Carta as CPO
- What led you to Carta? What was the state of the company when you got there?
- What was the nature of the network effect at Carta that fueled the business?
- What are your observations on some of the problems with equity today?
- What are some trends you’ve seen in the talent and equity market?
- Founding story and vision for Continuum
- What is Continuum and what problems are you solving?
- What are you hearing from companies and execs on fractional opportunities?
- What is your vision for Continuum?
- What has been the most humbling part of being a first-time founder?
- Recruiting and HR at startups
- What is your HR advice for early-stage founders?
- How should founders think about HR strategically?
- When should a startup hire their first recruiter?
- What do you look for when hiring recruiters?
- How do you think about the value of an advisor?
- What makes someone a great recruiter?
- Closeout questions
- What is the most difficult feedback you’ve received?
- What are you optimizing for at this point in your career and how has that evolved?
- What are some of your superpowers that you find yourself leaning on often?
Links
- Follow Nolan on Twitter
- Read Nolan’s thread on he helped DoorDash grow from 50 to 800+ employees
- Check out Continuum— to hire an exec or join as an exec
Hit subscribe to keep up with new episodes!
- Follow Ashish and Zane on Twitter for summaries
- Click here to give feedback — it only takes a minute
Sairee is a serial entrepreneur and Founder/CEO or Sheroes. Sheroes is a social network with over 15M women. It helps empower them with a broad set of tools, community, jobs, entrepreneurial opportunities and financial services. It’s profitable and has quickly grown to several million in top line revenue. Sairee is also the founder of Mahila Money and serves on the board of PayTM Payments Bank.
In this episode we discuss:
- Founding and growing Sheroes to a profitable community of 15M women
- What led you to tech entrepreneurship?
- What led you to found Sheroes?
- What problems do you solve for women?
- What are gender rankings and how do they work?
- How are users using Sheroes today?
- How does Sheroes unlock more opportunities for women?
- How did you grow to a 15M community?
- How do you build and maintain trust in the product?
- How do you make money and what’s your current revenue?
- Fintech and startup ecosystem in India
- What led you to found Mahila Money— banking for women?
- What is the current state of fintech in India?
- Where do you see the biggest fintech opportunities in India?
- Closeout questions
- Who is the most talented person you have worked with and why?
- What are some things you believe that would surprise most people?
- What are some of your superpowers that you’ve learnt to lean on often?
Links
- Follow Sairee on Twitter
- Check out Sheroes and Mahila Money
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Kedric is a serial entrepreneur who co-founded and teaches the DeFi Masterclass, a hands-on workshop that has helped 100s onboard into the world of DeFi, learn how to research crypto opportunities, and make a passive income.
Before DeFi masterclass Kedric was co-founder of Unblockable which builds crypto and NFT/sports prediction games. He also co-founded performance marketing agency Playbook Media, and was Chief Business Officer at Exitround, a marketplace for private company M&A.
In this episode we discuss:
- The hook that got Kedric to go down the DeFi rabbit hole
- What was your first DeFi experience and aha moment?
- What led you from skepticism to curiosity to excitement?
- What DeFi is and how does it work?
- How to understand risk, returns and yields?
- How DeFi yield farming works and generates passive income
- How does DeFi work in a decentralized way and eliminate middlemen?
- How do transactions between two assets or parties happen in DeFi?
- How does decentralized finance increase automation, lower costs, and increase access to yield/revenue from automated market making?
- What is driving yields and rates of return on assets in DeFi?
- How to identify, research and evaluate yield opportunities/risks
- What are the different ways to invest and earn a return in DeFi?
- How do you research opportunities and filter signal from noise?
- How do you evaluate potential based on narrative/speculation, and cashflow/DCF?
- What are some examples of crypto projects with low DCF valuation right now?
- How do find information/data to analyze yield farming opportunities?
- What are the categories of risks a crypto investor should bear in mind?
- What is your framework for evaluating risk, returns and constructing portfolios?
- What are typical returns for low risk, med risk and high-risk opportunities?
- How to earn 32.9% ROI per year through a simple risk management portfolio framework?
- How do you think about counter-party risk for stable coins?
- Outlook on future of DeFi and yields
- What are the biggest barriers to more trust and adoption of DeFi?
- What is your take on government oversight and the regulatory landscape?
- Whats your outlook on yield farming opportunities in the current crypto landscape?
- Closing questions
- Who is the most talented person you have ever worked with?
- What is something you believe that would surprise most people?
- What superpowers do you like to lean on day to day?
- Who are some people that have helped you along the way?
Links
- Follow Kedric on Twitter
- Check out DeFi Masterclass and sign up for the hands-on workshop! We couldn’t recommend it more highly. We made our class fee back in just a few months.
- Learn more from Kedric on yield farming portfolio construction to earn best in industry returns while managing risk and how DeFi can reduce the wealth gap
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Sean is founder and CEO of HealthTap which makes primary care affordable and easy to access for all Americans.
In this episode we discuss:
- HealthTap’s virtual primary care clinic
- Affordable solution for all Americans regardless of whether they have insurance
- How it works from user experience to business model
- Types of conditions and issues that can be treated through primary care
- How HealthTap approaches different use cases and care scenarios
- Building a healthcare product and company
- How to get early traction
- Importance of patience and resilience
- Maximizing luck surface area
- Being early to telehealth and growing with the market
- Impact of pandemic to tele-health
- Exploring multiple business models in healthcare
- Connecting consumers online with 90k physicians
- Building a trusted Doctor powered UGC powerhouse
- Leveraging UGC to build a subscription telehealth business
- What makes for a great subscription in healthcare
- Opportunity size around content and telehealth SaaS
- How they built a content machine online
- User experience decisions that drove engagement and quality
- Regulatory challenges when innovating in healthcare
- How Sean has remained engaged building HealthTap for over a decade
- Impact of pandemic— what was over-hyped and what accelerated
- Closing questions
- Most talented person Sean has worked with and why
- Whats something you believe that would surprise most people
- Who Sean’s heroes are and what inspires him
- What superpowers do you lean on day to day
Links
- Follow Sean on Twitter
- Read more about HealthTap
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Mari has held a variety of incredible roles in Silicon Valley as a product veteran, company builder, and now board member. Mari started her career in startups. She was one of the first 30 people at Intuit and helped grow the company grow over 10 years into a public company with thousands of employees.
At Intuit, Mari went from being a Product Manager for Quicken to SVP and got to work closely with industry legends like Scott Cook and Bill Campbell to shape Intuit’s products and culture. Intuit of course is well known for having one of the most customer centric product cultures and has successfully navigated multiple technology and platform shifts— from Command Line to GUI, PC to Web, and Web to Mobile. Mari shares some incredible lessons and insights from the early days that shaped Intuits product culture.
We also talk to Mari about her more recent work serving on the boards of Stanford, and Blue Shield of California. We talk about how University boards work, Mari’s role in founding the Stanford Women’s Leadership Innovation Lab to tackle the under-representation of women in our industry, and opportunities for innovation in the healthcare space.
This is an incredibly wide-ranging conversation where we cover so many interest topics spanning Mari’s incredible career as a product builder, company builder and board member.
In this episode we discuss:
- Starting out in Silicon Valley and being early at Intuit
- What was the valley like at the start of the PC revolution?
- Intuit’s first product was Quicken (for personal finance), what was the original insight?
- What made you join Intuit when it was a small startup?
- How big was Intuit when you got there and when you left?
- How Intuit has built customer obsessed products across multiple decades
- Intuit was known to be extremely customer focus, how did y’all approach that in the early days and build the product culture?
- How did Quicken (personal finance) lead to Quickbooks (SMB accounting)?
- How did Mari approach marketing at a time when people were new to computers and software?
- Working with Scott Cook and Bill Campbell to shape Intuit products and culture
- How did Scott Cook approach product management during early days of software?
- How did Intuit build its customer centric culture?
- You got to work closely with Bill Campbell. What were his superpowers that helped him become such a legendary leader?
- Serving on the Board of Trustees at Stanford and setting up the Stanford Women’s Leadership Innovation Lab
- What does the Board of Trustees role at Stanford entail?
- What led you to setting up the Stanford Women’s Leadership Innovation Lab?
- Serving on the board of Blue Shield of California which is a non-profit insurer with 4.5m members and $21b in revenue
- Where do you see the biggest opportunities for technology to transform healthcare especially in a post Covid world?
- What’s your advice for healthcare founders trying to figure out trade-offs between B2B vs B2C business models?
- Closing questions
- Who is the most talented person Mari has ever worked with and why
- What’s something you believe that would surprise most people
- Who are some of Mari’s heroes that she admires
- What superpowers does Mari lean on day to day
Links
- Follow Mari on Linkedin
- Stanford Women’s Leadership Innovation Lab
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Dmitry is the founder of Tortoise ($11m raised), which is building remote-controlled mobile vending machines, which are the world’s first “smart stores”. It takes less than 15 seconds to complete a transaction with frictionless tap-to-pay user experience and Tortoise is piloting these robots in at least a dozen cities around the world. In this episode we talk about how Dmitry approached building a robotics and automation startup, and the many decisions that led Tortoise to where it is today.
We also talk about Dmitry’s stellar early career and lessons learnt from being part of the early team at Facebook, Pulse, Linkedin and Uber. Dmitry shares his best career advice, some incredible stories from the early days of Facebook/Linkedin, and his experience at Uber where he championed the JUMP acquisition and overall multi-model mobility strategy.
In today’s episode we discuss:
- Early Facebook experience
- What Facebook got right in the early days, and lessons from that experience
- How Dmitry managing the Zynga partnership from early days to it becoming the biggest single largest source of revenue for FB in 2009/10
- Some of the people Dmitry learnt the most during that experience
- Advice on how to navigate hyper growth, and Dmitry’s best career advice
- Pulse, LinkedIn, and Uber experience
- How the culture at Linkedin differed from FB
- How Dmitry ended up at Pulse working on early mobile/tablet experiences
- How the environment at Uber changed from before/after the media storm
- How Dmitry framed the strategy that led to the JUMP acquisition
- How Uber thought about the business case for new modalities
- Dmitry’s view on the big opportunity for micro-mobility (Bird, Lime, JUMP, etc.)
- Founding Tortoise and building autonomous delivery robots
- Core pillars to bring robotics / automation products to market
- Last mile, middle mile and mobile vending use cases
- How the Tortoise mobile smart store works (world’s first!)
- How Dmitry thinks about cost strategy for autonomous robots
- How Tortoise built a 15-second frictionless tap-to-pay checkout experience
- How much the mobile stores sell every hour and how many are live (dozen cities so far)
- What it takes to build and manufacture a robot (hardware iteration loops)
- Dmitry’s fundraising advice for a hardware and robotics startup
- Closing questions
- Most talented person Dmitry has ever worked with
- What superpowers does Dmitry lean on day to day
- Who are some people that have given him a break
- Who are some of Dmitry’s heroes that inspire him
Links
- Follow Dmitry on Twitter
- Read more about Tortoise
- Tortoise mobile smart stores
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Don Stalter is a Partner at Global Founders Capital (GFC) and has an incredible portfolio of investments including Brex, Deel, CultureAmp, Checkr, FamPay and many more. Before transitioning into an investment role, Don was a co-founder of CityDeal which he sold to Groupon, and subsequently led International at both Groupon and Airbnb.
In this conversation we talk about Don’s learnings from working on two of the most explosive marketplace companies of the last decade (Groupon and Airbnb), and trends/opportunities he’s seeing in Marketplaces, Future of Work, and Fintech.
In today’s episode we discuss:
- Early career
- What led you into investment banking and M&A work early in your career?
- Having worked on blockbuster deals like Google/YouTube, Google/DoubleClick, Disney/Pixar, what were your biggest learnings from those experiences?
- Founding CityDeal and selling to Groupon
- What led you to founding CityDeal and ultimately sell to Groupon?
- What was your approach to running international at Groupon?
- What did Groupon get right in the early days, and what could they have done better?
- International at Airbnb
- What was your approach to international growth at Airbnb?
- How did you prioritize what to focus on during hypergrowth?
- Marketplace investments
- How do you evaluate marketplace businesses as an investor?
- What are your thoughts on B2B marketplaces which seem to be a new trend?
- What have been some of your learnings investing in digitization of older industries?
- Future of work investments
- What was your original thesis that led to investments like Deel, CultureAmp and Checkr?
- In a pod covid world, how do you think about remote tooling opportunity for productivity?
- Fintech investments
- What are some trends and thesis you’re most excited about?
- What are your observations on crypto and NFTs?
- Transition to VC
- What do you think makes a great operator vs a great VC?
- Has your operating background helped you as a VC?
- Closing thoughts
- What are your superpowers that you like to lean on day to day?
- Who are some people that have given you a meaningful break?
- What books have had an outsized impact on your life?
Links
- Follow Don on Twitter
- Some companies mentioned in the episode: Blueland, Cedar.ai, Checkr, Deel, Brex, Karat
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Qiao Wang is the co-founder of Alliance DAO, which is the leading web3 accelerator and builder community. In terms of impact, Alliance has helped accelerate 10% of the top crypto projects by market cap. Their most cohort had 30 companies building web3 products across DeFi, Social, NFTs and Gaming. Before Alliance, Qiao was the Head of Product at Messari which is a market intelligence product that provides advanced analytics for crypto.
Special thanks to Roberto Riccio and Brian Ma for providing questions for this conversation.
In today’s episode we discuss
- Crypto Landscape
- What led to a perfect storm for decentralized technologies?
- How has pace of innovation progressed vs expectations?
- What could web3 native social networks/products look like?
- Opportunity Areas across DeFi, SocialNets, Gaming
- What are opportunity areas where Qiao is seeing startups get traction?
- What are some examples of interesting projects in different verticals?
- What are the main motivations for people playing games like Axie?
- What are some opportunities for financial products to build social experiences?
- Getting Messari off the ground to provide advanced analytics for crypto
- What was the unique insight when founding/building Messari?
- What were the first products / features that got PMF?
- How much to rely on intuition vs user feedback/research for crypto products?
- How did they approach pricing for their paid plans?
- How did they approach governance and tokens?
- Accelerating web3 with Alliance accelerator and community
- What is Alliance today and how did it start?
- How big is each cohort and what categories are most projects/companies in?
- How does the accelerator work and how does Alliance accelerate teams?
- What makes for a great Alliance founder?
- How to build Crypto Native products and companies
- When and how to launch a token?
- What are regulatory implications?
- How to fundraise for web3? How to vest?
- How to manage trade-offs between PMF and Tokens?
- How do SAFEs and SAFTs work?
- When and how to decentralize without losing vision and execution leadership?
- How to leverage DAOs in an effective way?
- Future of DAOs as Digital Nations
- How might DAOs re-shape society?
- What is the core value proposition of a DAO?
- How to build the right incentives with tokens and DAOs?
- How might DAOs enable digital nations with property rights and laws?
- Crypto and web3 trajectory
- What has to go right for crypto products to continue to go mainstream?
- Has crypto and web3 reached escape velocity? What are the biggest risks?
- Closing thoughts
- What are your superpowers that you like to lean on day to day?
- Who are some people that have given you a meaningful break?
- What books (or articles or podcasts) have had an outsized impact on your life?
Links
- Apply to the next cohort of AllianceDAO
- Follow Qiao and AllianceDAO on Twitter
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In this wide-ranging conversation, we chat with Blake about his experiences starting out his professional career as a musician, and all the key experiences and trends that led him to founding the Goldfinch decentralized lending protocol (recent $25m Series A from a16z, and $500M DAO).
This is an incredibly rich conversation where we explore so many interesting topics. Some select highlights: the similarities between being a musician and an engineer, and between being in a band and a startup. How the Goldfinch protocol works and Blake’s most ambitious vision for it. Advantages of setting up Goldfinch as a DAO. Predictions on NFTs. The areas where crypto really shines and the trends that are moving more and more economic activity on chain.
Blake is a brilliant and clear thinker, and we learned so much from this conversation. We hope you enjoy it as much as we did.
Episode Highlights
- Being a full-time musician after college
- Putting small things together to make big things as a musician, and engineer
- Joy of working on a small group, and being in a band vs startup
- Learning to code after college and transitioning over to software engineering
- Early inflection points at Hint Health (Employee #1) and Coinbase
- Approach to hiring engineers at Goldfinch
- How Blake got into crypto and what got him interested
- Magic of decentralization and many interfaces sitting on top of the same data
- Recent LooksRare token launch
- What Goldfinch does and how it’s different from other crypto lending protocols
- Under-collateralized lending for real-world scenarios in a decentralized way
- Approach to finding the right market and getting early PMF traction
- How the lending protocol works — across borrowers, backers and LPs
- More liquidity as one of the places where crypto really shines
- Most ambitious vision for the protocol
- Trends moving more economic activity on chain
- Goldfinch is setup as a DAO — how that works
- Tradeoffs between DAOs and Centralized Organizations
- Thoughts on the current bear market cycle
- Blake’s secret to making rapid progress with Goldfinch
- What mission-driven means to Blake
- DeFi advantages: natively global and interoperable by default
- Prediction on profile NFT pics coming true
- Crypto wallets as bottomless digital backpacks
- Predictions on NFTs— “can’t lose” way for brands and creators to engage super fans
- Building great co-founder relationships and handling high pressure situations
- Recruiting his initial boss at Coinbase to Goldfinch
- Superpowers and book recommendations
- Structure of Scientific Revolutions— the book that coined the term “Paradigm Shift”!
Links
- Goldfinch: the protocol bringing crypto loans to the real world
- Hummingbird Notation (early side project)
- Blake’s Op-Ed on NFTs from April 2021
- Follow Blake on Twitter
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In this conversation we chat about Don’s experiences in the crypto world as Managing Partner of QuantStamp, and through multiple cycles over the last decade. We spend most of our time talking about his recent experience co-founding OrangeDAO which is a collective of 1k+ YC founders helping build an accelerate web3.
Don walks us through how he thinks about building communities, why DAO’s are exciting, and shares a breakdown of how the OrangeDAO was setup— across the early community, token design, building products, raising a venture fund, and how everything fits together.
This is an inside look into how cutting edge DAO communities work today and why they’re such an exciting glimpse into the future. We hope you enjoy this conversation!
Episode Highlights
- Growing up in Silicon Valley around people doing seemingly wacky, wild, strange things
- Investing in Vietnam and facing remittance issues that led him to Bitcoin
- Crypto as Financial Rails 3.0 and a wrapper to solve coordination problems
- QuantStamp as a Verisign of crypto with over $40b of value secured
- Most surprising things since being early to crypto— rate of consumer adoption
- Decentralize everything vs just things where crypto drives user value
- How B2B opportunities in crypto have evolved since 2017
- How to build a great community, and how to build a DAO
- Why people organize- to express themselves and feel a sense of belonging
- Keys to enduring communities- clear purpose on what they’re trying to achieve, and why people should be joining
- What is a DAO- communities that have a software layer and ownership component, with embedded incentive based coordination layer
- DAOs as a more scalable version of Co-Ops, on a blockchain
- How to start a DAO, and how and why OrangeDAO was founded
- OrangeDAO: largest collective of builders wanting to build or invest in Web3.. going from a WhatsApp group to a DAO to keep up with interest; today a collective of 1k+ YC founders
- Raising an Orange Fund with $10m+ to invest in early Web3 companies
- How to setup a fund, and setup a DAO as the coordination layer
- How ownership and governance works in a DAO
- Designing token economics for OrangeDAO and how everything fits together
- How DAOs incorporate, get bank accounts and hold assets
- Products developed by OrangeDAO: YC gem for web2 to web3 oAuth and token gated communities, and LFG reputation game to bet on founders and companies on chain
- Don’s super powers and vision for OrangeDAO
Links
- OrangeDAO: collective of 1k+ YC founders helping build and accelerate web3
- QuantStamp: leaders in blockchains security and solutions
- Great tools for DAOs: Syndicate, Multis, Bank Mercury
- Follow Don on Twitter
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In this conversation we chat about Linda’s journey from a traditional consulting career to startup rocket ships (Snap and Faire), product management, and entrepreneurship.
We start out talking about the early days at Faire and key growth unlocks that helped it quickly grow from $50m to $2.5b, and now a $12b valuation. Linda was an early product leader, and saw it grow from 14 to 300 employees. We then talk about challenges when growing that quickly and reflections on ideal culture at fast growing startups. Finally, we talk about Linda’s path towards starting Product Lessons, and building an engaged audience through her terrific writing.
We hope you enjoy this amazing episode!
Episode Highlights
- Early career at Bain and transitioning to startups
- Consulting as a professional bootcamp
- Operational and product culture at Snap
- Transitioning into PM roles at a startup
- Faire: b2b marketplace for brands/makers and retail stores
- What drew her to Faire ($12b co now) and early culture
- Key growth unlocks at Faire, and building b2b virality
- Going from as Employee 14 ($50m valuation), to 300 employees ($2.5b valuation), and 1000 employees ($12b valuation)
- Transitioning to being a being a solo entrepreneur
- Ideal culture at fast growing companies
- Importance of talent density
- Writing/creating, building product toolkit, and starting product lessons
- Power of building email lists
- Top Startups project to help people find great startups and jobs
- Building an audience: find a format that works for you
- Having a “red pill”: what are you willing to say or share that no one else is saying or sharing?
- Mastering your own psychology
- Superpowers, lucky break and books
Links
- Product Toolkit
- Product Lessons
- Top Startups
- Follow Linda on Twitter
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In this conversation we chat about so many key moments in Sanders journey cofounding, building and scaling Thumbtack into a $3.2b business with 900+ employees over 13 years.
We start with the founding story and weekly brainstorm calls that led to the company. We then talk about the four key phases of building a successful marketplace startup, from finding product-market fit to hyper-scaling. And finally, we talk about how Sander and his co-founders built incredible long term relationships, working together for 13+ years.
We hope you enjoy this amazing episode!
Episode Highlights
- Growing up in DC and going to Law School
- Two big levers to make a difference— Politics and Technology
- Thumbtack founding— weekly phone calls brainstorming ideas for a year
- Thumbtack today 13 years later— 900+ employees, over $500m raised, $3.2b valuation
- How to come up with good ideas, and innovation as a deliberate process
- Alternate ideas and names explored (like “TimeStrapped!”)
- Marketplace liquidity as most important thing in early days
- Early days: solved supply first, then focussed on demand for 18mos
- Key moment in unlocking demand: early SEO insight and strategy
- Key to growing fast: one big channel where you go super deep
- Barriers to entry for more founders that prevent taking risk
- How Sander overcame those barriers and how it shaped his thinking on risk
- Challenges raising early VC based on user growth alone— 45 A-round passes
- Four key phases: building supply, building demand, finding the right revenue model, hyper scaling
- Challenges and frustrations during the hyper scaling phase
- Reflection on power of focus, and also narrative/PR
- Power of hiring exec coaches to scale as founders and a team
- Building strong co-founder relationships: structured approach, and long term focus
- Advice for founders and building successful long term working relationships
- Putting on blinders and focussing on what you can control
- Scaling as a founder and building out multiple different areas
- Operating in your zone of genius to stay energized for 13+ years
- Thumbtack’s culture and how they built and shaped it
- Framework for giving/recieving feedback and turning it into an action plan for growth
- Reflections on Thumbtacks superpowers and shadows of those strengths
- Book recommendation: Design Your Life
- New projects: (1) Scaled- bringing innovation to recruiting (2) New mobile dog grooming business that can train and up level anyone to earn $100k+
- Sander’s super power, lucky breaks, and book recommendations
Links
- Start using Thumbtack to find local professionals for pretty much anything
- Hire People, Finance, Legal talent with Scaled
- Follow Sander @sanderdaniels
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In this conversation with Alanna we talked about pivotal moments in Alanna’s journey from working on emerging markets research on Wall St, to founding a YC backed marketplace startup, to growth marketing leader at Afterpay. Alanna has a broad and unique perspective on startups, fintech and crypto, and in this conversation we cover a wide range of topics across all three.
Episode Highlights
- Starting her career on Wall St during the 2008 financial crisis
- Culture working in finance vs tech
- Founding VIVE — what drove her to marketplaces
- Vision to build a marketplace that helps salons acquire customers
- Explosive early demand — 14,000 customer waitlist
- Challenging unit economics — trade-offs between unlimited usage and credit system
- Explorations — marketplace vs SaaS vs bundling CPG products
- Key learning — PMF is about finding and meeting demand in a scalable way, unit economics and margins important even at early stages
- Joining AfterPay to lead growth marketing for engagement and retention
- Approach towards consumer vs merchant, and checkout product vs standalone app
- Thoughts on fintech and potential risks in the system
- How startups build/validate a new lending product as a startup and risks to manage
- Thoughts on DeFi and NFTs — both quickly going more and more mainstream
- How NFTs and e-commerce could merge and enable new products and marketing levers
- Thoughts on what might happen if interest rates go up — mental model on opportunities if markets retreat or become more volatile
- Super powers on spotting talent and hiring, people who have her a break, and books
Links
- Follow Alanna @alannaeve on Twitter
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Summary
In this conversation with Vrinda we cover a wide range of topics including how the current credit system works, why women are more likely to have negative credit experiences, and how Sequin solves that inequity gap with a new debit card for women that helps build credit. We also talk about the process of launching a new card based product at a bank vs. a startup, and both opportunities and challenges to innovate in the space.
Episode Highlights
- Working on Chase Sapphire card at Visa and getting rejected for it
- Challenge of credit: needing credit to get credit
- How credit score gets calculated and factors contributing to bias
- Why women get rejected for a credit card more often than men
- Speed of launching a card at a bank vs. as a startup
- Considerations in designing a new card
- Building Sequin as a debit card that builds credit
- How to think about benefits as a fintech startup vs at scale
- Surprising insights: huge appetite for knowledge, community and card design
- Approach to education and community building as a fintech
- Vision for Sequin: full suite of credit products for women across every life stage
- Going from fintech idea to prototype/MVP as a non-technical founder
- Insight: importance of credit utilization to build credit
- Moving fast without breaking anything as a fintech
- Early next year: re-launching the debit card that builds launch with rewards partners
- Opportunity to create hyper personalized products that grow with customers
- Superpowers: capacity for empathy and how she's built it, and ability to pattern match
- People who gave Vrinda a break, and book recommendations
Links
- Read more about Sequin ($5.7m Seed) and get the card: https://www.sequincard.com/
- Follow Vrinda @vrinda_tweet
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Summary:
Conversation with Shamir Karkal, co-founder of Sila. Prior to Sila, he was co-founder of Bank Simple, which was the first US neobank and early fintech pioneer. For many it was one of the most exciting and groundbreaking products of the last decade. We talk about the Bank Simple story, banking and fintech landscape, and his new company Sila. Sila makes it easy for any business to program money through APIs for digital wallets, linked accounts, ACH, money storing, transferring and payouts.
Episode Highlights:
- Career path from software engineer to consultant at McKinsey with financial services clients
- Founding story and vision for Bank Simple — first US neobank, founded in a Brooklyn basement
- Why starting a bank in 2009 was crazy, and how the landscape evolved after the 2008 financial crisis
- Inventing the modern fintech bank partnership model and path to market with a simpler bank that replaced retail branches with software and no-fees
- Story behind selling to BBVA for $117m after raising only $20m
- Getting excited about building fintech platforms to make access to banking infra easier, and founding Sila
- How Sila makes it easy for any business to program money through APIs for digital wallets, linked accounts, ACH, money storing, transferring and payouts
- History of regulatory landscape around getting a full banking charter — 100s a year before 2008 to just a handful in the following decade, and how its becoming more feasible again
- Pros and cons to having a banking charter— ability to lend FDIC insured deposits and fully leverage the "3, 6, 3" business model
- How cyclical nature of credit industry and credit crunches makes stable FDIC deposits high-value for the lending business model of banks
- Bank Simple's business model, unit economics and strong early growth
- Activation and direct deposit as a key product lever for newer neobanks
- Looking forward, why global financial services industry is exciting— $17T annual revenue industry, 30x larger than $600b global advertising industry (out of ~$100T global GDP)
- Opportunity for fintech to go from 1% market share to 10% this decade
- Prediction: fintech and crypto in 2030 could be as big as all of tech in 2020, with few $1T+, few dozen $100B+, and 100s of $1B+ companies
- Crypto doesn’t change underlying trends but might accelerate through faster/easier permissionless innovation on a global scale
- Regulators can’t control on chain work but can regulate on/off ramps and how Sila enables on/off ramps and connectivity between crypto and traditional banking through flexible APIs
Links:
- Read more about Sila: https://silamoney.com/
- Follow Shamir on Twitter: https://twitter.com/shamir_k
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Summary:
Conversation with Paul Sawaya, co-founder of Human Interest, $1b company that makes it easy for SMBs to provide 401k savings plans to their employees, and helps employees save for their retirement.
We cover so many interesting topics in this conversation across the Human Interest story, numerous lessons learnt, and technologies he's most excited about for the future.
Episode Highlights:
- Early experiences like building an FB app at Bloomberg
- Interviewing with Emmett Shear to interview at Justin.TV
- How big company vs tiny startup experience made him want to start a company
- Spending 2 years exploring problems and ideas
- Challenges and lessons from wandering the wilderness
- Key lesson: focussing on problems first before jumping into futuristic projects
- Got excited about solving 401k access problems which led to Human Interest
- Only 20% small companies offered 401ks due to setup, admin and cost challenges
- Product innovation: automating operational work to lower cost structures and expand access
- Building on top of back-office solutions to learn/move fast, then moving in-house
- How they moved fast to get early customers for feedback and validating demand
- How to spend time during exploration/sabbatical: establish a routine and talk to lots of people
- Approaching GTM through an effective partnership and integration strategy
- Cleaning up some shady 401k practices by offering better, sustainable solutions
- Transitioning out of day to day Human Interest work to spend time with early stage startups
- Exploring new ideas for his new project and things he's excited about
- Exciting breakthroughs other people might be under-appreciating: Web Assembly to run high intensity server side compute locally in the browser, and AI to reimagine user interfaces
- Prototyping to explore and learn new things
- Ability to enter ambiguous, messy situations and find a path forward
- People who gave him an early break that he is grateful for
- Power of developing personal values as a guiding light
Links:
- Read more about Human Interest: https://humaninterest.com/
- Follow Paul on Twitter: https://twitter.com/automin
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Conversation with Jim Brusstar, co-founder of Treasury Prime, which is building APIs to connect a network of banks to fintechs. They make it easy for fintechs to partner with the right bank, and reduce the time to market for a neo bank or embedded banking product from years to months.
We cover so many interesting topics in this conversation — starting with being early at Sidecar and lessons learnt from competing with Uber and Lyft, being early to fintech with Standard Treasury which built banking APIs and sold to Silicon Valley Bank, how banks work under the covers, and why he decided to found Treasury Prime (with same mission as Standard Treasury).
We also talk about why Jim is excited about fintech and how most people underestimate how early we are in fintech overall— with lots of headroom for innovation and growth.
Episode Highlights:
- Why Jim decided to start a company
- Early days at Sidecar — and inventing ride sharing
- Sidecar — getting out executed by Lyft and Uber
- Thanksgiving 2012 — cease and desist to all ride sharing companies
- Early fintech — building "Banking in a box" APIs at Standard Treasury and being too early
- Acquisition by Silicon Valley Bank and how banks work under the covers
- Banking business model (incentives) — buying deposits and selling loans
- Starting Treasury Prime — with same mission as Standard Treasury
- Building a network of banks — infra layer with modern APIs + match Fintechs with right bank
- How infra layers and APIs unlock innovation — reducing time to market from years to months
- Use cases and business models on top of Banking APIs
- Benefits of using Treasury Prime to connect with a network of banks
- Why Fintech is super early — less than 1% of all deposits today and where next gen will bank
- Thoughts on crypto use cases — international remittences and programatic settlement
Links:
- Read more about Treasury Prime Use Cases and Banking APIs
- Follow Jim on Twitter at @JimBru
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Conversation with Sam Corcos, CEO of Levels health, who is a prolific serial entrepreneur and building one of the most exciting companies in healthcare today. Levels is a groundbreaking product that helps people track their blood glucose in real-time to understand and improve their metabolic health.
We talk about key lessons Sam learnt from his first few startups, why he took a year off before starting levels, how he honed in on the idea for Levels, his approach towards building a radically open company, and areas he's most excited about for the next 5-10 years.
This episode is packed with real insight into what it's like to be a serial founder, and full of actionable advice on how to explore ideas, find purpose, and work hard without burning out.
Episode Highlights:
- Early startups and nomadic adventures
- Building a high-trust culture that supports risk taking
- Thoughts on hiring as a matching problem
- Why (and how) he's building a radically open company
- Biggest lessons from Sightline Maps and CarDash
- Building effective co-founder / interpersonal relationships
- Sam's framework for choosing what problems to work on
- Why he took a year off before Levels and how he structured his time
- Approach to network management and maintenance
- Approach to time management while exploring ideas
- How he converged on the Levels idea and product
- What Sam's excited about for the next 5-10 years
- Thoughts on synthetic biology
- Sam's superpowers and how he's honed them
Links:
- Check out Levels' product and unlock your metabolic health
- Follow Sam on Twitter at @SamCorcos
- Read more about why Levels is building in public
- Levels' internal company podcast
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Conversation with Brian Ma - who interned at Zillow when it was 15 people, joined as employee #32, and went on to become a prolific serial entrepreneur. We talk about his entrepreneurial journey founding Decide.com, Weave, Divvy Homes ($2b unicorn), and most recently, a SE Asia focused Seed fund and accelerator.
Some highlights from the conversation include how he skipped high school, why he joined Zillow, his first few companies, going on a "vision quest", his approach to exploring new ideas, the early days at Divvy Homes, and his recent fund and why he is excited about investing in South East Asia.
Episode Highlights:
- Brian's life mission and how it led him into startups
- Skipping high school and doing early-entry and Univ of Washington
- Interning at Zillow when it was 15 people and being an early employee
- First company: Decide.com
- Moving to Silicon Valley, starting Weave, and YC experience
- Going on a vision quest
- Approach to exploring new ideas
- Working with Max Levchin to incubate Divvy Homes
- Early days and finding PMF at Divvy Homes (now $2b unicorn)
- Why he started Iterative.VC and is excited to invest in SE Asia
Links:
- Follow Brian on Twitter at @zealoustiger
- Read more about Divvy Homes and how rent-to-own works
- If you're a startup in South East Asia, apply to the next cohort of Iterative.VC
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Conversation with Bo Jiang - founder and CEO of Lithic, which offers an API for card issuing. We talk about Bo's incredible journey starting out as a consumer focussed company (Privacy.com), and pivoting to Lithic, which is an easy to use API for card issuing.
Today, Lithic is one of the fastest growing company in Fintech and recently announced a Series C at an $800m valuation. In this conversation, we focus on the early days and pivotal moments in Bo's journey.
Episode Highlights:
- Growing up in the midwest
- How Bo got started building products
- Story and insight that led to Privacy.com
- Challenges building on a legacy processor
- Anatomy of a card transaction - acceptance vs issuance
- Why they built their own infrastructure for issuance
- Lightbulb moment to pivot from Privacy.com to Lithic
- Programmable money and new use cases the Lithic API enables
- Impact of Covid - metrics and remote work
- Thoughts and reflections on crypto
Links:
- Follow Bo on Twitter @bolingj
- Read this terrific analysis on Not Boring to learn more about Lithic
- Check out the Lithic website to explore use cases and get started with the API, and Privacy.com for personal payments
- Lithic is growing fast and hiring across almost all areas -- explore their open opportunities
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Conversation with Prasanna Sankar - whose most recent company, Rippling, went from zero to $1.35b valuation in less than 4yrs. We talk about his experiences working on startups for over 10 years, finding and scaling success at Rippling, and why he believes crypto will be a transformative new economic engine.
Episode Highlights:
- Getting started as a programmer in high school
- Approach to building from first principles and becoming the top ranked coder in India
- Moving from Microsoft Bing team to Silicon Valley and pitching to Paul Graham
- Building LikeALittle - hyper-growth phase, passing on M&A, eventual crash and burnout
- Joining Zenefits and the visionary genius of Parker Conrad
- Founding Rippling - clear and ambitious vision requiring a large up-front build
- Path to $1.35b valuation in under 4 years, leading to hyper growth and scaling phase
- The blockchain movement and why it could be the next big thing
- Thoughts on crypto use cases and framework for how adoption will grow over time
- Ethereum as the gateway into crypto-native activities
- Exciting infrastructure being built today - faster Ethereum, and high speed bridges between chains
- Why blockchain will be the economic engine for the future, and how it allows creators to maximize wealth creation
- Thoughts on planned move from the US to Singapore which is becoming the "crypto capital of the world"
- Recommended reading: Tendermint white paper on Consensus without Mining
Links:
- Follow Prasanna on Twitter at @myPrasanna, check out his terrific blog, and his AngelList fund
- For more of Prasanna's thoughts on crypto/blockchain, check out his blog post on Building a Trillion Dollar Crypto Business, and his talk on Blockchain- The New Steam Engine
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Interview with Jonathan Wegener -- one of the most innovative product thinkers we know. We talk about his experience founding Timehop, working on Evan Spiegel's design team at Snap, and what he's working on next ("active" audio-based products).
Episode Highlights:
- How Jonathan got started building products
- How he got into startups and started building online businesses
- How Timehop started at a Foursquare hackathon
- Timehop early traction and explosive growth
- Lessons from raising Series A and hyper growth phase
- Facebook launches competing "on this day" product
- Timehop's evolution and new advertising business
- Joining Evan's design team at Snap
- Snap's vision driven design culture "Willy Wonka chocolate factory of tech"
- What he's working on now-- Active Auditory Experiences
- Framework for Active Audio (Eg: Detour), Passive Audio (Eg: Music), Active Video (Eg: Gaming) and Passive Video (Eg: Netflix)
- How and why Active Audio experiences could be a big new category
Links:
- Follow Jonathan on Twitter at @JWegener
- Download his latest app GoGoGames! to experience active audio adventures
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