Every week, I interview brave founders, uncover the epic stories, and elicit profound insights about what has helped them achieve breakthroughs in their business.
Over the years, as I’ve met hundreds of founders and talked about their challenges, I’ve often had this illusion that there are a million different problems holding startups back.
But recently – as I really dug into it – I’ve realized that there is really 1 problem that defines whether or not a startup is going to go to the moon – or fizzle out and die.
Today’s guest, Alex Kottoor has made a similar observation.
The distinction is around whether or not you achieve product market fit or PMF.
And the path to get there – Go To Market or GTM – requires an amazing amount of vision, action, and most importantly persistence.
Alex and I had a fascinating discussion where we boiled down what separates founders who are able to make it through this journey – and those who give up.
How to know when you need to buckle down and push harder – vs when you need to step back and get new options.
And why startups need to keep their energy focused on GTM and not get sidetracked by all of the other temptations along the way.
It was a fascinating discussion – and I hope you get some gems out of it.
Links:
Alex: https://www.linkedin.com/in/alexkottoor/
Dena Startup Lab: https://www.denastartuplab.com/
We’ve talked quite a bit on the pod about Product Market Fit – and hammered home how critical that milestone is to the success or failure of any startup.
But there’s an even more important factor that needs to be considered – and that’s founder market fit.
Before starting his current venture, today’s guest, Shawn Miller, developed a deep understanding of the problem he wanted to solve through his own direct experiences.
Not only does founder market fit make it easier to persevere when the going gets tough – it also makes sure you have the right lens to catch opportunities as they arise, and to separate the signal from the noise.
I had a ton of fun talking about Shawn’s background – how it informed his idea for inbound – and how it has drastically increased the odds of the company achieving product market fit.
I gained so many great insights talking with Shawn – and I hope you do as well.
Links:
Shawn Miller: https://www.linkedin.com/in/shawndavidmiller/
Inboundr: https://www.inboundr.ai/
Today’s episode features a conversation with Lee Lorenzen, a seasoned entrepreneur - and self proclaimed Forrest Gump of founders - who’s been building startups for over five decades.
From mowing lawns as a kid to working at Xerox during its golden years of innovation, Lee has seen the tech industry evolve in some fascinating ways.
In this conversation, we dive into:
• How seeing the future at Xerox helped shape his entrepreneurial journey
• Navigating major technology trends over the years
• The tension between seeing the future and living in the present
• Building startups with a mission-driven mindset
• How founders can take advantage of a non-traditional funding approach outside of VC circles
It’s an engaging discussion filled with valuable insights and stories from Lee’s incredible career.
Links:
Altura Ventures: https://www.altura.net
The gig economy is booming, but there's still a gap when it comes to odd jobs and local services.
Derreck Stratton, the founder of HUDU – who we first interviewed back in episode #2 – is looking to bridge that gap with an innovative platform.
During our conversation, we talked about:
· How Hudu is revolutionizing the way people find help for odd jobs and tasks
· The challenges of building and scaling a two-sided marketplace
· The importance of focusing on your core markets before rapid expansion
· How AI is being integrated to make the user experience seamless
· The potential for Hudu to enable a new kind of "physical nomad" lifestyle
· And the journey from launch to achieving product-market fit
You can learn more about Derreck and HUDU at:
HeyHUDU.com
The entrepreneurial journey is full of ups and downs, pivots and persistence. Our guest today has lived that roller coaster and is now helping other founders navigate it.
Jessica Lynch is a tech founder turned investor, and during our conversation, we talked about:
How early entrepreneurial experiences, even failures, can plant the seeds for future success
The importance of customer discovery and market research before building a product
How to pivot a business model when faced with major external challenges
Navigating the emotional and practical challenges of the M&A process
How founders can set themselves up for success by learning from those who've gone before them
Jess shares some incredibly valuable insights from her own founder journey and her current work investing in and accelerating promising startups.
Links:
Jessica Lynch: https://www.linkedin.com/in/jessicallynch/
Raiz Capital: https://raiz.vc/
Like all of us, today’s guest had to face the hardships brought on by the global pandemic in 2020 – one of which was having her children learn at home instead of in school.
But for her and her kids, something peculiar happened – and they actually thrived in the online experience.
She later learned that other parents and their kids did not, unfortunately, thrive to the same degree – and this led her to try to figure out what worked for her – and how she could share that. This inspired the creation of Edify – a tutor matchmaking service which is on a mission to help neurodivergent kids everywhere thrive in an optimal learning experience.
We had a fascinating conversation where we talked about how she was able to bottle the inspiration – and figure out what actually made the experience work. How putting extra effort into matchmaking up front pays dividends later on, and how she is working to scale the business without losing the magic at its core.
I learned a lot from the interview – and hope you do as well.
Links:
Priya: https://www.linkedin.com/in/priya-tron/
Edify: https://www.edifylearningspaces.com/
The startup journey is full of twists and turns – but it can also present new opportunities as you go down the path.
Today’s guest, Katelyn Alberts started her journey with the idea of building a marketplace – and quickly transformed it into something even greater than that.
During our talk, we covered some really timely topics for any founder:
How Katelyn, as a nontechnical founder, was able to navigate the tough question of whether to hire a tech team or recruit a tech founder – and how she discovered an even better approach.
How to go from seeing a problem that needs to be solved – to deciding to take action on it yourself.
What to do when you get started – and how to define your MVP
The challenges of building a 2 sided marketplace – and knowing how to recruit participants on both sides.
How adding a community mastermind to the mix can add huge value to the core members of the audience – and generate more revenue to help grow the business
The importance of getting the formula right in one location – to achieve “density” – before scaling
Links for Katelyn:
VERVERY: https://www.ververy.com/
LinkedIn: https://www.linkedin.com/in/katelynalberts/
Starting and building companies is an amazing rollercoaster of ups and downs – and for many founders, achieving a successful exit at the end of the process is the ultimate goal.
I’ve been fortunate enough to experience 2 major exits in my founder career – and I learned a ton from both of them. Today’s guest, Mac Lackey – has gone through a total of 6 major exits in his startup career.
Starting out in the midst of the first web explosion of the mid-90’s, Mac quickly built and sold his first company – and has then learned how to capitalize on opportunity after opportunity since.
I had a fascinating conversation with Mac about the ups and down, the huge takeaways – how he improved his craft with each exit. And – how we all can learn from his experiences to drive something he called optionality into our own startup experience.
I hope you get as many gems out of our conversation as I did!
Links:
Exit DNA: https://exitdna.com/
Book: https://exitdna.com/book/
We’ve all seen products over the years that fizzle out or go sideways – and other products in the same category that achieve explosive growth and quickly scale to millions
Likewise, we’ve seen companies enter red oceans with tons of competitors – only to quickly go viral there and dominate. Google did this in the crowded search space of 1998. Facebook did this to Myspace.
But – how do they pull this off?
I’m so excited to bring you today’s guest – Vince McPhillip.
A trained social scientist and entrepreneur, he’s spent his career thinking about how to design for massive virality.
And he’s already done it once, launching the Pi network to over 3 million users during his tenure – and over 45 million users at its peak.
Now he’s at it again with Knomad – tackling one of humanity’s longest standing challenges – trust.
LinkedIn provided a huge breakthrough to the space back in 2003 – but has been about as innovative as a snail since then, and may have set itself up for a Myspace moment of its own.
Vince and I had a fascinating discussion about what goes into the DNA of products to make them go viral – and I hope you enjoy it as much as I did as you hear his plans for launching Knomad.
Links:
Knomad: https://knomad.io/
If you’re involved in selling – and especially B2B selling for a SaaS business, then you’re going to love today’s episode. In the last episode, we talked with Stephen Steers about how storytelling is important to sales. Today’s guest – Matt Wolach – shares a masterclass on another aspect of B2B sales that will help you massively increase your close rate.
In sales, it can be tempting to share all of the unique features and bells and whistles of your product. Especially after you’ve spent to much care bringing it to life. But Matt explains how a different frame – based on deep curiosity for your customer’s challenges – is going to help you improve your results.
I had a blast talking to Matt – and learned a ton of nuance along the way. I hope you get some gems as well.
Links:
LinkedIn: https://www.linkedin.com/in/mattwolach/
Website: https://mattwolach.com/
There’s one skill that every founder has to master in order to build a successful startup.
I’m talking – of course – about sales. But – there are a lot of misconceptions out there about what sales is and what it isn’t.
Today’s guest – Stephen Steers – has mastered the art of Startup Sales and codified it into a method he calls Contact Sales.
During our discussion, we talked about the importance of story – and why it’s critical to help your prospect see themselves in the story.
We talked about how to eliminate the pressure of closing – and help your prospect from the same side of the table.
We talked about how to structure your sales call for maximum effectiveness – and a lot more.
It was a value packed discussion – and I hope you enjoy it as much as I did.
To learn more about Superpower Storytelling & Stephen:
https://www.stephensteers.com/
The modern startup ecosystem has been evolving for decades – since the evolution of Silicon Valley from farmland to the hardware companies of the 60’s and 70’s – to the modern tech startup space of today.
But – even after all of these years, a founder looking for support can still feel like they’re living in the wild west.
At the elite levels, accelerators like Y-Combinator and Techstars certainly offer transformational support. But outside of the top 1% or so – the rest of the space can be a bit confusing.
Today’s guest, Jonny Boyarsky is looking to help founders cut through the noise and get better advice.
His company, called “Literally Helping Startups” – is, wait for it – literally helping startups make sense of the journey.
We had a great in depth conversation around all of the challenges founders face today, what they can do to make more sense of the world – and what Literally Helping Startups is doing to help move things forward.
We’ve talked a lot on the podcast about the importance of asymmetric upside – or luck – in helping to drive entrepreneurial success.
Today’s guest, Vlad Mkrtumyan, has made stacking the deck into a science in his ventures.
In his first company, he launched an app featuring Drake quotes that got 2,000 downloads in week 1 - then he rinsed and repeated the process into hundreds of thousands of downloads.
He then turned what he learned into a method he uses for evaluating and executing new opportunities to make sure he and his agency’s clients are constantly in the flow of asymmetric upside.
We had an amazing discussion going deep into a whole bunch of rabbitholes – peeling back the layers of the onion and finding new insights on what makes founders win – and getting dangerously close to solving puzzles around success in general.
I had a blast talking to Vlad – and I hope you enjoy our discussion as well.
Every startup needs to make money – but some startups are architected with a much bigger purpose in mind.
Today’s guests, Mike Mills and Nick Spoors of Infinitary Fund – have found a unique way to fund their mission.
Their core innovation has enabled them to sell a product today that gives them cashflow and runway to build the business – while also funding a Think Tank that is going after some pretty amazing breakthroughs.
Their runway business keeps the lights on – and their think tank enables them to shoot for the moon.
I can’t even imagine how much innovation could be unlocked if more companies were designed this way.
We had a fascinating discussion going deep on this new model for doing business – and I hope you find it as inspiring as I did.
Timing is one of the hardest challenges for founders.
Execute an idea too soon – and you’ll run out of runway before someone gets there when the time is right.
Execute it too late – and you face still competition from the incumbent that got there first.
Today’s guest, Ace Bhattacharjya of MedicalRecords.com gives us a masterclass on how to stay true to a timeless vision while also leveraging timing to take advantage of opportunities as they arise.
Over 20 years, he’s built multiple successful iterations of the business – while also being poised to pounce on huge trends as they’ve emerged.
Ace & I always have fascinating conversations – and I’m super excited to be sharing this one with you.
I hope you gain as many takeaways from our conversation as I did.
One of the common themes I see with top entrepreneurs is that they find a way to get experience from multiple viewpoints within the startup ecosystem.
Today’s guest, Stephane Nasser of Open VC is no exception – having had stints from the large corporate world building software for startups, then working within accelerators to help startups get launched, then – of course – working as an entrepreneur, and finally landing in the venture capital side of the world.
During our talk, we did a lot of deep dives around all of these angles while also pulling out the common themes that apply across all of them.
I gained a lot of great insights from his wide range of experiences across the startup world – and I hope you are able to get some gems out of our conversation as well.
You can learn more about Stephane and Open VC here:
OpenVC: https://openvc.app
Stephane: https://www.linkedin.com/in/stephanenasser/
Today’s guest, Peter Mann, found out that he had autism in a late diagnosis as an adult. But – buried in this so called diagnosis was actually the operator’s manual for his supersuit.
While working a full time 8-5 at Dell, Peter was able work another 8 hours per day launching his first side hustle – and he was able to find flow and focus throughout these long days.
What might be exhausting or cause burnout for others – actually lit Peter up with motivation and purpose.
Over several decades, he has turned this drive into multiple successful businesses – including his current venture, Oransi, which he decided to start when his son had trouble breathing and he wanted to find a better way to solve the air purification problem.
We had a fascinating conversation about how Peter has been able to apply his hyper-focus to methodically build and grow several successful businesses.
There are a lot of paths into the world of entrepreneurship, but today’s guest has one of the most fascinating ones I’ve found yet. While running a popular Miami nightclub, Shaun Gold had front row seats to a parade of some very interesting and diverse people.
By being curious – and making connections – Shaun built a network that would take him on a whirlwind through the entrepreneur world. From startup founder, to investor, to the world of Hollywood and screenplays, and even a stint on jeopardy – Shaun’s ability to connect with varied people have taken him on some pretty amazing adventures.
During our talk, we discussed the common thread that ties all of these experiences together – and also how they apply to the current environment for funding and launching startups.
I’ve gotten to talk with a lot of amazing founders on the show over the past 6 months.
In today’s episode, I had the chance to speak to an expert with a unique vantage-point and mix of experiences.
Elad Granot is a serial entrepreneur, the Dean of the Boler College of Business at John Carroll University, an active investor in startups, and also host of the Bottom Line podcast.
From his unique vantage-point as the dean of a business school – and an investor – Elad is able to keep his pulse on what upcoming entrepreneurs are thinking about – and then apply that knowledge to his ongoing funding thesis.
We had a great conversation talking about what things have changed over the past 3 decades, and what principles have stayed the same.
And we also how the major disruptions of the day – like Artificial intelligence – are increasing the pace of change in the startup world.
It was a super fun talk – and I hope you learn as much from it as I did.
One of the themes that keeps re-appearing on the show is that industries that look like they have been locked down for years or even decades – can suddenly go through a renaissance and lead to a new jump ball.
Today’s guest is taking advantage of a massive shift that’s happening in the online selling space.
As influencers flock to sell items on the multiple prominent marketplaces, they’re stuck with the challenge of managing listing across 4 or 5 networks for every product they sell.
With SellStuff, David Brown is building a platform to tackle this issue head on.
We had a fascinating discussion on how he leveraged his experience at big tech firms to conceive of and now launch his new app which will enable influencers to enter their information once – and list across the marketplaces.
Beyond removing friction – he sees the opportunity to help transform the marketplaces themselves – and the community of influencers that sell on them.
I got so many gold nuggets out of our discussion – and I hope you learn as much as I did.
It’s easy for founders to look at an industry and think that you’ve already missed the boat. I could have done this with travel in 2003 and missed the destination wedding trend – and it would be easy to conclude that ride management has already been won by Uber and Lyft.
But today’s guests – Zach Castaneda and Steven White are approaching the transport space with a unique spin that is starting to catch waves. As industries mature, they leave holes for new entrants – and that’s exactly what Zach and Steven see in transport.
Their company Shofeur is helping re-invent a segment of the transport space by helping fleet operators level up with their customers.
We had a fascinating talk – where Zach and Steven explained what was missing in the space, why they saw the opportunity, and how they are gaining steam going after it with Shofeur.
On July 16, 1945 at 5:29 am – the world changed.
Up until that point – there was strong theory supporting the idea that enormous amount of energy could be unleashed by splitting an atom.
At 5:29 on that day – that theory became indisputable reality – and the world was never the same.
That test on July 16, 1945 was code named Trinity – and today we’re going to talk about how founders can pursue their own Trinity moment in their startup – and how this type of nuclear demonstration can give them huge momentum.
For most startups, the main task of launch and validation is to figure out if the market has any interest in the idea at all – and if it’s possible to gain traction. Today’s guest, Rachel Cossar – took a different approach. She was already operating a successful coaching practice helping her clients optimize nonverbal cues during sales calls.
She knew this process was valuable - but her question was – could it be automated through technology and AI?
We had a fascinating conversation about how this question led to the formation of Virtual Sapiens – and how she has been able to transfer her existing validation of her process into a way to deliver the same value through AI.
She’s had an amazing step by step journey – from initial validation of automating the process – to multiple iterations that have built trust in the AI and started to deliver results to her clients automatically.
I learned so much in this conversation – and hope you do as well.
To learn more about Rachel and Virtual Sapiens:
Virtual Sapiens: https://www.virtualsapiens.co/
Rachel Cossar: https://www.linkedin.com/in/rachel-cossar/
Todd Sullivan is co-founder and CEO of ExitWise. After building and exiting a series of his own companies, Todd now helps founders plan and maximize their own exits when the time is right.
During our talk, we covered:
- How solving your own burning need can be the best launchpad for a startup
- How decisions you make now can set you up for a strategic acquisition later down the road
- The dangers of depending too much on someone else’s ecosystem – and how to mitigate them
- The importance of timing in acquisition – and how one founder was able to 20x their exit outcome by planning this well
- How to manage the 3 different types of exit scenarios
- Why bringing an experienced M&A team to the table can make a deal go much smoother
- How to make sure time works for you and not against you in any deal process
- And how the current funding environment is affecting M&A – and which companies are poised to win
You can learn more about Todd and Exitwise here:
One morning just over 11 years ago, I met up with my friend Dr. Michael Connell in a Panera to talk about a startup idea he was working on in the education space.
He told me about a groundbreaking research study that had been done during the 90’s that could have revolutionized how children learn math – but how previous attempts to deliver it at scale had failed to move the needle.
During our breakfast, we pondered whether the newly introduced iPad could create an opportunity to take a new approach to bringing the research to life.
And thus began one of the most incredible journeys of my career.
A year later – we released Native Numbers into the iPad app store. 6 months after that – it ranked up to #2 in the education section, and 10 years later – it’s helped over 700,000 kids and counting learn math.
On this episode – Mike and I talk about the story behind Native Numbers – and also get some of his prescient insights about what’s happening in the ed tech space.
Akash Magoon's company Adonis is innovating the healthcare billing space – hoping to reduce enough friction so it feels much more like stripe than what patients and providers have to deal with today.
We hit a lot of great topics today:
- How having a strong relationship with your co-founder can set the stage for candor in your startup
- How healthcare space has changed in the past 10 years – and how to approach a space once the low hanging fruit has been picked
- How the proliferation of best of breed point solutions can create an integration burden on the end user
- What to do when an ecosystem has misaligned incentives
- How a diagnostic can be the perfect way to open a client relationship and uncover the most pressing challenges
- The importance of knowing whether your market is in a build or buy cycle, and
- Why startups should earn the burn if they’re looking to raise money
You can learn more about Adonis at:
https://tryadonis.com
Matthew Turner is the author of the book Beyond the Pale. In writing his book, he interviewed over 100 founders to learn how they found balance in their lives as entrepreneurs.
We talked about:
- The downside of so called hustle culture – and why founders should try to avoid it
- How founders can tap into the creation vortex – to drive their best ideas
- How sometimes skills we take for granted are actually super valuable to our customers
- The right way to frame mistakes so you can make the most learning from them
- Why it’s important to have a clear definition of what success means to you
- The importance of having something called a “Hell Yeah” – and how to use this to drive all of your important decisions.
It was a fun conversation – and it was super insightful to hear what Matthew learned from the 100+ founders he spoke with.
David Sorbara is the founder of Barkley HQ – a software as a service product that helps pet groomers run their businesses.
I learned so much from David – not just about his experiences growing Barkley HQ into a successful business – but also in how he is working to take his experience to launch even more businesses now – all while continuing to benefit from BarkleyHQ.
During our talk, we discussed:
- Why some businesses still use pen & paper to operate – and how this spells opportunity for startup founders
- How making your customers customers look good creates a halo for your customers – and for you
- How you can get started with youtube, organic, and other cold outreach methods
- Why it’s important to know where your customers are – so you use the right channel to communicate with them
- How leverage comes from actually solving customers problems at a deep level
- And – how to go from 1 successful SaaS business to launch multiple new ones
It was a super exciting discussion – and I learned so much about how to go deep on customer experience to create a great startup.
Mark Herschberg - has worn many hats in his career including Founder, Chief Technology officer, Author, and Instructor at MIT.
A lot of episodes have focused on the startup, today we went deep on the path and growth of the founder behind the startup.
We talked about:
- How the startup world presents challenges differently than how you were trained in the past
- A great method for modeling a problem so you can then figure out how to solve it
- The open ended nature of startups – and of the career of a founder, and how to navigate through this
- The magic of patterns – and how to get better at spotting them
- How to intentionally build your skills as you navigate the founder career path
- And quite a few surprises in terms of which companies win – and which ones get defeated
Mark's Resources:
1) The Career Toolkit Book:
https://www.thecareertoolkitbook.com/
2) Brain Bump App:
https://brainbumpapp.com/
Every few years, there is a massive shift in the tools and platforms available to founders who are building out their dreams. On this episode, I had the pleasure of speaking with John Rush, the Founder of Mars X – which is a new development platform that is reinventing how software gets developed.
We discussed a lot of great insights during our chat:
- The dangers of building a startup without getting active customer feedback – and how this can waste years of time
- Why you need to talk with customers to figure out which problems need solving
- The inspiration for a whole new way of developing software called Mars X
- How solving your own problem is often the best inspiration for a startup
- Why it’s absolutely critical that you focus on your evangelists before wasting time converting skeptics
- And how you can multiply your team by attracting a community and ecosystem around your product
As a lifelong programmer, it was exciting to learn about how MarsX is changing the way software gets built.
There is a missing ingredient from all of the advice, strategies, tactics, and approaches given to founders on how to build their company. Today we dive deep into that missing ingredient:
On this episode, we're joined by expert marketer Josh Wilkinson to share insights on how founders can master the art of marketing to launch and grow their startups. During our talk, we discussed:
The online course space is exploding - but it's created a massive gap where video quality has made it into the 21st century, but we're still stuck using antiquated tools to do the exercises and learn the material. Jake Press is founder of Workbookable.com - a company that is looking to fill this gap and help bring the entire online learning experience into the 21st century.
In this episode, I explore the 2 main ways businesses create value - and how startups often fail because they focus on the wrong mechanism. Large companies make money through exploitation - or maximizing value of what they've already discovered. Startups that try to exploit before they've properly explored get into serious trouble - or never leave the launchpad.
Last week Sam & I talked about the challenge founders face when they try to get feedback on their startup idea. This episode, we peel back deeper to talk about how founders can actually start getting better feedback - and how they can make sure they are able to create a killer pitch for their idea.
I interview my brother and business partner Sam Durso about the challenges founders face right now in the current funding environment. We talk about how easy it is for founders to get bad advice - and how this sends them down the wrong path. We also cover how founders often invest an enormous amount of time and effort building something that they could have validated much easier - and finally, we talk about an approach you can take instead.
Last episode, we talked about how "luck" is created by consistent testing and experimentation - and how this leads to the big breakthroughs in business. Today's guest executed this plan to build the largest digital health care provider in the middle east. By running repeated experiments with multiple niches - he's been able to build his business from 0 to 5,000 consultations per day.
In the ongoing debate about what factor most contributes to startup success - between "Luck" and everything else, we settle the debate with some bad news (Spoiler Alert: It's all about luck). But, then we go on to talk about how once you accept that "it's all about luck" - you can focus on maximizing the amount of luck you experience in your startup.
Last episode, we first talked about the subject of fundraising - and introduced a framework for understanding fundability. Today's guest, Mike Miranda, started his company during the pandemic with a great idea - but later discovered an even more valuable idea when interviewing his customers for feedback. By focusing on his customers' biggest problem - he was able to develop a more relevant MVP - and successfully complete a $2m+ fundraise for his startup.
Today, we look at the age old question, "should I raise money, or not?" and reframe it into a hierarchy that goes from Unfundable, to Fundable, to a secret level called "Un-Unfundable". Once you understand the difference among these levels, you can decide at each phase whether your best move is to focus on fundraising, building, or both.
Marc Andreesen famously gave his chilling prediction on the gig economy, saying that in the future "either you'll be telling the API what to do, or the API will be telling you what to do." Today's guest, Derreck Stratton, takes a fresh perspective on the gig economy - and he's building HUDU to put the power into the hands of gig economy workers.
One of the single biggest levers that determines whether a startup is going to succeed or fail is the depth of its "Why". In this inaugural episode of Founder Breakthroughs, I peel back the layers on how "Why" impacts a startup's trajectory through some stories of where Why made a difference.
Introducing the Founder Breakthroughs podcast - where every week, serial entrepreneur Jeff Durso interviews founders to hear their amazing stories and glean insights that can help other founders achieve success.