A Product Market Fit Show | Startup Podcast for Founders

AI startups don’t necessarily have to beat incumbents. Some will start entirely new markets instead. 

Like Canva to Photoshop, Shopify to Amazon or Pickleball to Tennis, many of these won’t even have to compete. They create 10x easier to use products and through that open up an entirely new space. They solve problems people didn’t even know they had. In many cases they expand the market for incumbents too— pickleball didn’t steal tennis players, it became a gateway and created even more. 

We discuss the 3 factors a startup needs to be able to create a new market and why there is plenty of opportunity left in the AI space. 

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"I was technically homeless at the time. I was sleeping on my buddy's couch. I had declined $250,000/ year at McKinsey... I had no idea what I was doing." Now, Blake has $150M in ARR, growing 30% per year, with 80% gross margins. He's raised $400M and his startup ID.me is worth over $1B.

This is the story of how pivoted for a Groupon-like model to an identity verification platform. Blake talks about how he raised the initial round, closed the first few enterprise contracts, and why he thinks finding product-market fit is more of a science than most founders think.

After his pivot, ID.me doubled its user base every year. Now, over 40% of Americans have an ID.me account.

Why you should listen
•Learn how even successful founders are often much closer to failure than you'd expect
•How to get credibility as a founder and close enterprise deals.
•Why fear of failure can be a powerful motivator if used constructively.
•How to use a niche market to quickly find product-market fit
•Why staying close to customers is the best way to pivot into the right problem/solution set.

Keywords
ID.me, military, tech founder, product-market fit, startup, business model, capital raising, mentorship, scientific approach, user base, revenue growth

Timestamps:
(00:00:00) Intro
(00:01:56) The Origin of ID.me
(00:04:44) The Two Parts of Credibility
(00:11:16) To Win Big, Start Small 
(00:14:53) Fear of Failure Can Be Positive
(00:20:54) Paypal for Identity
(00:23:59) Moving to DC and Raising 500k
(00:27:53) Belief in the Person Over the Business Model
(00:30:55) Pivoting to Identity Wallets
(00:41:07) The first big contract: Under Armour
(00:48:06) Getting to a Million
(00:49:39) One Piece of Advice

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Every startup needs to compete with incumbents. But it's different with AI.

AI startups need to create websites or apps from scratch and drive traffic. Incumbents can just add AI as a feature. They have distribution built in.

AI is not like previous tech revolutions. Unlike mobile, the internet, or the PC revolution, AI is not a new distribution channel. Startups are at a much bigger disadvantage than they've ever been.

In this episode, we discuss the 3 key elements you need to consider to answer the most important question:

Will you get distribution faster than incumbents get product?

Keywords
AI, startups, incumbents, distribution channels, technological shift, mobile, internet, PCs, sustaining innovation, disruptive innovation, product versus distribution, founders

Why you should listen

• This time it's different. AI is easier for incumbents and harder for startups than previous tech revolutions.
• Startups need to consider the incumbents they are up against, the power dynamics in the market, and the primary use case they are targeting.
• Understand how to think through the race and what elements are most important

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Andrew spoke with 120+ VCs to raise a $1.5M pre-seed round. He closed $2.7M and had demand for many millions more. He devoted 90% of his time to fundraising, but only took weeks from the first meetings to close. 

99% of founders I meet do not fundraise at this level. It takes them longer to close, they have fewer choices and raise less. 

This is a specific, detailed and tactical guide to closing a round. If you're ever going to raise, you need to listen.

Why you should listen

• Why talking to more investors will help you raise 10x faster.
• How to use an investment memo to articulate your thoughts and as a base to build a pitch deck
• How to get warm introductions to VCs
• How to take control of investor meetings and put VCs on their heels

Keywords
fundraising, seed round, investors, memo, deck, pitch, negotiating terms, trust, conviction, dilution

Timestamps:
(00:00:00) Intro
(00:02:02)How Taxwire Thought About Fundraising
(00:04:02) The Start of Taxwire
(00:06:32) Making a Memo Before a Deck
(00:09:50) Reaching Out
(00:16:10) Wanting to Oversubscribe
(00:21:32) Keeping Control and Qualifying Investors
(00:31:10) The Basic Structure of the Pitch
(00:34:24) Target Close Day
(00:39:01) The Timeline for Fundraising and Meetings
(00:44:41) Deciding Who to Accept Funds From
(00:50:18) One Piece of Advice

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Zoom was THE work-from-home stock. It's down 90% from peak. The same hype that fuelled work-from-home stocks is now fuelling AI. What happened to Zoom will happen to many AI companies. 

 AI startups today need to carefully position against foundational models and incumbents. Here's how to think through it.

Why you should listen:

• Learn why what happened to Zoom will happen to many AI companies
• How to position yourself against the two AI giants: Foundational models & incumbents.
• How to think through the product vs distribution race all AI startups face. 

Keywords
Zoom, AI, positioning, foundational models, incumbents, use cases

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Chris shares the story of how he grew Refine Labs to $22M ARR, what he did to grow so fast, and also why he regrets spending so much on growth instead of focusing on profitability.

He goes exceptionally deep on sales and marketing and provides tactical advice you can steal. 

Chris is the founder of Refine Labs & Passetto. He's also a LinkedIn Top Voice with 150K followers.

Why you should listen:

• Learn when to switch away from founder-driven sales 
• Why sales velocity is the key metric you need to track
• How to use customer feedback to drive a consistent marketing campaign and drive organic inbound. 
• How to know if you have product-market fit based on customer satisfaction and retention.
• Why Chris regrets not focusing more on cash flow profitability vs growth.

Keywords:
entrepreneurship, founder sales, marketing, customer insights, zero-to-one growth, go-to-market strategy,  product management, growth strategy, product-market fit

Timestamps:
(00:00:00) Intro
(00:01:21) Starting e-commerce companies on the side
(00:04:56) Going all in
(00:11:30) Balancing sales and marketing
(00:18:05) Focusing on Customer FeedbackLanding the first customers
(00:27:19) Why you should not spend on advertising
(00:37:55) His most viral marketing campaign
(00:41:04) Finding Product Market Fit

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Sam Altman is playing chess not checkers. He partnered with Microsoft. He partnered with Apple. He grew to $3B in ARR in 2 years. Hate him or love him, he's a strategic genius.

You'll recognize a pattern: Sam has an idea, positions correctly, lets the bets play out, and goes all-in on what works.

Rinse, repeat, rinse, repeat, rinse, repeat.

In under 2 years, he has over 10M paying subscribers.

A brand name the average 60-year-old recognizes.

And, of course, his company OpenAI has $3.4B in ARR.

Keywords
ChatGPT, OpenAI, revenue growth, strategic decision-making, positioning, Sam Altman, Microsoft, Apple, AI technology, 

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We interview Chris Slow the CTO and Founding Engineer at Reddit. Reddit is now a ~$10B company, with nearly $1B in revenue. Their 1B+ monthly active users are so powerful they can move markets.  This is the story of how it all began.

On this episode, we interview Chris Slowe, Reddit's current CTO and Founding Engineer. Chris was in YC's first-ever batch with Steve and Alexis. He was their roommate. When Chris's own startup failed, he moved over and joined them to build Reddit. This was almost 20 years ago, in 2005.

It only took them a year to hit 1 million monthly active users. But it took them well over 5 years to hit $1M in revenue. Here's the story of how they hit product-market fit and built the world's most powerful online community. 

Why you should listen:
- Learn how Reddit got started in 2005 and why it took them many years to monetize
- See how word of mouth & organic growth are the key to building a community like Reddit
- Hear Chris's perspective on scaling teams and organizations, preserving culture, and signs of clear product-market fit
 - Why applying lessons from your first startup to your second one is not as easy as you think it might be

Keywords
Reddit, Y Combinator, growth, startups, founders, acquisition, Conde Nast, community-driven platform, culture, word of mouth, Google, organic growth, Hipmunk, monetization, product-market fit, scaling, startup advice

Timestamps:
(00:00:00) Intro
(00:01:55) The Start of Reddit
(00:07:13) Joining Reddit
(00:12:56) Building Communities
(00:20:37) The First Year of Reddit
(00:22:56) The Acquisition
(00:26:50) Staying Lean
(00:28:58) Leaving Reddit to do Hipmunk
(00:37:14) Hiring for Hipmunk
(00:41:08) Coming Back to Reddit
(00:45:05) Making the Mobile App
(00:47:13) Monetization
(00:50:05) Finding True Product Market Fit
(00:50:41) One Piece of Advice

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Wardah was a PhD graduate working at a biomedical imaging startup. But all it took was two different dentists giving her two totally different diagnoses for her to quit her full-time job.

She was unemployed with no idea what to build.

All she knew was that something was broken—and she had to fix it. Her startup Overjet is now the #1 dental AI platform, valued at $550M.

Why you should listen:
- Why founder obsession is a key trait
- Why learning speed is the main KPI early on
- Why staying close to customers is how you build the right product.
- How to get customers to share data with you and let you spend time in their office, watching how they work.

Keywords
dental AI, startup journey, funding challenges, product-market fit, impact on dental industry, speed in startups, biases in fundraising


Timestamps:
(00:00:00) Intro
(00:00:52) The Start of Overjet
(00:05:05) Obsession Increases your Chances
(00:08:15)A Bad Dentist Appointment
(00:11:35) Surpassing Dentist's Analysis Using AI
(00:15:52) Finding a Co-Founder and Fundraising
(00:24:22)Finding True Product Market Fit
(00:27:33) One Piece of Advice

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Dane was the CEO of Squarespace from 2007 to 2011. He grew the company from ~$2M in revenue to ~$15M. He's a multi-time founder with multiple exits. His current startup, Odeko,  raised $227M.

He takes us through his long journey as a founder of multiple companies and shares the key startup lessons he's learned.

Why you should listen:
- Why 7-day trials led to higher conversion than 30-day trials at Squarespace
- Why you should talk to customers every single day.
- Why SMB usage doesn't always translate into revenue.
- Why you need to follow customer problems over business models and TAM.

Keywords
Squarespace, Odeko, product-market fit, PMF, blogging, freemium model, trial period, data analytics, startup,, customer relationships, business model, pivot, success factors, logistics, hiring, purpose

Timestamps:
(00:00:00) Intro
(0:00:0:37) Before Odeko
(00:06:54) Leaving Squarespace
(00:07:31) SumAll
(00:13:01) Conversion Rates with Free Trials
(00:16:10) The Start of Odeko
(00:20:05) Staying Close to Clients
(00:26:36) Realizing the New Model was Working
(00:31:47) Landing the First Few Customers
(00:37:00) Overhiring
(00:39:17) Finding Product Market Fit
(00:41:32) One Piece of Advice

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