A Product Market Fit Show | Startup Podcast for Founders

Sahil was 18 when TechCrunch published a hit piece calling him a copycat. His co-founder Aaron was 16. They'd just raised $6 million from YC and top VCs for their crypto startup, then got subpoenaed by a state government and watched their business implode. 

So they fired everyone, moved back to their parents' homes, and spent months cold-calling dentists and lawn care companies to find a real problem. What they discovered:...

Jon spent 3 years building Gamma with barely any traction—just a few hundred users after burning millions. Then ChatGPT dropped. In desperation, he pivoted to AI-powered presentations in March 2023 with one year of runway left. What happened next was insane: Paul Graham publicly mocked their launch tweet calling it worthless—then it went viral. 

They went from 2,000 signups a day to 60,000. Their servers crashed for three days, but ...

Soham co-founded Rubrik by taking what he learned from building Google's data center tech to enterprises desperate for cloud migration. Two quarters later, he hit $1M ARR. And a few years later, a $16B IPO. 

Soham breaks down why paid pilots beat free trials, how to sell enterprise hardware before it works, and why early customers become your biggest champions when you solve real pain. 

Now building WisdomAI after watching the C...

Stéphan bootstrapped AODocs to $55M in revenue and 250 employees without taking a dime of VC money—while competing directly with venture-backed competitors. Starting as a services company in 2012, he spotted the cloud migration wave early and built document management for enterprises moving to Google Workspace. 

In this episode, Stéphan breaks down why doubling every two years beats hypergrowth, how to win enterprise deals with zero...

Andrew bootstrapped Wrike and grew it from 0 to a $2.2B exit by doing the exact opposite of what every startup book tells you. No pivots. No talking to customers before launch. No narrow niche. Just 17 years of relentless focus on one problem while everyone else was pivoting every 18 months. 

In this episode, he breaks down exactly why bootstrapping saved his company (and why VC would have killed it), why he ignored customer develop...

Peter Walker from Carta drops the hard data every founder needs. Based on actual cap table data from 1000s of startups, this Q2 update reveals the brutal new reality.

It takes 2+ years to go from seed to A (up from 1.6), you need 3X the revenue you used to, and if you're not AI, you're getting half the attention. 

But there's good news too—teams are finally getting leaner, exits are picking back up, and the worst of th...

Hedra CEO Michael Lingelbach breaks down how his generative video app went from zero to millions of users and an eight-figure run rate in months — then deliberately slowed down to rebuild a V2 that enterprises would pay for. We dig into the prosumer-to-pro upsell, why free users are a false signal, and how a creator-seeded launch can outpull ad spend. 

Michael shares the GTM that signs enterprise contracts every few days with no out...

Ross went from lawyer to self-taught engineer to CTO at a 1,600-person unicorn—then quit to build Wordsmith AI. 

In 18 months, he's raised $30M and grown to mid-single-digit millions in ARR by doing everything differently. He tested co-founders by starting fights. Built in Slack for 10 months before adding a web interface. Kept his team at 8 people while competitors hired dozens. 

This episode breaks down his exact playbook: how...

Rick built Persona into a $100M+ ARR unicorn, but he never thought it would work. In fact, Rick started Persona believing it would probably fail, and that mindset might be exactly why it succeeded. 

In this episode, Rick reveals how a casual project with zero expectations turned into a billion-dollar business, why early-stage startups should avoid hyper-optimization, and the secrets he learned at Square about identity fraud that bec...

Neil Patel just flipped everything you know about startups upside down. He says product-market fit is overrated, giving away your software for free can make you rich, and the real secret to scaling isn’t charging customers—it’s monetizing the leads your free product generates. 

Neil breaks down his playbook on how startups can leverage free products to grow exponentially, why your churn doesn’t matter if you monetize correctly, and ...

Roy Lee went from getting kicked out of Harvard and Columbia to building Cluely, one of the fastest-growing AI startups ever—going from 0 to $5 million ARR in just 3 months. 

We go deep on Roy’s playbook for using controversy, virality, and content to get millions of views—and millions in ARR. You’ll learn why Roy intentionally designs content to spark outrage, how he leveraged Twitter to raise millions from top VCs within 24 hours,...

Mary Beth Snodgrass shares the raw and real story behind Healthiby—an innovative healthcare startup that succeeded in delivering measurable health outcomes but ultimately failed commercially. Hear firsthand what went wrong, from unclear payer dynamics and sales friction, to macroeconomic shifts and storytelling gaps. This episode pulls back the curtain on why having a working product isn’t enough and why mastering the market dynami...

Tanay started coding at 10, built a product with millions of users by 11, and never stopped. In this episode, he shares how he created Wispr Flow—one of the fastest growing AI startups today. He's built the world's best voice to text app. I use it myself every single day. And he just raised a $30M Series A from Menlo Ventures 

This is a must-listen for any founder obsessed with building something users can’t live without.<...

We go through some lessons I learned from my own startup journey. I also go through  why almost every business challenge beyond product-market fit is actually a people issue—and how to quickly spot and fix these hidden problems. You’ll learn why staying in direct contact with your customers accelerates your path to true product-market fit, and hear a powerful story of how making something radically different—even free—can disrupt e...

Immad grew Mercury to $500M in annualized revenue and profitable. Mercury is one of the fastest-growing fintech startups ever. No wonder they just raised $300M from Sequoia at $3.5B. 

Immad breaks down exactly how he structured a viral launch, why fundraising is easier with zero customers than you think, and how he unlocked massive word-of-mouth growth. If you’re building a startup, especially in fintech, you can’t miss this episode...

Ever wonder why some startups follow every “right” rule and still fail, while others break every norm and dominate? Mike Maples (Floodgate, author of Pattern Breakers) reveals how true breakthrough startups aren’t built by checking boxes—they’re created by founders bold enough to reject consensus, ignore conventional wisdom, and rewrite the rules entirely. 

This episode explains why your biggest risk isn’t failure, it’s wasting year...

Zuben turned his personal experience with crippling overdraft fees into Brigit, a fintech he sold for $460 million after hitting $100M ARR. This episode gives early-stage founders the unfiltered truth: how Zuben discovered massive market pain hidden in plain sight, validated the idea with real customers, built bulletproof unit economics early, and navigated brutal early-stage fundraising. It’s a real story about solving problems ba...

Joseph built Freshline to $3.5 million in revenue and nearly $2 million raised. It looked like a marketplace success story—until it wasn’t. In this episode, Joe shares the hidden reasons marketplaces fail, critical lessons on how to spot the right market, and why traction alone doesn’t guarantee success. It’s a raw, real look at what happens when hype meets reality.

Why You Should Listen

• How a $3.5M startup stalled despite tracti...

Andrew Rubin raised $40M in 6 months before writing a single line of code—and another $100M before seeing his first dollar of revenue. Today, Illumio is valued at billions and counts Morgan Stanley among its earliest customers. But Andrew’s journey wasn’t smooth or easy. Listen in to learn how he navigated the fine line between being early and being too early, how he raised venture capital at unprecedented speed, and why he believe...