A Product Market Fit Show | Startup Podcast for Founders

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 b...

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, h...

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...

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...

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...

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 episod...

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...

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 ma...

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 mi...

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

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...

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 radicall...

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...

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...

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 r...

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....

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 unpr...

Forget what you thought about early-stage growth. In this must-listen episode, you’ll hear firsthand how startup success truly happens—and spoiler alert, there’s no playbook. From companies like Carbon6 using roll-up strategies to Graphite pivoting multiple times before exploding, we unpack real founder journeys that prove getting to $1M ARR fast isn’t what matters. You’ll see why the real winners...

Rob Woollen, founder of Sigma Computing, shares the unfiltered reality of going from 0 to $100M ARR. After spending seven years grinding without product-market fit, Sigma finally hit an inflection point—tripling revenue year over year. Rob dives deep into the pivots, setbacks, and critical decisions that turned early failure into a massive success. If you’re an early-stage founder feeling stuck, t...

This is the brutally honest startup story every founder needs to hear. Benedetta  shares how she built a fintech app to half a million users and raised $10M—yet still failed.  You’ll learn why chasing big partnerships can backfire spectacularly, how a seemingly successful startup can quietly fall apart, and how to set yourself up to avoid common but deadly fundraising mistakes.  This isn’t just an...

How do you build a $100B business without hypergrowth or endless funding rounds? Hernan Kazah co-founded Mercado Libre, the Latin American ecommerce giant, at the peak of the dot-com bubble. But when the market crashed, funding disappeared, and competitors doubled down on spending, Mercado Libre focused relentlessly on building a rock-solid, profitable core product—ignoring pressure to chase faste...

Four founders prove you don’t need Silicon Valley, a technical degree, or a massive seed round to build a massive company. We go through the key observations from the last 4 episodes: How Skip created a $200M business in a third tier city, Polarsteps’ NPS‑obsessed rise, Jobber’s decade‑long compounding engine, and why a small decision was key to Public.com’s huge success.  You’ll learn when to ign...

Jordan Dearsley spent 3 years building a startup stuck at $500K in revenue—then he burned it all down and moved to San Francisco. A year later, he was at $10M ARR. This episode walks through Jordan’s decision to abandon a profitable business, why solving a painful customer problem was the key to explosive growth, and how finding product-market fit is as simple—and as brutally difficult—as discover...

Two founders, two wildly different paths to $100M ARR: Arvind Jain, founder of Glean, walked away from a unicorn to start over—raising $15M without revenue and ignoring lean startup rules. Kyle Hanslovan, founder of Huntress, faced brutal rejection, slept in his car, maxed out credit cards, and still crushed it. This episode is packed with raw lessons on fundraising, product-market fit, and why re...

Avery Pennarun raised $160M for Tailscale—without even meaning to. What started as a small, simple project exploded into an unstoppable force in network connectivity and security. This episode reveals exactly how Avery turned a tiny seed round into millions of dollars in ARR, powered by nothing more than word-of-mouth and an obsession with solving everyday developer headaches. Learn why your start...