A Product Market Fit Show | Startup Podcast for Founders

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, this episode will show you how patience, resilience, and radical product decisions can transform your startup. Why You Should Listen * How Sigma went from $0 to $100M ARR—but spent 7 years figuring it out. * The pivot that turned years of failure into explosive growth. * Why obsessing over speed to product-market fit is the wrong game. * How to handle the psychological toll of startup uncertainty. * The hidden power of building features your customers never ask for. Keywords product-market fit, Sigma Computing, pivot, startup growth, business intelligence, Snowflake, early-stage startup, SaaS growth, cloud analytics, founder stories 00:00:00 Intro 00:02:49 Debating speed to product–market fit 00:10:14 Quitting Salesforce and the EIR leap 00:23:12 Two years of prototypes that went nowhere 00:36:53 The Snowflake meeting and spreadsheet pivot 00:45:41 Dealing with Investors 00:52:30 Tripling three years straight to $100M ARR 00:54:46 Why most people shouldn’t start a company Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]

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 another success story; it’s a real guide on how not to fail. Why You Should Listen * Discover why even rapid growth and millions raised might not save you. * Find out the hidden dangers of relying on corporate VCs. * Learn why equal founder equity splits might not be a good idea. * Hear the biggest fundraising mistakes early-stage founders make (and how to avoid them). * Get practical advice on how to truly validate your startup before building tech. Keywords startup failure, fundraising mistakes, fintech startup, founder lessons, corporate VC, startup partnerships, product validation, founder equity split, early-stage fundraising, startup growth challenges 00:00:00 Early Days at Uber and Moving into Fintech 00:07:00 Launching a Consumer Fintech App in Europe 00:13:37 Validating Without Tech Building an MVP by Hand 00:19:22 Why US Startup Models Don’t Work in Europe 00:23:07 Raising Money Quickly—and the Hidden Costs 00:28:56 Running Out of Cash When COVID Hit 00:32:15 Tough Decisions Layoffs, Sales, and Shutdown 00:37:53 How Big Partnerships Can Sink Your Startup 00:43:41 Staying Optimistic Even When Everything Falls Apart 00:46:38 Crucial Fundraising Advice for Early-Stage Founders Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]

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 faster growth. Hernan shares how they turned extreme constraints into a secret weapon, why getting profitable early was a game-changer, and why the biggest businesses are built by doing fewer things, better. Why You Should Listen * How Mercado Libre survived going bankrupt by pivoting overnight. * Why most startups die chasing growth—and what to do instead. * How to build unstoppable momentum by nailing one thing first. * The simple test to know if your startup has real product-market fit. * The one thing all $100B companies do differently. Keywords Mercado Libre, product market fit, Hernan Kazah, startup advice, ecommerce growth, marketplace strategy, profitability, venture capital, early-stage startups, Latin America startups 00:00:00 Intro 00:04:07 Why We Chose the eBay Model 00:08:56 The Early Hack That Got Us Our First Users 00:14:23 Raising Money at the Worst Possible Time 00:21:37 Becoming Profitable and Going Public 00:26:34 How Mercado Libre Stayed Patient While Competitors Chased Growth 00:34:05 Why We Expanded Across Latin America From Day One 00:45:11 Our Secret to Winning Against Better-Funded Competitors 00:50:04 The Most Important Advice for Early-Stage Founders 00:52:16 Why AI is Different From the Internet and Mobile Revolutions Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]

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 ignore best practices, how to choose one north‑star metric, and why slow, relentless improvement beats silver‑bullet fantasies. Perfect fuel for scrappy founders hunting product–market fit. Why You Should Listen * The single‑metric focus that took a travel app to $10M ARR through Covid * Turning six months of “no’s” into $100M ARR: the slow‑burn playbook * Why mastering your craft first can unlock your next billion‑dollar idea * Picking the rules to break: using “unconventional” as an unfair advantage 00:00:00 Intro 00:01:30 Why location odds matter less than you think 00:02:50 Skip the Dishes proves huge wins can start in tiny markets 00:05:30 Polarsteps shows what happens when one metric rules them all 00:09:00 Jobber’s decade‑long slow burn to compounding growth 00:14:40 Public.com and the power of diving deep into your craft 00:21:40 The real skill: knowing when to ignore conventional wisdom 00:24:30 Key takeaways and next steps for your own playbook Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]

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 discovering a 10/10 burning pain.  If you’re a founder struggling to find breakout growth, this episode is your blueprint. Why You Should Listen * How to pivot from a dead-end idea to $10M ARR in one year. * The power of solving a 10/10 burning pain. * When customer anger becomes your biggest growth signal. * Why chasing local maxima can trap your startup. * How true conviction unlocks explosive growth. Keywords product-market fit, startup pivot, explosive growth, voice AI, founder stories, SaaS startups, early-stage startups, customer pain points, San Francisco startups, developer tools 00:00:00 Intro 00:02:35 Stuck at $500K ARR & Burning the Boats 00:07:15 Knowing When It’s Time to Quit 00:08:49 The Side Project that Became Vapi 00:16:28 Early Growth and Finding First Customers 00:23:32 The Product Hunt Launch that 3X’d Growth 00:27:57 Surviving Explosive Growth 00:35:17 Competing Against OpenAI and Big Tech 00:41:26 How to Identify a True 10/10 Pain 00:48:53 The Moment of Real Product-Market Fit Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]