A Product Market Fit Show | Startup Podcast for Founders

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 believes an entrepreneur’s conviction—backed by customer insights—is the real key to startup survival. Why You Should Listen * How to raise $40M in 6 months with no product or revenue * Why “too early” often means bankrupt—and how to avoid it * Why activity ≠ funding (and what to do instead) * The hard truth about selling enterprise early * Why market timing matters more than product genius Keywords product market fit, fundraising, early-stage startups, startup fundraising, venture capital, enterprise sales, market timing, Andrew Rubin, Illumio, cybersecurity 00:00:00 Intro 00:08:15 Why Being Early Can Bankrupt You 00:16:09 Creating a Market That Doesn’t Exist 00:27:55 Activity Does Not Equal Funding 00:38:06 Landing the First Enterprise Customer 00:49:57 Surviving Enterprise Sales Cycles 00:54:56 Navigating the Emotional Rollercoaster 01:00:46 The Truth About Product Market Fit 01:01:55 Andrew Rubin’s Best Advice for Early Founders Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]

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 chase true product-market fit, why copying competitors is a trap, and why patience in the early stage might be your biggest competitive advantage. If you’re building a startup, stop what you’re doing and listen now. Why You Should Listen * Discover why getting to $1M ARR fast is NOT the goal (and what really matters instead). * Learn how randomness and serendipity shape startup success—straight from real founder stories. * Understand why chasing product-market fit beats obsessing over short-term revenue milestones. * Hear why copying existing playbooks can sabotage your startup’s long-term growth. * Find out how radically different paths—roll-ups, pivots, or total serendipity—can all lead to success. Keywords  product market fit, startup growth, early-stage startups, founder stories, zero to one, ARR milestones, startup pivots, product differentiation, scaling startups, startup playbook 00:00:00 Intro 00:02:47 Carbon6’s $210M Exit—Roll-ups and Serendipity 00:04:27 Lightspeed’s Unplanned Journey to $1B 00:06:04 Graphite’s Pivots—How a Failed Idea Led to Success 00:07:27 Vapi’s Rapid Rise After Three Years of Flat Growth 00:08:55 Why There’s No Single Path to Product Market Fit 00:11:19 The Million-Dollar ARR Myth Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]

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]