A Product Market Fit Show | Startup Podcast for Founders

Simon spent 10 years at Shopify scaling databases to millions of requests per second. Then he discovered vector databases were so expensive that companies couldn't launch AI features. So he solved it.  When Cursor emailed about their crushing costs, Simon flew to San Francisco unannounced. They migrated their entire workload within a week, cutting their bill by 95%. Then came Notion. Justin pulled 24-hour coding marathons during their POC, fixing 300 milliseconds of latency in three hours. They signed on July 25th—the same day Simon's daughter was born.  Now TurboPuffer powers Cursor, Notion, and Linear while staying profitable with just 17 people. Simon shares why he turned down easy Series A money and his framework of exactly 6 legitimate reasons to ever raise capital. Why You Should Listen: * The power of making something 10-100x cheaper * Why you need to be willing to fly to early customers (how that landed Cursor) * The 6 reasons to raise money (and why you often shouldn't) * How working 24-hour sprints during POCs converted enterprise customers * Why staying profitable with 17 people beats raising $30M you don't need Keywords: startup podcast, startup podcast for founders, TurboPuffer, Simon Eskildsen, vector database, Cursor, Notion, bootstrapping, database startup, AI infrastructure 00:00:00 Intro 00:07:52 Finding the problem 00:12:25 Building alone 00:22:27 Going viral on X 00:26:18 Closing Cursor 00:40:17 Closing Notion 00:45:26 Why he didn't raise $30M when everyone expected him to Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]

Guy spent 2 years and $4M building Snyk to $100K ARR. Thousands of developers loved the product. They just wouldn't pay. Then he figured out the problem: he had product-user fit, but not product-buyer fit. Developers loved Snyk. Security teams (the actual buyers) didn't care about it. The distance between user and buyer was killing him. So Guy spent a year building governance features, reporting, and enterprise capabilities—all the stuff developers didn't care about but security teams needed to write checks.  Four months later, Snyk hit $650K ARR.  A year after that, $4.5M.  Then $19M.  Today it's over $300M ARR. This episode breaks down the brutal reality of PLG when your user isn't your buyer, why Guy thinks the worst outcome for a founder is getting stuck (not failing), and how he's now raising $125M for his next company Tessl. If you're building PLG, selling to enterprise, or wondering why your users love you but won't pay—this is required listening. Why You Should Listen: * Learn why thousands of users loving your product means nothing if they won't pay * Discover the difference between product-user fit and product-buyer fit * Understand why the worst outcome isn't failure—it's getting stuck in the grey zone * Master the art of anchoring in the future instead of just filling today's gaps Keywords: startup podcast, startup podcast for founders, product market fit, PLG strategy, product-user fit vs product-buyer fit, developer tools, security startup, enterprise sales, bottoms-up GTM, Snyk founder Chapters: (00:00:00) Intro (00:01:37) The first start up :Blaze.io" (00:06:16) The Beginning & Concept of Skyk (00:15:27) Why use Snyk (00:23:41) The Product Led Growth for Snyk (00:33:08) Raising for Snyk (00:38:58) The Beginning & Concept of TESL (00:46:39) Raising for TESL (00:48:52) Finding PMF (00:49:26) One Piece of Advice Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]

Amar is a 5x founder who helped birth Tinder (it was the 10th project—after the first 9 failed), then sold his next company to Ford for putting a platform in every single vehicle they make. But the wildest part? He got Ford to commit in under a year by doing something most founders would never do: he asked for SO MUCH money that only the CEO could approve it. That one move made him "part of the transformational change" instead of a vendor they could ignore. In this episode, Amar breaks down the exact pricing strategy he used to land an 8-figure deal, why founders who sell discounted pricing are sabotaging themselves, and what it actually takes to compete against billion-dollar incumbents like Carta (his current company, Mantle, is doing exactly that). If you're trying to sell to enterprise, wondering if you should bootstrap or raise, or questioning whether your market even exists—this episode will reset how you think about all of it. Amar's built companies in mobile, vehicles, security, and fintech. He knows what works. Why You Should Listen: * Learn the pricing trick that got a CEO to sign off to an 8-figure deal. * Discover why asking for MORE money (not less) is how you win enterprise deals * Why getting told "you're nuts" might mean you're dead right * Master the one metric that matters more than ARR in the early days Keywords: startup podcast, startup podcast for founders, enterprise sales, 5x founder, product market fit, pricing strategy, Tinder origin story, competing with incumbents, bootstrapping vs raising, SaaS pricing Chapters: (00:00:00) Intro (00:03:56) The Start & Finding PMF for Tinder (00:09:04) Xtreme Labs (00:12:18) Autonomic (00:17:03) The Contract Turned Acquisition (00:22:04) The origin of Mantle (00:28:56) Going into a Dominated Category (00:32:39) Raising & Pitching for Mantle (00:40:01) One Piece of Advice Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]

Ben Alarie spent 8 years building Blue J with "partial product market fit"—real customers, real revenue, but no real market pull. Then he made a bet that would either kill the company or 10x it: he put the existing product in maintenance mode and gave his team 6 months to rebuild everything from scratch using a technology that barely worked. Two years later, Blue J went from $2M to $25M in ARR. They're adding 10 new customers every single day. NPS went from 20 to 84. This isn't a story about getting lucky. It's about a founder who knew—with absolute conviction—that the market would eventually arrive, and made sure he was ready when it did. But it's also about the danger of fooling yourself into thinking you have PMF when you only "kind of have PMF." Why You Should Listen: * Learn the brutal difference between fake and real PMF * Discover when to abandon millions in existing ARR to go all-in on something else * Why "time to value" might be the single most important metric for word-of-mouth. * See what it takes to survive until the market is ready. Keywords: startup podcast, startup podcast for founders, product market fit, founder journey, early stage startup, startup pivot, AI startup, SaaS growth, founder advice, hypergrowth startup Chapters: (00:02:00) Starting BlueJ (00:9:26) Introducing AI to Tax Research (00:12:44) Starting to Build (00:17:03) Not Having True PMF (00:19:44) Believing in Retrieval Augmented Generation (00:25:34) Updating to V2 of BlueJ (00:30:58) The Necessity of Time to Value (00:33:47) When You Knew You Have PMF (00:38:19) One Piece of Advice Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]

Dean thought he'd have to bootstrap Axonius because no investor would fund a solution to a problem that had existed for 20 years. He was wrong—they've raised $500M.  The breakthrough came when a Fortune 500 company was actively being hacked by Chinese state actors. Their first customer almost said no—they had 20 bugs during the POC. But Dean's team fixed each one within 48 hours while their competitors took quarters to respond. That speed changed everything.  They went from zero to $100M ARR in under 5 years, created an entirely new category (cyber asset management), and achieved an NPS score in the 80s—unheard of in cybersecurity.  His framework for the three types of enterprise journeys will change how you think about positioning. Why You Should Listen: * Why responding to customer issues in hours changes everything. * How to turn a "dormant pain everyone accepts" into a $500M+ company. * Why speed beats everything. * The 3 types of enterprise software journeys and which one VCs won't fund. Keywords: startup podcast, startup podcast for founders, Axonius, Dean Sysman, cybersecurity startup, enterprise sales, Unit 8200, cyber asset management, B2B SaaS, YC alumni 00:00:00 Intro 00:02:25 From Hacker to CyberSecurity 00:14:46 The three types of enterprise software journeys 00:18:41 Why time to value beats everything 00:29:33 Thought they'd bootstrap but VCs validated the problem 00:35:14 Failed POCs and landing first customer with 20 bugs 00:40:10 Zero to $100M ARR in under 5 years 00:45:24 When to know you have product-market fit Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]