A Product Market Fit Show | Startup Podcast for Founders

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]

Casey  turned hackers into a marketplace and built Bugcrowd to $180M+ raised. But the real story isn't about cybersecurity—it's about how he validated a two-sided marketplace with almost no product, refined his pitch by literally testing it on Uber drivers until it clicked, and cracked the code on category creation when everyone thought hackers were the enemy.  You'll learn about the exact moment he knew he had product-market fit, why he blew every pitch to top VCs until he reframed his vision, and how giving away 500 t-shirts did more for growth than any paid marketing.  If you're building a marketplace, creating a category, or just trying to figure out how to explain what you do—this is required listening. Why You Should Listen: * Master the 30-second Uber pitch test—Casey's framework for refining your message until anyone gets it. * Learn why problem-solution fit without product-market fit is worthless  * Validate your marketplace with $500 and no code * Why your network is your only real asset pre-Series A * The surprising ROI of early brand marketing  Keywords: startup podcast, startup podcast for founders, marketplace startup, go-to-market strategy, product-market fit, category creation, B2B sales, early-stage fundraising, founder pitch, cybersecurity startup 00:00:00 Intro 00:01:36 From white label pen testing to the Bugcrowd idea 00:18:58 Testing with MailChimp and 5000 hackers signed up 00:21:46 Landing Google as customer in month four 00:24:24 Blowing every pitch meeting in Silicon Valley 00:33:21 The Uber pitch technique for simplifying the message 00:36:57 Early go-to-market tactics and hitting $1M 00:43:37 Open heart surgery and stepping back as CEO Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]

Zach spent 8 years at Google leading engineering for Google Docs, then left to build a photo sharing app with zero go-to-market plan.  Reality hit hard: "At Google, anything you launch gets millions of users. At a startup, the challenge isn't building—it's getting anyone to care." After writing a brutal postmortem documenting everything that went wrong, he started Warp with strict principles: only hire product-obsessed people, document every process, build pure software not services.  For three years, Warp had hundreds of thousands of free users but no revenue. Then they pivoted to AI-powered development in 2024. Here's how they went from taking 300 days to hit their $1M to now adding $1M ARR every 10 days.  Why You Should Listen: * Why working at Google can set you up to fail as a founder * How to know when to quit your own startup * Why you should write down every operating principle before starting * The shift he made to grow insanely fast * Why competing directly with fast-growing startups is actually smart Keywords: startup podcast, startup podcast for founders, Warp, Zach Lloyd, Google alumni, developer tools, AI coding, product-market fit, startup pivot, Series B 00:00:00 Intro 00:01:48 From law school to Google via Craigslist 00:05:01 Why Google makes you a terrible startup founder 00:10:36 Joining SelfMade as technical co-founder 00:19:00 Writing a brutal post-mortem of the startup experience 00:27:15 Building Warp and getting 10,000 signups day one 00:38:08 Raising $50M Series B with zero revenue 00:41:50 Pivoting to Agent Mode and AI development 00:46:27 From 300 days to $1M to adding $1M every 10 days Retry Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]

Alex had $2,000 in his checking account when Microsoft acquired his last company. For years, he paid himself $30K while his friends made six figures at corporate jobs. He had only 2 months of runway for 18 straight months.  Then retail media exploded and everything changed—he went from grinding against the current to riding a wave. After selling to Microsoft, he took 6 months off, got bored, and started Bluefish AI with the same team. This time they called Fortune 500 CMOs before building anything.  His #1 advice for early-stage founders: Get on the plane. And go meet your customers. You'll be shocked by how big a difference that makes.  Why You Should Listen: * How to survive on 2 months of runway indefinitely * How to validate your next startup before writing any code * Why second-time founders often have more blind spots than first-timers Keywords: startup podcast, startup podcast for founders, PromoteIQ, Microsoft acquisition, Alex Bluefish, retail media, product-market fit, MarTech, enterprise sales, second-time founder 00:00:00 Intro 00:01:58 From management consulting dreams to startup world 00:04:44 Trying to return $200K to investors after 30 days 00:07:19 Pivoting through iterations to find retail media 00:12:13 Finding product-market fit like a river reversing 00:21:28 Microsoft acquisition with $2,000 in the bank 00:24:30 Post-exit sabbatical and starting Bluefish 00:35:08 Building for AI marketing with Fortune 500 design partners 00:43:12 Always get on the plane Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]