A Product Market Fit Show | Startup Podcast for Founders

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]

Brett had a drug dealer's car for 13 days. By day 11, the death threats started coming. This is the reality of building ServiceUp, the "DoorDash for auto repair."  Brett literally stole DoorDash's entire playbook—city launches, three-sided marketplace, everything—but discovered even if he got 90% right, 10% of B2C customers can end you.  He raised from Tiger just as the firm exploded. The DoorDash partnership that seemed like salvation turned into their worst nightmare. But then they pivoted to B2B and saw their average order value grow 5x overnight. "Work-life balance is BS. If you can work seven days a week, you'll fail faster, fix faster, and find product-market fit faster." Why You Should Listen: * Why just 10% of your customers can destroy your business  * How to close funding in the middle of a macro crisis * Why work-life balance is BS if you want to build something big * How stealing another startup's playbook can lead to 5000% growth * Why your worst customers might actually show you your best pivot Keywords: startup podcast, startup podcast for founders, ServiceUp, Brett Carlson, marketplace startup, B2B pivot, Tiger Global, auto repair tech, fleet management, startup growth 00:00:00 Intro 00:01:40 Failed auto shop becomes ServiceUp idea 00:03:27 Pulling co-founder out of retirement 00:09:30 Raising $2M seed from angels 00:13:23 Building the MVP in Puerto Rico 00:15:01 Early Bay Area operations and getting shops 00:17:50 The drug dealer death threat incident 00:21:17 Tiger Global loses $8B during Series A 00:26:57 DoorDash partnership disaster 00:28:36 Pivoting from B2C to B2B fleets 00:30:00 Finding product-market fit Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]

Doug Scott and the Ethic team spent years building technology before landing real customers. While other startups were growing fast, Ethic was focused on building, and after two years had only a modest amount of AUM. Until he and his team found a way to help his customers help them WIN new clients they couldn't land before. That shift took them to ~$250M AUM in one year. He reveals why he left investment banking in Australia, sold everything, and moved to the Bay Area within three weeks with no idea what company to start.  He pitched over 100 investors to raise early rounds, survived years of building with no traction, and discovered the enterprise sales playbook that unlocked distribution in wealth management. Today Ethic manages $7 Billion and has raised over $160 Million in funding. "If I knew how difficult it would be, maybe I wouldn't have done it." This is the reality of building a decade-long overnight success. Why You Should Listen: * Why helping customers win new business is the killer ROI * How to survive a 3-year build phase when everyone else is growing fast * Why you should pitch 100+ investors even if only 5 will say yes * How to figure out distribution and go-to-market * Why the best value-add investors never pitch their value-add Keywords: startup podcast, startup podcast for founders, Ethic, Douglas Scott, wealth management, ESG investing, fintech, B2B2C, Series A, distribution strategy 00:00:00 Intro 00:01:47 What Ethic does 00:08:15 Leaving Australia for Bay Area with no plan 00:17:06 The breakthrough for 5x YoY growth  00:29:42 Three years building with no traction 00:38:36 Distribution partnerships unlock growth 00:42:44 Finding product-market fit Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]