Something Ventured -- Silicon Valley Podcast

In this episode of the Something Ventured podcast, I talk with Sam Shank, the founder of HotelTonight—the groundbreaking last-minute hotel booking app that was acquired by Airbnb in a deal reportedly valued at nearly half a billion dollars. Sam takes us on an incredible journey: from his early days in Hollywood as a production assistant on Wes Craven's iconic horror film Scream (yes, he has an IMDb credit!), to pivoting to tech during the dot-com boom, surviving the crash, and founding multiple startups in the brutal travel space. After two tough swings that taught him invaluable lessons about product-market fit, distribution, and avoiding incremental ideas, Sam spotted a massive opportunity in mobile same-day hotel bookings. Sam shares how HotelTonight cracked the App Store rankings, turned perishable hotel inventory into gold, and ultimately became a perfect strategic fit for Airbnb. Now, Sam is back at it with his new venture in wildfire insurance—using cutting-edge science and AI to make high-risk homes insurable and literally save lives. We also dive into Sam's reflections on Silicon Valley's evolution, the future of AI in travel distribution, self-driving cars, and why building things still excites him after all these years. Hopefully you'll find it a candid, inspiring conversation with a resilient founder who proves that great outcomes often come on the third try. Timestamps 00:00 – Intro & How Kent Met Sam 03:29 – From Hollywood (Scream) to Silicon Valley 09:41 – Early Startups & Lessons from Failure 19:35 – The HotelTonight Origin Story 27:18 – The Airbnb Acquisition 29:52 – New Venture: Wildfire Insurance with Science & AI 38:48 – Silicon Valley Then vs. Now + AI's Impact Something Ventured Podcast 8-Bit Capital

Lee Edwards is a General Partner at Root VC, a San Francisco-based deep tech seed fund. They recently raised their 4th fund of $190 million. But before he became a venture capitalist, Lee was an engineer. He was most recently CTO at Teespring. Previously, Lee was a mechanical engineer at iRobot, a software engineer at Pivotal Labs, Lead Engineer at SideTour (acquired by Groupon in 2013), and engineering manager for GrouponLive. He graduated from Olin College of Engineering with a degree in Systems Engineering. So not the type of person you'd expect to become a venture capitalist. In this episode he talks about unconventional leap from hands-on engineering at Pivotal Labs and Teespring to the high-stakes world of seed-stage investing in devtools, AI, and hard tech. We discuss – it gets a bit technical -- the magic of pair programming (and why it's the ultimate anti-slacking hack), the ADHD-fueled superpowers of VC life, and Lee's early days tinkering with QBASIC on a Gateway 2000. We also cover AI's overhyped (yet underappreciated) revolution, the wild west of Web3 engineering, and why San Francisco remains the epicenter for autonomous dreamers (shoutout to Waymo dodging NIMBY drama). Plus, we take on fake "AI-native" posers, the next Bill Gates hacking LLMs in their basement, and why technical VCs are the real unicorn hunters. An AI suggested I end the description of the podcast with "Whether you're a builder, investor, or just love origin stories that skip the Ivy League script, Lee's chill vibe and sharp takes make this a must-listen. Tune in for laughs, lore, and lessons on staying hands-dirty in tech." AI has a way to go. Oh – we also discuss the perennial favorite question around AI: Will we have to blow up the data centers? Root.vc 8-Bit Capital Lee Edwards on X Kent Lindstrom on X

In this episode of the Something Ventured podcast, I spend time with Danielle Strachman and Michael Gibson, the people behind 1517 Fund. 1517 is a venture capital firm that defies Silicon Valley's fixation on elite credentials from Stanford, Harvard and the like. Their paths to venture capital are anything but typical. Danielle shares how her 20 years in alternative education, from founding a tutoring company to launching a San Diego charter school rooted in homeschooling principles, shaped her belief in lifelong learning for all. Michael, a former philosophy PhD 'dropout', recounts how he joined Peter Thiel's orbit through the Seasteading Institute and helped launch the Thiel Fellowship, which famously paid young innovators to skip college. Together, they explain how their time at the Thiel Foundation inspired the 1517 Fund—named after Martin Luther's 1517 theses, a nod to challenging modern "indulgences" like college diplomas. We unpack the flaws in traditional education, from the "higher education bubble" and soaring tuition costs to the growing acceptance of gap years and autodidacts. Danielle and Michael discuss how 1517 Fund bets on non-degreed, often teenage founders tackling ambitious tech challenges, with standout investments like Luminar (autonomous driving sensors that IPO'd in 2020), Lambda Labs (now a GPU cloud computing leader), and Positron (AI inference chips). Michael also explains the title of his book Paper Belt on Fire, a critique of failing institutions—from universities to banks—that rely on outdated "paper" authentication. We wrap up by exploring AI's game-changing potential, especially for young founders pushing the frontiers of knowledge. 1517 Fund 8-Bit Capital Danielle on X Michael on X Kent on X

In this episode I talk with Frank Rotman, Founding Partner and Chief Investment Officer of QED Investors, a leading fintech-focused venture capital firm managing $4.3 billion that has backed over 200 companies. A seven-time Forbes Midas List honoree, Frank shares his remarkable journey—from shaping Capital One's groundbreaking, data-driven strategy during his 13 years there, to co-founding QED Investors, which has since become a global powerhouse in the fintech ecosystem. Frank is also a widely respected thought leader—you may know him as @fintechjunkie on X—where his essays and insights on startups, investing, and market cycles reach tens of thousands. In this conversation, he reflects on lessons from three decades in finance and venture capital, his philosophy on backing founders, and where he sees fintech heading next. Fintech Junkie Something Ventured 8-Bit Capital

Eric Ries, entrepreneur and author of the bestselling book "The Lean Startup," ignited a movement that reshaped how founders and corporations build and scale businesses worldwide. Drawing from his experiences in Silicon Valley startups, Ries introduced a methodology centered on rapid experimentation and iterative development that encouraged entrepreneurs to create minimum viable products (MVPs), test assumptions with real customers, and pivot quickly to maximize success. He is host of The Eric Ries Show where he discusses with founders and business leaders how to build profitable companies for the long-term benefit of society. In this episode we discuss: • Origins and Rise of the Lean Startup Movement • Misconceptions and Applications of Lean Startup Principles • Expansion to Corporations and Broader Contexts • Founder Well-Being, Business Philosophy, and Governance • AI Developments, Risks, and Eric's Current Projects And, of course, much more! The Eric Ries Show Something Ventured