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, General Partner at Root VC, is a former engineer and CTO with experience from iRobot to Teespring. He shares his unique journey from hands-on tech to venture capital, highlighting the magic of pair programming as an anti-slacking tactic. The conversation dives into the misunderstood realm of AI, the messy landscape of Web3, and why San Francisco remains the hub for innovation. Lee discusses the qualities of true technical VCs and why they’re key to finding the next big tech breakthrough in hard tech and robotics.

Danielle Strachman, co-founder of 1517 Fund and an educator with two decades in alternative education, teams up with Michael Gibson, a former philosophy PhD dropout and fellow co-founder, to discuss their contrarian approach to venture capital. They challenge the traditional higher education system, citing its flaws and the rising acceptance of non-degreed, often teenage founders. Their successful investments in companies like Luminar and Lambda Labs highlight the potential of young innovators. Michael also shares insights from his book, critiquing failing institutions and the diploma's role as a modern indulgence.

Frank Rotman, Founding Partner and Chief Investment Officer of QED Investors, is a notable figure in the fintech world with over three decades of experience. In this conversation, he discusses his journey from Capital One’s innovative strategies to co-founding QED. Rotman delves into his philosophy on backing founders, the balance of expertise and opportunity in fintech, and the evolution of the music industry alongside technology. He also addresses the impacts of financial nihilism and offers insights into the future of fintech and entrepreneurship.

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

Kobie Fuller is a partner at Upfront Ventures. He came to the firm after investing at Accel and leading marketing efforts at EVOLVE, the large global fashion ecommerce platform. Highlights from our conversation. -- we covered a lot of ground, so this is just a small part: Kobie's Athletic Background and Vision for Track and Field: Kobie, a former track and field athlete who competed in the 400m and 200m, believes the sport deserves greater mainstream attention due to its purity and universal accessibility. He discusses a new professional track league, Grand Slam Track, started by Olympian Michael Johnson, aimed at elevating the sport's profile, potentially rivaling soccer's popularity. 2 Journey into Venture Capital: Kobie's entry into venture capital was sparked during the dot-com boom when he co-founded a soccer portal in college. Exposure to VCs visiting his startup led him to pursue a career in VC, despite initial rejections. His persistence, including sending physical letters to Boston VCs, eventually landed him a role at Insight Partners. Decision to Pass on Oculus: We've all done it! At a career crossroads, Kobie chose not to join Oculus as CMO, opting instead for a VC role at Accel. He later invested in Oculus. He remains optimistic about AR/VR's future, noting improved devices like the Oculus Quest, though he notes it's not his primary investment focus. Advocacy for Black Founders: Kobie addresses the underrepresentation of Black founders in tech, emphasizing the need for more diverse capital allocators and intentional outreach beyond traditional networks. He founded Valence, a platform to connect Black professionals, which grew to 30,000 members, highlighting his continued commitment to fostering inclusivity in the startup ecosystem. AI's Transformative Potential in Venture Capital: Kobie is bullish on AI, particularly its ability to augment human capabilities in enterprise software. He cies examples like portfolio company 1Up, which reduces RFP completion from weeks to minutes. He contrasts this with concerns about AI's potential to erode human connection, as illustrated by a great story about an essay his son wrote. dUpfront Ventures 8-Bit Capital Something Ventured Podcast

David Anderman is co-founder and General Partner of Stellar Ventures, a venture capital firm focused on early-stage space technology startups. He spent 16 years at Lucasfilm Ltd., creator of the Star Wars franchise. As Chief Operating Officer and General Counsel, he notably negotiated Lucasfilm's $4 billion sale to Disney in 2012. Moving from imagined space to real space: David became General Counsel at SpaceX, where he played a key role in landmark projects like the launch of Starlink and the first private human spaceflight to the International Space Station. David is also founder of Red Rock Media Group, which is the media company for humanity's expansion into the cosmos. This episode covers a lot of ground (well, space): - What it's like to work for George Lucas - What it's like to work for Elon Musk (and what motivates him) - The media rights to SpaceX's journey to Mars ('Big Brother' in space?) - Timeline for humans on Mars - How space has been opened up to entrepreneurs and investors who support them Stellar Ventures Something Ventured

Cyan Banister of Long Journey Ventures is truly one of the most successful and interesting early stage venture investors. And by 'successful investor', I mean "invested early in Uber and SpaceX" kind of successful. She overcame a challenging childhood that included periods of homelessness (a surprisingly uplifting story, covered deeply in Tim Ferriss' interview with Cyan). Here we discuss Cyan's journey from these early struggles to becoming a prominent figure in Silicon Valley. Along the way she learns to program computers, and co-founds Zivity – an early social networking site one might compare to OnlyFans. She was a partner at VC juggernaut Founders Fund (the VC fund founded by Peter Thiel, that invested in AirBnB, Spotify and OpenAI among others). She also is author of "The Ugly Duckling" substack. This episode also includes her brush with Star Wars' "Lucasfilm" (the singular matters), her meeting with Marc Andreesen and her (incredible) plans for the future. Ugly Duckling Long Journey Ventures Something Ventured 8-Bit Capital

Roger Ehrenberg, a seasoned investor and founder of IA Ventures and Eberg Capital, dives deep into his multifaceted career. He shares insights on the evolution from Wall Street trading to venture capital, emphasizing the importance of founder liquidity and humane investing. Ehrenberg explains why he sees sports as a ripe area for investment, discussing strategic stakes in franchises like the Miami Marlins and trends in sports betting and media convergence. He also touches on revitalizing Detroit through targeted investments while highlighting the critical role of community services in urban renewal.

Mark Scianna, the founder of venture firm "Forward Deployed," which targets sectors like Defense, Energy, and A.I., was spotlighted as a 'top emerging manager' in 2022. Starting his journey as an engineer and an early investor at Palantir, Scianna offers an insider's perspective in this episode, unraveling the enigma of Palantir's inception and meteoric rise. Scianna delves into what makes Palantir so unique, shedding light on how its unconventional management style has been a cornerstone of its success. He doesn't shy away from the intense realities of being 'forward deployed'—a term that for him meant being physically stationed in war zones to deploy Palantir's groundbreaking solutions firsthand. Scianna also talks about the newly popular trend of investing in 'defense tech' – and who should (or shouldn't) be doing it. Links: Forward Deployed 8-Bit Capital Something Ventured