Something Ventured -- Silicon Valley Podcast

In this episode of Something Ventured I dive into the explosive controversy shaking Silicon Valley: California's proposed one-time 5% "Billionaires Tax" ballot initiative. Filed by the powerful healthcare workers union SEIU-UHW, the measure would impose a retroactive 5% levy on the net worth of individuals worth $1 billion or more (as of January 1, 2026), aiming to raise around $100 billion to shore up the state's healthcare system and support education amid looming federal funding cuts. I break down why this has sparked panic among the ultra-wealthy — including Google co-founders Larry Page and Sergey Brin, who have already moved business entities out of state (along with others like David Sacks) — potentially costing California trillions in departing wealth and innovation. I explain key concerns: The tax applies to unrealized gains and even control/voting shares in companies (which could hit founders like Page and Brin far harder than a simple 5% of their personal stock holdings).  Fears that a "one-tim

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

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 overh

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”

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

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 VC

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 suppo

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 Somethin

Roger Ehrenberg's career spans three remarkable acts, each of which would be impressive on its own.  He founded IA Ventures, a seed-stage venture capital firm, in 2010.  IA Ventures invested in numerous successful startups, including Datadog, Digital Ocean, The Trade Desk, and Wise. His work with IA Ventures has earned him recognition as a three-time winner of the “Midas Award” – the coveted ranking of venture capitalists by Forbes. Before founding IA Ventures, Roger spent 17 years on Wall Street at Citibank and Deutsche Bank, specializing in derivatives and quantitative trading, managing over $10 billion in investor assets at its peak. In 2021, Roger stepped back from day-to-day operations at IA Ventures to focus on Eberg Capital, which he founded with his two sons to invest in sports franchises, sports betting, media, and entertainment. Through Eberg Capital, he has made strategic investments in sports teams like the Miami Marlins, Real Salt Lake, and the Utah Royals, as well as in the Alpine Formula 1 Raci

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

Winter Mead is the author of How to Raise a Venture Capital Fund: The Essential Guide on Fundraising and Understanding Limited Partners.  He is also founder of Coolwater Capital, a new model that helps launch, build, and scale emerging fund managers While there are a lot of investors (known in the parlance as “LPs”), and certainly a lot of funds – the set of people who sit at the intersection of these two is much smaller. So Winter has an unusual perspective and point of view to share. Winter shares his journey from Harvard and Hall Capital to Sapphire Ventures and ultimately to founding Coolwater. He explains the complex and often overlooked challenges new fund managers face in securing funding, managing portfolios, and building effective business strategies. With insights on the evolving venture ecosystem, the role of emerging managers in fueling innovation, and the rising focus on sectors like AI, climate tech, and longevity, Winter offers a compelling look at how Coolwater helps guide and co-build alongsi

Max Altman and Ben Braverman were both pretty close to Silicon Valley royalty before they started Saga Ventures.  Max had built Alt Capital with his brothers Sam and Jack.  Ben had helped Ryan Peterson build Flexport as its Chief Revenue Officer.   Recently, they came together with a third partner (Thomson Nguyen, who does not appear in this episode) to form Saga Ventures. In this episode, Max and Ben talk about building their new fund, discussing its structure, goals, and the nature of VC partnerships.  We continue with a look at the Silicon Valley Ecosystem: There is a focus on people, the interconnected nature of Silicon Valley, and how certain patterns of behavior and community dynamics influence the startup and venture capital space. We finish by covering a range of other topics:  - How venture capital lost its way - The rise of VC podcasting - Billionaire VCs fighting over politics Join us as Max Altman and Ben Braverman discuss building Saga Ventures. https://www.sagavc.com/  https://8bitcapital.com/ h

If you don’t already know about Alexis Gay, you’re about to. Alexis is the creator and star of her solo comedy show, “Unprofessional”. Recently, her show was a hit at the world-renowned Edinburgh Fringe Festival, and she's now touring the show for audiences across the United States.  Alexis previously worked in the tech industry running Business Operations and Creator Partnerships at Patreon.   Outside of work, she started creating videos featuring dead-on takes on tech culture -- and everyday life.   These soon went viral, racking up more than 24 million views across social media. Her sharp insights into startup life and its absurdities resonated far and wide, transforming her into a favorite amongst both tech insiders and comedy fans alike. From viral videos to her successful podcast, Alexis has kept audiences hooked. She’s been profiled by Fast Company, Nightline, Business Insider, SFGate, and CNBC.  And now, she's stepping onto the stage as a standup comedian. Now comes her debut solo show, “Unprofessiona

In this episode of Something Ventured, I talk to Adeyemi “Ade” Ajao, co-founder of Base10 Partners, one of the largest Black-led venture capital firms in the world. Ade shares his journey from growing up in Nigeria and Spain to building multiple successful companies, including Tuenti, which was sold to Telefonica. He also discusses his transition into venture capital, his mission to empower underrepresented founders, and the impact of Base10’s Advancement Initiative, which partners with top universities to support a diverse new generation of entrepreneurs. Other topics include:  Sci-Fi Inspiration: Adi and his brother are avid readers of science fiction, which shaped their belief in the power of human imagination and technology. Global Entrepreneurship: Adi reflects on the scarcity mindset found in some parts of the world, like Spain and Mexico, and contrasts it with the abundance mindset in Silicon Valley, where entrepreneurs help each other succeed. Technological Evolution: The conversation touches on how

Nick Sturiale reflects on a career working in venture capital, in which he invested early in companies such as Splunk, Bill.com, and Reputation.com. Nick shares insights from his extensive career, which spans roles at Ignition Partners, Icon Ventures, Seven Rosen Funds, and the Carlyle Group, among others. He reflects on the evolution of the venture capital landscape, the challenges of finding product-market fit, and the critical role of timing and luck in a startup's success. Nick also delves into the complexities of being a CEO as a company grows, discussing the shift from being a hands-on founder to potentially needing to bring in a new leader with different skills. He emphasizes the importance of understanding customer needs through active listening and the pitfalls that entrepreneurs and VCs alike must navigate. This episode is a must-listen for anyone looking to gain a deeper understanding of the venture capital world and the nuanced journey of building successful startups. (I had an AI write that last

Eric Paley is a General Partner at Founder Collective, one of the great seed-stage venture capital brands - and one of the relatively few venture firms led by startup founders. As the name suggests, Founder Collective is a "founder stage" venture capital fund that focuses on providing the first professional round of capital to “entrepreneurs with compelling business concepts”. Eric himself also founded several companies before becoming a VC.  Founder Collective's investments include:  Coupang, Cruise, Kaggle, Pill Pak, The Trade Desk, Uber and Venmo.  In this episode we discuss the importance of Founder-led VC firms, and the evolution of seed VC firms - which barely existed when he started, and now number in the hundreds.We also discuss: ·      * Why the unique name "Collective" ·      * Fuzzy VC math ·      * VC 'revisionist history"      ·      *  What's next for Founder Collective Please subscribe to Something Ventured! Eric Paley on X (Twitter)  Founder Collective Something Ventured 8-Bit Cap

Homebrew is one of the great venture firm names.  It hearkens back to the 1970s era computer hobbyist group that included people like Steve Jobs.  Hunter Walk and Satya Patel are the partners who founded and built Homebrew (the venture capital firm). Nevertheless, if you say “Hunter and Satya” in Silicon Valley, people will know exactly who you are talking about.  Hunter Walk came to homebrew with experience as a product leader at YouTube and Google.  Meanwhile, Satya Patel's background was as a seasoned investor at Battery Ventures and product leader at Twitter. In this episode we discuss the power of partnerships in Silicon Valley.  In particular we talk about the power of the 2 -person partnership (see also:  Andreessen Horowitz), why the alchemy has to be right, and why some don’t make it. We also discuss the evolution of Homebrew from a firm backed by outside capital (from Limited Partners or “LPs”) to one in which the two founders deploy their own capital. Finally, we cover Hunter and Satya’s newest fun

Nolan Bushnell’s career is extraordinary.  Nolan has ignited two entertainment revolutions: first with Atari, birthing the video game industry through classics like Pong, and later with Chuck E. Cheese, merging pizza and arcade games for family fun. A serial entrepreneur, he's founded over 20 companies, venturing into robotics, personal computers, and beyond, forever changing the landscape of leisure and inspiration. Nolan has turned his thoughts to the state of education in the US and has teamed up with Dr. Leah Hanes to form ExoDexa, a developer of educational games that seek to ‘gamify’ education.  Together, they’ve published a book “Shaping the Future of Education” outlining their ideas. Dr. Leah Hanes is a force to be reckoned with as well.  Dr. Hanes has been a champion for STEAM education (Science, Technology, Engineering, Arts, and Math) for years, leading the Two Bit Circus Foundation since 2013 and using her expertise to advocate for a more engaging and future-proof approach to learning.  In this

Richard Socher is a visionary computer scientist, entrepreneur, and AI researcher who has dedicated his career to pushing the boundaries of what's possible in AI. With a Ph.D. from Stanford University, Richard's groundbreaking work in deep learning, neural networks, and NLP has paved the way for remarkable advances in AI applications. It may seem like everyone is an AI expert these days:  Richard Socher really is.  Richarrd is founder of the AI-focused venture firm AIX, and founder of the AI-powered search engine You.com. He is the former Chief Scientist at Salesforce and founder of the groundbreaking MetaMind AI startup (which was acquired by Salesforce).  In short, when it comes to AI, Richard is the real deal. In this episode, we delve into Richard's insights on the latest AI trends, ethical considerations in AI development, the future of human-AI collaboration, and much more. Whether you’re new to AI – or have been investing in it for 10 years -- Richard's engaging discussions and visionary ideas will cap