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-time" tax on billionaires could expand into an ongoing wealth tax affecting the middle class (just like the federal income tax did).

How deceptive ballot naming, union funding power, and shifting political winds (including support from Rep. Ro Khanna) make passage seem scarily plausible — despite opposition from Gov. Gavin Newsom.

I also also consider the value billionaires create (think iPhones, Amazon deliveries, and massive charitable giving), highlight how the top 1% already pay a huge share of California's taxes, and contemplate stifled innovation, capital flight, and long-term damage to the state's economy.

From ghost-town fears for Silicon Valley to broader debates on wealth, fairness, and government overreach — this is the inside story straight from the heart of tech. Stay tuned for more unfiltered takes on what's really happening in Silicon Valley and beyond.

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

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'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 Racing Team.

In this episode he discusses building IA Ventures as well as why he thinks sports is the next great investing opportunity.

https://www.ebergcapital.com/

https://somethingventured.us/

https://8bitcapital.com/