Spooky News: California's Billionaire Tax is on the Ballot!

My explainer on California's "Billionaire Tax". In this episode I break down California's proposed billionaire tax, which is now officially on the ballot as Proposition 40. It's a one-time 5% tax on the assets of billionaires, put forward by a healthcare union. It's opposed by Governor Gavin Newsom and several other major unions. I walk through the core arguments against it: the risk that billionaires and high-potential entrepreneurs leave California (noting that figures including Mark Zuckerberg, the Google founders, and David Sacks have already relocated), the historical failure of wealth taxes in other countries, and the practical problem of identifying and valuing billionaires' assets. I also highlight a key concern in the actual text of the measure—that the legislature could later expand it beyond billionaires, make it recurring, or lower the threshold. I cover related ballot measures (Props 41 and 42) designed to neutralize or limit the tax, the constitutional complications of a national wealth tax, and the broader reality that California's richest residents already pay a large share of the state's taxes. This is my update on what's at stake if Prop 40 passes this November.

I sat down with David Tisch from BoxGroup. If you've looked at a seed firm's website and seen one famous logo, that's usually the whole list. David's list is Ramp, Plaid, ID.me, Stripe, Airtable, Warby Parker, Clay, Zipline — and Cursor, which just got acquired for $66 billion. Then he shrugs and says it probably just means he's been doing it awhile. We talk about the part of this job that doesn't show up on a website. Seed is messy. The feedback loop is five, ten, fifteen years. The founder is living inside the dream; we're a line item and a phone number. David's view is that most of us should end up as extras in the credits. If they need to listen to you, that's already a problem. Unsolicited VC advice is close to worthless. The few people worth listening to are obvious, and the third partner at the thirtieth-best firm is not one of them. What he actually underwrites is the why. Not the slide that says what they're building — the reason they're the person who can drag it through a decade of moving parts. Early tell: can they recruit? The smartest friends on campus. The band from Palantir or Anthropic or Ramp. Cursor started as a person Claire met in Dorm Room Fund, before there was a product. Two college friends, giants attacking from every side, and they still held the thing together. We get into the ugly middle of the companies everyone now treats as inevitable. Facebook, Uber, Airbnb all did down rounds. Fundraising is permission to make progress, not progress. A lot of AI "revenue" right now is companies trying not to miss something. Pets.com and Amazon were in the same business in the same moment. One of them was the company. David lives in New York because that's home, not because he's running a geography thesis. SF is the deep talent pool. Most other cities can build a few companies. Israel has a real early network — if a seed is leaving the country, he wonders why you're seeing it. Nobody is calling to do you a favor. Collaboration exists. Sharp elbows exist more. He won't pretend he's smart enough to tell you whether we blow up the data centers. He will say technology has been a force of good, this moment is early, and his job is still the same as it was sixteen years ago: wake up tomorrow and find someone who might actually change the world.   If you want to reach him: [email protected].

As Burning Man rolls around once again, is it still relevant to Silicon Valley? Reports of lower attendance this year, as the newer arrivals to Silicon Valley say "pass". A deep dive into this crazy event in the desert. li>ol]:list-[lower-alpha] [&_ol>li>ol>li>ol]:list-[lower-roman] [&_ol>li>ol>li>ol>li>ol]:list-[list-decimal] [&_[data-user]]:text-primary [&_:is(pre)]:overflow-auto [&_:is(table)]:w-full [&_:is(table,th,td)]:border [&_:is(table,th,td)]:border-collapse [&_:is(table,th,td)]:border-gray-300 [&_:is(table,th,td)]:p-2 [&_:is(strong,h1,h2,h3,h4,h5,h6)]:font-semibold [&_:is(h1)]:text-2xl [&_:is(h2)]:text-lg [&_:is(h3)]:text-md [&_h1:not(:first-child)]:mt-8 [&_h1:not(:last-child)]:mb-6 [&_h2:not(:first-child)]:mt-6 [&_h2:not(:last-child)]:mb-4 [&_h3:not(:first-child)]:mt-4 [&_pre]:bg-palette-gray-200 [&_pre>code]:bg-transparent [&_pre>code]:px-0 [&_pre>code]:py-0 [&_pre]:px-[6px] [&_pre]:py-[2px] [&_pre]:m-0 [&_pre]:rounded-[4px] [&_code]:bg-palette-gray-200 [&_code]:px-[6px] [&_code]:py-[2px] [&_code]:m-0 [&_code]:rounded-[4px] [&_blockquote]:m-0 [&_blockquote]:px-[16px] [&_blockquote]:py-0 [&_blockquote]:text-subtle [&_blockquote]:border-l-[4px] [&_blockquote]:border-palette-gray-200 overflow-x-auto [&_ol]:pl-5 [&_li]:my-2 [&_:is(p,ul,ol):not(:first-child)]:mt-3 [&_:is(p,ul,ol):not(:last-child)]:mb-3" data-testid="render-markdown"> Kent and Michael discuss the evolution, culture, and commercialization of the Burning Man festival. Event History Kent and Michael trace the origins of Burning Man from its 1986 beginnings on a beach to its current location in the Nevada desert. They discuss the documentary Spark: A Burning Man Story, noting how the event transitioned from an anarchic, unorganized gathering of "counterculture weirdos" to a highly structured society. The early era was characterized by a lack of formal infrastructure and a sense of pure anarchy. A turning point occurred around 1996 following incidents involving safety and deaths, leading to increased organization. The modern event functions with significant infrastructure, including a dedicated Department of Public Works (DPW) and professional management teams that resemble military operations. Cultural Shifts The conversation focuses on the tension between the original "burner" ethos and the influx of wealth from Silicon Valley. Michael notes that while many claim the event is about escaping society, participants have actually built their own complex bureaucracy and meritocracy. Plug and Play camps allow wealthy participants to fly in and experience the desert without the traditional labor of building camps or art. The introduction of ticket lotteries and scarcity has changed the social dynamic, moving away from open access toward a curated experience. There is ongoing debate regarding whether the event has "sold out" due to the presence of high-net-worth individuals and luxury amenities. Silicon Valley Influence Michael and Kent explore why Silicon Valley has effectively "hijacked" the festival, treating it as a massive networking event for tech elites. They reference an article by Nick Bilton in the New York Times regarding how tech leaders often pretend to be indifferent to money while simultaneously dominating spaces like Burning Man. The event serves as a primal networking roadshow where executives can interact outside of traditional corporate settings. The transition toward a more organized, "curated" festival is seen as an inevitable result of managing large populations and scarce resources. How does the increasing corporatization affect the long-term survival of the original artistic mission?

Sheel Mohnot is co-founder of Better Tomorrow Ventures, a venture firm that leads rounds in pre-seed and seed-stage fintech companies. It is one of the most active fintech investors in the world. Sheel has spent the last decade in fintech — first as an operator and angel, then as a founder of his own firm. In this conversation, he walks me through the unconventional path that led him into venture, including time spent in India working in microfinance, and why he believes a focused fintech strategy makes sense. We dig into some of his biggest early misses, including passing on both Robinhood and Chime, and what those decisions taught him about recognizing real customer shifts. Sheel also gives a clear-eyed view of today's hypergrowth environment, the gap between flashy numbers and durable businesses, and how AI is actually showing up in the day-to-day work of venture capital. We also talk about the growing political involvement of tech leaders, the challenges facing San Francisco, and what he's most excited about looking ahead — from self-driving cars to the quieter, more practical uses of AI. A candid conversation with one of fintech's more thoughtful investors. Better Tomorrow Ventures Sheel on X

In this episode of Something Ventured, Kent Lindstrom sits down with Mark Suster, Managing Partner at Upfront Ventures and one of Los Angeles' most prominent venture capitalists. Mark shares his unconventional journey from early computer programming in the 1980s, building and selling software companies, to becoming a VC — including the surprising challenges of the transition and why he created Launch Pad LA to stay connected to founders. The conversation explores the fundamental differences between being a founder and a venture capitalist, particularly the emotional "amplitude" of highs and lows, crisis frequency, and the long-term nature of measuring success in VC. Mark also dives deep into why Los Angeles has become a major hub for hard tech, aerospace, space, national defense, maritime innovation, and next-generation energy solutions (including nuclear applications on ships and in space). He makes a compelling case for LA's strengths in manufacturing, trade, and deep tech versus Silicon Valley's dominance in software and AI. Additional highlights include Mark's thoughts on nonconformity in investing, returning capital to LPs, the importance of government relations for startups, and his optimistic view of LA's future despite recent challenges. A thoughtful, wide-ranging discussion full of historical context, contrarian insights, and forward-looking vision on American innovation and resilience. Books Mark mentions in this podcast:   Miller, Chris. Chip War: The Fight for the World's Most Critical Technology. Scribner, 2022.   Herman, Arthur. Freedom's Forge: How American Business Produced Victory in World War II. Random House, 2012. Mark Suster: Upfront Ventures. |  LInkedIn | X  Thoughts? Drop a comment.

Andy McLoughlin is Managing Partner at Uncork Capital (formerly SoftTech VC). We discuss Andy's journey from co-founding Huddle -- racking servers in the Docklands and building their own payment system before Stripe -- to Silicon Valley. He was an early angel investor in companies like Postmates, eventually joining Jeff Clavier's venture firm SoftTech, now Uncork Capital. We dive into the golden era of "super angels," collaborative seed rounds, and famous near-misses like Uber and Twilio. Other topics include how seed funds like Uncork stay relevant in a world dominated by mega-funds, why specialized early-stage investors often serve founders better than big brand names, and how to find those non-obvious deals before they become consensus. Andy also shares what it felt like to step away from operating a company, the power of "knowing thyself," and how he's helping build Uncork into a firm that stays sharp through founder empathy and relentless context-switching. We also cover: The story behind Founders Pledge and giving back The British "GBx" network in Silicon Valley San Francisco's turnaround, tech getting political, and why local government actually matters The AI revolution — why everything feels like an AI company right now, what's overhyped, and why we're still in the very earliest innings Uncork Capital Something Ventured

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