Katelin Holloway's Billion-Dollar Box Scores

Venture capitalist Katelin Holloway—founding partner at 776— unpacks the new math of sports investing. From incubating Angel City FC and LA Golf Club to why women’s sports offer the biggest upside, Holloway explains where value is created (media, sponsors, merch) and how pay equity should be built from first principles. Plus: the origin of “776,” TGL’s tech-arena gamble, and the story behind her three citizen’s arrests.

Ireland is making an aggressive play to strengthen its ties with the West Coast. IDA Ireland—the nation’s foreign investment agency—has launched a trade mission aimed at securing €250 billion (about $300 billion) in new capital and creating 75,000 jobs over the next five years. Already, a West Coast company opens or expands in Ireland every month, with Apple, Google, Anthropic, and Microsoft among the major investors. Scott McGrew sits down with Ivan Houlihan of IDA Ireland to talk about Ireland’s evolving industries, the impact of Brexit, why U.S. tech companies keep choosing Ireland, and how the country is balancing record foreign investment with challenges like housing.

NEA partner Aaron Jacobson joins Sand Hill Road to discuss the next wave of robotics and AI — from warehouse automation and drone manufacturing to autonomous construction and defense innovation. Jacobson explains why the future of robotics isn’t humanoids but specialized machines that perform one task perfectly. He shares insights on startups like Outrider, Built Robotics, Second Front Systems, and Firestorm, and why he believes AI-driven intelligence and flexible manufacturing will reshape industries from green energy to national security.

Steven Lee raised $40 million in five weeks to fund his own venture firm — with just his reputation, network, and a bet on AI. From being the last kid picked up at school to becoming one of Silicon Valley’s earliest investors in breakout companies, Lee shares his journey from his parents’ clothing store in Los Angeles, to Twitter, to launching his own fund.

Steven Lee’s journey from waiting outside his L.A. high school to launching Seven Stars Capital is one of grit, timing, and intuition. In this episode, the former SV Angel partner explains how he raised $40 million in five weeks—without a product or pitch deck—relying on relationships, reputation, and a sharp eye for AI. Lee reflects on lessons from Twitter and SV Angel, his immigrant roots, and why being the earliest money in isn’t just about speed, but trust. Plus: how AI is transforming overlooked sectors, from law enforcement to accounting.

Rehan Jalil has sold three companies. His fourth, Securiti AI, might be his first to go public. A decade after we first met him as the founder of Elastica, Rehan returns to explain why protecting enterprise data is the gateway to unlocking AI’s full potential—and why building companies will always be his passion. From reading market signals to redefining data security, Jalil shares what it takes to keep winning in a fast-changing tech landscape. 

Kanyi Maqubela’s journey is nothing short of extraordinary—from fleeing apartheid South Africa as an infant, to living in a homeless shelter in New York City, to becoming a venture capitalist in Silicon Valley. As managing partner at Kindred Ventures, Maqubela sits at the intersection of culture, finance, and technology. In this episode, he talks with Scott McGrew about why he believes crypto has already succeeded—even if it doesn’t look the way early critics expected.Maqubela argues that value isn’t just stored in physical assets or spreadsheets—it can also be stored in memes. Whether it's gold, real estate in Las Vegas, or Dogecoin, he suggests that cultural momentum and shared belief can give something staying power and real economic weight. “Mimetic value is value,” he says, making the case that virality itself is a form of capital.This conversation explores why the blockchain matters, how meme coins might be more serious than they seem, and why the next generation is right to question the financial systems they inherited. It's a provocative look at the future of value—and the stories we tell to justify it.

Scott McGrew sits down with Tom Drummond, co-founder of developer-first VC firm Heavybit, fresh off the announcement of the firm’s fifth fund and second opportunity fund.Drummond explains why the traditional enterprise sales model is fading, and why developers now hold the keys to software adoption. He talks about resisting the temptation of early revenue, the dangers of “cargo cult” startup thinking, and what it means to build for a future where code is free and infrastructure is everything. As Tom puts it: “We’re entering a world where code is free. Anyone can generate it. The consequence? We’ll need an entirely new layer of infrastructure." Sand Hill Road is produced by Andrew Mendez under the leadership of Sara Bueno and Stephanie Adrouny.

It's our annual tradition—venture capitalists and startup founders share the books that shaped them. From sci-fi and civil rights to artificial intelligence and management, this year's reading list offers insight into the minds of Silicon Valley’s most thoughtful leaders.Highlights include:Master of the Senate by Robert Caro, recommended by Casber Wang of Sapphire Ventures for its deep exploration of power and politicsTraffic by Ben Smith, cited by Joe Alalou of Daring Ventures as essential reading on how the social web shaped our modern worldThe Sentence by Louise Erdrich, praised by Initiate Ventures’ Jessica Owens for its emotional depth and powerful storytellingRead Write Own by Chris Dixon, a pick from Bobby Franklin of the NVCA to better understand the potential of blockchain beyond cryptoEven Cowgirls Get the Blues by Tom Robbins, a personal favorite of Wharton’s Lori Rosenkopf for its message on turning perceived flaws into strengthsMindset by Carol Dweck, currently on Larry Gadea’s reading listThe Foundation Series by Isaac Asimov, a longtime source of inspiration for Imvaria's Joshua ReicherHigh Output Management by Intel legend Andy Grove, recommended by Avery Pennarun of TailscaleTomorrow, and Tomorrow, and Tomorrow by Gabrielle Zevin, the book Amit Kumar of Accel is gifting to friendsPrediction Machines by Ajay Agrawal, a favorite of Terry Doyle from TELUS Ventures for making AI approachable—even for his 89-year-old motherAnd anything by Isaac Asimov, says James Joaquin of Obvious Ventures, who’s now funding a factory that grows diamondsMore than just a beach read list, these titles reflect the philosophies and obsessions of today’s investors. Dive into the full episode of Sand Hill Road for all the recommendations—and check our archives for past years’ picks.Sand Hill Road is produced by Andrew Mendez under the leadership of Sara Bueno and Stephanie Adrouny

Stanford lecturer and venture investor Robert Siegel argues the lone-wolf CEO is not just outdated—but dangerous. In this episode, he joins Scott to explain why today's most effective leaders are those who can hold competing truths at once: acting with empathy and accountability, being tactical and strategic, thinking locally and globally. Drawing from his new book The Systems Leader, Siegel shares stories from Silicon Valley and beyond, reflects on the next generation of founders, and explains what it really takes to lead in a world defined by constant crisis and accelerating change.Sand Hill Road is produced by Andrew Mendez under the leadership of Sara Bueno and Stephany Adrouny