StrictlyVC Download

This week on StrictlyVC Download, Connie Loizos talks with Bill Gurley, longtime venture capitalist, former Benchmark partner, and author of the new book Running Down a Dream. After stepping back from day-to-day investing, Gurley has turned his focus to a different question: how people build meaningful, enduring careers—and what they might do differently if given the chance to start over.In this conversation, Gurley reflects on why nearly 60% of professionals say they would rethink their career paths, how to know when it’s time to pivot, and why “regret minimization” can be a powerful decision-making framework. He shares his views on mentorship, peer networks, and the risks of following conventional career tracks in the age of AI. Gurley also weighs in on Silicon Valley’s shifting work culture, the resurgence of 996-style intensity, and why he believes the best way to future-proof your career isn’t to avoid technology—but to run straight at it. It’s a candid discussion about ambition, reinvention, and designing a career you won’t second-guess.
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This week on StrictlyVC Download, Connie Loizos talks with Stacy Brown-Philpot, founder and managing partner of Cherryrock Capital. After a decade at Google and leading TaskRabbit through its acquisition by IKEA, Brown-Philpot is now building a venture firm focused on Series A and Series B software companies led by under-invested founders—targeting what she sees as a critical gap in today’s venture ecosystem.

In this conversation, Brown-Philpot explains why she launched Cherryrock in a difficult fundraising environment, how the firm evaluates product-market fit at scale, and why quality revenue matters more than headline ARR. She discusses how AI is reshaping enterprise software, how her board roles at HP and StockX inform the way she assesses companies, and why she believes strong businesses will continue to get funded despite a bifurcated venture market. It’s a grounded look at building durable companies—and backing them at a pivotal stage of growth.
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This week on StrictlyVC Download, Connie Loizos talks with Paolo Ardoino, CEO of Tether, the company behind USDT, the world's largest stablecoin. With 536 million users globally, Tether has quietly become one of crypto's most powerful players—and now it's evolving far beyond stablecoins. Ardoino is transforming Tether into what he calls "the stable company," a diversified operation making bold bets on decentralized AI, agriculture, telecommunications, and gold-backed tokens.In this conversation, Ardoino explains how Tether generates billions in profit from U.S. Treasury holdings, why the company is building AI platforms that run locally on smartphones for emerging markets, and how its relationship with U.S. regulators has shifted dramatically. He also discusses Tether's geographic expansion, particularly in El Salvador and across Latin America, and makes the case that all of these seemingly disparate investments—from cattle ranching to brain-computer interfaces—are part of an interlocking strategy to serve the billions of people left behind by traditional finance.
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This week on StrictlyVC Download, Connie Loizos and Alex Gove talk with Howie Liu, co-founder and CEO of Airtable. On Tuesday, Liu announced the launch of Superagent, Airtable’s first standalone product outside of its core platform—and this isn’t just another AI feature bolted onto an existing product. Superagent represents a bit bet on autonomous agents that handle tasks end-to-end, rather than chatbots that provide text-based answers.

In this conversation, Liu walks us through why he decided to build Superagent as a separate product rather than just another Airtable feature, how it actually works under the hood—from native integrations to browser automation—and the early signals that suggest he might be onto something big.
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In this episode, Connie Loizos speaks with Mary Jane Rubenstein, a professor of religion and science and technology studies at Wesleyan University and author of "Worlds Without End: The Many Lives of the Multiverse"—a book that served as research material for the Oscar-winning film "Everything Everywhere All at Once."

As the space economy heats up and venture capital pours into startups promising everything from asteroid mining to lunar gas stations, Dr. Rubenstein offers a critical perspective on the ethics and values shaping humanity's expansion beyond Earth. Dr. Rubenstein discusses how religious stories have shaped space exploration from the Apollo missions to today's commercial ventures, examines how science fiction has influenced the industry (sometimes as cautionary tales that get misread as instruction manuals), and makes the case for why space debris might be the issue that brings nations together—ultimately challenging listeners to consider whether we're truly imagining new possibilities in space or simply extending the worst of what we have here on Earth.
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