Uncapped with Jack Altman

It was a pleasure to sit down this week with Josh Kopelman, one of the original architects of seed stage investing who continues to re-invent what it means to operate within venture. Josh co-founded First Round Capital, which has invested at the earliest stages in companies like Square, Uber, and Roblox. Some of Josh’s more recent investments include Notion, Pomelo Care, Loyal, and Perpay. Since First Round’s inception in 2004, Josh has invested in 500+ startups and has frequently made the Forbes “Midas List” which ranks the top 100 tech investors. Josh has been a founder three times (four if you include founding First Round). In 1992, while in college, he co-founded Infonautics Corporation – and took it public on NASDAQ in 1996. Josh co-founded Half.com in 1999 and led it to become one of the largest sellers of used books, movies and music in the world. Half.com was acquired by eBay in 2000, where Josh remained for three years. In late 2003, Josh helped to found TurnTide, an anti-spam company that created the world’s first anti-spam router. TurnTide was acquired by Symantec just six months later. We covered: His “Venture Arrogance Score” The role of relevance in venture Making money in disequilibrium Overlooking margin superiority Decision-making as a product Timestamps: (0:00) Intro (0:25) Current landscape (4:39) Venture Arrogance Score (10:49) Comparing fund models (14:24) The role of relevance in venture (21:03) Small funds vs large funds (26:36) Making money in disequilibrium (33:57) Overlooking margin superiority (43:17) First Round’s strategy (49:02) Operating like a company (56:49) Future of First Round Linktree: https://linktr.ee/uncappedpod Twitter: https://x.com/jaltma Email: friends@uncappedpod.com

Garry Tan, CEO of Y Combinator and a prominent figure in early-stage startups, discusses his journey from co-founding Posterous to leading one of the most influential startup accelerators. He shares insights on running YC like a founder and the evolving landscape of startups influenced by AI. Garry highlights the importance of empathy in successful leadership and the rise of compound startups. He also touches on the role of YC in hard tech and his engagement in local politics to address community challenges.

Elad Gil, a serial entrepreneur and startup investor, shares insights from his impressive background, including his time at Google and co-founding Color Health. He discusses the importance of optimizing for market needs and cultivating optionality in career growth. Elad reveals his secrets for achieving long-lasting success and leveraging time effectively. He also dives into investing outside of AI and emphasizes the significance of getting the right theme in business. Listeners will gain valuable perspectives on navigating the evolving tech landscape and scaling startups.

In this engaging conversation, Sarah Guo, founder of Conviction and former General Partner at Greylock Partners, shares her insights on the ever-evolving world of venture capital. She discusses the compounding qualities that make firms endure and the critical role of branding in investment success. Guo also delves into navigating the AI landscape, emphasizing the shift from focusing on inputs to outputs. Additionally, she highlights the importance of equipping future generations with essential skills, preparing them for the challenges ahead.

Adam Guild, the founder of Owner, shares his inspiring journey as a young entrepreneur who dropped out of high school to build a successful software company for small business owners. He discusses the vital role of premium domain names in establishing trust and authority, and how navigating early challenges fueled his commitment. Guild emphasizes the importance of understanding customer needs, persistence in recruiting top talent, and maintaining health and resilience amidst startup pressures, all while illustrating how learning from others enhances growth.

Aaron Levie, Co-founder and CEO of Box, shares how he revolutionized cloud storage at just 19. He delves into the transformative impact AI has on enterprise management, revealing its potential to unlock hidden insights. The discussion also touches on market dynamics, showcasing how startups can outpace established firms. Levie reflects on his early cloud challenges and emphasizes the significance of adaptability. Lastly, he critiques the shifting political landscape and its implications for innovation and the tech industry.

Keith Rabois, a Managing Director at Khosla Ventures and CEO of OpenStore, shares insights from his impressive investing journey, which includes backing giants like DoorDash and Stripe. He discusses the vital traits of top founders and the importance of instinct in decision-making. Rabois emphasizes the role of venture capitalists as strategic advisors, especially with ambitious founders. He also reflects on the evolving relationship between tech and government, along with the implications for innovation in AI and healthcare, providing a deep dive into the complexities of startup investing.

Shaun Maguire, a Partner at Sequoia Capital, has a rich history, leading investments in groundbreaking companies like SpaceX and The Boring Company. In this conversation, Shaun dives into the complexities of investing in tech versus hard tech, advocating for a 'beginner's mind' in leadership. He also discusses the impact of trust and media biases, reflecting on the challenges of open expression in today's information-rich landscape. His insights into evaluating extraordinary founders and navigating the shifting dynamics of tech and politics are particularly thought-provoking.