This week Patrick takes a deep dive in the world of Venture Capital with Craig Shapiro, founder and CEO of the New York based Collaborative Fund, which was an early investor in companies like Lyft, Kickstarter, and Reddit. We cover Craig’s investing roots, his process for sourcing and evaluating investment opportunities, and the very useful “villain test.” ... Show More
Oct 27
Cliff Sosin - Owning the Complements to Intelligence - [Invest Like the Best, EP.497]
Cliff Sosin is the founder of CAS Investment Partners, which he started in 2012. Roughly 80% of his portfolio is in Carvana. We discuss why Cliff thinks there are hard limits to what even the smartest AI can predict, which businesses benefit as intelligence gets cheap, and what t ... Show More
1 h
Oct 20
Christina Cacioppo - Building an Enduring Software Company in the Age of AI - [Invest Like the Best, EP.496]
My guest today is Christina Cacioppo, founder and CEO of Vanta, which helps more than 16,000 companies manage security and compliance. Five years after our first conversation, we discuss how Vanta became a category leader, what it takes to reinvent a successful software business ... Show More
57m 29s
Oct 13
David Vélez - Building Nubank and the Future of Global Banking - [Invest Like the Best, EP.495]
David Vélez is the founder and CEO of Nubank, which serves 140 million customers across Latin America. David believes the industry is still in its Blockbuster era, with most of the world's banking still running through branches and incumbent banks, and that AI will make digital b ... Show More
1h 11m
Nov 2015
#5 Chris Dixon: The State of Venture Capital
In this episode, a16z partner Chris Dixon and I discuss the history of venture capital, artificial intelligence, what makes a great entrepreneur, and why companies fail. *** Go Premium: Members get early access, ad-free episodes, hand-edited transcripts, searchable transcripts, m ... Show More
57m 41s
Dec 2021
TIP401: The Most Important Company Is Going Public w/ Chris DeMuth Jr.
Trey Lockerbie brings on the founder and principal of Rangeley Capital, Chris DeMuth. After discussing a company called Planet with Josh Wolfe on episode 399, Trey wanted to explore the SPAC merger with DMY Technologies which has a definitive vote scheduled for December 3rd, 2021 ... Show More
1h 4m
Apr 2025
TIP714: Bet Big, Bet Rarely: The Dhandho Investing Playbook w/ Kyle Grieve
On today’s episode, Kyle Grieve dives deep into Mohnish Pabrai’s The Dhandho Investor, unpacking its nine core principles through vivid case studies and personal reflections to help investors embrace simplicity, asymmetric bets, and the power of cloning proven ideas. IN THIS EPIS ... Show More
1h 1m