Invest Like The Best

Conversations with the best investors and business leaders in the world. Patrick explores their ideas, methods, and stories to help you better invest your time and money.

Patrick O'Shaughnessy Host Patrick O'Shaughnessy

Patrick is the Founder and CEO of Positive Sum. He founded Colossus in 2020 to build on the success of Invest Like the Best.

Investors

Leaders

Invest Like The Best

Ep.249

Building The Local Graph

Sarah Friar is the CEO of Nextdoor. We cover what excellence looks like in a number of different executive roles, the lessons Sarah ported over from her time as an equity analyst, and how Nextdoor is fostering connections between people and businesses in their local areas.

11.02.2021

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Invest Like The Best

Ep.248

Investing in Operating Systems

Alex Rampell is a General Partner at Andreessen Horowitz. We cover Alex’s framework for positive selection in investing, why the best investments are often operating systems or systems of record, and Alex’s views on the future of fintech.

10.26.2021

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Invest Like The Best

Ep.247

Creating a Perfect Market

Sam Bankman-Fried is the founder and CEO of leading cryptocurrency exchange, FTX. We cover the building blocks of a perfect market, the key areas of inefficiency in today’s exchanges, and Sam’s north stars of product design and effective altruism.

10.19.2021

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Invest Like The Best

Ep.246

Becoming Your Own Bank

Nick Neuman is the CEO and co-founder of Casa. We cover the history of asset custody from ancient temples to decentralized ledgers, look at the mechanics of how private keys work, and explore why people are better off holding the keys themselves.

10.12.2021

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Invest Like The Best

Ep.245

The Go-to-Market Motion

Jenny Lefcourt is an equal General Partner at seed-stage venture firm, Freestyle Capital. We cover Jenny's investment frameworks, why she believes a deep understanding of the customer is key for founder success, and what makes great go-to-market strategies.

10.05.2021

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Invest Like The Best

Ep.244

Calibrating Market Adoption

Jay Hoag is the co-founder of TCV. We cover his own journey founding TCV, what advice he has for visionaries, and why he sees advantages for private to public crossover investors.

09.28.2021

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Invest Like The Best

Ep.243

Paint Outside the Lines

David Fialkow is the co-founder of General Catalyst. We cover what makes a great founder, the importance of storytelling, and the value of effectively convening people within your network.

09.21.2021

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Invest Like The Best

Ep.242

Enabling Creators Everywhere

Daniel Ek is the CEO and founder of Spotify. We cover differences between the world of bits and atoms, how Daniel gets up to speed in challenging new fields, and how Spotify aims to nurture the evolving creator ecosystem.

09.14.2021

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Invest Like The Best

Ep.241

Building a Great Endowment

Scott Malpass was the CIO of Notre Dame's endowment for 32 years, building it into a powerhouse of the endowment world. We cover the qualities he looks for in great investors, how he recruited top talent to work at Notre Dame’s endowment, and how asset classes have evolved over his 30 years of investing,

08.31.2021

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Invest Like The Best

Ep.240

Investing at the Supercritical Stage

Renata Quintini and Roseanne Wincek are co-founders and managing directors of Renegade Partners. We cover their investing philosophies, what it means to invest at the “supercritical stage” in venture, and what worries them most in search of businesses with outsized potential returns.

08.24.2021

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