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.253

Design-led Hospitality

Francis Davidson is the founder and CEO of Sonder. We cover his unique views around customer-centric focus, the nuances of hiring a team, and Sonder's approach to decision making.

11.30.2021

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Invest Like The Best

Ep.252

Developing Every Skill

Niraj Shah is the CEO and co-founder of Wayfair. We cover how the competitive frontiers in e-commerce have changed, what it was like to build out a proprietary logistics operation, and what makes the home goods market more attractive than other physical goods markets.

11.23.2021

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Invest Like The Best

Ep.251

Indexing the Earth

Will Marshall is the co-founder and CEO of Planet. We cover the untold space story, how space is going through an internet moment where cost reductions and performance enhancements have led to a seismic shift in what’s possible above our atmosphere, and how that can drastically improve life on Earth through unique datasets like the one Planet is piecing together.

11.16.2021

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Invest Like The Best

Ep.250

Sequoia’s Crucible Moment

Roelof Botha is a partner at Sequoia. We cover the seismic change Sequoia is making to its investing model, what's changed over the course of his career, and what he’s learned from businesses like MongoDB, Square, YouTube, and Unity.

11.05.2021

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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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