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.

Invest Like The Best

Ep.438

Performance During Pain

Mark Bertolini is the CEO of Oscar Health. We cover the near-death experience that shaped so much of his life and leadership framework, how a decision to raise wages actually increased shareholder returns, and what Oscar's strategy for disrupting the healthcare industry has in common with pirate ships.

08.19.2025

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Invest Like The Best

Ep.437

Backing The Best Managers In Private Markets

Peter Lacaillade is the Chief Investment Officer for Private Investments at SCS Financial. We cover the wealth management industry's problem with adverse selection, how SCS built an institutional-grade platform that offers the same access as endowment funds, and Peter's framework for identifying top-tier managers before they become household names.

08.12.2025

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Invest Like The Best

Ep.436

Full-Contact Capitalism

Andrew Milgram is the founder of Marblegate Asset Management. We cover how one-third of the economy has had its earnings and pricing power hollowed out, why he made a $600 million bet on taxi medallions, and his firm's unique approach to distressed investing built on variant views and data-driven research.

08.05.2025

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Invest Like The Best

Ep.435

Building Abstract

Ramtin Naimi is the founder of Abstract Ventures. We cover the parallels between art collection and venture investing, the unconventional approach that financed his earliest deals, and the value of being a small fish in the biggest pond.

07.29.2025

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Invest Like The Best

Ep.434

Powering the Future

Zach Dell is the co-founder and CEO of Base. We cover how the energy grid is struggling to keep up with the rising demands of AI compute and the electrification of industry, why batteries solve this problem by allowing energy to move through time, and the vertically integrated distribution framework that lets Base deliver batteries at a lower unit cost.

07.22.2025

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Invest Like The Best

Ep.433

Building Sixth Street

Alan Waxman is the co-founder and CEO of Sixth Street. We cover the power of flexible capital in a world of siloed funds, why so many investors take risk for granted, and the thesis that led to major partnerships with both Real Madrid and Barcelona.

07.15.2025

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Invest Like The Best

Ep.432

Rebuilding CLEAR

Caryn Seidman-Becker is the Chairman and CEO of CLEAR. We cover how she rebuilt CLEAR with a focus on free cash flow following its bankruptcy, the applications of secure identity verification beyond airports, and the importance of leading by example in periods of crisis.

07.08.2025

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Invest Like The Best

Ep.431

Building SKIMS

Jens Grede is the co-founder and CEO of Skims. We cover how nostalgia for the past supplanted optimism for the future in popular culture, the importance of continuous adaptation in building enduring brands, and why first-mover advantage is overrated.

07.01.2025

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Invest Like The Best

Ep.430

Music & Markets

Alex Pall and Drew Taggart are The Chainsmokers and the founders of Mantis VC. We cover their journey from aspiring DJs to global superstars and successful venture capitalists, what it means to be authentic in an age of algorithms, and how the creative process has guided their approach to venture.

06.24.2025

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Invest Like The Best

Ep.429

Keys to Successful Growth Investing

Jay Hoag is the co-founder of TCV. We cover the decline in consumer-focused investing, why the trend of companies staying private for longer can't continue forever, and his favorite lessons from TCV's 30-year history.

06.17.2025

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