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.323

Trail Magic

Highlights from three of our most popular episodes, featuring Sam Hinkie, Boyd Varty, and Charlie Songhurst. These classic conversations are a source of timeless lessons on life and investing.

04.04.2023

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Invest Like The Best

Ep.322

The Long and Short of Investing

David Einhorn is the President of Greenlight Capital. We cover the highs and lows of an illustrious career, his views on the current issues facing the banking sector, and how he has evolved as an investor over time.

03.28.2023

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Invest Like The Best

Ep.321

The Economic Impact of AI

Avi Goldfarb is a Professor at the University of Toronto. We cover the pace of AI's development compared with other technologies, the transition from a world governed by rules to one governed by decisions, and the disruptive effects of AI on existing businesses and professions.

03.21.2023

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Invest Like The Best

Ep.320

A Deep Dive on Data

Auren Hoffman is the CEO of SafeGraph. We cover his definition of a great business, the characteristics of a good data set, and the most common struggles for data entrepreneurs.

03.14.2023

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Invest Like The Best

Ep.319

Find Good Quests

Trae Stephens is a partner at Founders Fund. We cover the importance of investing in firms that advance society, why the high-tech defense firms of the past became stale, and why disagreeableness is a valuable trait in founders.

03.07.2023

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Invest Like The Best

Ep.318

Lessons from a Titan

Doug Leone is a Partner at Sequoia Capital. We cover his lessons from four decades at Sequoia, what makes for great go-to-market motions, and survey the changing landscape of venture and founders.

02.28.2023

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Invest Like The Best

Ep.317

Idea Labs and High-Rung Thinking

Tim Urban is the author of Wait But Why. We cover the concept of social golems and genies, the media and technology’s role in shaping our ideas and values, and the importance of having the courage to not leave things unsaid.

02.21.2023

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Invest Like The Best

Ep.316

How Stunning Founders Operate

Dan Rose is the chairman of Coatue Ventures. We cover the story behind Amazon’s Kindle, the relationship between innovation and constraints, and how he would build a Frankenstein of effective leadership styles.

02.14.2023

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Invest Like The Best

Ep.315

Modernizing Advertising

Jeff Green is the CEO and co-founder of The Trade Desk. We cover the parallels between The Trade Desk and an equity exchange, why Jeff chose to align with ad buyers instead of sellers, and how he shaped the culture of his firm.

02.07.2023

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Invest Like The Best

Ep.314

Dealing with Regime Change

Carl Kawaja is a portfolio manager at Capital Group. We cover the biggest changes in markets over the last two years, what everyone can learn from Apple and oil companies, and his approach to finding diamonds in the rough.

01.31.2023

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