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.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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Invest Like The Best

Ep.313

Systems Thinking in Sports

Daryl Morey is President of Basketball Operations for the Philadelphia 76ers. We cover what makes for a great sports match, using systems thinking to improve decision-making, and why superstar athletes are key to success in basketball.

01.24.2023

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Invest Like The Best

Ep.312

The DNA of Software Companies

Miles Grimshaw is a General Partner at Benchmark. We cover his biological approach to investing, the differences between pure API companies and other software businesses, and why software development is as much art as it is science.

01.17.2023

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Invest Like The Best

Ep.311

Creating Magic for Consumers

John Fio is a product inventor and entrepreneur who has bootstrapped multiple products. We cover his thoughts on product positioning, how to create an enduring brand that is separate from its founder, and what he learned from working for Justin Bieber.

01.10.2023

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Invest Like The Best

Ep.310

The Future of Software Creation

Amjad Masad is the founder and CEO of Replit. We discuss the Steve Jobs black pill, how to reduce friction for developers, and how emerging AI tools will affect the incumbent tech giants.

01.03.2023

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