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.293

The Business of Gaming

Mitch Lasky is a partner at Benchmark. We cover the most important features of the modern gaming business model, how platforms like Twitch and Discord have re-shaped the industry, and what to look for when investing in gaming businesses.

09.06.2022

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Invest Like The Best

Ep.292

Passion & Pain

David Senra is the creator of the Founders podcast. We cover what made him obsessive about studying history's greatest entrepreneurs, the most common themes he's discovered in his studies, and the role obsession plays.

08.30.2022

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Invest Like The Best

Ep.291

Investing in Enterprise Software

Robert Smith is the founder, Chairman, and CEO of Vista Equity Partners. We cover what makes a business an ideal fit for Vista, the importance of capital cycles on price and sentiment, and what he's learned from building an iconic investing franchise.

08.23.2022

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Invest Like The Best

Ep.290

Investing for America

Katherine Boyle is a general partner at Andreessen Horowitz. We cover American Dynamism in detail, what matters most to her as an investor today, and the biggest problems facing the education system.

08.16.2022

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Invest Like The Best

Ep.289

Focus

Ravi Gupta is a partner at Sequoia. We cover the importance of keeping the main thing the main thing, why the best leaders are both demanding and supportive, and how mentorship works within Sequoia's culture.

08.09.2022

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Invest Like The Best

Ep.288

The Power of Long Holding Periods

Will Thorndike is author of The Outsiders and host of 50X. We cover the hallmarks of great compounders, how the best serial acquirers deliver outsized returns, and what he's learned about developing conviction.

08.02.2022

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Invest Like The Best

Ep.287

Searching for White Space

Alok Vasudev is the co-founder of Standard Crypto. We cover what advice he would give to crypto skeptics, whether the recent bubble in cryptoassets meets the definition of productive speculation, and look at some underestimated big ideas.

07.26.2022

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Invest Like The Best

Ep.286

A Manual to The Metaverse

Matthew Ball is the Managing Partner of EpyllionCo. We cover the 3D engines powering the Metaverse, why interoperability is so important, and the types of companies that stand to do well under a shift to the Metaverse.

07.19.2022

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Invest Like The Best

Ep.285

Building a Start-Up Machine

Alice Bentinck is a co-founder of Entrepreneur First. We cover how EF helps talented entrepreneurs find co-founders, what markers of success to screen for in candidates, and why there aren't more incubators like EF.

07.12.2022

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Invest Like The Best

Ep.284

Designing Investment Products

Jess Lee is a partner at Sequoia Capital. We cover Sequoia's approach to product design, what ComicCon and Burning Man can teach us about the importance of communities, and the recipe for building great teams and companies.

07.05.2022

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