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.64

Capital Light Compounders & Reinvestment Moats

Connor Leonard runs the public equity portfolio at Investors Management Corporation. We cover IMC's backstory, business models Connor likes best, and who is on his Mt. Rushmore of capital allocators.

11.21.2017

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Invest Like The Best

Ep.63

Adventures in Sports, Business, and Investing

Dhani Jones is a former NFL player and current investor & businessman. We cover his transition from the NFL to the business and investing world, his business experience in the creative agency space, and investing in diverse & minority owned businesses.

11.14.2017

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Invest Like The Best

Ep.62

How to Value a Cryptoasset

Chris Burniske is a partner at venture capital firm Placeholder. We cover concepts of utility-value of crypto assets, the differences between cryptocurrencies, crypto commodities, and crypto tokens, and the pros and cons of centralized vs decentralized networks.

11.07.2017

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Invest Like The Best

Ep.61

What Happens When You Hit Buy

Brad Katsuyama is the founder of the IEX exchange and the protagonist of Michael Lewis’s famous book, Flash Boys. We cover the business model of the financial exchanges, what IEX is and the problem they are solving, and what it was like to be the topic of a best-selling book.

10.31.2017

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Invest Like The Best

Ep.60

Ladder: The Fitness Marketplace

Brett Maloley is a founder of Ladder, a fitness market platform. We cover origins of the health clubs, the differences between franchise vs. license models, and fixing the commercial fitness industry by changing it.

10.24.2017

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Invest Like The Best

Ep.59

Grand Theft Life

Tim Urban runs the blog "Wait, But Why" and Andrew is his business partner. We cover what it means to be a cook and not a chef, what he learned from writing about Elon Musk, and what human progress implies about the future of our species.

10.17.2017

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Invest Like The Best

Ep.58

Hash Power – Part 3

With various investors and players in crypto as our guides, we cover regulation and storage of cryptos, forking in blockchains, and the need for increased security in cryptos.

10.10.2017

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Invest Like The Best

Ep.57

Hash Power – Part 2

The founders of Polychain, Metastable, and Blocktower Capital are our primary guides as we cover why we need bitcoin and blockchains, investing in cryptocurrencies and ICOs, and the lifecycle of a token.

10.03.2017

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Invest Like The Best

Ep.56

Hash Power – Part 1

We cover the potential of blockchains, the idea of scarcity in digital assets, and hashing. Our guides are leaders in this field such as Naval Ravikant, Olaf Carlson-Wee, Fred Ehrsam, Ari Paul among others.

09.26.2017

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Invest Like The Best

Ep.55

Tech Investing Outside of Silicon Valley

David runs Box Group, a seed-stage VC firm. We cover the tech accelerator model, how things have changed for tech startups over the last 20 years, and the biggest mistakes David sees startups make.

09.19.2017

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