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.42

Building Something People Want to Buy

Andy Rachleff is the co-founder and CEO of Wealthfront. Previously he co-founded and was a long-time partner at Benchmark Capital. We cover Benchmark's founding strategy, product market fit, and Andy's transition from venture capitalist to operator at Wealthfront.

06.20.2017

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Invest Like The Best

Ep.41

Quant vs. Traditional Investors and How Alphas Become Betas

Leigh Drogen has worked as a statistical arbitrage portfolio manager is the founder of Estimize, a data company that works with some of the world's largest hedge funds. We cover traits that help funds perform well, crowdsourcing in funds, and algorithms and automation.

06.13.2017

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Invest Like The Best

Ep.40

Bail Street, with NYC’s Leading Bail Bondsman

Ira Judelson is the leading bail bondsman in New York City. We cover the business of being a bail bondsman, some of his most memorable clients including Dominique Strauss-Kahn and DMX, and his advice for younger people just starting out in their careers.

06.06.2017

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Invest Like The Best

Ep.39

The Human Blitzkrieg

David Chilton is a venture capitalist, author, investor, and television personality from Waterloo, Ontario. We cover business, investing, and writing.

05.30.2017

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Invest Like The Best

Ep.38

The Art of Asset Allocation

David Salem was the founding president and CIO for The Investment Fund for Foundations and currently is CIO of the Windhorse Group. We cover foundations of asset allocation, first principles thinking, and the history of the Yale and Harvard endowment models.

05.23.2017

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Invest Like The Best

Ep.37

Man + Machine, Moats, and Power of the Outside View

Michael Mauboussin is the Head of Global Financial Strategies at Credit Suisse. We cover moats and base rates, the active-passive debate, and the shift from public to private markets.

05.16.2017

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Invest Like The Best

Ep.36

How Skilled Capital Allocators Compound Capital

Will Thorndike is an author and investor whose book The Outsiders is one of the best examinations of CEOs and capital allocation. We cover how these CEOs were contrarians in business tactics, lessons for business capital allocation, and Will's experience in private equity.

05.09.2017

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Invest Like The Best

Ep.35

The Bet With Buffett

Ted Seides is the host of the Capital Allocators podcast. We cover the details of his bet with Warren Buffett, how anyone can replicate hedge fund strategies with public market alternative, and assess the performance of the S&P 500.

05.02.2017

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Invest Like The Best

Ep.34

The Big Short and Beyond

Danny Moses has worked on Wall Street for 20 years and was the head trader at FrontPoint during the 2008 crisis. We cover his part in the Big Short story, how the sell-side has evolved over the years, and how he thinks about valuations as part of the bottom-up framework.

04.25.2017

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Invest Like The Best

Ep.33

REALLY Private Equity

Royce Yudkoff and Rick Ruback are Harvard Business School professors. We cover how students in their class practically learn to search for, acquire, and run a small business directly after graduation.

04.18.2017

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