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.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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Invest Like The Best

Ep.32

The Art of Tracking

Boyd Varty is a lion tracker, life coach, and storyteller. We cover tracking and how the same strategy for pursuing animals in the wild can be applied to all aspects of our lives, the dangers of a goal-oriented mindset, and what he learned from spending time with Nelson Mandela.

04.11.2017

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Invest Like The Best

Ep.31

Quant Hedge Funds and the Fear of Death

Khe Hy rose to be one of the youngest MDs at Blackrock. We cover the hedge fund landscape, what investors should look for in hedge fund managers, and the four pillars that he lives by.

04.04.2017

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