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.13

Small Bets, Huge Payoffs

Chris Cole is the founder and CIO of Artemis Capital Management. We cover the benefits of being long volatility and convexity, how to implement them in portfolios as well as daily life, and the lessons that Dennis Rodman can teach investors.

11.29.2016

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Invest Like The Best

Ep.12

Exploring the Frontier

Kevin Simler has a background in technology and was one of the earliest employees at Palantir Technologies. We cover start-up culture and activities he did at Palantir to help create the culture, the economics of social status, and why people search for meaning in their lives.

11.22.2016

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Invest Like The Best

Ep.11

Better for You, Better for the World

Craig Shapiro is the founder and CEO of the New York-based Collaborative Fund. We cover the investment philosophy of "better for you and better for the world", his advice to entrepreneurs, and the biggest misses of his career.

11.14.2016

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Invest Like The Best

Ep.10

Cultivating a Disaster Resistant, Compound Interest Machine

Brent Beshore is the CEO and founder of adventur.es. We cover how he got started and built his company, how they source, evaluate, and acquire businesses, and how he and his team work to improve profitability at their portfolio companies after acquisition.

11.08.2016

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Invest Like The Best

Ep.9

The State of Automated Investing

Jon Stein is the founder and CEO of Betterment. We cover how Betterment was started, how Betterment can serve financial advisors as a technology support tool, and the future of robo-advisors.

11.01.2016

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Invest Like The Best

Ep.8

An Internal Locus of Control

Kiley Adams is a track and field star, valedictorian, varsity soccer player, Taekwondo master black belt, and philanthropic researcher. We cover the lessons from Taekwondo that translate into other aspects of her life and the importance of having an internal locus of control.

10.28.2016

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Invest Like The Best

Ep.7

A Deep Dive into Hedge Funds

Ted Seides was the founder, president, and co-chief investment officer at Protégé Partners and also the author of "So You Want to Start a Hedge Fund?". We cover David Swensen’s model for investments at Yale, the current state of fundraising, and his advice for hedge fund investors.

10.25.2016

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Invest Like The Best

Ep.6

Vanguard’s Gerry O’Reilly and Jim Rowley

Gerry O'Reilly is the portfolio manager and Jim Rowley is a senior investment analyst at Vanguard. We cover the particulars that make Vanguard and its funds tick, how buybacks play into re-balancing, and factor investing.

10.18.2016

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Invest Like The Best

Ep.5

The Quantified Self

Christian Rudder is the co-founder of OKCupid and the best-selling author of Dataclysm. We cover interesting and unsettling trends in OKCupid's dating data, artificial intelligence, and his favorite book recommendations.

10.11.2016

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Invest Like The Best

Ep.4

Walking and Thinking

Morgan Housel is a prolific writer, researcher, and partner at the Collaborative Fund. We cover the differences in investing in private vs public markets, why the timing of innovation matters, and advice that Morgan would give to young investors.

10.04.2016

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