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.303

Building a Compound Company

Parker Conrad is the co-founder and CEO of Rippling. We explore Rippling's place in the B2B infrastructure stack, the notion of a compound startup, and what Parker has learned about leadership, motivation, and communication.

11.15.2022

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Invest Like The Best

Ep.302

A Macro Tour

Bob Elliott is the CEO and CIO of Unlimited. We cover the relationship between rates and inflation for different asset classes, why we're seeing a return to boring economic cycles, and how to find alpha in private markets through quantitative strategies.

11.08.2022

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Invest Like The Best

Ep.301

Investing in Consumer Change

Kirsten Green is the founder and managing partner at Forerunner Ventures. We cover the frameworks for identifying brands early, how to build deal flow, and the shift in power between buyers and sellers.

11.01.2022

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Invest Like The Best

Ep.300

Building Uber Eats

Jason Droege is a venture partner at Benchmark. We cover what he learned building Uber Eats, transferrable lessons for other marketplace businesses, and what it's like to work in a business that evokes strong public opinion.

10.25.2022

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Invest Like The Best

Ep.299

It’s About the Money

Paul Orfalea is the founder of Kinko's. We cover his leadership style, what he learned about hiring well, and why entrepreneurship was his only path out of school.

10.18.2022

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Invest Like The Best

Ep.298

How to Price Products

Madhavan Ramanujam is the author of Monetizing Innovations. We cover different monetization models, common mistakes when pricing products, and why positive feedback doesn’t necessarily equate to dollars spent.

10.11.2022

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Invest Like The Best

Ep.297

Non-Traditional Endowment Investing

Scott Wilson is the CIO of Washington University’s endowment. We cover the qualities Scott looks for in good partners, what he's learned from investing in China and emerging markets, and red flags in the venture space.

10.04.2022

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Invest Like The Best

Ep.296

Investing in Latin America

Julio Vasconcellos and Mate Pencz are partners at Canary and Atlantico. We cover the state of investing and business in Latin America today, the nuts and bolts of building a digital payments system for emerging markets, and the most interesting insights from their report on digital transformation in the region.

09.27.2022

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Invest Like The Best

Ep.295

Billion Dollar Scrubs

Trina Spear is the co-founder and CEO of FIGS. We cover the original insight that led to FIGS' founding, what the basic financial profile of an apparel retailer looks like, and the biggest lessons for builders of product-centric businesses.

09.20.2022

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Invest Like The Best

Ep.294

Building the Entrepreneurship Company

Harley Finkelstein is the President of Shopify. We cover the different dimensions of entrepreneurship, the most interesting trends in e-commerce today, and the lessons learned from Shopify's transition to public markets.

09.13.2022

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