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.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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Invest Like The Best

Ep.293

The Business of Gaming

Mitch Lasky is a partner at Benchmark. We cover the most important features of the modern gaming business model, how platforms like Twitch and Discord have re-shaped the industry, and what to look for when investing in gaming businesses.

09.06.2022

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Invest Like The Best

Ep.292

Passion & Pain

David Senra is the creator of the Founders podcast. We cover what made him obsessive about studying history's greatest entrepreneurs, the most common themes he's discovered in his studies, and the role obsession plays.

08.30.2022

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Invest Like The Best

Ep.291

Investing in Enterprise Software

Robert Smith is the founder, Chairman, and CEO of Vista Equity Partners. We cover what makes a business an ideal fit for Vista, the importance of capital cycles on price and sentiment, and what he's learned from building an iconic investing franchise.

08.23.2022

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Invest Like The Best

Ep.290

Investing for America

Katherine Boyle is a general partner at Andreessen Horowitz. We cover American Dynamism in detail, what matters most to her as an investor today, and the biggest problems facing the education system.

08.16.2022

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Invest Like The Best

Ep.289

Focus

Ravi Gupta is a partner at Sequoia. We cover the importance of keeping the main thing the main thing, why the best leaders are both demanding and supportive, and how mentorship works within Sequoia's culture.

08.09.2022

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Invest Like The Best

Ep.288

The Power of Long Holding Periods

Will Thorndike is author of The Outsiders and host of 50X. We cover the hallmarks of great compounders, how the best serial acquirers deliver outsized returns, and what he's learned about developing conviction.

08.02.2022

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Invest Like The Best

Ep.287

Searching for White Space

Alok Vasudev is the co-founder of Standard Crypto. We cover what advice he would give to crypto skeptics, whether the recent bubble in cryptoassets meets the definition of productive speculation, and look at some underestimated big ideas.

07.26.2022

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