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.313

Systems Thinking in Sports

Daryl Morey is President of Basketball Operations for the Philadelphia 76ers. We cover what makes for a great sports match, using systems thinking to improve decision-making, and why superstar athletes are key to success in basketball.

01.24.2023

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Invest Like The Best

Ep.312

The DNA of Software Companies

Miles Grimshaw is a General Partner at Benchmark. We cover his biological approach to investing, the differences between pure API companies and other software businesses, and why software development is as much art as it is science.

01.17.2023

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Invest Like The Best

Ep.311

Creating Magic for Consumers

John Fio is a product inventor and entrepreneur who has bootstrapped multiple products. We cover his thoughts on product positioning, how to create an enduring brand that is separate from its founder, and what he learned from working for Justin Bieber.

01.10.2023

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Invest Like The Best

Ep.310

The Future of Software Creation

Amjad Masad is the founder and CEO of Replit. We discuss the Steve Jobs black pill, how to reduce friction for developers, and how emerging AI tools will affect the incumbent tech giants.

01.03.2023

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Invest Like The Best

Ep.309

Finding Your Customers

Rebecca Lynn is the co-founder of Canvas Ventures. We cover the biggest lessons from her time at P&G, why you should say no to customers, and the differences between an interesting topic and one that has investing potential.

12.27.2022

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Invest Like The Best

Ep.308

Sharpening Investor & Executive Toolkits

Michael Mauboussin is the Head of Consilient Research at Counterpoint Global. We discuss his research on market share and capital allocation, examples of the relationship between value creation and market power, and which recent market phenomena have provided the biggest surprises.

12.20.2022

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Invest Like The Best

Ep.307

Explaining the New AI Paradigm

Jeremiah Lowin is the founder and CEO of Prefect. We cover the new class of AI models, what's happening under the hood of the popular chatbot ChatGPT, and what else he’s watching closely in the space.

12.13.2022

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Invest Like The Best

Ep.306

Investing in Commercial Real Estate

Bill Lenehan is the CEO of Four Corners Property Trust. We cover the impact of trends such as COVID and climate change on commercial real estate, how rising rates are influencing its return profile, and how retailers are adapting to rising costs in today's economy.

12.06.2022

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Invest Like The Best

Ep.305

Box Office Business

Ron Howard and Brian Grazer are co-founders of Imagine Entertainment. We cover how they've kept their their creative spark alive through their careers, the value of trust and curiosity, and the biggest storytelling mistakes they've come across.

11.29.2022

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Invest Like The Best

Ep.304

The No-Stats All-Star

Shane Battier is a two-time NBA Champion. We cover the best stories from his acclaimed career, what he's learned from various coaches, and how to use data to gain advantages in basketball and business alike.

11.22.2022

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