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.409

Graham Duncan: Talent Whisperer

Graham Duncan is the co-founder of East Rock Capital. We cover the pivotal moments of ignition in his career, his frameworks for pricing talent and matching the perfect person to a role, and how mindset and intensity separate masters from professionals in any field.

02.04.2025

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Invest Like The Best

Ep.408

Combat, Service, and Innovation

Blake Hall is the CEO and co-founder of ID.me. We cover what his time in the military taught him about leadership and service, the staggering true cost of identity fraud, and his frameworks for building trust and culture in organizations.

01.28.2025

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Invest Like The Best

Ep.407

Designing The Future

Dylan Field is the co-founder and CEO of Figma. We cover the hardest part of building in private, his principles for avoiding common design pitfalls, and why human creativity is still as relevant as ever despite the growing capabilities of AI models.

01.21.2025

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Invest Like The Best

Ep.406

Bridging Science, Medicine, and Returns

Tal Zaks is a Partner at OrbiMed. We cover the challenges that make investing in biotech different from fields like software, the importance of seeking lessons in your successes as well as failures, and why the pursuit of returns makes large-scale capital flows into science and innovation possible.

01.14.2025

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Invest Like The Best

Ep.405

Building Captions

Gaurav Misra and Dwight Churchill are the co-founders of Captions. We cover the idea of solving bounded versus unbounded problems, the process of building a business model and setting pricing for a generative AI product, and the most salient point investors in this space are missing.

01.07.2025

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Invest Like The Best

Ep.404

Building AlphaSense

Jack Kokko is the CEO and founder of AlphaSense. We cover the evolution of language models and how they've enabled product builders, the role of M&A as a tool to help business owners realize their vision, and why he's motivated by improving the research experience for investors.

12.31.2024

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Invest Like The Best

Ep.403

The Mechanic

Jared Kushner is the founder of Affinity Partners. We cover his formative experiences as a real estate investor, the major accomplishments from his time in government, and the people who have shaped his investing and geopolitical worldviews.

12.20.2024

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Invest Like The Best

Ep.402

Building Cognition

Scott Wu is the co-founder and CEO of Cognition. We cover the history of programming from punch cards to LLMs, how AI agents like Devin can 10x a software engineer's productivity, and why he's optimistic about the future of jobs in the industry.

12.17.2024

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Invest Like The Best

Ep.401

Building Ribbit

Micky Malka is the founder of Ribbit Capital. We cover the founding principles behind Ribbit's mission to innovate financial services, the exciting possibilities enabled by the intersection of crypto and AI, and why there's no such thing as having too much conviction when a team is aligned.

12.10.2024

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Invest Like The Best

Ep.400

Capital, Compute & AI Scaling

Chetan Puttagunta is a General Partner at Benchmark and Modest Proposal is a money manager who is one of the most respected thinkers in financial markets. We cover the current scaling challenges of frontier AI models, the incredible proliferation of open source models, and the investing implications across private and public markets.

12.06.2024

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