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.429

Keys to Successful Growth Investing

Jay Hoag is the co-founder of TCV. We cover the decline in consumer-focused investing, why the trend of companies staying private for longer can't continue forever, and his favorite lessons from TCV's 30-year history.

06.17.2025

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Invest Like The Best

Ep.428

A Father’s Call To Action

Dinakar Singh is the founder and CEO of Axon. We cover the story and inspiration behind Axon, what it means to deploy capital towards outcomes that matter, and why research into rare diseases is in need of a structural overhaul.

06.15.2025

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Invest Like The Best

Ep.427

The Gift and The Curse of Staying Private

Bill Gurley is a former General Partner at Benchmark Capital. We cover the breakdown of incentives that created over a thousand "zombie unicorn" companies, how late-stage venture firms have largely eliminated the need to go public to access funding and liquidity, and the investing implications if AI turns out to be the single greatest platform shift of our lifetime.

06.10.2025

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Invest Like The Best

Ep.426

Inside Apollo

John Zito is the Co-President of Apollo Global Management. We cover the secrets behind Apollo's origination engine, their plan for capturing a greater share of client portfolios, and why companies are abandoning banks and embracing private credit for financing deals.

06.03.2025

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Invest Like The Best

Ep.425

Building Alpine

Graham Weaver is the founder and Managing Partner of Alpine Investors. We cover the three North Stars shaping Alpine's outperformance, how it became the most coveted destination for business school graduates, and why executives should seek the same level of coaching as professional athletes.

05.27.2025

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Invest Like The Best

Ep.424

How Spotify Thinks

Gustav Söderström is the Co-President, Chief Product Officer and Chief Technology Officer at Spotify. We cover how AI might revolutionize the music-listening experience, the systematic process behind all of Spotify's successful innovations, and why it's become the effective R&D department for the entire music industry.

05.20.2025

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Invest Like The Best

Ep.423

Entrepreneurship Through Acquisition

Royce Yudkoff and Rick Ruback are professors at Harvard Business School. We cover the bifurcation of search funds, how acquisition entrepreneurs achieve returns that consistently outperform private equity, and the common red flags that can break otherwise promising deals.

05.13.2025

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Invest Like The Best

Ep.422

The Focused Few

David Senra is the creator and host of the Founders podcast. We cover how obsessive focus can transform a simple idea into a billion-dollar business, the importance of optimizing for durability over growth, and why the best entrepreneurs seek wisdom from unrelated industries.

05.06.2025

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Invest Like The Best

Ep.421

Investing in Carvana

Cliff Sosin is the founder of CAS Investment Partners. We cover how taking concentrated positions in companies with brilliant business models created a billion-dollar fund, the remarkable turnaround story behind Carvana, and the critical decision-making processes that set successful investors apart during market crises.

04.29.2025

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Invest Like The Best

Ep.420

Investing at the Frontier

Matt Huang is the co-founder of Paradigm. We cover the building blocks of Paradigm's highly technical investing approach, how navigating illegible frontiers leads to outsized returns, and why crypto plays an important role in preserving economic freedoms.

04.22.2025

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