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.

Invest Like The Best

Ep.435

Building Abstract

Ramtin Naimi is the founder of Abstract Ventures. We cover the parallels between art collection and venture investing, the unconventional approach that financed his earliest deals, and the value of being a small fish in the biggest pond.

07.29.2025

Play

Invest Like The Best

Ep.434

Powering the Future

Zach Dell is the co-founder and CEO of Base. We cover how the energy grid is struggling to keep up with the rising demands of AI compute and the electrification of industry, why batteries solve this problem by allowing energy to move through time, and the vertically integrated distribution framework that lets Base deliver batteries at a lower unit cost.

07.22.2025

Play

Invest Like The Best

Ep.433

Building Sixth Street

Alan Waxman is the co-founder and CEO of Sixth Street. We cover the power of flexible capital in a world of siloed funds, why so many investors take risk for granted, and the thesis that led to major partnerships with both Real Madrid and Barcelona.

07.15.2025

Play

Invest Like The Best

Ep.432

Rebuilding CLEAR

Caryn Seidman-Becker is the Chairman and CEO of CLEAR. We cover how she rebuilt CLEAR with a focus on free cash flow following its bankruptcy, the applications of secure identity verification beyond airports, and the importance of leading by example in periods of crisis.

07.08.2025

Play

Invest Like The Best

Ep.431

Building SKIMS

Jens Grede is the co-founder and CEO of Skims. We cover how nostalgia for the past supplanted optimism for the future in popular culture, the importance of continuous adaptation in building enduring brands, and why first-mover advantage is overrated.

07.01.2025

Play

Invest Like The Best

Ep.430

Music & Markets

Alex Pall and Drew Taggart are The Chainsmokers and the founders of Mantis VC. We cover their journey from aspiring DJs to global superstars and successful venture capitalists, what it means to be authentic in an age of algorithms, and how the creative process has guided their approach to venture.

06.24.2025

Play

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

Play

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

Play

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

Play

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

Play

Investors

Leaders

Contact

Get in touch at help@joincolossus.com