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Invest Like the Best with Patrick O'Shaughnessy

Brad Jacobs - Think Big and Move Fast - [Invest Like the Best, CLASSICS]

25 Jul 2025

Transcription

Full Episode

0.031 - 19.946 Patrick O'Shaughnessy

Welcome to this Classics episode. Classics are my favorite episodes from the past 10 years, published once a month. These are end-of-one conversations with end-of-one people. Brad Jacobs' simple principle of think big, move fast is one I think about often. He is a true force of nature, and I hope you enjoy this episode. Hello and welcome, everyone.

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20.107 - 37.672 Patrick O'Shaughnessy

I'm Patrick O'Shaughnessy, and this is Invest Like the Best. This show is an open-ended exploration of markets, ideas, stories, and strategies that will help you better invest both your time and your money. If you enjoy these conversations and want to go deeper, check out Colossus Review, our quarterly publication with in-depth profiles of the people shaping business and investing.

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37.872 - 53.191 Patrick O'Shaughnessy

You can find Colossus Review along with all of our podcasts at joincolossus.com. Here's a puzzle. What do OpenAI, Cursor, Perplexity, Vercel, Plaid, and hundreds of other winning companies all have in common? The answer is that they're powered by today's sponsor, WorkOS.

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53.732 - 69.593 Patrick O'Shaughnessy

If you're building software for enterprises, you've probably felt the pain of integrating SSO, SCIM, RBAC, audit logs, and other features required by big customers. WorkOS turns those deal blockers into drop-in APIs with a modern developer platform built specifically for B2B SaaS.

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69.573 - 88.9 Patrick O'Shaughnessy

Whether you're a seed stage startup trying to land your first enterprise customer or a unicorn expanding globally, WorkOS is the fastest path to becoming enterprise ready and unlock growth. It's essentially Stripe for enterprise features. Visit WorkOS.com to get started or just hit up their Slack support. Yes, they have real engineers in there who will answer your questions fast.

89.461 - 98.854 Patrick O'Shaughnessy

WorkOS allows you to build like the best with delightful APIs, comprehensive docs, and smooth developer experience. Go to WorkOS.com to make your app enterprise ready today.

99.475 - 126.175 Unknown

To learn more, visit psum.vc.

128.247 - 142.404 Patrick O'Shaughnessy

My guest today is Brad Jacobs. Brad's resume is remarkable. He's founded seven companies, all of which are billion-dollar or multi-billion-dollar businesses. He's done 500 M&A transactions and raised $30 billion of debt and equity capital.

142.965 - 157.242 Patrick O'Shaughnessy

Currently, he's the executive chairman of XPO, a commercial trucking company that he started in 2011 and has grown into one of the largest logistics businesses in the world. He's also written a book that will be out in January titled How to Make a Few Billion Dollars. What a title.

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