How Would Warren Buffett Invest if He Started Today? | Ryan O’Connor

Ryan O’Connor is the Founder and Portfolio Manager at Crossroads Capital, a Private Investment Partnership based out of Kansas City, MO. In this conversation, Ryan tells me the story of why he is (successfully) running an investment fund modeled after Warren Buffett’s early partnership.

Enjoy This Episode of The Reformed Financial Advisor – A Kansas City Podcast

Featured in this episode:

Why Launch A Boutique Hedge Fund in Kansas City?

In our conversation, Ryan explains how his location in Kansas City is an advantage and a homage to his idols Warren Buffett and Charlie Munger.

You have as an individual investor a gigantic structural advantage over the professionals. – Ryan O’Connor, Crossroads Capital

Ryan O’Connor

What Would Warren Buffett Do If He Were Starting Today?

My favorite part of Ryan’s background is his superhero-like origin story from an investor’s point of view.

Ryan’s grandfather, Bill O’Connor, was an Irish Catholic Omaha father of 10. His early claim to fame was being the first to sell the famously cheap Warren Buffett a typewriter while working in sales at IBM. A poker game with Warren convinced the elder O’Connor to liquidate the family’s life savings and invest in his early partnership.

This lifelong tutelage under his grandfather inspired Ryan to follow in Buffett’s footsteps.

If I was running $1 million today, or $10 million for that matter, I’d be fully invested. Anyone who says that size does not hurt investment performance is selling. The highest rates of return I’ve ever achieved were in the 1950s. I killed the Dow. You ought to see the numbers. But I was investing peanuts then. It’s a huge structural advantage not to have a lot of money. I think I could make you 50% a year on $1 million. No, I know I could. I guarantee that. – Warren Buffett

– With permission from Ryan O’Connor


Andrew Flattery, CFP®

Andy Flattery is a CERTIFIED FINANCIAL PLANNER™ and Owner of Simple Wealth Planning. He serves young and affluent families that are working to lower their time preference and achieve financial sovereignty. Flattery is the host of The Reformed Financial Advisor Podcast, where he relates stories in Kansas City history to pivotal themes in personal finance. When he’s not helping individuals build wealth, you can catch him playing rec sports, reading Austrian economists, and spending time with his wife and three children.