In this episode, we delve into the remarkable journey of Chad Hutchinson, one of only seven individuals to have played in both the NFL and the MLB. Chad was both a pitcher for the St. Louis Cardinals and a quarterback for the Dallas Cowboys. But he didn't just hang up his boots and call it quits after his pro-sports career: he went back to the bottom of the finance world and worked his way to becoming a Partner at the successful PE firm Arctos, pioneering sports franchise acquisition.

Discover how Chad transitioned from the ultra competitive world of sports to a thriving career in finance. Chad shares insights on his decision-making processes, from choosing between MLB and NFL offers to navigating complex negotiations with sports team owners in private equity. Learn about the values and lessons Chad acquired from his mentors and the pivotal moments that shaped his path. Don't miss Chad's inspiring story and his practical wisdom on achieving success in multiple high-stakes arenas.

00:00 Introduction to Winning and Success

00:19 Meet Chad Hutchinson: Dual-Sport Athlete

01:03 Chad's Early Life and Sports Beginnings

01:58 High School Breakthroughs and College Decisions

04:32 Negotiation Lessons from Scott Boris

08:19 Transition to Professional Baseball

10:24 Steroid Era and Lessons from Mark McGuire

16:25 Transition to Professional Football

20:03 Negotiating with Jerry Jones

26:13 First NFL Game Against Peyton Manning

28:03 Transition from Sports to Finance

29:12 Facing the Daunting Transition from Sports to Finance

29:47 Building Marketable Skills and Networking

30:39 Humbling Beginnings in the Workforce

32:20 Navigating the Financial Crisis and Buying Distressed Assets

33:26 Grit and Persistence in Business

34:38 Experience at Sixth Street and Learning Agriculture

39:21 Transition to OSE Partners and the Business of Sports

51:56 Investing in College Sports and NIL

58:20 Rapid Fire Questions and Final Thoughts