The incredible story of Logan Rose, who built Big League Wiffle Ball from his backyard during COVID at age 13—and now counts David Blitzer, Mark Lasry, Gary Vee, Dude Perfect, Rob Walton, and Kevin Costner among his team owners.
Jordan Rose (his mom, also minority owner of the Arizona Diamondbacks and TGL’s Motor City Golf Club) shares the journey, while Brent Montgomery (Wheelhouse, creator of Pawn Stars) and Adam Friedman (CAA/Connect Ventures, investor in TGL) break down why YouTube distribution is reshaping sports valuations and why emerging leagues are the hottest bet in the industry.
From a teenager renting Scottsdale Stadium for a national tournament to hosting the World Series at AT&T Stadium with the Dallas Cowboys—this is the blueprint for building a sports league in the content era.
Timestamps:
0:00 Introduction
8:44 Forbes 30 Under 30 at 19
9:23 “In chaos, you create great things”
9:40 He rented Scottsdale Stadium at 13
10:20 The Dallas Cowboys called him
11:01 The owner list
14:32 “I go to my kids to find out what shows to pitch”
21:32 Sports is the last real live programming
Key topics:
- How Logan Rose built Big League Wiffle Ball starting at age 13
- Why the Dallas Cowboys cold-called a teenager
- TGL team valuations hitting $100 million range
- YouTube as CapEx: self-distribution before media deals
- Why “sports is the last real live programming”
- The owner roster: Blitzer, Lasry, Gary Vee, Dude Perfect, Kevin Costner, Rob Walton
Speakers:
- Jordan Rose, President & Founder, Rose Law Group
- Adam Friedman, Head of Consumer Investing; Venture Partner, CAA & Connect Ventures
- Brent Montgomery, Founder, Wheelhouse
Recorded at Global Alts Miami 2026 | Presented by iConnections
