Tom Digan & Greg Stewart - Building the World’s Best Fitness App
Invest Like the Best with Patrick O'Shaughnessy
- Published
- January 13, 2026
- Duration
- 1h 14m
- Summary source
- description
- Last updated
- Apr 17, 2026
Discusses business, investing, technology.
Summary
My guests today are Tom Digan and Greg Stewart. Tom is the co-founder of Ladder, and Greg is its CEO. Ladder was my first angel investment. What followed over the next seven years is one of the most unlikely and dramatic business stories I’ve been a part of. Today, Ladder is the number one grossing fitness app in the App Store, approaching $100M in ARR wi…
Show notes
My guests today are Tom Digan and Greg Stewart. Tom is the co-founder of Ladder, and Greg is its CEO. Ladder was my first angel investment. What followed over the next seven years is one of the most unlikely and dramatic business stories I’ve been a part of. Today, Ladder is the number one grossing fitness app in the App Store, approaching $100M in ARR with more than 300,000 paying members. But the path from near death to dominance involved debt collectors, leadership changes, and a full reset d
Themes
- business
- investing
- technology