Invest Like The Best

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 during the pandemic. Tom and Greg built Ladder by being relentlessly empirical about their customers, ruthless about prioritization, raising money wherever they could, and doing whatever it took when most founders would have quit. We cover the messy early years when survival meant negotiating creditors, how they found PMF by reading thousands of app store reviews, and how they built a TikTok growth engine with no performance marketing experience. They share their long-term vision for becoming the category winner fo