Tom Digan & Greg Stewart - Building the World’s Best Fitness App - [Invest Like the Best, EP.454]

Introduction

PatrickLadder was my first angel investment ever. It was made entirely on trust in Tom Digan at a point when I had no idea what I was doing in venture capital. What followed over the next seven years is one of the most unlikely and dramatic business stories that I've been a part of. Today, Ladder is the number one strength training app. They're approaching $100 million in ARR and more than 300,000 paying members. But the path from near death to dominant fitness app involved debt collectors, leadership changes, and a full reset during the pandemic pivot.

At one point, Greg Stewart entered what he calls a cave process, where a huge amount of effort and time went into cracking the TikTok algorithm just to make short-form content work as a growth engine. Tom and Greg built Ladder by being relentlessly empirical about their customers, ruthless about prioritization, raising whatever amount of money they could from any investor, and willing to do whatever it took when most founders would have quit.