Tom Digan

.@joinladder was my first angel investment, made entirely on trust in @ThomasDigan when I had no idea what I was doing in venture. What followed is one of the most unlikely and dramatic business stories I've been part of. Today, Ladder is the number one strength training app approaching $100M in ARR with over 300K members. But it should have died several times and survived through sheer force of will from Tom and CEO @GregoryFStewart. Tom left a lucrative hedge fund career and moved his family to Austin. He raised money from me, my family and his friends. Tom talks about how when you take money from people that close to you, you have to know deep down that you're willing to do whatever it takes. During the early years, they were in constantly in debt with no customers and no sign of PMF. They celebrated raising $10k checks at night while negotiating with creditors and rebuilding the product during the day. Greg describes copying thousands of App Store reviews into Word documents and color-coding them by theme to know exactly what feature to build next. He talks about going into what he calls a "cave process," disappearing to study a single problem until he masters it. He spent months cracking TikTok with no background, dissecting every minute detail -- the hook in the first three seconds, what the coach was wearing, the gym setting -- to grow from $3M to nearly $100M in ARR in four years. Ladder is becoming the operating system for health and fitness, but this conversation is about how hard it really is to build something valuable, told by two people who were willing to do absolutely anything to make it work. Enjoy! Timestamps: 0:00 Intro 1:07 The Genesis of Ladder 3:04 Engineering DNA vs. Content Libraries 4:31 Scaling to 300,000 Paying Members 5:36 Leaving the Safety Net 9:00 Restructuring 13:58 Survival Mode 25:48 Ruthless Prioritization 27:15 Integrating Nutrition and Listening to Members 33:53 Cracking the TikTok Growth Loop 44:25 Expanding the Brand Beyond Short-Form Video 46:54 Financing Growth 51:10 Leveraging AI 58:10 Long-Term Vision 1:05:32 Kindest Thing