Patrick O'Shaughnessy as interviews Tom Digan and Greg Stewart. Tom is the co-founder of Ladder, and Greg is its CEO. Ladder is the #1 strength training app with 300,000+ paying members and nearly $100M ARR. This episode reveals the dramatic journey from near-bankruptcy to market dominance, including how they pivoted from a failing marketplace to an engineering-first fitness platform. Learn their secrets to cracking TikTok's algorithm, building an empirical product development process, and scaling from $3M to $100M ARR in just two years. The conversation covers their unconventional fundraising strategies, data-driven approach to understanding customers, and plans for expanding into nutrition and beyond. A masterclass in consumer company building, persistence, and the power of truly understanding your customers. #LadderFitness #StartupStory #ConsumerTech #FitnessApp #TikTokMarketing #ProductMarketFit #Entrepreneurship #StartupFunding #MobileApps #FitnessIndustry 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 Presented by Ramp: https://ramp.com/invest Sponsored by WorkOS, Rogo, Vanta and Ridgeline: https://workos.com/ https://rogo.ai/invest https://www.vanta.com/invest https://www.ridgelineapps.com/ ****** Patrick O'Shaughnessy is the CEO of Positive Sum. All opinions expressed by Patrick and podcast guests are solely their own and do not reflect the opinion of Positive Sum. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of Positive Sum may maintain positions in the securities discussed in this podcast. To learn more, visit psum.vc