Tom Digan & Greg Stewart - Building the World’s Best Fitness App - Invest Like the Best with Patrick O'Shaughnessy Recap

Podcast: Invest Like the Best with Patrick O'Shaughnessy

Published: 2026-01-13

Duration: 1 hr 14 min

Summary

Tom Digan and Greg Stewart share the remarkable journey of building Ladder, the leading strength training app, emphasizing the challenges and strategies that propelled their success in a crowded market.

What Happened

In this episode, Patrick O'Shaughnessy interviews Tom Digan and Greg Stewart, co-founders of Ladder, the number one strength training app that has grown to nearly $100 million in annual recurring revenue and over 300,000 paying members. They recount their early struggles, highlighting a phase they refer to as the 'cave process,' during which they dedicated immense effort to cracking the TikTok algorithm for growth. This relentless pursuit of understanding their customers and their needs laid the groundwork for the app's eventual success.

Digan and Stewart discuss how they built Ladder by focusing on three pillars of personal training: programming, coaching, and accountability. They aimed to replicate the benefits of hiring a personal coach, making these advantages accessible to a broader audience. Their approach combines empirical analysis of customer behavior with a ruthless prioritization of tasks, allowing them to adapt quickly and decisively in the face of challenges. The conversation also touches on their vision for the future, which includes becoming the system of record for health and fitness and their unique organizational structure—operating without managers in a 30-person team.

Overall, this episode provides a candid look at the entrepreneurial journey, illustrating the hard work, adaptability, and innovative thinking required to build a successful product in a competitive landscape.

Key Insights

• The importance of understanding customer needs and behavior is critical for product success.
• Adapting to market changes, like leveraging social media algorithms for growth, can be a game-changer.
• Creating a product that mimics the benefits of personal training can attract a wider audience.
• Unique organizational structures, such as operating without managers, can foster innovation and agility.