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

Podcast: Invest Like the Best

Published: 2026-01-13

Duration: 1 hr 14 min

Guests: Tom Digan, Greg Stewart

Summary

Tom Digan and Greg Stewart share the remarkable journey of Ladder, a fitness app that rose from near failure to become the top-grossing fitness app in the App Store. They discuss the strategic pivots, customer-centric approaches, and innovative marketing tactics that fueled their success.

What Happened

Ladder, co-founded by Tom Digan and led by CEO Greg Stewart, has become the top-grossing fitness app in the App Store, achieving nearly $100 million in annual recurring revenue with over 300,000 paying members. Despite its current success, the journey was fraught with challenges, including financial struggles and a need to pivot from their original business model as a managed marketplace for personal training to focusing on strength training software.

The early years of Ladder involved navigating financial turmoil, which required personal investments and strategic decision-making. At one point, Tom Digan had to sell personal assets and lead a crucial inside round of funding to keep the company afloat. Greg Stewart joined as CEO during a pivotal reset in 2019, bringing a renewed focus on empirical decision-making and customer feedback.

Ladder's growth strategy heavily relied on customer input, with the team spending significant time analyzing app store reviews and conducting surveys. This customer-centric approach led to the development of features like group programming and a nutrition component, which were introduced to address user dissatisfaction with existing solutions like MyFitnessPal.

A key turning point for Ladder was their innovative use of TikTok as a growth engine. Without prior experience in performance marketing, the company managed to rapidly grow their TikTok presence from zero to 250,000 followers in just 45 days. This approach involved investing in full-time TikTok creators to ensure high-quality, engaging content.

The company is exploring the integration of AI and GLP-1s to enhance its offerings. AI has been instrumental in scaling operations efficiently, with tools like Maeve AI handling 90% of customer support. This focus on technology and data-driven decisions positions Ladder as a potential system of record for health and fitness.

Ladder's strategic partnerships, such as with General Catalyst, have provided a stable foundation for controlled cash flow and further growth investments. Despite being a top app in its category, the team acknowledges that brand awareness remains low, presenting an opportunity for future expansion.

The founders emphasize the importance of integrity, personal investment, and relentless focus on customer needs in building a successful company. They see a significant opportunity in the underserved strength training market and aim to expand their offerings to include a marketplace for supplements and fitness-related products.

Key Insights

• Ladder, a top-grossing fitness app, has achieved nearly $100 million in annual recurring revenue with over 300,000 paying members, transitioning from a managed marketplace for personal training to a focus on strength training software.
• The company's growth strategy includes leveraging TikTok, where they amassed 250,000 followers in 45 days by employing full-time creators for high-quality content, despite having no prior experience in performance marketing.
• AI plays a crucial role in Ladder's operations, with tools like Maeve AI managing 90% of customer support, enabling efficient scaling and positioning the app as a potential system of record for health and fitness.
• Ladder's strategic partnerships, such as with General Catalyst, provide a stable foundation for controlled cash flow and growth investments, while the team plans to expand into the underserved strength training market with a marketplace for supplements and fitness-related products.