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

What It Covers

Tom Deegan and Greg Stewart explain how Ladder grew from near bankruptcy to approaching $100M ARR as the number one strength training app, scaling from 9,000 to 300,000 paying members through empirical product development and TikTok mastery.

Key Questions Answered

• •Customer research methodology: Read thousands of app store reviews manually, color-coding themes into 100-page documents. Survey users with 200+ questions taking 50 minutes average to complete. Talk directly to members weekly to identify pain points, not features. This empirical approach reveals what actually drives workout completion versus investor opinions.
• •TikTok growth strategy: Started coach accounts from zero, analyzed every viral video element (hook words, clothing, gym setting, movements). Created content in-house with full-time creators rather than agencies to enable rapid iteration. Moved ad budgets 7-10 times daily, ignoring Facebook-based rules that TikTok reps recommended, treating it like active trading.
• •Ruthless prioritization framework: Half the team works on workout completion, half on trial acquisition from TikTok. Every feature must prove it increases workout completions before building. Delayed Android app for years despite pressure because it would split focus and serve lower-revenue users. Earned each level before expanding to next product category.
• •Survival fundraising tactics: Negotiated with creditors at 20 cents on dollar. Led inside rounds personally while selling any liquid assets. Called existing limited partners to buy out positions at discounts during market crashes. Raised money from anyone willing, focusing on conviction and skin-in-game rather than terms or valuation during desperate periods.
• •AI implementation phases: First used for synthesizing 5,000 survey responses and creating TikTok hooks from user data. Built custom tools like Maeve AI handling 90% of support tickets and Ladder Pulse analyzing chat conversations to tell coaches exactly what content to create. Team stayed at 30 people (excluding coaches) during hypergrowth because AI replaced hiring needs.