Tom Digan & Greg Stewart - Building the World’s Best Fitness App - [Invest Like the Best, EP.454]
Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
Podcast Summary
This episode tells the remarkable story of Ladder, now the number one strength training app with nearly $100 million in ARR and over 300,000 paying members. (04:26) Tom Digan and Greg Stewart discuss their journey from near bankruptcy to building a dominant fitness platform, sharing candid insights about surviving debt collectors, leadership transitions, and cracking the TikTok algorithm with no performance marketing experience.
- Main Theme: How to build something truly valuable by being empirical about customers, ruthlessly prioritizing features, and persisting through seemingly insurmountable challenges when most founders would quit.
Speakers
Tom Digan
Tom is the co-founder of Ladder, leaving a lucrative hedge fund career to pursue the startup world. He moved his family to Austin and raised money from friends and family to fund the venture, personally investing multiple times to keep the business alive during its darkest moments.
Greg Stewart
Greg is the CEO of Ladder and a Notre Dame alumnus who joined the company in 2019 during its most challenging period. He previously worked in banking and had experience building startups, bringing a team of engineers and product specialists to help transform Ladder into the successful platform it is today.
Key Takeaways
Listen Obsessively to Your Customers, Not Investors
The founders discovered their breakthrough by reading thousands of App Store reviews and conducting extensive surveys with members. (31:51) Greg emphasizes that investors often give prescriptive product advice based on their personal use cases, but real insights come from systematically gathering feedback from actual users. They would color-code customer feedback, organize themes, and let member data guide every product decision. This empirical approach led them to discover that personalization wasn't the key – good programming relevant to specific personas was what mattered.
Be Willing to Do Whatever It Takes When Others Would Quit
During their darkest period, the founders negotiated with creditors at 20 cents on the dollar and Tom personally invested multiple rounds to keep the business alive. (16:40) Their survival mindset meant there was no task too small or too difficult. This included Tom calling debt collectors daily, learning to negotiate payment plans, and even trying to sell equity stakes to fund operations. The key was having conviction that success was inevitable, even when circumstances suggested otherwise.
Master One Growth Channel Completely Before Expanding
Rather than spreading efforts across multiple marketing channels, Greg went "into a cave" to become an expert at TikTok growth. (43:53) He studied the platform obsessively, making budget changes 7-10 times daily while others recommended waiting weeks. They created content organically first, growing one account from zero to 280,000 followers in 45 days, before investing in paid advertising. This deep expertise in one channel became their primary growth engine and competitive advantage.
Ruthless Prioritization Based on One North Star Metric
Every product decision at Ladder is evaluated against one question: will this increase workout completions? (31:58) Greg explains they don't build features just because they can or because they seem interesting. Each potential addition must prove it will improve the odds of members actually completing workouts and staying with the platform. This laser focus prevents feature bloat and ensures resources go toward what truly matters to their core value proposition.
Build Your Own Tools When Existing Solutions Don't Fit
Rather than relying on external agencies or generic software, Ladder built custom AI tools for their specific needs. (61:01) They created "Maeve AI" for customer support and "Ladder Pulse" to help coaches identify the most important member questions without scrolling through thousands of messages. By building internal capabilities, they could iterate faster and maintain better control over the user experience than competitors who outsourced critical functions.
Statistics & Facts
- Ladder grew from 9,000 paying members at the beginning of 2023 to over 300,000 paying members today, representing explosive growth in just two years. (09:14)
- The company is approaching $100 million in ARR and is the top 100 app of all US apps in the App Store, demonstrating significant market penetration in a crowded fitness space.
- Their custom AI customer support tool "Maeve" now handles 90% of support tickets with over 300,000 paying members, requiring only one person for customer support operations. (61:48)
