Invest Like the Best with Patrick O'Shaughnessy · Colossus | Investing & Business Podcasts

Tom Digan & Greg Stewart - Building the World’s Best Fitness App

·1 hr 14 min·5 clips

Tom Digan describes negotiating with debt collectors at 20 cents on the dollar to keep Ladder alive.

Tom Degan and Greg Stewart lead Ladder, the number one strength training app with over 300,000 paying members and nearly $100 million in annual recurring revenue. The business started as Tom's side hustle in 2017 when he left a lucrative hedge fund career to move to Austin and build a fitness startup with a high school classmate. Greg Stewart, a Notre Dame classmate who had been building startups for 10 years, joined at the end of 2019 when the company was out of money with no product-market fit. The original Ladder was a managed marketplace for personal training that proved operationally complex and unprofitable. By late 2019, Tom proposed significant leadership changes including naming Greg as CEO, describing his role as steward of the business since he was the largest financial shareholder and had raised money from friends and family. The team spent mornings in early 2020 negotiating with debt collectors and creditors like American Express, getting settlements at 20 cents on the dollar, while afternoons were devoted to building a new product. Tom raised money constantly through small checks, at one point selling his Permanent Equity stake at a 50% discount to investor Bill to kickstart a funding round. The breakthrough came from studying their existing marketplace and noticing that successful coaches weren't actually personalizing training—they used big bucket personas while charging premium prices. Trainer Lauren was earning $4,000 monthly but hit a capacity limit, so in February 2020 they created a trial where she programmed for a group of New York women via Instagram, generating 100 signups at $100/month with 90%+ renewal rates. Members spontaneously met in parks and posted about the experience, revealing demand for quality programming, coach interaction, and social accountability rather than pure personalization. The company ruthlessly prioritizes features based on one metric: increasing workout completions. They read every App Store review, organize feedback into 100-page color-coded documents, and send surveys with up to 200 questions to thousands of members. A recent survey of 5,000 members revealed that one-third track macros, 90% use MyFitnessPal and hate it, leading to their nutrition feature launch. They discovered members view fitness as one problem set—inputs and outputs—but were forced to manage it across multiple apps. The conversation style is candid and detailed, with founders sharing specific dollar amounts, failure points, and tactical decisions. Both speakers exhibit a survival-oriented mindset, emphasizing that they never doubted eventual success despite dire circumstances. This episode suits founders facing near-death business scenarios, product leaders seeking customer research methodologies, and investors wanting to understand the messy reality behind eventual success stories. The emphasis on empirical customer understanding over competitor analysis offers actionable frameworks for product development.

As heard by us

A practical look at how Ladder turns member signal into product decisions.

The discussion keeps its attention on the plain mechanics of building Ladder as a fitness app that changes behavior. Its central point is easy to follow: product choices need hard priority, every addition has to earn its place, and the real North Star is workout completions, not…

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Why you'd press play

You want to hear how a fitness app decides its next big build.

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