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

In a near-death scenario, Ladder successfully negotiated with major creditors by convincing them of the real possibility of getting zero. This little-discussed survival tactic was key to cleaning up their balance sheet, demonstrating that even large institutions will negotiate when faced with a total loss.

Ladder's CEO argues that consumer startups cannot succeed without simultaneous, world-class expertise in both product development and customer acquisition. A great product with no growth engine, or a great growth engine with a leaky product, are both fatal flaws in the B2C space.

During a pivot with no new product to show, Ladder's fundraising relied entirely on selling the team's conviction. Co-founder Tom Digan personally leading the round despite being financially stretched was the ultimate signal of "skin in the game" that convinced other investors to join.

By analyzing their initial marketplace, Ladder found that coaches were charging premium prices for "personalized" plans that were actually just templates for broad customer personas. This insight led them to pivot to a scalable, one-to-many model focused on high-quality programming for specific groups.

Instead of relying on investor feedback or intuition, Ladder's product strategy is deeply empirical. The CEO manually copied, pasted, and color-coded thousands of App Store reviews into Word documents to identify core customer pain points, forming the blueprint for their roadmap.

To succeed on TikTok, Ladder's team obsessively analyzed their winning organic content on whiteboards, breaking down every variable: the hook, the creator's clothing, the gym setting, the specific words used. This deep qualitative analysis was crucial for understanding what the algorithm would amplify.

Ladder's success stems from prioritizing aggregate customer data over individual opinions, especially from investors. They view an investor's product suggestion as a single, biased data point that often contradicts what their broader user base actually wants and needs.

When facing a new business bottleneck, Ladder's CEO Greg Stewart enters a "cave" of intense, focused study to become an expert. He went from a non-creator to mastering the TikTok algorithm, demonstrating that founders can learn and execute on critical functions themselves without immediate hiring.

Instead of guessing when a new feature is ready for public launch, Ladder uses a beta group of 2,000 members. They repeatedly surveyed these users with the question, "How likely are you to switch from your existing app?" They only launched when the metric climbed from an initial 20% to 85%.

To kickstart a critical funding round, Ladder's co-founder needed to lead with his own cash but was tapped out. He creatively found liquidity by convincing the GP of a fund he was an LP in to let him sell his stake to another investor, who then also joined the new round.

Ladder built custom AI tools to handle operational tasks at scale. "Maeve AI" manages 90% of support tickets, while "Ladder Pulse" synthesizes group chats for coaches. This strategy uses AI for leverage, allowing a small team to deliver a high-touch experience without a large headcount.

Instead of following standard performance marketing playbooks, Ladder's CEO learned TikTok from scratch. He treated it like a trading desk, making 7-10 budget changes a day—a strategy that baffled even TikTok's own team but proved highly effective by challenging established platform heuristics.