Episode Summary
Executive Summary: This episode traces Ladder's unlikely rise from a near-death personal training marketplace to the number one strength training app, nearing $100M ARR and 300K+ paying members. Founders Tom Deegan and Greg Stewart explain how ruthless customer research, product simplification, TikTok mastery, and AI tools turned survival into durable growth.
Main Topics: Ladder's product thesis (Priority: 5/5): Ladder repackages personal training into programming, coaching, and accountability. From collapse to reset (Priority: 5/5): The business nearly died pre-2020, then reset leadership and strategy during COVID. Customer-led product development (Priority: 5/5): They read reviews, ran surveys, and used member feedback to decide what to build. TikTok as the growth engine (Priority: 5/5): Greg built a proprietary short-form video machine by learning TikTok from scratch. Nutrition expansion (Priority: 4/5): Nutrition became the next major feature by connecting inputs and outputs for members. AI as leverage, not replacement (Priority: 4/5): AI now powers synthesis, support, and coach tools without removing the human layer. Long-term platform vision (Priority: 4/5): The goal is to become the system of record for health and fitness with future commerce.
Key Arguments: Ladder won by understanding its users better than fitness competitors do. The original marketplace model was too operationally complex and didn't scale. They built around workout completion, not one-time conversion or content libraries. TikTok growth came from iterative creative testing, not paid-media playbooks. Nutrition was only launched when member data showed clear demand and timing. AI let a small team ship faster and add personalization without bloating headcount. The company uses a long game: product expansion, user expansion, then monetization.
Data Points: Paying members: more than 300,000 - Current size of Ladder's subscriber base ARR: approaching $100 million - Revenue scale discussed by the founders Paying members at start of 2023: 9,000 - Shows the pace of growth since the reset Renewal rate: 90% plus - Early trial cohort on the new persona-based product Beta members for nutrition: 2,000 - Initial test group for the nutrition feature Switch intent rate: 20% - Early survey answer from users asked to switch from existing nutrition apps Switch intent rate: 85% - Later survey result after product iteration Meals logged: almost 4 million meals logged - Week six after nutrition launch TikTok growth: zero to 250,000 people in 45 days - First account built for short-form acquisition Starting revenue of TikTok journey: 3 million - Early revenue level before the paid TikTok push Revenue during TikTok scale-up: 4 or 5 million of era - Revenue level as the channel started working Team size: 50 people, including 20 full-time coaches - Current operating footprint described by the founders Survey responses: 5,000 responses - Annual member survey used to guide roadmap decisions Survey length: 230 of our most burning questions - Questions asked in the annual survey App store position: top three or four in our category - Current awareness and ranking discussion Cash negotiations: 20 cents on the dollar - How they negotiated with creditors during the turnaround
Pivotal Quotes: "There are really two Ladders or two different companies here. Same name." — Tom Deegan: Describing the pre- and post-2020 reset "We didn't look at fitness almost ever." — Greg Stewart: Explaining how they avoided copying competitors "If that was the frontier then, what is the frontier now?" — Tom Deegan: Framing the next growth and product stage
Implications: Ladder's next test is whether it can broaden awareness and expand into adjacent health categories without losing the focus that made the core product work.
From the Transcript
There are really funny stories where Degan was pitching, I'm pitching, and you're basically trying to figure out what the investor likes. You're like, let me tell you about this one-to-one business we got. It's like super exciting. Oh, you're like that? We're thinking about this social concept. You just live in this world of figuring out how do I make it through? And there were enough wins. The micro wins on survival felt big to us. And there was enough to celebrate to keep going and wake up and go do it again. If you were to teach a class on fundraising for startups now, you've done this as massively. As anyone with the cards you were dealt, what would the lesson plan look like? One of the biggest lessons, particularly from that moment, is selling people on your conviction. In that moment, we were selling both the product that we were about to shut down, but we didn't really even have visuals yet for the new product. So it was as much just selling the team and the conviction on what you were about to build. I think the best example of that is a story about another friend of ours, we'll call him Bill, in March of 2020 trying to kickstart a round. But no one's going to lead this round naturally because who would lead a round in our business?
This media agency that was figuring it out across all these different creators that we controlled, that we weren't just waiting and hoping that somebody on the other side of the fence would throw us the right thing. If that was the frontier then, what is the frontier now? What we're thinking about now is the short-form video strategy will always be a core part of our strategy. That's not going away. But I think what we learned. It's expanded well beyond TikTok at this stage. Exactly. I think what we learned last year, though, is that we certainly don't have a product problem. We have a very special product. Our customers love us and they're asking us to go deeper with them. But most people still don't know who Ladder is. We're consistently top three or four in our category in the app store, and yet the awareness is very low. I think that's largely a function of the short-form video strategy that we had that was speaking with creators in these winning formats to a specific persona that wasn't really leading with the ladder brand. Now we're excited to go and think about celebrity partnerships and out-of-home and TV. And we're already making these campaigns. Now we're just going to go and put them in these other channels. So that's certainly a big focus.
About Invest Like the Best with Patrick O'Shaughnessy
Conversations with the best investors and business builders in the world.
View all episodes from Invest Like the Best with Patrick O'Shaughnessy