Episode summary
How Ladder Became #1 Strength Training App
Invest Like the Best
· · Hosts: Patrick O'Shaughnessy · Guests: Tom Digan, Greg Stewart
Summary
Ladder grew from a struggling managed marketplace for personal training into the #1 strength training app by rebuilding around what its members actually wanted: structured programming, coaching, and accountability without the friction of a human trainer. The host and the guests argue that the company’s real edge was not fitness content volume, but an engineering-first culture that used member interviews, app reviews, and experimentation to find the right product shape. By 2023, Ladder had grown from 9,000 paying members at the start of 2023 to more than 300,000 paying members and was nearing $100 million in ARR.
The early business was close to failure. Tom moved the company to Austin to separate himself from his old career and force the startup to work, but the original marketplace model was operationally complex, money-losing, and hard to scale. When the company reorganized in late 2019 and Greg became CEO, the focus shifted to survival: cleaning up debts, negotiating with creditors, and raising enough capital to keep the business alive while the team rebuilt the product.
The breakthrough came from studying the least obvious customers and building around their behavior. Greg and the team found that strength-training enthusiasts wanted relevant programming, not endless personalization, and that a social, cohort-based experience created real accountability. Later, the same empirical playbook drove growth on TikTok and informed new product expansion into nutrition, which the guests described as another way to solve the same fitness problem more completely.
Key takeaways
- The guests say Ladder won by replacing a marketplace for personal trainers with an engineering-led strength-training product built around programming, coaching, and accountability.
- Tom says the company nearly died before 2020 and required a reset, debt cleanup, and new leadership, with Greg named CEO during the turnaround.
- Greg says the product team learned from members that workout planning was the pain point, not endless personalization, and that cohort-based programming improved retention.
- The guests say TikTok became a major growth engine because they treated it like a new media platform, owned creative in-house, and iterated quickly on content.
- Greg says nutrition is the next major product bet because members see fitness and food as one problem set, not two separate apps.
Notable quotes
“Ladder is the number one app for strength training. We've built a system that's designed to make it as easy as possible to maintain a consistent routine”
“I think it's it's going to sound simple, but it's understanding your customers and really being an engineering first business”
“We were kind of out of money the whole time. We didn't have really any customers to speak of”
“I would call ladder 1.0 as everything pre2020 and after 2020”
“what we learned was we have a third of our members who are tracking macros”
How the episode opens
Today's episode is a conversation with the founders of the company that was my very first ever angel investment, a company called Ladder. At the time, I had absolutely no idea what I was doing. I didn't know the first thing about venture capital, startup investing, technology, software, all things I've learned a lot about through Invest Like the Best and elsewhere since.
But at the time, I was betting on my friend Tom. As you'll hear Tom and Greg discuss the story of building this company together. This is a classic example of what it really takes to build something special and valuable in the world of startups.
It has not been a straight line. It's a company that easily could have died and probably should have died many times. But it has survived and gone on to thrive, reaching almost hund00 million of recurring revenue and building what they hope is the system of record for fitness and health.
I believe this story is a great example of what it really takes to go the distance. Of course, the story is still being told, but I love this episode with Tom and Greg because it's an inside look at the difficult things that any founders will have to go through on the way to an ultimately great story. We try to get into all the nitty-gritty details.
What went wrong, what they did to fix it, and why they're now on the right trajectory. Please enjoy this great conversation with Tom and Greg, the founders of Ladder. So, Ladder was the first ever angel investment that I made, which effectively was a bet on Tom.
This was before I had any idea what I was doing in private markets. And uh I've learned a lot from watching you guys build over the years.
From the episode’s captions: roughly the first two minutes, lightly cleaned. Keep watching on YouTube →
Topics
- strength training app
- tiktok growth loop
- product development process
- scaling revenue arr
- fundraising and financing
Companies and tickers mentioned
- Ladder
Watch the episode
Watch “How Ladder Became #1 Strength Training App” on YouTube
Summary, takeaways and quote selection by Octagon. Quotes are short excerpts; the full conversation is in the episode.
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