
38 segments available
Patrick O'Shaughnessy as interviews Tom Digan and Greg Stewart. Tom is the co-founder of Ladder, and Greg is its CEO. Ladder is the #1 strength training app with 300,000+ paying members and nearly $100M ARR. This episode reveals the dramatic journey from near-bankruptcy to market dominance, including how they pivoted from a failing marketplace to an engineering-first fitness platform. Learn their secrets to cracking TikTok's algorithm, building an empirical product development process, and scaling from $3M to $100M ARR in just two years. The conversation covers their unconventional fundraising strategies, data-driven approach to understanding customers, and plans for expanding into nutrition and beyond. A masterclass in consumer company building, persistence, and the power of truly understanding your customers. #LadderFitness #StartupStory #ConsumerTech #FitnessApp #TikTokMarketing #ProductMarketFit #Entrepreneurship #StartupFunding #MobileApps #FitnessIndustry Timestamps: 0:00 Intro 1:07 The Genesis of Ladder 3:04 Engineering DNA vs. Content Libraries 4:31 Scaling to 300,000 Paying Members 5:36 Leaving the Safety Net 9:00 Restructuring 13:58 Survival Mode 25:48 Ruthless Prioritization 27:15 Integrating Nutrition and Listening to Members 33:53 Cracking the TikTok Growth Loop 44:25 Expanding the Brand Beyond Short-Form Video 46:54 Financing Growth 51:10 Leveraging AI 58:10 Long-Term Vision 1:05:32 Kindest Thing Presented by Ramp: https://ramp.com/invest Sponsored by WorkOS, Rogo, Vanta and Ridgeline: https://workos.com/ https://rogo.ai/invest https://www.vanta.com/invest https://www.ridgelineapps.com/ ****** Patrick O'Shaughnessy is the CEO of Positive Sum. All opinions expressed by Patrick and podcast guests are solely their own and do not reflect the opinion of Positive Sum. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of Positive Sum may maintain positions in the securities discussed in this podcast. To learn more, visit psum.vc
An introduction by the host about his first angel investment in the company Ladder and the upcoming conversation with its founders.
"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..."
Tom and Greg share how Ladder differentiates itself in the fitness app market and their approach to customer understanding.
"and unlikely and dramatic, which is why I'm excited to do this with you guys to tell the story of the business that you've built so far and and where it might go. The idea, I think, for our conversati..."
The founders discuss why Ladder has succeeded where many other fitness apps have not, focusing on engineering and customer understanding.
"How has it been so successful? Because I feel like this is almost like a Silicon Valley meme like you have a fitness app like there's 4,000 million fitness apps to what would you attribute the fact th..."
The founders share significant metrics showcasing Ladder's growth and their revenue milestones.
"Just to give people a sense of scale, like roughly, you know, how many people use it? What sort of revenue does the business do? Just like give people a sense of of how big the business is. >> Yeah, w..."
Tom recounts the early struggles of Ladder and the challenges faced during the initial years of the company.
"So sort of having like laid that quick simple groundwork for what the thing is. I would love to rewind time and Tom have you talk about actually we've literally recorded podcast at the same table. I d..."
Tom describes the evolution of Ladder's business model from a marketplace to a focus on strength training solutions.
"there's really two ladders or two different companies here. Same name. I would call ladder 1.0 as everything pre2020 and after 2020. The name's ladder and we're in the fitness space, but it was a it w..."
Tom shares how he met Greg and how they redefined Ladder's mission and direction during its struggles.
"really any customers to speak of. There was no signs of product market fit at that point. Fortunately, this is where Greg answers the the picture. So Greg and I went to went to Notre Dame. I should di..."
Tom explains the leadership changes made in late 2019 to reset the direction of Ladder for future success.
"we were back to where we had started in a lot of ways. It was the end of 2019 and I'm realizing that we have this opportunity to reset and to really think about like what what can ladder 2.0 be. But i..."
Tom reflects on the emotional stakes involved in building Ladder, including risks taken with personal relationships and finances.
"Just to put like a finer point on the situation for you personally. You've left this job. We're making a bunch of money. You're in Austin. You moved your family. You've gotten most of your good friend..."
Both Tom and Greg discuss the intense personal commitments they made to ensure Ladder's success amidst challenges.
"Why not? You have to just like know deep down that you'd be willing to do whatever it takes, you know, including like, you know, some very difficult conversations with your wife and you're building a ..."
Greg shares his reasoning for joining Ladder during its challenging time and the vision he had for the company's future.
"Why did you decide to join it? You know, if you think about the circumstance that you were opting into, uh he said it best, you know, no money, no product market fit, like need needing a whole new tea..."
Greg describes the restructuring process and the work of refining the product plan after they joined forces.
"Talk about what a given day was like in when you guys joined forces there's still this mess to clean up and then there's this thing you have to go build and it's like two sides of the coin. How what w..."
The founders share their approach to survival during challenging times, particularly regarding finances and operations.
"But it it was survival and like when you're in a moment where it literally is survival it's not hard to know what to work on where it wasn't hard for us to know what mattered. We needed to not run out..."
Insights gained from negotiating with creditors during tough financial times and strategies developed to manage debts.
"What's the key to that? What's the lesson? uh begging you money. >> Like when when you get them to really believe and it was true that there's a chance you get zero, there's a door to negotiate. Like ..."
Discussion on strategies for fundraising during the tough times, leveraging personal conviction and creative fundraising techniques.
"If you were to teach a class on fundraising for startups now, you you've done this as masterfully as anyone with the with their cards you were dealt. What would the lesson plan look like? >> One of th..."
Greg explains the importance of cultivating relationships with investors and the role personal connections played in fundraising efforts.
"Again at this point I'm trying to figure out how to sell anything that's not nailed down. And so it's you know 401k put that in done. Uh what else can we do? And um this story here is funny because I'..."
Exploration of insights learned about the product and customer needs through trial and error in development.
"So he bought your steak and then also invested in the round that you were that you were investing in. >> I think he matched what he was what he was sending me which was which was awesome and that kind..."
Discussion on the importance of understanding customer behavior to inform product decisions in the fitness industry.
"And what I noticed was like the coaches could set their own price and like some people had crazy high prices, some people had more approachable prices. And they're building this as customizable progra..."
The founders discuss the development of a new product concept based on insights about customer needs and market gaps.
"Like you've capped how big this can get. You the constraint is human human time. So these two insights of calling [ __ ] on personalization, kind of watching what Lauren was doing and seeing how she w..."
The founders recount the excitement of engagement and community among their users as they trialed new features and products.
"We’re in process of dying in this moment. She went out to her Instagram audience and we had like a 100 people sign up at 100 bucks a month very fast. Like that was the most exciting thing I'd seen yet..."
The conversation covers how user feedback shaped the development of their product and community.
"So all these like little glimmers of hope on this concept of programming that's not personalized, but it's high quality. It's meant for a specific persona. This social accountability element. all thes..."
The founders emphasize the importance of an empirical approach to product development based on user needs and feedback.
"Did anything surprise you in those conversations? >> It validated a lot of things we were learning in in real time. It's like why did you join? I'm tired of thinking about what workout to do. I'm alre..."
Discussion on using customer insights as a cornerstone of their product development strategy.
"Your finance team isn't losing money on big mistakes. It's leaking through a thousand tiny decisions nobody's watching. Ramp puts guard rails on spending before it happens. Real-time limits, automatic..."
Exploration of Ladder's iterative improvement process built around user feedback and prioritization.
"If you think about the uh everyone's very fond of the Elon algorithm for company building now, uh it's been kind of passed around as like one one method for doing this. If you had to distill your like..."
The discussion emphasizes building products based on member feedback and identifying core pain points in user experiences.
"and what can we go build to go improve the odds of you doing that and and staying with us? And how we get to that is we don't guess. Like we absorb every piece of information that's coming in and it's..."
The founders delve into why they decided to integrate nutrition tracking alongside fitness in Ladder's platform.
"And out of that work it became very clear that it was nutrition. And what we learned was we have a third of our members who are tracking macros. And of of that third, 90% are using an app. And of that..."
Exploration of potential new features related to nutrition tracking as part of Ladder's comprehensive service.
"and then once we have that kernel like we go very we do another survey we go very deep on nutrition like extremely deep to understand and we all review it, read everything, we synthesize it and it giv..."
Discussion on the feedback mechanisms utilized to refine Ladder’s product post-launch.
"What did you learn there? What do people want on nutrition? >> There are two halves to this. And from my perspective, it's looking backwards and looking forwards. What they were doing is tracking look..."
The founders discuss their strategy of building trust by providing essential functionalities while keeping user experience seamless.
"So we we made a a conscious decision not to charge for it. So we're going to give this part away. We want to go build trust with this group and win over tracking with ladder. We're not going to convin..."
The concept of user engagement is highlighted as a critical factor for fostering innovation and product development.
"If we think about what nutrition does for us, it gives us the whole math equation of inputs and outputs. There's no product in the world that that has that. So the picture around the consumer, it's th..."
A discussion about Greg's experience troubleshooting ad tech amidst the Texas freeze and insights gained from the book 'Crossing the Chasm.'
"like the ad tech was very new and so Greg was very much like triaging and troubleshooting their ad tech in real time. The other story that just speak to Greg going into his cave. Um it's it is winter ..."
Details of how the team used TikTok to overcome challenges and create successful growth through targeted content.
"Like you have unlimited time right now to talk to us about solving this problem and like how you've how you cracked the code of growing through something like Tik Tok like the more detail the better. ..."
Insights into the differences between TikTok and other social platforms, emphasizing content creation strategy.
"He's got the creative mind. and we grabbed a coach and we said, "Hey, we're going to start an account from scratch. Uh, you're not on TikTok. We want to go learn. Give us all your raw video that you h..."
Discussion of performance marketing strategies on TikTok and the importance of creative ownership.
"So we got views, we had proof points of traction and then we said all right we have blink and bio. Can we get somebody into the app and and we did very quickly and we're getting the right people into ..."
A personal take on the exhilarating feeling of driving growth in a marketing-driven context.
"I launched my first ad. Okay, like we could do this. But like very quickly it was getting people into the app and then it just became a drug addiction. I mean it's like trading. I'm bad at mental math..."
Elaborating on the importance of analyzing content performance to improve marketing strategies.
"And we had a lot of bad content that didn't work. And then we had stuff that started to work. And we have these whiteboards. We dissected every inch. It's like, what is she wearing? What word was firs..."
Exploring new growth strategies and channels outside TikTok as the company matures.
"So, we started investing in creators full-time. We had JDs on the website in 2023. It said full-time Tik Tok creator. People were like, "What the hell is this job?" But it's no different than social m..."
Evaluating strategies for leveraging celebrity endorsements and partnerships to boost brand visibility.
"So, if it's a celebrity partner, we need to know exactly who that audience is. Is this someone that resonates with our user? Are they going to amplify the right message that represents ladder? And lik..."