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

“We had no performance marketing team, no agency. I committed to learning how to be a performance marketer on TikTok. We didn't come from Facebook, we had no preconceived notions of how things should go. I make budget changes 7 to 10 times a day. TikTok would say you shouldn't touch it for 2 weeks, it's the learning phase. Those people came from Facebook and all the rules were Facebook rules.”— Greg Stewart

Strategy & Decision Making · Business & Entrepreneurship · Technology & Engineering

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No prior model advantage on new platform

“In February 2020, we said, what if we jimmy-rigged the existing app and we created an experience where there could be more than one person? You're going to program for a group of women. You'll go out to your Instagram audience and say, this is for busy women in New York, kettlebell training, very specific persona. We had like 100 people sign up at $100 a month. Very fast. That first month, these people had found each other in the app. They started posting on Instagram about Lauren and Ladder.”— Greg Stewart

Business & Entrepreneurship · Psychology & Behavior · Operations & Execution

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Community formed around shared persona

“We owed some hardcore creditors like American Express, who doesn't really mess around. I learned you can learn all about how to negotiate creditors. What's the key to that? Begging. Tell them you have no money. Get them to really believe it was true that there's a chance you get zero. There's a door to negotiate. And we were negotiating with big creditors at 20 cents on the dollar.”— Greg Stewart

Business & Entrepreneurship · Psychology & Behavior · Operations & Execution

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Credibility of insolvency opens negotiation

“One of the biggest lessons is selling people on your conviction. In March of 2020, trying to kickstart a round, no one's going to lead this round. I was about to lead another inside round where I'm pricing the round and passing the hat to all the boys. I need some more cash. I'm looking at the line items on the balance sheet and I see permanent equity. That's Patrick's friend Brent Beshore. I called Brent and said, I need your investor list.”— Tom Digan

Business & Entrepreneurship · Psychology & Behavior · Strategy & Decision Making

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Personal capital signals conviction to investors

“We had Lauren, a trainer in New York. She was filling up all of her downtime with online clients with Ladder, making $4,000 a month. But her earnings aren't growing. She figured out she had this Instagram profile with 5 or 10,000 people and she was telling a story to her audience and they were coming in, but she filled up all of her time and she couldn't take on any more clients. I'm like, that's a bad business. You've capped how big this can get. The constraint is human time.”— Greg Stewart

Strategy & Decision Making · Business & Entrepreneurship · Economics & Markets

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One-to-one model hits time ceiling

“We started handles in the coaches' names on TikTok, then we started to create content. Very quickly we started to learn what was the content that worked. What worked multiple times in a row? Why? What are the commonalities? How is this product used? It's not Instagram, it's like TV. People are consuming content for entertainment. It's not a social platform, it's a media company. You have to create content that the algorithm knows who to put in front of.”— Greg Stewart

Business & Entrepreneurship · Creativity & Innovation · Technology & Engineering

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Algorithm as media company not social network

“Ladder started as a side hustle for me. I then raised the rest of the money, ended up joining him as co-founder and president of the business. And my condition for joining the business was to move the company to Austin, Texas. That was less about warm weather and change in lifestyle. It was about separating myself from safety nets and putting distance between New York and my Bloomberg terminal and the easy way out, because I assumed it would get hard.”— Tom Digan

Psychology & Behavior · Strategy & Decision Making · Leadership & Management

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Distance as commitment mechanism

“We spent time studying the current business. The coaches could set their own price and they're billing this as customizable program, building it for you based on your very specific goals. On the back end, we can see that it really wasn't personalized. It was big bucket personas. The names were Sally Pilates. We're like, okay, maybe personalization isn't the secret here, but it's having good programming that's relevant to you.”— Greg Stewart

Business & Entrepreneurship · Strategy & Decision Making · Operations & Execution

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Claimed personalization vs actual bucketing

“Number one is don't listen to investors on product feedback. For us, it's two things. Ruthlessly prioritize. You have to prove to each other that this is going to be additive to the product. Additive to the product means we have a thesis that is going to increase workout completions. That's our North Star. We're solving not for getting you to pay one time, we're solving for you to actually complete workouts with Ladder.”— Greg Stewart

Business & Entrepreneurship · Strategy & Decision Making · Operations & Execution

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Ignore investors, measure usage not payment

“Most software companies try to maximize your time on their app to juice engagement. Ramp does the exact opposite. Ramp understands that no one wants to spend hours chasing receipts, reviewing expense reports, and checking for policy violations. So they built their tools to give that time back, using AI to automate 85% of expense reviews with 99% accuracy.”

Strategy & Decision Making · Business & Entrepreneurship · Operations & Execution

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Minimize user time as competitive advantage

“The nutrition survey, that was probably a couple hundred questions. We read all of them. In the beginning, I would copy and paste App Store reviews into a Word doc. I would read every single one of them and I'd organize the words by buckets and I would color code them. I have these documents that are 100 pages long and it's all just deconstructing words from our members. And now you can use ChatGPT to synthesize all this. What is the biggest bet that we can make on behalf of our members?”— Greg Stewart

Business & Entrepreneurship · Operations & Execution

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Manual dissection before AI synthesis

“We learned about hooks, what you say in the beginning, the first 3 seconds, it matters. What should a hook look like? What do I need to say? It's a billboard that I need to get your attention very quickly. We have these whiteboards where we dissect every inch. What is she wearing? What word was first? What was the setting of the gym? What was the movement? All of the insights come from knowing your customer.”— Greg Stewart

Creativity & Innovation · Business & Entrepreneurship · Psychology & Behavior

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Whiteboard dissection of every variable

“We started investing in creators full-time. We had JDs on the website in 2023. It said full-time TikTok creator. People were like, what the hell is this job? That's not a job. Well, it is a job. It just wasn't a job yet. Complete control over the creative. We have these coaches on our team, gave us this edge on compounding learnings, this mini 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...”— Greg Stewart

Strategy & Decision Making · Business & Entrepreneurship · Operations & Execution

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In-house creators enable learning velocity

“If you want to get into consumer, you got to love talking to people. You got to love extracting information from human beings to go create solutions for them. It's not like, I think it should be. That's how consumer companies die, because they just guess and it doesn't match what the consumer is looking for. You have to be excellent at both sides of the house. Half our team works on workout completion, half of them works on trials off TikTok. That's the business. Very simple.”— Greg Stewart

Business & Entrepreneurship · Strategy & Decision Making · Leadership & Management

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Consumer needs dual black-belt capability

“We absorb every piece of information that's coming in, and it's all driven by our members. If you ask the right questions and you have people that are talking to you, you can start forming a picture of what are the huge buckets that actually move the needle. You can do some work to figure out how complex is this to go build and go do it. And don't do 10 other things just because it's interesting. Just do the one thing and do it really well and then do it again.”— Greg Stewart

Operations & Execution · Strategy & Decision Making · Business & Entrepreneurship

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Sequential single-focus execution

“I'm realizing that we have this opportunity to reset and to really think about what can Ladder 2.0 be. But in order to do that, we need to refocus, restructure. I found myself in a position where I was our largest financial shareholder. I felt naturally this obligation and my role and mindset shifted from one of co-founder to trying to be a steward of the business. Came to the board and proposed that we needed to make some pretty significant leadership changes, including naming Greg CEO.”— Tom Digan

Leadership & Management · Strategy & Decision Making · Psychology & Behavior

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Steward role over founder ego

“The mornings were for the messy stuff. It was figuring out how to untangle some of the situations we found ourselves in, debt collectors, and actually just trying to fix things so we can move forward. In the afternoons, we're actually building product. We're raising money at any moment during that. The world has stopped, everyone's at home.”— Tom Digan

Operations & Execution · Leadership & Management · Psychology & Behavior

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Survival clarity plus celebration rituals

“There was nothing we weren't willing to do to make it work. I should have learned that lesson and said, I need to not raise money from friends and family. Instead, they were the only people at that moment that I needed to double or triple down. You just had to go even further all in. Your motivation was delivering to everyone in your life that sits with you every single day. I don't think there was a moment where we thought we weren't going to figure it out.”— Tom Digan and Greg Stewart

Psychology & Behavior · Leadership & Management

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Obligation converts to fuel