How Ladder Became #1 Strength Training App

1. The Genesis of Ladder

Today's episode is a conversation with the founders of the company that was my very first 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, or software—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 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 $100 million in 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.

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 I've learned a lot from watching you guys build over the years. The story is fairly amazing, 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 where it might go.

The idea for our conversation today is to show people how incredibly hard it is to build something that ends up being very valuable, and the twists and turns that happen along the way. It's amazing that you've ended where you are, but I find it all the more interesting how you got here. Of course, we'll also talk about where you're going. Maybe to begin, since not everyone will know what the business is, describe what the actual product and business is. Then I want to tell the real, dirty version of the story of how you got here.

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. We spent a lot of time thinking about personal training. Arguably, the most reliable way to get to the results that you're looking for is hiring a coach.

It's unattainable for most, inaccessible for most. But personal training, if you think about how it breaks down, is programming, coaching, and accountability. Programming: you know exactly what to do. Someone's prepared it for you. There's no guesswork. There's no thinking.

With coaching, you have an expert there to guide you and answer your questions. And with accountability, you have a coach standing in front of you. You don't want to piss off your coach, which is a really powerful motivator. Then we took those 3 pillars and designed an experience from the ground up to get as close as possible to that experience.

2. Engineering DNA vs. Content Libraries

How has it been so successful? I feel like this is almost a Silicon Valley meme: you have a fitness app, and there are 4,000 fitness apps. What would you attribute the fact that this is the one that seems to have come to dominate in a sea of competition?

I think it's going to sound simple, but it's understanding your customers and really being an engineering-first business. If you look at most companies in our space, they're started by creators, and they're good products, they're good companies, but the creator is the face of that business. They make every decision, and they don't have a DNA that's rooted in engineering, in problem-solving.

When you look at these apps, they're mostly just content libraries, and the motion is just constantly creating more and more content. But what we saw was that nobody was spending time thinking about how to use these incredible levers to deliver an experience that actually increases the odds of you continuing on.

We looked at apps like social networks and Duolingo—all these apps that are using powerful motivational mechanics and pointing them at an action. For social media networks, it's selling your attention. For Duolingo, it's learning a language. So we took that mentality: How do we use software to create an experience that's totally different from what exists today, that isn't reliant on a never-ending content machine?

3. Scaling to 300,000 Paying Members

It's been guided by our members. We spend more time than you could imagine just speaking to our members, dissecting exactly what we should focus on based on what they care about. I think it's just not looking at other companies for inspiration. We just don't look at fitness almost ever.

Just to give people a sense of scale, roughly, how many people use it? What sort of revenue does the business do? Just give people a sense of how big the business is.

We're north of 300,000 paying members today. I think at the beginning of 2023, we were at 9,000 paying members. The growth has been exciting. We're getting pretty close and knocking on the door at $100 million of ARR. It's been very exciting from a revenue-growth perspective, but it all boils down to the fact that we've created a product that gets people the results that they want and they stay with us.

So, having laid that quick, simple groundwork for what the thing is, Tom, actually, we've literally recorded a podcast at the same table. I don't know—do you know what year that was? 2017, maybe.

4. Leaving the Safety Net

The beginning chapter of the business, call it 2017 to 2020 or so, was a struggle to stay alive, and you personally put so much of your time and your reputation on the line to do this thing. You left a really lucrative, successful hedge fund career to do it. Maybe you can just tell the story of those early years—what was going on and why it was such a struggle.

Again, I want to paint the story of how $100 million of ARR is awesome. Congratulations. That's really fantastic. I'm very happy as an investor, but the more interesting part of this is what it takes to get there. So maybe set the stage for us.

Ladder started as a side hustle for me. A high school classmate whom I went to school with up in Boston had pitched me on a fitness startup. The product didn't exist yet. I think it was a pitch that I was looking to swing at the time. I was very interested in startups and technology.

He asked me to put some money into the business, which I did. I then raised the rest of the money and ended up joining him as co-founder and president of the business. My condition for joining the business was to move the company to Austin, Texas. For me, that was less about warm weather and a change in lifestyle. It was about separating myself from safety nets and putting distance between New York, my Bloomberg Terminal, and the easy way out, because I assumed it would get hard.

I didn't know it would get quite as hard as it did. There are really 2 Ladders, or 2 different companies here, with the same name. I would call Ladder 1.0 everything pre-2020 and Ladder 2.0 everything after 2020. The name's Ladder, and we're in the fitness space, but it was a different team. It was a different product.

What we were originally building was more of a managed marketplace for personal training. We thought that it was about personalization, with a heavy emphasis on a relationship with another human. We thought that was really the opportunity. What we'd come to find out was that the business would be operationally complex and difficult to scale.

Ultimately, as you scale that business, it starts to look more like a call center, and you'd be inclined to start to automate away the very human element you were selling in order to build anything that had margins worthy of venture-type economics and scale. So it was uninteresting.

But what we were seeing was that all of the innovation in the space was focused on the casual fitness consumer. We were noticing that it was all very cardio-based, and we saw that this fitness-enthusiast customer was really being ignored. Strength training in particular—there was no one selling strength-training solutions.

We got excited that there was this fitness-enthusiast customer who was already working out and had a huge pain point around planning their workouts daily. We got excited that this is something we can solve with software. We found ourselves in Austin, Texas. By the time I got down there, I realized startups are really hard, and it didn't quite look like what I had been hearing on your podcast as far as the iterating and the learning.

It was hard. It was messy. We were out of money the whole time. We didn't really have any customers to speak of. There were no signs of product-market fit at that point. Fortunately, this is where Greg enters the picture.

Greg and I went to Notre Dame. I should disclose that all 3 of us were classmates at Notre Dame. Greg and I reconnected in Austin, Texas. He had left banking and had been building startups for a period of time. It was very obvious that he had this small team that believed in him very much, and it was clear that he wanted to build something very meaningful and consumer-focused.

So I spent my time tricking him into joining us, if you will. Eventually, I got him under the hood and excited about what we were building.

5. Restructuring

Why I was so interested in startups myself is that I had this sense that you could make something happen in the startup world. It just felt like if you were willing not to stop and just keep going, through sheer force of determination, you could build something that was appealing. Because in the hedge fund space, I can promise you, in the finance world, that's not possible. You can't just will hedge fund returns into existence. I think Bernie Madoff tried to do that, and it doesn't work.

It was obvious to me that he shared that same belief. We'd be in the middle of doing something messy, like a debt collector, whatever it was—something hard—and in that same next conversation, he's talking as if our success is inevitable. We're going to build this enduring business. I was attracted to that. I've always felt that way. I could just tell that Greg seemed like the type of guy you wanted to be in a foxhole with.

So now it's the end of 2019, and I'm realizing that we have this opportunity to reset and really think about what Ladder 2.0 could be. In order to do that, we needed to really refocus and restructure. I was thinking about what a leadership transition could look like. I found myself in a position where I was our largest financial shareholder. In addition to being in the company as a co-founder in the early days, it was people like yourself who had put money in because they trusted me personally.

I naturally felt this obligation, and I think my role and mindset shifted from one of co-founder to trying to be a steward of the business. The day after Christmas in 2019, I came to the board and proposed that we needed to make some pretty significant leadership changes in order to really reset the business. As part of that, we had some changes at the executive level, including naming Greg CEO.

It felt like, at that moment, we had this sense of, “We can go build this thing now.” Our problems were hardly solved, but it felt like the problems were now worth solving.

Just to put a finer point on the situation for you personally: you've left this job where you were making a bunch of money. You're in Austin. You moved your family. You've gotten most of your good friends and your family—as far as I understand it, my family—so many people that you cared about and that cared about you too, to invest in this thing. What did that feel like? What was the darkest point, and what did it feel like for you personally?

It just felt like there was nothing you weren't willing to do to make it work. I think that's why it was appealing to meet someone else who felt that way, who was going to be in that foxhole. I should have learned the lesson and said, “I need not to raise money from friends and family.” Instead, they were the only people at that moment that I needed to double- and triple-down on.

You just had to go even further all in. I'm not sure I would do it again or recommend that other people take that path.

Why not? You have to know deep down that you'd be willing to do whatever it takes, including some very difficult conversations with your wife. You're building a family, and you're leaving a lot on the table—a much easier, cushier, hedge-fund, country-club-type existence here in the Northeast—and you want to go and do something hard. It turns out it's pretty fucking hard.

I think that dynamic is why Ladder is here, though. Your motivation was delivering to everyone in your life, and that sits with you every single day. I don't think there was a moment when we thought we weren't going to figure it out. I can't think of 1 day when we were like, “It's not going to happen.” We were going to figure it out.

On my side, I don't have that same dynamic—I do now, but it wasn't true when I first joined. Not everybody was invested in Ladder. But I had a conversation with my wife where she said, “This is the last one. If you don't figure this one out, there are no more startups.”

It had been 10 years of not a lot of success tied to a lot of work. My wife married an investment banker who was a closeted entrepreneur, and I've been an investment banker for 18 years. It's been a long time of, “I'm going to the clubhouse. I'm going to figure it out today. I promise it's coming. It's coming.” That's been an enormous motivator: no, this is going to work. I mean, there's just no scenario where we can let this not get to the vision that we've set ourselves on.

Why did you decide to join it? If you think about the circumstance that you were opting into, he said it best: no money, no product-market fit, needing a whole new team. Why not just start a new company or something? Why come into this?

It was a perfect moment that is very unlikely to ever happen again. I was building a company inside of a big real-estate private-equity business—a consumer company—which had all kinds of complexities involved in trying to be an innovator inside of a really established company.

6. Survival Mode

But I had this amazing team of people, some who had been with me for a couple of ventures, and some who I'd worked with for 2 to 5 years. It was a really powerful team that could build anything. This was product, engineering, and marketing—a core group that we wanted to just keep working together. We wanted to be in consumer, and we wanted to work on a hard problem.

But we had a group of people who were not at a stage of life where they could take zero salary and start something from a garage. People were starting to have kids. Life was starting to happen. We had spouses, and just starting something from scratch seemed like a hard task if we wanted to keep the group together.

That was my number-one focus: keep this group together. It's special, and I wanted to hold on to it for dear life. That's what I was solving for: consumer, bring my most important people, and let's take another swing together.

Talk about what a given day was like when you guys joined forces. There's still this mess to clean up, and then there's this thing you have to go build. It's like 2 sides of the coin. What would a day look like in those early days?

It was literally late March 2020 when we'd zeroed in on the concept for this new product, and we were having to go fully remote. The teams knew, so everyone was working from home other than Greg, myself, and Johnny.

The mornings were for the messy stuff. It was figuring out how to untangle some of the situations we found ourselves in—debt collectors, actually just trying to fix things so we could move forward. In the afternoons, we were actually building product, and Greg was focused on winding the team up and iterating on what we were about to build and launch a few months later.

We were raising money at any moment during that. I was spending every moment redialing people who were already investors and reaching out to new people.

What I remember most about those days, though, because it was hard but also so exciting, was that at night, at around 10:00, we'd finish. The whole world had stopped. Everyone was at home. We'd been in the office grinding since 6:00 a.m. At 10:00, it would be like, “All right, whatever win we had that day, let's celebrate.”

It was like—you've seen that scene in Goodfellas when they're all in prison. When wise guys go to prison, it's not like everyone else. They've got lobsters coming in and slicing the garlic.

Slicing the garlic with the little razor blade.

Yeah, slicing the garlic with the little razor blade. For us, our version of that was cooking steaks on the grill. We were smoking cigars in the office because no one else was coming in. I was shaking martinis up there, and we were high-fiving about raising $10,000 checks.

That was exciting because, frankly, it felt more like the startups that were romanticized by podcasts and books and all the fun stuff.

But it was survival. When you're in a moment where it literally is survival, it's not hard to know what to work on. It wasn't hard for us to know what mattered. We needed not to run out of money.

Digan was spending time trying to solve that problem. We were in debt and owed a lot of people a lot of money, and it's a startup, so it's really hard to get a clear picture of the financials and where money is going. The first thing I worked on was, “Where's the money going?”

We put that piece together, and no one can really see this or is looking at it, and you realize money's going in different places that we're not totally aware of. Mission number 1 was to figure out the cash flow, and we got visibility into that.

Then we had some money that we owed to people, and we owed some hardcore creditors, like American Express, who doesn't really mess around. Digan and I learned all about how to negotiate with creditors, and that was a new skill set for me.

What's the key to that? What's the lesson? Begging for money?

When you get them to really believe—and it was true—that there's a chance they get zero, there's a door to negotiate. We were negotiating with big creditors at 20 cents on the dollar.

We knew the list of groups that we owed money to, and it was like sales. We were like, “All right, we have to go one by one and figure out how to close the door on this and not let it overhang the business.” So: raise money, get money back to the right people, clean up the house to survive.

And then we had this moment around this time where we had this existing business. It wasn't working. There were some insights coming out of it, but it really wasn't working. But we were still trying to maintain it.

So we were living in this in-between moment of, “Keep that thing alive so we can pitch something to folks on the outside,” but also, “What are we going to do? What are we going to build?” There was no path in this thing that we had built.

There were really funny stories where Digan was pitching, I was 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 super exciting. Then you're thinking about this social concept, and you're just living in this world of figuring out how to make it through.

There were enough wins—the micro-wins on survival felt big to us—and there was enough to celebrate to keep going, wake up, and do it again.

If you were to teach a class on fundraising for startups now, you've done this as masterfully as anyone with the cards you were dealt. What would the lesson plan look like?

[Speaker?]

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 selling the team and the conviction on what we 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. We were trying to kickstart a round, but no one was going to lead this round. Naturally, who would lead a round in our business at that moment? So I was about to lead another inside round where I was pricing the round and passing the hat to all the boys and whoever would listen.

What happened there was that I needed some more cash. I think Braden knows how many times I wrote checks into the business. This was another example of being like, “All right, the only way to get this going is to write the first check and then lead with that conviction, showing that you had skin in the game here.”

At this point, I'm trying to figure out how to sell anything that's not nailed down. My 401(k)—put that in, done. What else can we do?

This story here is funny because I'm looking at the line items on the balance sheet, if you will, and I'm like, “Oh, Permanent Equity.” That's Patrick's friend, likely Brent Beshore. Brent came and told his story on this podcast. He has an unbelievable strategy, and it's called Permanent Equity for a reason.

He buys these family-owned, awesome businesses and then holds them forever. There isn't necessarily a liquidity profile here, but I read the documents, and it said that if you found another LP to sell to, you could sell.

So I called Brent and said, “Hey, I need your investor list.” He's like, “The market—the S&P—is down 35%. We're in a global pandemic. Of course I'm not giving you my investor list. You're my smallest investor.” But he did me a solid and said, “Hey, you should call Bill.”

Bill's a friend. He's Patrick's friend, another Notre Dame guy. So I called Bill, and Bill's a gamer. He's just like, “What are you looking to do? When do you need this by?” And he's like, “What are you thinking? How do we mark this?”

I'm like, “Well, the market's down this much. What about down 10%?” And we did the dance and ended up somewhere in the middle. I'm like, “You're in, but I need the money tomorrow.” And he's like, “I'll send you the money tomorrow, and I'm investing in whatever this is going into.”

He didn't even really know what Ladder was, but he was like, “I'm in.” I think the point there is that, particularly in those early days, it's important to have skin in the game in whatever way you can.

For us, it was about being able to show that level of conviction and urgency. Bill didn't need to see a deck. We didn't have a new product yet. He knew you were involved, and he was just like, “If you're willing to do this, I need to be involved too.”

So he bought your stake and then also invested in the round that you were investing in.

[Speaker?]

I think he matched what he was sending me, which was awesome, and that kind of kicked it off.

We're glossing over a lot. Maybe we'll keep returning to fundraising. I love that story. But let's get to the point now where things are starting to feel like, okay, now we have to build this next thing.

Maybe this is a good opportunity to ask you what you now know about the world of fitness and people who want to get fit. What becomes your north star for what product can we build here that's scalable, that can get to what it's become?

Yeah. There was no magic bullet that said, “Go do this and you'll win.” But we spent a lot of time in the first 2 or 3 months I was there trying to dissect the current business.

The current business was essentially this one-to-one marketplace connecting an independent-contractor coach with a consumer who was looking for personal training. We were studying the behavior and watching what was going on here.

What I noticed was that the coaches could set their own price. Some people had crazy-high prices, and some people had more approachable prices. They were building this as a customizable program: “I'm building it for you based on your very specific goals, and that's why I'm charging you this amount.”

On the back end, we could see that it really wasn't personalized. It was big-bucket personas, and the names were like “Sally Pilates.” That was being built as super-personalized programming and charging like you would work with a coach. But we could see these big-bucket personas.

We thought, “Okay, maybe personalization isn't the secret here, but having good programming that's relevant to you is.”

At that same moment, I went through the list of coaches. There weren't a lot of coaches who were making a lot of money on this, but we had a couple who were making 4 or 5 grand a month. I spent time with them and asked them, “What are you doing differently? How are you making this a thing when everybody else is struggling with it?”

We had one in particular, and I was like, “All right, so you're making 4 grand a month. Your earnings aren't growing. What's going on? How did you get there, and why isn't it growing anymore?”

Lauren was a trainer in New York, a high-ticket trainer in person, and she was filling up all of her downtime with online clients through Ladder. We had no idea how to grow.

She figured out, “I have this Instagram profile. I have 5,000 or 10,000 people, and I'm telling a story to my audience. They're coming in.” But she filled up all of her time and 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.”

These 2 insights—calling BS on personalization, watching what Lauren was doing and seeing how she was growing—and piecing them together became a trial, a test, or an MVP of this vision. We didn't know what we would build, but we said, “There's something in these concepts.”

In February 2020, we said, “Okay, you can't take on any more business, Lauren. What if we jimmy-rig the existing app?” We created an experience where there could be more than 1 person in there.

“You're going to program for a group of women. You'll go out to your Instagram audience and say, ‘Hey, I'm in New York, and this is for busy women in New York: kettlebell training. I'm an experienced coach. I'm going to give you new workouts every week. It's not customized, but it's a very specific persona that I'm talking to. We're going to have this chat in the app where we can all talk to each other.’”

The app looked like shit. The functionality barely worked, but the concept was clear. We were in the process of dying at this moment. She went out to her Instagram audience, and we had about 100 people sign up at 100 bucks a month very fast.

That was the most exciting thing I'd seen yet, other than getting wins against American Express and our creditors. We were like, “Okay, there's demand.” Lauren's audience came in, and it was very clear that there was interest in this concept.

That first month, we were just watching what was happening because there was nothing else to look at from a product perspective. I think the most amazing and impressive thing to me was that these people had found each other in the app.

7. Ruthless Prioritization

They had similar personas. They lived in a similar place—busy women following the same workouts every day, interacting with the coach and each other. They'd never met each other, but they started posting on Instagram about Lauren and Ladder.

Then we saw them meeting up in New York at the park together. They had never met each other before. That was magical. We were like, “We have these community and social elements, and they're happy.”

We had never seen anything like that in the original version of the product. So there were all these little glimmers of hope around this concept of programming that's not personalized but is high quality.

It's meant for a specific persona. This social-accountability element—all these things were bubbling up as real, tangible proof points of something that could be interesting to go work on. And that group, the renewal rate was 90%-plus; people paid again. We were like, damn, they're doing the workouts and they're staying with us. If you looked at the app, you would go, “This is garbage.” But the promise was being delivered on what we were proposing.

We ran 1 more trial with another coach. It was the exact same outcome. I talked to almost all those women on the phone. It was, “Who are you? How did you find Lauren? Why did you go into this app? What problem were you trying to solve?” We talked to all of them and built a relationship, and all those were inputs.

Did anything surprise you in those conversations?

8. Integrating Nutrition and Listening to Members

It validated a lot of things we were learning in real time. It was, “Why did you join?” I’m tired of thinking about what workout to do. I’m already into fitness, but I spend time actually planning this. It’s a pain point for me. I don’t want to go spend $1,000 on a coach. I need something more approachable, but I need help with a plan. I need to know that I’m doing the right thing. I want a coach that’s helping me, and I want to have confidence that it’s the right thing to do. That was a real thing.

Then we saw them meeting up, and they would say, “Oh, I met someone just like me.” They had the same pain points, they became friends, and they worked out together. That was magic. All these little kernels, just speaking and forming a picture that got clearer and clearer and clearer, were the beginning of what that product would be.

If you think about it, everyone’s very fond of the Elon algorithm for company building now. It’s been passed around as 1 method for doing this. If you had to distill your algorithm for how you proceeded from that initial kernel of an insight—“Here’s something that people are paying for, and we can do something with this”—all the way through to where the product is today, what’s been your algorithm, as the CEO, for that iterative improvement to get from the original kernel to now?

I can tell you: number 1 is don’t listen to investors on product feedback. That is by far number 1. For us, it’s 2 things. It’s prioritization—ruthlessly prioritize. We 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 it’s going to increase workout completions. That’s our North Star. We’re solving not for getting you to pay 1 time. We’re solving for you to actually complete workouts with Ladder. What can we go build to improve the odds of you doing that and staying with us?

How we get to that is we don’t guess. 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 who are talking to you, you can start forming a picture of what the huge buckets are that actually move the needle. You can do some work to figure out how complex this is to build, and then go do it.

Don’t do 10 other things just because they’re interesting or you can do them. Just do the 1 thing and do it really well, and then do it again. That’s still the case today. We just launched nutrition. It’s the biggest thing we’ve built since the first version of the product.

People on the outside were like, “That should be a separate app,” or, “That’s a different business.” We were like, well, to our customer, it’s not. We did this survey a year ago. We had 5,000 people spending 50 minutes on it, and it was qualitative and quantitative. We were trying to figure out what the biggest bets were that we could make. We were ready for a big project, and we didn’t want to guess.

Out of that work, it became very clear that it was nutrition. What we learned was that we have a third of our members who are tracking macros. Of that third, 90% are using an app. Of that 90%, most are using MyFitnessPal, and they hate it. They’re really tired of managing their problem set in 2 different spaces.

What we learned through that experience and talking to members was that, for the consumer, it’s 1 problem set: I want to lose weight. I want to gain muscle. There are inputs and outputs to that math equation. The output is activity and exercise; the input is what you’re eating. They’re managing this in 2 places, and they know that’s not the right way to do it, because if you worked with a coach, these things are all symbiotic together.

It all started with a kernel from our members, and we had really clear line of sight that this would move the needle. They were telling us, “I want you to use all of these things—motivational mechanics, streaks, badges, celebrations—and help me with the other side of the equation, which is going to dictate success or not.”

Once we have that kernel, we do another survey. We go very deep on nutrition—extremely deep—to understand. We all review it, read everything, synthesize it, and it gives us a blueprint. When you do that, it becomes obvious what to build.

What does “very deep” mean?

The nutrition survey was probably a couple hundred questions. We read all of them. Now you can put them in ChatGPT. In the beginning of this, I would copy and paste App Store reviews into a Word document. I would read every single one of them, and I’d organize the words by buckets. I’d color-code them, and I would use ChatGPT. I have these documents that are 100 pages long, and it’s all just deconstructed words from our members.

Very similar to survey work in the beginning, we would do that with surveys. We dissected the themes: What do people care about? Now you can use ChatGPT to synthesize all this: What is the biggest bet that we can make on behalf of our members?

Then we’ll think about what the building blocks of this should be. Is this nutrition coaching? Is it macro tracking? What does the feature set do? You aim questions at uncovering the pain point and what they’re looking for, and that becomes the guide on the 1st version.

What did you learn there? What do people want on nutrition?

There are 2 halves to this. From my perspective, it’s looking backward and looking forward. What they were doing was tracking, looking backward: “Make it really easy to track macros. I want to know if I’m in a surplus or a deficit. I want good visualizations, and I want it to be really easy in terms of how to log.” It’s very tedious. It’s very hard with some of the existing legacy products, so give me an easy way to do this.

The looking backward, to us, was basically the table stakes. We need to give a really easy path to tracking macros, logging your meals, logging your food, and telling you what’s happening as a result. Then, if we do that—and we do that really, really well—there’s going to be a whole other opportunity to tell you what to do. Not what you did, but what to do.

People want to—our members want to—know what to eat specifically. Where should I get it? I’m at a restaurant. Here’s the menu. What’s the best choice right now based on my goals? They want prescriptive advice.

But the looking backward was what they were using the apps for at that moment. It was mostly MyFitnessPal. There was no brand affinity or love. It was just the tool that existed. There was trust because they had the biggest database and had done it for a long time. But there was just a lot of pain in these conversations about how they were doing this stuff.

9. Cracking the TikTok Growth Loop

We made a conscious decision not to charge for it. We’re going to give this part away. We want to build trust with this group and win over tracking with Ladder. We’re not going to convince the whole new group to do this. We’re going to go get the people who are already doing it. We’re going to do it better, and we’re going to win their trust.

Start compiling this data, and there’s a million products that we can now build. If you 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 has that. The picture of the consumer is the clearest of any other potential product or service around this consumer. We know exactly what’s happening on both sides of the equation, and that’s going to unlock a whole bunch of products and services to help our consumer.

And this would be things like, I could take a picture of my food?

We already have that. Take a picture. That’s easy. But also tell you what the level of confidence and accuracy is, because there are trade-offs if you take a picture versus scanning a barcode or entering very specifically an ingredient or a recipe.

We had to nail that use case, make it super slick, and make it very easy to use. That was the beginning of building trust. Even in that process, though, you have to ask: How do you figure out what to build? We built the 1st version.

We have a group of 2,000 members who are beta members, and we give it to them. But first, we do it as a team. That's the alpha. We're all giving feedback. We have a Slack channel, and everyone is communicating about what's happening. That helps the picture get clear.

Then we release it to our beta members, and it's in the wild. They're using it, and you hear right away: What's wrong? What are the gaps? What do you need? We would survey these users every week, and we had a question: How likely are you to switch from the existing app that you're using?

When it started, the number was around 20%. Pretty low, not super exciting for us. Then we would go build, make the picture clear, and help fill the gaps in what folks were experiencing. It kept going up, kept going up, kept going up. There's a point where you could keep building the MVP forever, but it was 85% one day, and it was like, "We're ready. We're there. We're done. This is ready for the wild."

Then we released it, and it's been a home run. We're in week 6. We're almost at 4 million meals logged, which is insane, thinking about those early stories where we literally knew all the people in the app. It was our buddies who were in the app. We knew the faces.

Yeah. So, a really amazing experience. You said before, "Don't listen to investors on product." Can you say more about that?

Well, I think, one, don't listen to any one person on product. Everyone has a unique use case, persona, problems, and solutions that they're looking for. No one person is the source of truth. If we get one piece of feedback, that's just one piece of feedback.

When we talk about investors, I remember earlier meetings where it would be really prescriptive advice: "You should go build this." And it's like, "Maybe. I don't know. That's what you want." Then we would go test that with our user base and ask them, and they would say, "No, I don't want that."

Yeah. Extremely empirical way of building.

So, it's just empirical. It doesn't have to be completely precise, but it becomes very clear what the big, chunky buckets are and everything else on the fringe. It's like, that's not that important. What is important becomes very, very obvious, even if it's in line with what an investor is looking for.

At various points throughout this business, you and I have had a call, and there will be some period where you describe him having gone into a cave-like process to study some new topic. Some new thing has become the bottleneck for the business, and I can think of several occasions when he was studying X, Y, or Z. Describe, from your perspective, this cave-like process that you've seen him go through to unlock these bottlenecks.

Probably 4 years ago, when we were trying to figure out growth, we'd built a product, people loved it, they were using it, and they were telling us what we needed to build and what features we needed to evolve to improve it. But we still hadn't figured out how to grow. The way you get from $0 to $1 million in ARR is very different from $1 million to $10 million.

For us, Greg's view was, "Look, let's go run some experiments." We were looking at some different ways to grow, saying, "Here are the different options right now." There's SEO, and we're thinking about how to start creating content on search. We have a lot of assets in the app that we can leverage there.

We were looking at some different channels, TikTok being the most obvious, where all the eyeballs were there but the brands weren't there yet. That was compelling to us. We understood that the consumer was very interested in engaging with short-form video. Meta hadn't quite copied that with their Reels product yet, but it was obvious that this was where consumers were going with their attention, and yet the brands weren't spending there yet.

We partnered with coaches, these world-class coaches who were all creators. None of them knew TikTok yet. They were all Instagram-native. In fact, I don't think any of them at that moment were even on TikTok. We were excited to go figure this out.

It was hilarious because Greg—I don't know if you've seen his Instagram—but it's not particularly cool. He's not a creator, but he was like, "I'm going to go and become the TikTok guy. I'm going to be the guy." I'm like, "All right, Mr. TikTok over here." I was like, "You got to go hire somebody."

I'm like, "I'll figure it out."

So, he goes all mad scientist, trying to understand every aspect of TikTok. Fast-forward 2 years, and the big-dog engineers from China are in our office because Greg would be calling and saying, "The algorithm is broken." They'd be like, "No, no, it's not." Then Greg would go get a bunch of information from Ryan Mott and send it through, and they'd be like, "Oh, wait. He's right. There's something wrong with Ads Manager."

The ad tech was very new, so Greg was very much triaging and troubleshooting their ad tech in real time. The other story that speaks to Greg going into his cave: It is winter 2021, probably March or February, and I don't know if you remember the Texas freeze, when the entire state shut down.

We had about an inch of snow, but we lost the power grid.

So, anyway, Greg goes into a cave because there's nothing else to do, and he's reading the book Crossing the Chasm, a great book that I think all founders have read. Greg's output from reading Crossing the Chasm was a 100-page slide deck that he sent me when the power came back on and we finally had internet again. He was just like, "I figured out who our customer is."

Ultimately, that was very important work because it set up what we were about to go do on TikTok. You couldn't have success without understanding who that customer is.

What did you find in the book?

Not trying to be all things to all people, especially early on. You can go after a big market problem, but you don't have to start there.

We were trying to tell a story to everyone. The world was upside down. Consumers were up for grabs because your gym folks were at home. Everything was a mess. All these other companies were launching, and we were saying, "We're weights, we're body weight, we're gym, we're home." It was all things to all people, and it wasn't working. We weren't getting to the right person.

Crossing the Chasm just helped me zone in on who is the most important person that we're talking to right now, who's finding success, and how do we speak specifically to that person? We didn't want to go try to tell a story that was relevant to a Peloton user. It helped me move away all the noise, narrow in on what mattered for this person, and build a whole growth strategy around that.

You have unlimited time right now to talk to us about solving this problem and how you cracked the code of growing through something like TikTok. The more detail, the better. I just think, obviously, it was a critical moment for the business early on, once you had figured out the product. Just riff on the experience—literally what you did.

Yeah.

And what you learned.

We had a whiteboard meeting. We were like, "What are the growth loops that we think are available to us, that we think we have an advantage on, that we think we can do within our own team, and that we can learn fast enough to get proof points and dive in on, go all-in on?" TikTok came out of that as the winner.

What we started to do was just make content, and we knew nothing. I had this breakfast meeting with Edel, who leads Brand and Creative, and I was like, "Hey, man, do you want to work on TikTok with me?" He was like, "Sure." This guy was building all of our amazing campaigns. He's shooting for Nike. He's done all these things. I'm like, "I need you to make TikToks with me. It's just going to be me and you."

He's got the creative mind.

We grabbed a coach and said, "Hey, we're going to start an account from scratch. You're not on TikTok, and we want to go learn. Give us all your raw video that you have on your iPhone." So, you have this inventory of video and a smart creative person. We started handles in the coaches' names, and we started to create content.

Very, very quickly, we started to learn what content worked, and we were dissecting every inch of it. 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, and it's not a social platform. It's a media company. You have to think about what the right content is that is educational, provides value, and gets to the right person.

Unlike Instagram, where you have an audience that you're creating content for, you have to create content that the algorithm knows to put in front of the right person. It's all about the content.

The advantage for us at that moment was that it didn't matter how many followers you had. You could start from scratch. Nobody knew how to do this. But that first account that we started—I remember being on the playground with my kids, and Edel was like, "Dude, one's ripping." It was like a million views. We were like, "Holy shit, that's amazing."

That video took you 2 seconds to make. It was like, “Do it again.” And we did it again. We took that account from 0 to 250,000 people in like 45 days.

We weren’t thinking about paid at all. We were thinking about: What is TikTok as a product? How is it being consumed? What content wins, and how do we create that content? We got views, we had proof points of traction, and then we said, “All right, we have link in bio. Can we get somebody into the app?” And we did, very quickly.

We were getting the right people into the app, and all these things were starting to compound. We started another account and did the same things. So we were like, “All right, we can do this organically.” It was like 3 months, and then we said, “Let’s start putting some money behind this and see how it goes.”

We had no performance marketing team. We had no agency. I was absolutely against hiring anybody outside the company, and I committed to learning how to be a performance marketer on TikTok because we didn’t come from performance marketing or Facebook. We had no preconceived notions of how things should go.

10. Expanding the Brand Beyond Short-Form Video

When you talk to Facebook marketers who were moving to TikTok, they were applying all these rules and heuristics of Facebook and Instagram to TikTok. But these are 2 separate platforms. You have this Chinese app and a different algorithm. Why would those rules matter over here?

I spoke at an all-hands for TikTok, and I was talking about some of our strategy. I had really high conviction in what we were doing, and I was like, “Yeah, I make budget changes 7 to 10 times a day.” If you talk to the TikTok group, they’re like, “You shouldn’t touch it for 2 weeks. It’s the learning phase,” and all these things.

All those people came from Facebook, and all the rules they were telling me were Facebook rules. At the end of the meeting, this woman comes up to me and she was like, “That was really interesting because the things you had the most conviction in are the opposite of what we’re telling our clients to do.”

I realized pretty quickly that everybody was taking this mental model over here and applying it, rather than trying to figure it out from scratch: If it works, do it again. Who cares what they tell me? It worked. Do it again. That was an important piece of thinking on our own about how this should go.

I launched my first ad. Okay, we could do this. Very quickly, it was getting people into the app, and then it just became a drug addiction. It’s like trading. I’m bad at mental math, but I’m also fascinated by traders.

When I was at Goldman, I would interact with traders. It was just magic to me—all the screens and the attention span. How does this happen? But it felt like that for me. I’m moving money around, driving growth for the business, and it became a video game. It’s like, how do we beat the video game today?

I had this amazing creative partner in Zel. I can figure out the ugly of how to be an ads manager person as my job. Those 2 things together unlocked that channel to just keep going, keep pushing on.

I feel like the rewards for doing this in a consumer business are extremely high. Lots of people have probably tried, but not many have succeeded. What do you think it was that let you start to win the video game? Was it the knowledge of how to cut a video together? Was it topics?

No. What we learned is the For You Page is making a decision about who your content is for, and then it’s shoving it to that person. The first game on the creative side was: Can we create content that gets to the right person for this coach? This is a CrossFit modality. Can we get to CrossFit people using content? That was just iteration.

What does a CrossFit person care about?

What do they care about? What’s their problem-solution statement? What should a coach say to get you in? We learned about hooks—what you say in the beginning. The first 3 seconds matter. What should a hook look like? What do I need to say? It’s a billboard. I need to get your attention very quickly.

11. Financing Growth

We had a lot of bad content that didn’t work, and then we had stuff that started to work. We have these whiteboards. We dissected every inch: What is she wearing? What word was first? What was the setting of the gym? What was the movement? What did we say?

All of the insights from that come from knowing your customer. It’s not like, “Hey, we magically figured out TikTok.” We did, but our edge was that we knew our customer inside and out. I had dissected these App Store reviews so deeply that we knew the words that were coming out of the mouths of people in CrossFit coming into the app.

We used that as our ammunition for how to speak to them and create compelling content hooks that got to that person and told the story very fast, which got them to keep going, to follow, to come into the app.

Just to orient in the history of the business, how much revenue or whatever was there at the start of this kind of S-curve, and how quickly did it accelerate?

Yeah, it was $4–5 million of ARR. We were getting some success, but at the beginning of the TikTok journey, it started at $3 million, and we were at $5 million when we started to put money into the machine.

And it sort of exploded since then.

It exploded. One of the things we learned that was critical to TikTok was that you have to own the creative. This was not typical for brands in our space. They would hire an agency, and the agency would make the creative.

But we were learning all this stuff organically, and we were learning that the iteration cycles are so fast. You can’t just hand it off to an agency and hope that it comes back correctly. So we started investing in creators full-time.

We had job descriptions on the website in 2023. It said, “Full-time TikTok creator.” People were like, “What the hell is this job?” But it’s no different from social media jobs 10 years ago. “That’s not a job.” Well, it is a job. It just wasn’t a job yet.

It was the same dynamic: complete control over the creative. We had these coaches on our team, which gave us this edge on compounding learnings—this mini-agency that was figuring it out across all these different creators that we controlled. 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 that the short-form video strategy will always be a core part of our strategy. That’s not going away.

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 3 or 4 in our category in the App Store, and yet awareness is very low. I think that’s largely a function of the short-form video strategy that we had, which 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 think about celebrity partnerships, out-of-home, and TV, and we’re already making these campaigns. Now we’re just going to put them in these other channels. That’s certainly a big focus of next year: thinking about telling a wider story that, frankly, is just going to amplify what we’re doing on short-form video.

How are you going to be empirical about that in the same way that you’ve been about product and marketing so far? It seems like a very different kind of thing—harder to be empirical about.

It is, but it’s small, controlled bets—big on scale, but limited in the bets that we’re making. If it’s a celebrity partner, we need to know exactly who that audience is. Is this someone who resonates with our user? Are they going to amplify the right message that represents Ladder?

To date, we had no leeway to spend money that didn’t turn into results. It was like, “Here’s the money in the bank; turn it into users. Keep doing it again.” This is a little bit different, but what we’ve realized very quickly is that we do have an awareness problem. People haven’t heard of Ladder.

We’re getting big. We’re the number-one-grossing fitness app in the App Store. We’re top 100 in the US of all US apps. It’s big. So we need to invest in really concentrated bets that speak very specifically to our user and leverage the creative horsepower in our team.

We have really special people on our team who can create stuff that no one in the world can from a brand perspective. It’s not as perfect of a science, and I kind of bucket it into 2 different paths. But my thesis is that, over time, it’s going to make the short-form engine a lot more efficient.

12. Leveraging AI

If people aren’t aware of Ladder, we have 1 video where we’re trying to convert you. They’re learning about Ladder in that video. If you’ve seen and built trust with someone who’s endorsing it, or you have even a nugget of awareness, there’s a higher likelihood that that person is going to take the first step.

I think the 2 play together. You asked what the supercharge was over the last couple of years. We did a deal with General Catalyst that changed the game for us through their Customer Value Fund.

Essentially, what we realized is that the capital markets aren’t funding CAC in consumer companies. We can’t just go raise a bunch of money to put into TikTok. The appetite’s not there, no matter how good the product is.

General Catalyst has solved that. They’re financing our investment growth every month, so the payback happens over time.

Not as much of a cash hit, but it lets me think about half the house as very performance-oriented and very controlled. You can underwrite it, which General Catalyst did. And now we're going to go invest in some squishy stuff that should be proven downstream to have an impact and make things more efficient, but it'll be iteration like nothing else. It will be a game of figuring out what works and what doesn't.

If you think about your experience—you said you've built some enterprise companies before this—versus consumer, it seems like, for a long time, no one invested in consumer. Actually, really up until I guess very recently, AI is of course unlocking things in interesting ways.

Maybe pitch it like this: if you were to pitch a young entrepreneur—a teenager or a young college student—on building a consumer business rather than the traditional B2B thing that's dominated the startup world for a long time, what would your pitch be? Why is it fun and different to build this kind of business?

The fun part is you get to see it every day, and it's impacting people, and that's real. We're providing real value. We're changing lives. I read these stories every day coming into our team about what happened to this person because of Ladder. What else could inspire you more than that?

We're not selling their attention to advertisers. We're helping their lives. That's really fun. And the feedback loop is fast. You make a change, you know exactly what happened, and that is exhilarating.

You have a report card that's your users, and no one user is the right answer, but collectively they are. I'd say what people don't realize in consumer is how freaking hard it is. There are no quick fixes. Growth hacks are not a real thing.

You have to be a black belt at building products for the consumer and growth. You have to have both those things within your own team to survive and then be able to raise money to go fund that, which is its own mission. So, in my mind, if you want to get into consumer, you have to love talking to people. You have to love extracting information from human beings to go create solutions for them.

It's not, “I think it should be.” That's how consumer companies die, because they just freaking guess and it doesn't match what the consumer is looking for. So it's really hard, and you have to be excellent at both sides of the house.

Half our team works on workout completions. Half of them work on trials off TikTok. That's the business. Very simple. But we are equal weight and black belt on both of those skills, and without either one of them, there would be no Ladder at this stage.

Great product, no growth, doesn't work, doesn't get funded. Great growth engine, no product, leaky bucket, doesn't become a big company. Both those things have to be true to be able to build a company that's durable and lasts.

And just be ready for 10 years. I mean, it's not going to be 6 months or a year. It's going to be a slog and constantly problem-solving along the way. So it's splashy. It's fun, but it's really fucking hard to do.

I'd probably say don't do it. There's probably easier things to get funded.

But listening to the stories, as Greg said, when you hear from one of your members about how Ladder has changed their life in some way, it's easy, when you're looking at the charts and everything, for that to get lost on you sometimes. But you're constantly pulled back by these stories.

I think our creative team does a great job of telling those member stories, and that's something we'll continue to do. Our customers, as Greg said, literally tell us what to do.

We sent our annual survey out this year. We already have 5,000 responses in the last 2 days, and people are spending an hour on average. They're answering 230 of our most burning questions about what to build from here, what companies to partner with, whether you'd be interested in supplements coming from Ladder—everything as it relates to all the different surface area that we could explore.

That's really exciting to us, just continuing to listen to them. They're huge advocates for us, and so we're going to continue to do that.

If you want to be by yourself with headphones on, working on consumer, it's a losing strategy. I see that all the time, where it's like you're just building shit. You've got to be talking deeply to the user.

If I think about the 2 big world things happening that probably most impact your business, that are out of your control, it's AI and GLP-1s. I'm really curious how you think about both of those things as creators of opportunity and as potential risks.

I'll mention GLP-1 fast, and then AI is a much bigger conversation. But on GLP-1, it's interesting because all the science would support that you need a strength-training plan alongside your GLP-1. You're at risk of so much muscle loss.

So we think that's actually a macro tailwind and something that will help us. It's not something that we've investigated to date, but could totally see us working with some of the bigger GLP-1 providers at some point. The science backs that relationship, and so that's not something that scares us. In fact, it's a question we asked in our survey, which we've never asked before.

Are you on it, or are you—

Yeah, these are people who are fitness enthusiasts. That doesn't mean that they're not on GLP-1s, so we're going to continue to learn more there.

On the AI, I think what gets exciting for us is that it feels like we can kind of have our cake and eat it too now. In the beginning, we felt like we needed to focus on a venture-scale business here and solve a problem that's solvable for a customer with software, which felt like one-to-many programming.

Now, with what's available to us in AI, we're able to deliver that personalization as well, which, 4 years ago, we couldn't have. 2 years ago, we couldn't have launched nutrition with our same team in a 6-month span like we did.

But I think beyond that, what I get excited about is that, in an age of a lot less differentiation in tech and commoditization of certain features, it's become so easy that people think you can just use ChatGPT to build an app. I would challenge someone to try to build the experience that we've built using AI.

I think we're going to continue to lean into the things that AI can't touch, which is that we've built a compelling brand. We have a tremendous amount of trust from our members, which is really exciting. We deliver a human experience at scale because of it.

13. Long-Term Vision

We've been thinking about it for 4 years. We've been using it as a tool for 3 years, and it's had chapters for us. In the beginning, it was a non-coding tool. It was, “How do I synthesize information?” It was amazing. I could take 5,000 responses and really understand what's happening.

Then it was everywhere. I could use it to think about how to create compelling TikTok hooks based on all of this survey data or user data. That's a tool. It saves time.

But it happened at the exact right moment. Our entire team is 50 people, and that includes 20 full-time coaches, so 30 people excluding coaches. We started scaling at the right moment, when AI started to become a use case that meant we didn't have to go hire and expand the team just to solve a problem that we were looking to solve.

The team would have been a lot bigger if this were 4 years ago, if we didn't have AI in every element of our business. The second chapter for us is using and incorporating it in the product, not replacing the human.

We believe in humans as motivation. It's really important to feel like we're having a relationship with the coach. But I don't want to have coaches reading chats all day and interacting one-to-one with users. I want it to feel that way and use tools to expand the capabilities of our coaches.

We have teams with 600 people that are in it. Now the chats are big, cumbersome, and complex. The coach's message isn't the only reason they're there, but it matters. The magic moment for a coach is saying the right thing at the right moment that makes the most people satisfied with what they're saying.

What isn't a great use of time, which was happening, is scrolling the chat for an hour to figure out what's happening here. So we built a product called Ladder Pulse that automatically, when you come in, reads every single chat that's come in and tells you, “Here are the 3 most burning questions. Here's the content you should create. Here's the member you should respond to because they've never been responded to by a coach.” Send. Done.

Now we've removed all the cognitive overload of what to say, and it's all powered by this tool that we built purposely for the business. We're building software now to support a better experience that's built on AI. Nutrition is a great example. We'd have never gone into nutrition if there was no AI.

MyFitnessPal had to build a database over time by hand that became the value of MyFitnessPal. That’s not the hard part anymore. The hard part is the consumer experience and knowing what to do with the data. So it opened up the capability to solve that problem without taking the business sideways for 5 years.

And then we’re inventing products from scratch. I’ll give you 2 examples. One, we have—I told you—north of 30,000 paying members. We have 1 person who touches support. It’s not even her full-time job.

We have tickets coming in every single day, and we spent time trying to understand who’s coming in, what they’re asking, and what the buckets are here. Then we built a product. That person’s name is Mave. We built Mave AI—M-A-I-V. We built a customer-support tool from scratch.

It’s purpose-built for our company. It now manages 90% of the flow coming in, and the experience is as good or better and faster than it was before. We made it ourselves, in our team. That would not have been possible 5 years ago. So that solved a huge problem.

Now we don’t have to expand that team, and we can deliver a better experience through that. We have a person on our team who only works in AI. That’s the job, and he’s been doing that for a long time.

How do you think about saying no to potentially juicy revenue opportunities that aren’t core to the subscription, completing a workout, and acquiring customers? I could imagine the Ladder data-dating service. I could imagine Ladder being an origination platform for GLP-1s.

Or Ladder coach tools.

Or Ladder coach tools. Absolutely, yeah. In the Ben Thompson sense of aggregation theory, you’re maybe a consumer aggregator.

You’ve aggregated a lot of demand in this specific space.

Historically, those companies have figured out how to monetize in lots of different ways. How do you think about the siren song of higher ARPU and new sources of revenue?

But a lot of those businesses have died, too, because of doing too much at the same time. We’ve had a multi-phase vision from the beginning of what this thing can become, and our goal is to be the de facto product in this category. We have stepping stones that we anchor to. They get moved around, but we have a vision for how to go do that.

I think about new ventures and new business as push versus pull. Are we being dragged into this area by our members? Is it so freaking clear that this is going to be really exciting and solve a really important problem for people who are relevant to us, like nutrition? Nutrition was on the board in an investor deck that you have from 5 years ago, but it didn’t make sense to build it until last year, when we had critical mass. It was very, very clear from our members that it was going to move the needle, and now we’ll build products on top of that.

We’re ruthless in prioritizing. You have to make a clear, clear case for what this does to the business. We have no Android app. People think that’s insane. But building an Android app requires basically pausing development on iOS, splitting the team’s focus and time, and playing this game of catch-up for a user that has much lower revenue potential. It could absolutely take the business sideways for a year.

Will we have an Android app? Yes. We won’t have it this year. It’s these levels in my mind: We have to go earn the next level. If we earn the next level, what should that be? Let’s figure it out and then start to work on that.

I think all these things that everyone talks about with Ladder, we’ll go do all of them. But I’m playing a long game here. This is not “go sell the business.” Let’s go build the generational business in consumer that solves the most problems for the most amount of people.

In that big, long-term vision, fitness, working out, and nutrition are 2 obvious major food groups of the vision. What else is on that understandably flexible list? What are the other big stepping stones that you think about?

It’s the system of record for health and fitness, which is kind of what Greg’s talking about and how we’ve talked about it for a while. There’s a category winner in every category. In transportation, it’s Uber. In short-term housing, it’s Airbnb. Spotify is the winner in music. There’s no clear winner in the health and fitness category.

Clearly, it needs to be a mobile-first company. It needs to be a product with engagement that looks like the social engagement we have. Nutrition was the next obvious step, and it increases the surface area for us to really think about these other product extensions and line-item extensions.

There’s so much commerce already happening in the app. We see it every day: “Hey, Coach, what’s that creatine you’re having? Should I be having whey or vegan protein? Love those new shoes. Where do they come from?” People are sharing links all day. There are different chats based on supplements or food or apparel, for that matter. We’re watching and we’re learning.

There’s an opportunity for us to reduce friction there and start to think about whether that’s a marketplace. Does it look more like an Amazon experience at first while we’re learning, and then we’re building our own kind of branded products? Our members want to tell us that they got a DEXA scan, and they would like this to be their system of record for their biomarkers. There are a lot of people building companies in the biomarker space. I think that would be a really cool partnership to start, or it could be a feature of our business.

We get excited about the opportunity if we build a compelling product and brand where people are opening this app 10, 15, 20 times a day. There’s a lot of opportunity for us to insert other products and experiences into it. So there’s a long list that’s been on the whiteboard since the beginning.

14. Kindest Thing

Yeah. What I think about is product expansion and user expansion. With product expansion, there’s no, “Oh man, that’s brilliant.” It becomes obvious when you look at it. We launched nutrition, and now we have inputs and outputs. Our members want us to tell them, “What supplement do I need to go take to make me whole?” They want to buy that from us, and those will become businesses for Ladder when there’s critical mass and it becomes very clear that this is a real problem that we can solve uniquely for the business. So all those things start to open up.

I think there’s user expansion, too. We have a very specific user. It’s a very big market, but it’s not everybody in fitness right now. So we think about Ladder: How do I get 100 million people to be working out with Ladder every day? It might be a different problem set than the current product right now.

We spend time thinking about how to get the people earlier in their fitness journey into Ladder. If you think about our product, it’s progressive programming, so they kind of already need to know that programming is valuable. They’ve got to be into strength training. That’s its own bucket. They need the ability to pay for that and to use a phone during a workout. All these things are big markets, but they’re inhibitors to broader fitness.

We’ve got this content library that is not valuable to our members. Our members are paying us not to think. They don’t want any choice. They want to know, on Monday, exactly what they should do. We asked this question in a survey. We said, “What would you pay for the whole library?” And it was like a dollar, because it’s not valuable to them. “What am I—I already have my Monday workout. I don’t need 10,000 workouts,” which is every other fitness product.

I think there’s going to be a path. It’s not this year, it’s not next year, where we give the individual content away—where we give away every other product, which is just the library—because the library isn’t valuable and isn’t what our members are paying for. But it starts to map to how consumers in the outer rings of fitness are consuming content.

Investors come in and say, “Who’s your biggest competitor? Is it Peloton?” It’s like, “No, it’s YouTube, by far. It’s not even close.” It’s people going to YouTube and typing, “45-minute upper-body dumbbell—give me a workout,” and then consuming it on YouTube. YouTube isn’t built for fitness, but the content lives there.

We need an on-ramp to Ladder that mirrors that consumption pattern. There’s amazing content, the best content. You’re getting it on YouTube. It all lives there. It’s free. There are motivational mechanics that are important. It amplifies the importance of social and the power there.

I think there will be a premium component, and it will be the right moment to hit on it. But we’ve been talking about and thinking about it for a long time: How do we get to the wider rings? Then, over time, you move those people, just like we do on TikTok, into this concept of a plan. “Hey, now you’ve done 40 workouts. They’re in 7 different teams, but you’re not really happy that your results aren’t there. I’ve got a different way. We can tell you exactly what it should be.”

The analogy I give to folks outside the business is that you’re working on a puzzle. You’re working on a puzzle. You’ve got the picture on the box and you’ve got all the pieces. You’ve got 10,000 pieces, and the picture is what you want to go build. Our members have the vision of themselves. That’s the box that they’re solving for. We give them each piece in order, 1 by 1, to construct the puzzle that they’re trying to solve. No thinking at all.

Most products in fitness are just a bunch of random pieces, and it’s like, “Pick up a piece that you feel like doing today.” That’s not a great strategy for getting to results.

One more question: What’s it like talking to investors now versus early on?

This thing has changed quite a bit. Your sources of capital have gotten—

We talk about push versus pull.

Yeah. Increasingly sophisticated over time. I was the least sophisticated at the start. You've gotten to much, much smarter, more institutional investors ever since the beginning. What would you say a little bit about that journey?

Well, I think what's exciting is that, just on the investor landscape in general, there's not much innovation being funded in fitness right now. When we first started trying to tell the story and raise money to institutional investors, it was like, “How could you possibly compete with Peloton?” They were a $50 billion company in that moment.

“You should build AI weights.” I remember multiple times that it seemed like, “Where's the hardware?” And then Peloton had its post-COVID troubles, and they were like, “Oh, well, Peloton basically didn't make it, or that story got very hard. How can you build a good business? It can't be done.” So we're like, “All right, so it's being used against us kind of twice now.”

But all the while, we've been iterating on product and shipping product every other day, listening to our customers, and building something that our members are telling us is really, really valuable. We have this amazing head start where we feel like we just don't really have any competition. So that's been really exciting.

It was hard for a moment. Now we find ourselves in a position where, when you get to this kind of growth stage, people can see the numbers. You can look at App Store metrics and see that our business is inflecting, and see that the growth rate has been really strong, so there's a lot of investor interest.

I think what's unique about conversations with investors now is we're in a strong position because of the General Catalyst deal. We kind of control the timeline on raising money. Our business now generates cash. It sustains itself. That doesn't mean we don't have huge ambitions—we do. As Greg just talked about, we want to be the system of record in health and fitness. That's going to require raising additional capital—at least another round—and continuing to invest, particularly in product and engineering.

Fortunately, we have some great investors already around the table right now. The way we've been approaching it is to start spending time with a small group of really high-quality investors, to get to know them outside of the context of a fundraising round, which is not something that we were used to. Now you have time to actually build rapport and get to know people when you're not raising money.

What I think is important there is that 4 or 5 years ago, it was, “It's cash. We just need cash. I don't care who it comes from. Terms? Sure, sounds great. We need money. We're dying.”

There was no selectivity, and this General Catalyst deal has given us a lot of leverage. We have more money in the bank than we did when we closed our Series B a year ago, and it's giving us time to really think about who are the people that we want in the boardroom, who are the people that we want advice from, and talk to companies in their portfolio.

Even before we're thinking about it, just knowing who the 5 human beings are—forget firms, because that's less important to me—who are the people that we're really excited about for the next leg of Ladder? We now have some cushion to go be smart on that, and that was not possible.

This remarkable journey is completely crazy. I know it's hopefully chapter 1 or 2, and there's a long story still to be written. What is the kindest thing anyone's ever done for you? You can take that either personally or professionally, however you want to take it.

I think it has to be my wife through all of this. She married an investment banker in New York and San Francisco, and that has a path and a vision for life that you can kind of predict and keep at steady state. Then I turned into this entrepreneur who's making no money, and we have 3 children. She is also working very hard, but she has given me the room to make this possible.

If that dynamic wasn't true, there's just no way that I could do this. There would be no path for me. It's a huge burden that she took on, and I think it's a huge component of how we got here.

Well, Greg just went with the wife, so I can't do that, even though that would be obvious. I've got to thank my wife, who's been putting up with me since we were 19. I would thank my dad, actually.

When I try to describe to my kids what it is I do or what my role is, I always say that I sell. That's what I do. And when I think about that, the quote that always got me excited was what Ken Griffin would say—though I don't even think it was his line—“If we're all going to eat, someone's got to sell.” That always kind of pumped me up: selling was important. It wasn't always something that was transactional.

But I learned sales watching my dad. It's not something he told me; it was something I learned just by being with him. My brother and I commuted to school for years, to 2 different private schools. It was about an hour commute and could be longer with traffic. This was the early '90s, mid-'90s. You had those old Zach Morris cell phones.

My dad was a mortgage originator, so he was always on the phone and was basically a traveling salesman, on the phone in the car the entire time. He was a lefty, so he would have his phone on his shoulder and his notebook in his left hand, taking notes, with the map, and he'd be driving with his knees. My brother and I would just be listening to my dad selling basically every day.

The 3 things that he taught me about sales are, 1, to be effective in sales, you need people to like you. Ideally, they want to root for you. If you're really good, you can get them to potentially quit what they're doing and want to join you. That would be the best thing.

The second thing is they need to trust you, because that's kind of all you have. Integrity is everything when it comes to sales. The third thing is that you need to be relentless, but not in an annoying way—just deeply persistent.

That's carried me well through 2 very different careers to date. He's been an awesome role model and someone I think about when I'm trying to teach my own kids lessons like that.

Amazing place to end. You are one of the best salespeople I've ever met. The car rides worked.

It was effective in getting me into Ladder.

Yeah. Thank you so much.

Let's go. Thank you.