The Decade That Built Gymdesk: A Founder's Journey from Solo Bootstrap to Scale

It's Monday, November 17th, and we're in a Las Vegas gym. Two people step onto the mat in gi—one is Eran Galperin, the founder of Gymdesk, and the other is Alex Cuevas, the company's CEO.

The last time they rolled together was exactly one year ago, just after Alex joined the company. Back then, it was no-gi—not Alex's favorite format. This time, they're in gi, and Alex jokes about hoping he's improved since then.

Eran responds with a laugh: "I'm definitely worse—I haven't trained in the gi for almost three years." He's been training mostly no-gi because of osteoarthritis and a herniated disc. The gi training involves more gripping and pulling that aggravates his condition, so he's adapted his practice.

This isn't just another training session. It's a sendoff. 

After nearly a decade of building Gymdesk from a nights-and-weekends side project into gym management software used by thousands of martial arts schools and fitness businesses, Eran is stepping away from day-to-day operations.

"It's going to be a decade in '26," Eran says, reflecting on the journey. "I'm ready to explore a little bit outside of that. That was my entire decade."

This is the story of how that decade unfolded—the struggles, the breakthroughs, the pandemic that could have ended everything, and the moment when Eran realized the best thing he could do for Gymdesk was to step aside.

The Beginning: When Everything Was Uncertain

In 2015, Eran was winding down a VC-backed startup in the Bay Area. It hadn't worked out. He'd moved from Israel to San Francisco to make it happen, but after years of trying, it was time to close that chapter.

"I did not like the VC track," Eran says. "I'm like, I want to build it completely bootstrap, completely self-reliant on revenue that it generates."

He'd been training Brazilian jiu-jitsu since 2006—nearly nine years at that point—going five or six times per week. He was deeply embedded in the martial arts community and wanted his next project to combine his two passions: software development and jiu-jitsu.

The obvious idea was gym management software. 

But, when Eran looked at the market, he saw established players: MindBody, Zen Planner, Pike13. It looked crowded. Maybe too crowded.

Then he talked to some gym owner friends. Gumby, from Heroes Martial Arts in San Jose, gave him the push he needed.

"Gumby literally told me, 'If you build something, we will move to yours,'" Eran recalls. "That kind of pushed me again in that direction."

Everyone was complaining about what they were using. There seemed to be a gap—not in the market itself, but in how existing products served customers. 

Eran had a background in user experience design. He believed he could provide something genuinely better: software that was actually user-friendly, not just software that claimed to be.

Looking back, Eran says his early hesitation about competition was misguided.

"What I now believe and know is that having competition in the market is actually a good thing," he says. "It validates the market. It shows there's already demand. Existing competitors do market education for you. You don't have to explain what your product is doing."

In late 2015, Eran started building. He worked fast—built the initial product in about three to four months—and launched in early 2016 under the name "Martial Arts on Rails."

Then came the hard part: getting customers.

The Learning Years: Customer Acquisition and Product Iteration

Eran had always been the technical founder in his previous companies. Someone else handled marketing, sales, and customer acquisition. 

With Gymdesk, it was all on him.

"I had zero idea how to do customer acquisition," he admits. "It was a long discovery process for me to figure out how to do that."

So he got a full-time job. 

In 2016, he moved to Los Angeles to work as CTO at an ecommerce company. He'd build Gymdesk at night and on weekends while drawing a steady paycheck. It wasn't glamorous, but it kept the lights on.

The first customer was Shawn from Honu BJJ in San Diego. 

Eran had trained at their gym when he briefly lived in San Diego to cut down living expenses. Shawn took a chance on a product that was, in Eran's words, "really not ready for prime time." 

Almost a decade later, they're still a Gymdesk customer.

Another early customer: Gumby, the friend who'd given Eran the initial push.

Those early customers were generous with feedback. Sometimes too generous. When someone said they couldn't figure out how to do something in the product, Eran's first instinct was to think: "They're holding it wrong. They just need to try harder." 

He'd build more help documentation, write more guides, answer the same questions over and over. Then he had a mindset shift.

"Eventually, I realized that if a customer tells me they don't know how to do something in the product, it's usually the product's fault, not the customer's fault," Eran says. "The product needs to be clearer. It's either too complicated or too hidden."

Instead of writing more help docs, he started solving problems through the product itself. Instead of just taking customer requests at face value, he learned to dig deeper.

"What I really learned with this company was how to do product," Eran says. "How to talk to customers and understand the core problem they're trying to solve, which is very, very important."

A customer would say: "I want the product to do X."

Eran would ask: "Okay, what are you trying to do with X in your business, not in the product?"

Once he understood the underlying business problem, he could often suggest a much better solution—one the customer hadn't even thought of. 

"They'd be like, 'Oh, it's amazing. I never thought about it like that.' Because I actually solved their business issue."

This became the foundation of how Gymdesk evolved. 

Over the years, the product got simpler and more intuitive—not because Eran built more features, but because he kept refining how those features worked until customers could intuitively understand them.

He also started building content. Gymdesk published resources on business topics relevant to gym owners. It was a slow build, but over time, it created an inbound channel. 

People found the content, understood what Gymdesk was about, and started signing up.

Between 2016 and 2019, Eran balanced his full-time job and Gymdesk. He was the only person at the company. 

Every customer conversation went through him. Every support ticket. Every feature decision. Every bug fix.

It was exhausting. But it was also the apprenticeship that would make everything else possible.

Going All In: The Redesign and Product-Market Fit

In August 2019, Eran finally made the leap. He left his CTO job, moved from Los Angeles to Austin, and went full-time on Gymdesk.

"That's what gave me the capacity to look back and say, okay, we learned this much. We have a bunch of stuff in our product that we didn't plan for. Let's reimagine the UI based on what we know now."

He brought in a UX designer named John. Together, they went through the product screen by screen, problem by problem. 

Years of customer feedback had revealed patterns—places where people consistently got confused, features that had been bolted on without a cohesive design system.

"John would design it, and that's how we went screen by screen, issue by issue, till we felt we had a pretty good solid base to move forward with," Eran says.

They launched the redesigned product at the beginning of 2020. 

Gymdesk also offered something none of the major competitors did: a generous 30-day free trial with no sales call required. Most competitors made you get on a call before you could even try the software.

"I believe that the product will win if you just let people try it versus the competitors," Eran says.

The approach worked. Gymdesk started seeing real growth. They hit what's called product-market fit (PMF)—that elusive moment when the product resonates so strongly that growth becomes easier, more organic.

"People seem to really enjoy using the product," Eran says. "Things were looking pretty good."

Then, in mid-March 2020, COVID-19 shut down the world.

Surviving the Pandemic

April 2020 was brutal. 

Gyms across the country were forced to close. According to IHRSA data, over 25% of gyms and fitness studios closed permanently during the pandemic. 

Customers called and messaged Gymdesk asking to freeze or cancel their accounts.

Eran worked with them. The team added features to help: support for capacity limits when gyms could only have ten people in the space at a time, tools for managing virtual classes, flexible payment options for struggling businesses.

"We added features to support them," Eran says. "A few tough months for the company—it wasn't clear if we'd make it through."

But they did. 

By the end of 2020, things stabilized. There were second and third waves, but with each one, gym owners were less anxious. They'd learned to adapt. Many had found new revenue streams. The ones who survived came back stronger.

And Gymdesk kept growing.

The Scale-Up Years: Building a Real Company

Between 2021 and 2023, Gymdesk transformed from a solo founder operation into a real company.

"We grew immensely from a team of one person—me—to a team of 13," Eran says. "We had a customer success department, marketing people, additional developers."

Thousands of businesses now used Gymdesk to manage their gym operations. 

Most were very happy with their decision. Eran would hear it directly from customers: the software was intuitive, the pricing was simple and fair, the support was responsive.

But scaling brought new challenges—specifically, maintaining quality as the team grew.

"When it's me answering all the customers' questions, it's the most accurate answer you can get," Eran explains. "I built the product. I talk to all the customers. I understand their businesses as much as anybody who's not actually running a gym can."

Once he hired customer success people, that knowledge had to transfer. They had to build up product knowledge and business understanding. 

"It's possible. It's a challenge, though. And as you continue to expand, the levels of separation between you and the frontline people just keep increasing."

The same challenge existed across every department: product, engineering, marketing. 

How do you maintain the founder's deeply ingrained intuition when that founder is no longer directly involved in every decision?

Despite the challenges, Gymdesk was in a strong position. When asked how he'd rate Gymdesk's progress, Eran used a martial arts analogy:

"As a product, I think it's definitely a competitive black belt, for sure. You always learn something new. You always improve your technique. It's definitely up there with everybody, and maybe even better than most of them."

He paused. "As a business, it's probably a purple belt. Just now getting into the advanced level, scaling up, building different operations, things that are no longer founder-dependent."

Purple belt in Brazilian jiu-jitsu is where things get serious. You're no longer a beginner, but you're not yet a master. You're in the long, hard middle—the place where most people quit or break through.

Eran was determined that Gymdesk would break through. But he was increasingly aware that he might not be the right person to lead that breakthrough.

Knowing When to Let Go

By the beginning of 2024, Eran was burnt out.

"I was so involved in the day-to-day in every aspect of the company. I could not take a real vacation for years. I'm just plugged in 24/7. People see me online at all hours of the day, all day, every day, over the weekend. It's not healthy."

That's when Gymdesk started conversations with Five Elms, an investment firm that partners with bootstrapped software companies. Five Elms saw what Gymdesk had built: a profitable, growing company with a product customers loved and a clear path to becoming much larger.

They asked Eran the critical question: "Do you want to continue as CEO?"

"I'm like, no," Eran says. "I would like to step down, maybe focus on product, and I want somebody else to take over the day-to-day operations of the company."

He'd been preparing for this mentally for years. The partnership with Five Elms made it financially possible. Now he needed to find the right person.

They interviewed several candidates. Some were excellent managers, skilled at building teams and scaling operations. But they had no connection to the martial arts or fitness industry.

Eran was worried. "As a founder that's from the industry, this is one of the main things that helped get Gymdesk to where it is—the understanding of what people are doing with the product, why they're building their business. I felt we would lose something if we went that direction."

Then Alex Cuevas showed up to the interview wearing a gi.

"I'm like, okay," Eran laughs. "There's something here."

Alex had trained judo for many years, practiced jiu-jitsu, taught taekwondo. His first job ever was teaching martial arts. He'd spent twenty-plus years in software but had remained connected to the martial arts community throughout.

"You understand—you trained judo for many years, you train jiu-jitsu now, taekwondo, all different aspects," Eran says. "Somebody that actually does all of those and experiences those businesses as a customer has so much more insight than somebody who is completely outside of the industry."

Alex felt the same way. 

"Everything that I've ever done in my entire career has led me to right here," he told Eran. "The first job I ever had was teaching martial arts when I was a young man, and now I get to pay it forward and serve the community that I care about."

The fit was obvious. Alex became CEO, and Eran began the process of stepping back.

What's Next: The Purple Belt Business Becomes a Black Belt

A year after that decision, Eran describes his current role with a sense of accomplishment: 

"I'm becoming more and more expendable at the company to the point where soon I won't be involved in the day-to-day. That's the accomplishment."

Some founders struggle to let go. For Eran, it feels right.

"I feel like I've done all I could as the founder," he says. 

"At this point, it might actually be a hindrance to a degree where some people defer to me too much. They just say, 'Let's just go with what Eran wants.' But people need to make their own mistakes. They need to grow in order for them to be able to provide the level of quality that we expect."

He's not leaving entirely. 

He'll stay involved strategically, helping guide product direction and long-term vision. But the day-to-day—the support tickets, the feature debates, the constant firefighting—that's in Alex's hands now.

And Gymdesk has ambitious plans for what's next:

• AI features are coming to help small gym owners do more with less. Many Gymdesk customers are solo operators or have very small staffs. AI can help them handle marketing automation, communications, and administrative tasks more efficiently.
• Major integrations are in the works—ClassPass, WhatsApp, and other tools that gym owners have been requesting for years. Gymdesk now has the team capacity to build these partnerships.
• Gymdesk Payments will launch, offering better merchant support than the current model, where gym owners work directly with payment processors. Instead of broken telephone games when something goes wrong, Gymdesk will be able to help directly.

Through all of it, the core philosophy remains the same.

"Some of our competitors, I've heard this from our customers, they just say, 'Yeah, the product is what it is,'" Eran says. "We will never say that. It's always getting better. If you have issues, let us know. Even if it takes a little bit of time, we will get back to you and resolve it."

That commitment—to keep improving, to never be satisfied—is what Eran built into Gymdesk's DNA. It's the legacy that will outlast his direct involvement.

To The First Believers: Thank You

Near the end of the conversation in Las Vegas, Eran's tone shifts. He wants to say something directly to the customers who were there at the beginning.

"First of all, thank you so much for taking on the product when it was really not ready for prime time, and you stayed with us all the way," he says. 

He calls out Shawn from Honu BJJ—that first customer who took a chance on "Martial Arts on Rails" back in 2016. Still with Gymdesk today.

He thanks Gumby from Heroes Martial Arts—the friend who gave him the initial push and became one of the first paying customers.

"You guys stuck with us when the product was barely a shell of what it is now," Eran says. "You're our first believers."

Alex adds his own gratitude: "Without you guys, I wouldn't be here either."

It's a small world. Alex once worked with someone who was roommates with Gumby and now owns a gym in Chicago that recently became a Gymdesk customer. 

The connections that brought everything together—the martial arts community, the software community, the gym owner community—they're all intertwined.

Eran trained at the University of Jiu-Jitsu in San Diego, where Alex also trained. 

They never met back then, but they rolled on the same mats, learned from the same instructors. Ten years later, they're building the next chapter of Gymdesk together.

"It's been an incredible ride," Eran says.

The decade is complete. The next chapter is just beginning.

Watch the whole episode here (and a preemptive apology for the audio issues):

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