He Sold Princess Dresses and Hoverboards Out of a Skate Shop. Then He Built the World's Largest Ninja Gym.

Most entrepreneur stories follow a clean arc. Guy has idea, guy builds thing, thing works. Maybe there's a pivot in the middle. Maybe a mentor shows up at the right time.

Wally Roskelly's story isn't that. It's a guy who sold longboards out of his bedroom, wired $7,000 to a stranger in China for frozen princess dresses, nearly made a million dollars on hoverboards before customs killed the deal at the port, became a world champion ninja warrior, and then built the largest ninja gym on the planet out of a backyard practice facility.

And he says he'll never sell it. Even at breakeven.

He sat down with Stu at a live Startups with Stu retreat recording. Here's what stood out.

$11 an hour, a boss watching him all day, and the moment it clicked

Wally's first real job was at an Allstate office. $11 an hour plus a small commission. He was outselling everyone. The owner sat across the room staring at him over a computer screen all day.

So he quit and opened his own insurance agency. Same product. Same work. Completely different feeling.

He wasn't even making more money at first. He was actually losing money. But he wanted to go to work. That was the shift. Not the revenue, not the business model. The feeling of building something that was his.

Most people skip that part of the founder story. They jump straight to the money. But Wally's point is real: if you can't wait to go to work, the motivation problem just disappears. You don't need a system for discipline when the thing you're doing already pulls you in.

The longboard shop and the first lesson that actually matters

Wally liked longboarding. He noticed something: tons of riders in Provo Canyon, almost nobody selling boards locally. Amazon wasn't the default yet. One shop in the area. Classic gap.

He started buying boards cheap and reselling on classifieds. Then his bedroom had 100 boards in it. His wife told him to move it out. So he opened a shop.

First day, first half hour, someone walked in and bought one.

He keeps coming back to this when he talks about starting businesses: passion is great, but passion without a supply-and-demand gap in your favor is a hobby. He saw the demand. He saw the lack of supply. Then he moved.

The shop turned into a community spot — free drinks, skate videos on the TV, a couch where local kids hung out. They thought he was 20. He was pushing 30 with a family. But the vibe worked. People came from all over. He ended up with 250 drop shippers running orders through a fulfillment operation in the back of the store, shipping boards and parts worldwide.

All from noticing that people wanted something and couldn't easily get it.

Princess dresses, tungsten rings, and the $450K hoverboard disaster

The China connection started when Wally manufactured his own longboard brand overseas. Once he had that relationship, he started seeing opportunities everywhere.

His daughter wanted a Frozen princess dress. Disney Store was sold out nationally. The employee told him moms were lining up on delivery days to fight over whatever came off the truck. Wally emailed his contact in China. $7,000 wire to someone he'd never met, never video-called, didn't know what the product would look like.

The dresses showed up. Sold out in two days.

Then tungsten rings. $8 delivered. Sold for $200.

Then hoverboards.

This is the one that hurts. Wally and a partner ordered two containers, roughly $450,000 worth, of what they were calling "self-balancing scooters" before anyone agreed on the name. Selling them at $500 with a cost around $130. The math said they'd each clear over a million in November.

Then other manufacturers' hoverboards started catching fire. None of Wally's did. But customs stopped the second container at the California port. He and his partner drove down. They could see the container from 100 feet away but couldn't cross the line. Customs inspected everything, rejected the shipment, and sent it back to China.

Million-dollar month became four grand.

Wally told this story at the retreat with a grin. Said he still felt good about himself and still looked pretty good. That's a joke, but it's also a real thing. The founders who stay in the game long enough to win are the ones who can take a financial hit without turning it into an identity crisis.

90,000 applicants, 600 spots, and pull-ups with a backpack full of food storage cans

Wally had been a competitive rock climber his whole life. Took second place at the Colorado state competition at 17. When American Ninja Warrior launched, he applied. That year had 90,000 applicants for 600 spots. He got the call.

His training? Pull-ups in his basement with a backpack full of food storage cans for weight. That's it.

He got on the show, did average, but it changed his trajectory. He met another competitor and they had the same thought: where do people practice this? There was no equipment to buy. No manual. Nobody had really built a facility for it before.

So Wally built one in his backyard. Then his basement. People started showing up from the neighborhood, then from across town. Which is cool until you start worrying about lawsuits from a random teenager falling off a homemade warped wall.

4,000 people on opening day with zero playbook

Wally and his partner opened the Ninja Playground. No franchise model to follow. No template. They figured out training, pricing, class structure, everything from scratch.

Opening day, they were hoping for a few sign-ups. An hour early, someone looked out the window. Over a thousand people in line. They have drone footage of it. By the end of the day, 4,000 people had come through.

The "problem" was getting people to leave so the next group could come in. That's a good problem.

A second location followed with a different partner — Impact Ninja Gym. It's the largest ninja warrior gym in the world. But the size isn't what Wally talks about most. It's what happens inside.

Kids who walked in on day one are now elite athletes. Adults who'd never done anything physical found something they were proud of. Wally runs monthly masterminds at the gym with speakers ranging from Olympians to Quinn Hastings from the Diesel Brothers. The gym hosts product launches, expos, community events that have nothing to do with ninja training.

Here's the thing most gym owners would never say: Wally told the retreat he'd never sell this business as long as he lives. Not because of the money. Because it checks every box: community, family time, fitness, purpose, relationships. Even at breakeven, he'd keep it.

That's a rare thing to hear from a serial entrepreneur. Most founders talk about exits. Wally built something he actually wants to keep.

The research nobody wants to do

For a guy who wired $7K to a stranger in China on a hunch, Wally is surprisingly obsessive about research when real money is on the line.

Before signing the lease on the second gym (millions of dollars), he spent months sitting in the parking lots of trampoline parks, bounce houses, and laser tag venues. Counting people going in and out. Going inside and asking the front desk kids how many customers they'd had that day. One kid told him 320 and didn't think twice about it.

He has hundreds of spreadsheets. His wife makes fun of him for it. Break-even calculations, pricing benchmarks from facilities across the country, minimum sales targets to cover the lease.

He calls it the Spider-Man test: is my excitement about this overtaking my analysis of whether it actually works? If the spreadsheets don't track, the passion doesn't matter. Good line.

1,003 pull-ups and the only happiness framework that holds up

At 45, Wally recently did 1,003 pull-ups in five hours. Nearly double David Goggins' pace during his 24-hour record. Three accountability coaches. A counter on his phone.

But the pull-up thing is really about his bigger point: progress is the key to happiness.

Not money. Not status. Progress. The measurable sense that you're further today than yesterday. He teaches his kids this. He sees it in the gym every day when a kid gets one inch further on an obstacle and the whole room cheers.

Most happiness advice is soft. "Be grateful." "Live in the moment." Wally's version is concrete: are you measurably better at something than you were last week? If yes, you feel good. If no, you don't. Everything else is noise.

The other piece is hope. Hope is the fuel. When you believe something could work, you'll do the spreadsheets, make the calls, take the risk. When hope dies, the venture dies. Wally's entire career has been about finding the next reason to be hopeful and then going hard on it before the feeling fades.

The thing he almost didn't talk about

Wally and his wife wanted kids. They went to the doctor. The answer was zero chance. Not low odds. Zero. The combination of their physical situations made it impossible, even accidentally.

That night was the worst of his life. They both cried themselves to sleep.

The next day, they started adoption paperwork. Usually takes 2–3 years. They had a newborn in six weeks.

They now have three adopted kids, all adopted at birth, all four years apart. His 11-year-old daughter is one of the best young ninja warriors in the country.

Wally processed the worst news of his life in about 24 hours. His wife took longer. He's honest about that — says she'll tell you he's a robot with no feelings. But his version is simpler: the path forward existed, it just looked different than expected. So they took it.

That's basically his whole philosophy in one moment. Bad news comes. You feel it. Then you find the next door and walk through it.

What stuck with me

I've sat through a lot of entrepreneur interviews. Most of them follow the same beats: humble beginnings, big break, lessons learned, call to action.

Wally's story is different because he genuinely doesn't seem to care about the narrative. He's not packaging his life into a TED Talk arc. He sold princess dresses out of a skate shop. He sat in parking lots for months counting customers. He did 1,003 pull-ups because he wanted to see if he could. He built a gym he'll never sell because it makes him happy.

There's no grand unifying theory. Just a guy who keeps noticing gaps, doing the math, and going.

Recorded live at a Startups with Stu retreat. More at startupswithstu.com.