Jesse Frey shows his invention, the Headlok hat retention clip. (Photo by Derik Holtmann)

Jesse Frey hasn’t forgotten his favorite hat, the one he bought at that little corner store near the beach at Hanalei Bay on Kauai’s north shore while on vacation from his U.S. Coast Guard job. He wore it all the time. Well, for about a year-and-a-half, at least.

One fateful day, Frey was riding his motorcycle up the iconic Pacific Coast Highway near where he was stationed in Southern California, as he loved to do. When he stopped, he realized the hat had vanished. The snaps on the back strap had failed, ripped apart by the wind pressure that enveloped the motorcycle. Poof.

There had to be a better way to keep a hat without cramming it in a backpack, Frey thought. Nobody wants a crushed hat. And his favorite fitted hats, the ones without a strap? Cramming was basically his only option. There had to be a better way to save a memory.

“That store had only that one location, and they designed their own stuff,” Frey remembers. “You can’t find the hat online. It’s stuff like that you hate to lose. With big brands, you can just buy another one. But with something like that? You have memories of that place, buying that hat.”

Frey, a senior at the University of Missouri­–St. Louis, still misses that Hawaii hat. And with that memory as motivation, he’s found a way to make sure he never loses another hat in a similar fashion. For years, he tinkered with different versions of a hat retention system for his motorcycle – “The first one is horrible, but I thought it was the coolest thing ever,” he said with a laugh – and it’s morphed into what’s now his patent-pending product, Headlok.

The design is beautifully simple – just a spring and a slope, using the button on the top of the hat as an anchor, locked and opened with a wrist twist. Frey uses the design for two similar products: One has a powerful magnet to attach to a motorcycle’s upper tank, and the other features a clip to throw on a backpack, belt loop or pretty much anything with an enclosed opening.

The first few prototypes of his fifth (current) iteration, he 3D-printed at the St. Louis Public Library using the Shapr3D software. Happy with the results, he bought his own 3D printer and can now print four at a time, with an ABS tough resin. He sells them on his website.

Frey is an intern with UMSL’s Anchor Accelerator program in the Entrepreneurship and Innovation Center. He showcased his invention on April 8 at the St. Louis Regional Entrepreneurship Educator Poster Competition, held at the Cortex Innovation Community.

Frey finished second out of 11 student entrepreneurs.

“I could only get him to the pitch event,” said Michael Butler, the director of operations for the EIC, “and from there Jesse had to sell himself, and without question he did an amazing job.”

For the competition, Frey put together a poster showcasing the schematics of his invention, along with information like his business concept and target audience. He gave a series of two-minute elevator pitches to folks who stopped by on a rotating basis, including a handful of “secret” judges. Stephanie Lynch, a senior partner at the St. Louis-based marketing company Braver Element, was one of those taking notes on the presentations.

“Since I’ve spent thousands of miles on the back of a bike, I could relate,” Lynch wrote on her LinkedIn page, shared with UMSL Daily. “Not to mention, Jesse engineered the prototype himself. To me, Headlok screamed lifestyle brand with a cult following.”

The presentations were a learning experience, each one a chance to gain a little bit more knowledge about how what he said impacted those who were listening. Frey admitted with a smile that his last pitch was better than his first one.

“Oh, definitely. You figured out how to flow, what information you needed to add, what stuff to leave out and how to shorten things,” Frey said. “I got it down pretty well. I was super shy kid in high school. I was nervous. But after the military? That kind of knocks it out of you. I don’t really get nervous. You don’t really get any better at something unless you throw yourself into the fire.”

Aside from the outstanding second-place finish, just being at the competition was useful.

“I connected with a bunch of cool business owners here in St. Louis, got a lot of information,” Frey said. “They just are so helpful and said, ‘Reach out if you ever need help with anything.’ It was more valuable just to get the help and the connection of those people.”

Frey spent six years in the Coast Guard – his first assignment out of basic training was on an icebreaker tasked with keeping the shipping lanes open in the Great Lakes during winter – and then two at Orange Coast College in Costa Mesa, California, before transferring to UMSL for the fall 2023 semester. He’s from the St. Louis area and wanted to return home, and UMSL felt like the right spot. Credits transferred and the G.I. Bill paid for his tuition, and he’s found a place that embraced his entrepreneurial spirit.

“I wouldn’t be as far as I am now without UMSL,” Frey said. “They’ve really helped. When I got here, I read about the accelerator program, how they worked with entrepreneurs and helped them get mentors. I was super excited about that.”

Frey is on track to graduate in December with a business administration major and a minor in marketing. Headlok has been a perfect real-life way to apply what he’s learning at UMSL. He designed the Headlok website himself, and he’s already collaborated with influencers in the motorcycle sphere of influence. Using his 3D printer, customization is definitely an option.

Even though he hasn’t fully ramped up his marketing efforts quite yet – he doesn’t want sales to outpace his ability to produce product – he’s still getting orders from Google searches and even his original Reddit post, asking if people might be interested. He’s in advanced talks with a manufacturer to produce them on a larger scale. Once that happens, he’ll expand, both online through outlets like Amazon, and he’ll pitch retail stores, too.

“The overall thought is, just go for it, basically,” he said. “I was so hesitant to try it and thought ‘Nobody’s gonna want this, nobody’s gonna buy it when you can just stuff your hat in a backpack.’ But just put it out there. Fail fast. That’s what I’m learning at the internship. Try something for a week and if you don’t get any traction, move on to the next thing. Fail fast. Even though I don’t like failing, it’s good because you might be going down a path that doesn’t end up leading to anything.”

But if you throw it out there and do get good traction – like a second-place finish at a student entrepreneur contest – that path almost certainly will lead to very good things.