Seminole Entrepreneur Turns an Old Horse Trailer into a Mobile Bar

SEMINOLE — When Krysten Strauser was 10 years old, her parents operated a snow cone food truck. During summer breaks and on weekends, she’d join them as they drove around the Tampa Bay area, setting up in Walmart parking lots, strip malls and outlet shopping centers.

“It was a great experience learning about how to run a business as a kid,” she said.

This wasn’t her parents’ only foray into entrepreneurship, she added. They owned a series of different businesses throughout her childhood.

“And they’ve owned many more since,” Strauser said.

But the one that stands out most for her the most is the mobile snow cone business.

“Growing up and seeing my parents run this business, seeing what they’ve done was inspiring,” she said. “Since then, I knew I wanted to own my own business, but I didn’t know what it would be.”

Until now.

In February, the Seminole resident launched the Tipsy Trotter Mobile Bar Co., one of the first mobile bars in the Tampa Bay area.

“I didn’t want to start a business until I had an idea that stuck with me,” Strauser said. “I’m the kind of person that needs an idea I fully believe in. I’m not going to start a business until I fully know what I want to do.”

From the beginning, she’s been consistently busy, booking several gigs every week.

“I didn’t expect it to grow as quickly as it did,” she said.

It’s been a long road to get to this point, though, she said.

Strauser spent the first 12 years of her life in Tarpon Springs. Then, her family moved to the greater Seminole area.

After graduating from Osceola Fundamental High School in 2008, she attended St. Petersburg College.

“Nobody in my family went to college. I wanted to be the first,” she said. “Everybody in my family were entrepreneurs. I wanted my own business, too, but I wanted to have a degree to back it up.”

College wasn’t a good fit for her, she quickly realized. Instead, she opted for real-world experience.

She began working for WingHouse Bar & Grill in 2006, even before she graduated from high school. Strauser started her career with the restaurant chain at its Pinellas Park location as a host and server, and worked her way up into management. She found herself as one of their go-to trainers to help open new WingHouses throughout the region. Her dream was to become a general manager for the company.

“I wanted to be a GM so bad,” she said. “I always thought that was the route I was going to go.”

Working for a corporate restaurant presented some difficulties as she pursued this dream, though. There was a nearly constant shake-up of the company’s leadership.

“They changed out the [vice president,] regional managers changed, there was a change in ownership,” Strauser said. “I was constantly proving myself to every new person that walked through the door.”

Eventually, she found herself working underneath a regional manager who wasn’t supportive of hiring female general managers, she said.

“After being told I was next in line to become a GM for so many years, I cut my losses and left the company,” she said.

Throughout much of her time at WingHouse, her mother was terminally ill. By then her parents, Robert and Lisa Williams, had moved to Wesley Chapel. In 2010, she followed them there to be closer to her mother.

Inspiration for the Tipsy Trotter struck as Strauser planned her wedding with her mother’s help. She dreamed of renting a mobile bar and photo booth for the event.

“But after researching it, there was nothing in the area,” she said. “In fact, there was no mobile bar in all [of] Florida at the time, I don’t think. And there was one photo booth all the way in Panama City.”

The wheels began turning for her, but the timing wasn’t right. In 2017, her mother passed away just months before her wedding. Around the same time, she left WingHouse.

After taking several months to grieve, she landed in her coveted general manager role at a family-owned restaurant in Dade City, Al’s Pizza Shop. Strauser only held the position a couple of months, though.

“It just wasn’t a good fit,” she said.

By then, her father had plans to relocate to Gainesville. So, she and her husband, Jack, decided to move back to Seminole.

“I wanted to be closer to home, closer to family, closer to what I know and what I grew up with,” she said.

She was hired as general manager of 1895 Kitchen Bar Market in downtown Tampa.

But a visit to her father before he moved north kicked her entrepreneurial spirit into high gear. Despite her new opportunity, something didn’t feel right to Strauser.

“I visited my dad crying. I felt like something heavy was sitting on me,” she said.

She told her father about her dream of owning a mobile bar.

“But I didn’t want to keep talking about it. I wanted to act on it,” she said. “I had been talking for so long.”

She was tired of working for other people and “restaurants that didn’t connect with [her.]”

“I needed to do this on my own. I don’t need to be working for anybody else, working for their paycheck,” she added.

Strauser was working between 70 and 90 hours a week, spending time away from her husband and their newborn.

Laying out her plans for the Tipsy Trotter to her father was “the motivation and push” she needed, she said.

He immediately went online and found an old horse trailer for sale in Wesley Chapel. They bought it that same day and towed it to her home in Seminole, surprising her husband.

This first trailer didn’t quite work out, though. It was too rusted to be of use as a mobile bar.

“Rust is like cancer,” Strauser said. “It spreads.”

She and her father found a second horse trailer, this time in Haines City.

“There was no rust. It was in perfect condition,” she said.

She and her husband immediately got to work on the trailer. She booked her first few gigs, scheduled for early February, even before the bar was completed, mostly through social media and word of mouth — her own wedding venue, a barn in Bushnell, and other vendors she’d hired helped spread the word about the Tipsy Trotter.

As Strauser launched her new business, 1895 was bought by new owners. She left the restaurant in January.

“So, it was perfect timing,” she said.

The word keeps spreading about the Tipsy Trotter, and the mobile bar is consistently booked each week. Sometimes she might have only one event, but, more often, other weeks she’s book for as many as four.

“It’s a unique concept,” she said.

Tipsy Trotter is licensed and insured to serve alcohol, but not sell it. This means, currently, they can only serve drinks at private events.

Those hosting the event – from weddings to birthday shindigs to business parties – purchase the alcohol they want served. Strauser brings the rest – ice, cups, fresh-made mixers and juices without the added sugar and preservatives, the bartenders, and, of course, the mobile bar.

This works in her clients’ favor, she added. Any unused alcohol can be returned after the event, which wouldn’t be the case if they hired a catering company, she said.

“Some people see the flaw in not having a liquor license, but to me it’s even better because people can save money,” she said.

The Tipsy Trotter is “versatile for [its] clients,” she added. They can serve a variety of drinks, even a creative menu of mocktails.

“And they taste even better than regular cocktails because they don’t have that strong alcohol taste,” Strauser said.

There are two taps which can be used for a number of beverages – draft beer, kegged wine, even nitro coffee.

It’s also “a fun photo prop,” she said.

Strauser and her husband bartend all the events Tipsy Trotter is hired for. But after more than a decade in the restaurant business, she has a number of potential employees waiting for the business to grow.

This growth will likely happen sooner than she thought, she said. She often receives inquiries for several events on the same dates.

“And right now we can only be in one place,” she said.

She’s already sending her father rigs to review for their next mobile bar project.

“I really want to grow the bar business,” Strauser said. “But who knows what’s down the road.”

Maybe even that mobile photo booth.

“You never know,” she said. “That’s something on the back of my mind.”