Sunlight filters through the large windows onto a pool table in the offices of custom software and integration services company Letter B Global Technologies. Instead of billiard balls and cue sticks, a jigsaw puzzle depicting a jaunty seaside town and harbor spreads across the felt tabletop, loose pieces strategically grouped together.
Trevor Bollers, the company’s founder and president and the CBJ’s 2026 Entrepreneur of the Year, contemplates the colorful cardboard riddle in front of him. The puzzle serves two purposes: as a brain break during the workday and occasionally, as an interview tool.
Mr. Bollers sometimes invites job candidates to help him with the puzzle during the interview, asking questions while trying to match shapes and patterns. It’s a peek into a candidate’s problem-solving method, a critical skill in this industry.
When considering any candidate, Mr. Bollers wants to know: “Can you solve a problem without me solving the problem for you?”
“I would tell any kid today that was getting into the workforce — if you can show your employer that if something arises, you’re strong enough to go and work through it, figure it out, and come up with ways to solve that problem or handle it or be part of the solution — that is a skill, that is a trait that people will pay for, because it takes that pressure off of the entrepreneur, (it) takes that pressure off of the owner, and says ‘no, I can handle this lane,” he said.
“(As) a small business owner, we’ve got to hire smart and strategic, we have to plan smart and strategic, and just roll with the punches as they come as things change, we need to be ready to change,” he continued.
Early days
Adapting to — and thriving in the midst of — change is a skill Mr. Bollers learned early in life. At age six, he and his family emigrated from Guyana, South America to Edmonton in Alberta, Canada. Twelve years later, he emigrated to the U.S. to play football for the University of Iowa, where he earned dual degrees in marketing and management information systems.
His interest in software and technology started in an Edmonton classroom with an Apple lle and Commodore PET computer. Mr. Bollers’ second-grade computer teacher, Mr. Chu, allowed him to experiment with the computers during lunch hour.
“It blew my mind that I could create things right when I sat down at it,” he recalled.
In addition to his nascent technical proclivities, Mr. Bollers showed enterprising spirit in his youth, as well.
“If you ask any of my teachers, they will tell you that I had always been the entrepreneur, from selling candy to their friends to delivering flyers to doing whatever,” he said. “It’s always been a dream of mine to own multiple businesses and be kind of the director of my own journey.”
That journey has led to many experiences that shaped the entrepreneur he is today — from software development to athletics to coaching and teaching, each role has been a puzzle piece to a much larger picture.
Return to Iowa
After graduating from the University of Iowa Tippie College of Business, Mr. Bollers was recruited to play fullback for the Jacksonville Jaguars. A torn ACL sidelined him during the season, after which he pivoted to playing for Jacksonville’s arena football team. During that time, he suffered another torn ACL.
As a result, “(I) started leaning on my education from Iowa,” he said, finding employment building training software and simulators for a defense contractor and training company.
He pulled up stakes a few years later to pursue a master’s degree in human-computer interaction and information science in Rolla, Missouri, before returning to the home of the Hawkeyes.
“My wife Jennifer and I always planned on coming back to Iowa to raise our kids,” he said. “We said, ‘Hey, when it’s family raising time, there’s no place like Iowa to raise your family,’ and so we worked our way back here.”
The couple returned to Iowa in 2008, and Mr. Bollers launched Letter B Global Technologies shortly thereafter, starting with three employees and amassing approximately 20 clients in those initial years; today, the company has 17 employees and serves 100 clients “consistently,” Mr. Bollers said.
At the same time he was starting his business, Mr. Bollers taught IT Management at Mount Mercy University (then Mount Mercy College), a position he held for four years.
Teaching eventually segued into athletics, and Mr. Bollers spent 13 years coaching football for Clear Creek Amana’s junior high and high school football teams, simultaneously volunteering for 10 years as director of the Clear Creek Amana Youth Sports Foundation.
A focus on culture at Letter B
Letter B Global Technologies provides integration services, augmented team support, software upgrades and creates custom software for businesses — everything from “automating shop floors, product tracking with RFID, custom configurable quoting, to responding to millions of insurance requests in a day,” according to its website, serving clients in Argentina, Canada, India, New Zealand and Vietnam, in addition to the U.S.
Letter B’s distinguishing feature from that of other tailored software companies is its focus on the culture of the clients’ business, Mr. Bollers said.
“We’re not going to sell you software that doesn’t take into consideration what your people do,” he said, adding that anyone can plug in the software “but plugging it into the point where the people in the office say ‘this works the way I understand our world, this enhances our world because it takes the things that we know are happening and then makes them visible across the organization’ — that is a critical piece to our success.”
With all new clients, the process starts with a visit to the company to observe its operations, followed by a series of meetings with management and staff alike.
“We want to talk (to) the people who are going to input the data for that report to be able to work … if we’re going to work with you, we want to make sure that the system that gets put in place is a system that’s going to get used because the data is going to get into it,” Mr. Bollers said.
7-on-7 football
Mr. Bollers’ entrepreneurial spirit has not been limited to software and technology. In 2018, he combined his passion for football and enterprising skills with the formation of Iowa 7v7 Football — rebranded last year as MidAmerica 7v7 Football — in response to growing concerns over head injuries and practice deficits due to the Midwest’s offseason, putting the region at a disadvantage compared to leagues from the West or South that can practice year-round.
He noticed as he was traveling for college recruiting visits with his son, TJ — a defensive tackle with the Jacksonville Jaguars — that Iowa recruits attracting the most college interest were overwhelmingly linemen.
“Why is this guy not as good as this guy from down south or this guy from out west?” he remembers asking. “The primary (answer) was, ‘They didn’t get the touches,’ and I’m like, ‘What do you mean touches?’”
He finally received an answer — it meant that in the off season, Midwestern kids aren’t playing football.
“Unless you were the coach’s kid and quarterback, you weren’t getting those discussions about how to read or how to push over or cause another defender to do something that would open up a play,” he said of the offseason.
Wanting to rectify that situation, he turned to 7-on-7 football, using his technical skills to help organize a league.
“Knowing what was needed and being able to put that in play, we were able to build technologies that also supported the 7-on-7 league,” he said. “Whereas a lot of people go into it trying to figure out how to run the tournaments, we were able to build the technology that was needed, and I could see how the technology was going to support our growth and track our numbers and everything else that (is) important to a league.”
Experience is the best teacher, and many things Mr. Bollers learned from the field have been applicable to running his own business.
“The first lesson is never stay stagnant. If you watch football, football’s always innovating,” he said. “It’s not easy staying in business with everything changing and adjustments … to the way things work, and with AI coming, and now the development world shifting, (Letter B) had to shift. We had to change. We had to modify our strategy, and that is a very football thing too.”
Leading by example
Football’s influence has also left imprints on Mr. Bollers’ leadership style.
“A lot of what I do on a day to day is coach,” he said. He also believes in leading by example, and encourages employees to be proactive.
“I’m not one that wants to be in control of everything,” he said. “I really want my people to come to me with solutions. If there’s a problem, I’d love it if you walked in the door and said, ‘Hey, here’s the problem, but here’s two solutions,’ and then we figure out what it is.”
With 7v7 football, “I lead by example,” he continued, a practice that entails observing what needs to be done and doing it, whether it’s picking up trash or folding T-shirts — regardless of job title.
Financial savvy and maintaining relationships
In the 17 years since founding Letter B, Mr. Bollers’ definition of success has shifted. Once equating success with developing a large client base, it’s now evolved to include client retention.
“Maintaining relationships has been a huge thing for us, and a critical piece of staying in business,” he said.
Cultivating an operation that stands the test of time is a goal for the majority of business owners, and those first few years can be challenging for many. For those in the embryonic stage of entrepreneurship, Mr. Bollers emphasized the importance of financial education.
“Make sure you’re on top of those, because those things will either sink or swim (your business),” he said. “Find a good accounting program. It’s standard, but make sure you have it in place, and then learn about your customer base.”
Leaving a legacy
When reflecting on his personal and professional legacy, Mr. Bollers wants to be remembered for giving back.
“I feel a lot of my life has come from the support of good people who gave me opportunities and opened doors,” he said.
Through Letter B and MidAmerica, he hopes to open doors for others, as well.
“We do internships that get people started in their tech journey. We do internships that get people started in their sports management journey, and (I) want to be able to leave back really good software that people can continue building on,” he said. Through MidAmerica, “we want kids from everywhere to be able to play together on the same field … we provide actual connections.”
Outside of work, Mr. Bollers enjoys traveling, tennis, attending his children’s sports events and picnics with his family — wife, Jennifer, and children TJ, 23, Teagen, 21, Texton, 16, and Tarissa, 14. He credits his family with the majority of his success.
“Having a support system with these (endeavors) really makes a difference,” he said. “For me it’s made a huge difference (having) my wife and kids be there as constant encouragement. There’s nothing like it, and I wouldn’t be here without them.”
