At 25, dealer buys Harley stores in Alaska

This article originally appeared in the December edition of Powersports Business.

Barry Matteson became a dealer as a side hustle, naming his Alaskan business Barry’s Custom Cycle. A meeting with a Harley-Davidson rep in the early ’70s inspired him to purchase a commercial building and take on the franchise. In 1975, he relocated his business and became a Harley-Davidson dealer.

“Back then, we were still living in a trailer house and not making that much money,” says Dia Matteson, his daughter. “Eventually, we moved upstairs in the dealership. We had a bed and breakfast there called Hog Heaven, and I remember making beds and doing laundry with my mom. We converted two of the rooms into an apartment where we lived and had guests in the other room.”

Under her father’s ownership, the business started providing stronger financial support for the Matteson family. “My dad was always advancing,” Matteson says. “He wasn’t afraid of technology, he was humble, he would go to 20 groups and he started to learn how to make the business profitable. Then we were able to buy a house.”

She was in elementary school at that time. “I just loved motorcycles. My dad and I would go on motorcycle trips. He would take me as passenger and we’d go down to Arizona, ride around Arizona, and go to New Mexico to visit my grandparents.”

At 14 years old, she started working at the dealership. “I loved the people and I loved the customers. I had a ton of fun. I worked at the dealership all through high school and my senior year I was pretty much working full time because I was only taking a couple classes.”

Wanting to explore a different part of the world, she attended college in South Carolina, returning home each summer to work at the dealership. She wanted to take over her father’s three dealerships, so he helped her learn every aspect of the business. She worked in different positions, from the parts department to service advisor to administration roles in accounting.

“I enjoyed my work,” she says. “I really liked being at the service counter.” She took on her first management position as service manager when she was 22 years old.

At just 25, she secured a loan and purchased her father’s three Harley-Davidson stores. “I finished my master’s degree and bought the dealerships all within a couple of months of each other,” she says.

Today, she owns House of Harley-Davidson, Denali Harley-Davidson and Kenai Peninsula Harley-Davidson in Anchorage, Wasilla, and Soldotna, Alaska.

From Alaska to Arizona

Eventually, Matteson hired a general manager at the Anchorage store to take over her day-to-day role. “I hired Trevor, who is still my general manager,” she says. “That freed me up to buy four more locations in Arizona.” At 33 years old, she acquired two dealerships and two retail stores in Arizona – Legends Harley-Davidson and Canyon Harley-Davidson.

“My dad passed away, but he was a huge part of the business and my development,” she shares. “That’s why my store in Arizona is named Legends – to give a nod to my dad and all the legends that came before me. I wouldn’t be where I am without his guidance and giving me the opportunity to buy the dealership.” She also credits her mother, Karen Matteson, for being her “prayer warrior.”

The Arizona acquisition came with challenges. “I didn’t really know the details of the structure of the deal when I bought the stores from my dad,” she says. “When this opportunity came up, it was intimidating. I didn’t hire a lawyer right up front to structure the deal, so me and the owner were structuring the deal.”

To prepare, she read books about business valuation and spoke to dealers with acquisition experience at 20 Group meetings.

“There were a few things I wish I would have known. I was learning as I was doing it,” she says. “I was able to structure the tax side of it well… It was intimidating but it was also fun and challenging.”

After the purchase, Matteson divided her time between Alaska and Arizona. “Those stores really needed a lot of attention,” she says about the Arizona Harley-Davidson dealerships.

Management

“It was harder to build culture in Arizona,” she explains. “In Alaska, we have a longstanding culture. My general manager has worked for us for 20 years. My operations manager has been with us for 28 years.”

She shares that if she acquired a dealership again, she would prebuild a team that would help run her stores. “We’re not a big dealer group. We didn’t have a whole team we could fly in to train everybody,” she explains. “I’ve always run lean, and there’s pros and cons to that with staffing. With my staffing, there’s not a lot of redundancy, but the ones I have, they make money and they stay because they’re part of a family. That was a little bit of a challenge in Arizona, to rebuild the culture. Not being there all the time and not having anyone there full-time that knew me and knew my culture, that was my biggest learning curve to overcome.”

After she acquired the Arizona stores, the Covid−19 pandemic changed travel and business operations. “I was the person flying every two weeks regardless of all the crazy that was going on in the world,” she says. This was her routine until 2023, when she received an offer and sold the Arizona businesses, keeping ownership of the properties.

Now, she is focused on the dealerships in Alaska. “We’re always trying to do better, find improvements, find efficiencies,” she says. When she interviews people, she often says, “If you are someone that thinks that we’ve gotten to a place that’s ‘good enough’ and we’re going to chill here, then you won’t like working for me.”

Spendard Bike Week and camping

Winters in Alaska are dark and cold, so the dealerships host events to keep the community engaged. Matteson started Spenard Bike Week, named after the famous road where House of Harley-Davidson is located.

“It’s super fun,” she says. “It’s never going to be Sturgis, it’s going to stay small, but it is super fun. The whole point is to support our local community. We don’t get a lot of money from organizations to sponsor it, but we get partnerships. We’ll do a scavenger hunt or a punch card that sends people to the businesses that are partnering with us.”

Next year, House of Harley-Davidson will celebrate its 50th anniversary during the bike week in August. Matteson is already planning the logo for apparel and t-shirts.

The dealership property also offers a campsite for motorcyclists. In 2002, Matteson’s father rebuilt the Anchorage store and added a campsite and shower house. “At that time, motorcycle camping wasn’t as big, but now the dealership is on every ADV rider’s list as a place to camp,” Matteson says. Riders from all over the world, some riding from the top of Alaska to South America, can camp, shower and change their oil.

Service technician apprenticeship program

Matteson has done many rides and solo rides around the country, so she understands the importance of needing somewhere to stay or needing service when your bike breaks down.

“We need to get them in and out as we can,” she says. To make sure the dealerships have top-notch service technicians, she and Nick Morton, her husband and a 10−year master technician at Volkswagen, developed an apprenticeship program that they implemented in 2023. “That’s a big focus for us,” she says. “Making sure we have highly trained technicians learning all the right things.”

Moving into 2025

“In Alaska, people could say or feel that we’re a little bit of a monopoly because there’s only one other dealer in our state,” Matteson says. “But I will never act like that. I will never be entitled to their business. I’m always working to earn and retain business.”

To do this, Matteson is focused on processes and training. “Sometimes you can make things overcomplicated and forget that you need to be training your staff on the perfect process to get a motorcycle back into service,” she says. “We want to be able to communicate with our customers and solve the problem faster. That’s what we’re doing next year, training and retention. Keeping the staff we have and making sure they’re happy and trained.”

“There’s a lot of pressure being an owner, and a lot of things people have no idea that we deal with as owners – threats of lawsuits, employment complaints – but at the end of the day, I love it,” Matteson adds. “I love the action, I love the pressure, I love to feel like I’m accomplishing something.”