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

Dia Matteson named one of her Arizona dealerships Legends Harley-Davidson to honor her father , Barry Matteson . Photos courtesy of House of Harley-Davidson

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