If you were “painted blue” in the 1970s, you were set for life. IBM dominated the computer market in the era before the PC, and people who worked for “Big Blue” usually stayed until they retired. Graduating from the South Dakota School of Mines & Technology (SDSM&T)with a degree in computer science in 1984, Don Roby thought he had been given the golden ticket when he landed a job with IBM. But Don didn’t know that the forces leading to a flat world were already eroding IBM’s dominance of the digital landscape.

Don grew up in Watertown, South Dakota, the youngest of five boys. The last to graduate from Watertown High School, Don played football, ran track and served as president of his senior class. He chose SDSM&T for the in-state tuition and on the recommendation of one of his older brothers who had already become a Hardrocker.

IBM recruited Don to the sales side of the business, using his technical expertise to help customers understand the potential uses of IBM’s systems. Over the next 11 years, he moved around the Midwest with assignments in Sioux Falls, Sioux City, Denver, Omaha and Minneapolis. Benefiting from IBM’s superior management training programs, he deepened his technical knowledge, improved his management skills and gained expertise in sales and marketing. Along the way he was climbing the corporate ladder. ”At IBM, your name was in a box on an organizational chart,” he says. ”The goal was to get your name in the box above.”

Unfortunately, IBM was in trouble. Blindsided by the rise of the personal computer and distributed networks, IBM was losing money in the mid-1990s. The company’s 1993 losses of nearly $5 billion set a record at the time for U.S. corporations. IBM’s financial woes, combined with Don’s growing interest in entrepreneurial organizations, led to his departure from Big Blue in 1995. He joined Minnesota-based Winthrop Resources, a leasing company helping to finance corporate acquisitions of high technology equipment and software. At Winthrop, Don discovered lots of new challenges.

He also met the love of his life. An administrator at Winthrop, Kelly was born and raised in Minnesota. She too had known a small town childhood. Married in 1997, Don and Kelly began their life together in central Minneapolis, but like many Americans today, when they started their family, they moved to a distant suburb. “To tell the truth,” Don says, “I never imagined living so far out of the city, but we wanted a big yard so the kids could be outside.” They also wanted better schools.

Stuck in morning and evening traffic on the days he wasn’t traveling to visit customers on the East Coast, Don thought about his own childhood. A friend from his youth was talking about moving back to Watertown. Don thought it would be good for his kids to be closer to their grandparents. “Since my sales territory was the Washington/Baltimore area,” he says, “living in Watertown wouldn’t really add much cost to what I did.”

When he approached his colleagues and the executive team at Winthrop, they were initially hesitant about the idea. Don realized that telecommuting would impact his relationships with the staff. He would have fewer opportunities to mentor the younger employees. Distance would probably impact his ability to be promoted. But he was resolved to make the move for quality of life reasons, and Winthrop was willing to give it a try.

Don and Kelly and their first two children moved to Watertown in 2003. Since the move, the family has grown with the birth of their third child. With the children sometimes coming in to check on dad, Don now works out of a home office and travels to the East Coast about once a month. Through family and the children’s activities, they have gotten connected in the community. Even though Don didn’t do business in Watertown, he joined the Rotary. Talking to local business leaders got him interested in the local economy. 

Recently, the wisdom Don gained at IBM and Winthop has begun to pay dividends locally. With a former high school football teammate who now lives in Dallas, Texas, Don has invested in a struggling manufactured homes company in Watertown. The pair brought in a new CEO, and with the fresh capital and marketing and management expertise that Don and his partner have brought to the business, the company has turned the corner. Employees are no longer worried about losing their jobs.

Don enjoys taking his kids to the lake outside Watertown in the summer, sharing some of the places he remembers from his childhood. On fall afternoons, they sit in the stands watching the football team. Instead of being painted blue these days, he once again cheers for the purple and gold of Watertown High.