Brenny Transportation Inc.
Inception: 1996
Headquarters: St. Joseph
Family members in the business: 4
Employees: 90

Joyce and Todd Brenny loved working in the trucking industry. But working for trucking companies? Not so much. That’s why they started their own. Brenny Transportation touts its customer service, of course. But just as important to the Brenny family is treating employees well. Need evidence that their approach works? The Brennys claim an employee retention rate of 85 percent, unusually high in the industry. Since its founding, Brenny Transportation has added three niche divisions: Brenny Specialized Inc., Brenny Global, and Brenny National.

Cox Insurance Associates Inc.
Inception: 1950
Headquarters: Falcon Heights
Family members in the business: 3
Employees: 26

How does a family-run insurance brokerage last for nearly 70 years and through three generations? Given the nature of the Cox family’s business, it’s not surprising that a big part of the reason is “plan, plan, plan.” The Coxes believe that it’s important to think at least 10 years out about what the business is going to look like and who’s going to be running it. Maintaining a strong but flexible transition plan has been key to the company’s durability. So is making sure that non-family employees are treated like, well, family. Both family and non-family staff share in shaping the company’s collaborative, customer-focused culture.

Discount Steel Inc.
Inception: 1992
Headquarters: Minneapolis
Family members in the business: 10
Employees: 95

Starting with a rundown office building and a warehouse containing 2.5 million pounds of structural steel, Discount Steel founders John and Diane Dormanen have built a sturdy business that provides a wide variety of industrial and construction-related metal products and services; the materials it sells now include copper, brass, and aluminum as well as steel. As the business and their family grew, the Dormanens saw an opportunity to open a second location, in Fort Worth, Texas. The Dormanens and their daughters now run a company with more than 350,000 square feet of operating space, which includes retail centers.

Evolve Systems
Inception: 2002
Headquarters: Little Canada
Family members in the business: 4
Employees: 15

Donald Raleigh and Marnie Ochs-Raleigh began selling computers and related technology to households and individual consumers in 1993. In 2002, they “evolved” their company into a B2B, selling an easy-to-use, self-directed system that lets its clients—small and midsize businesses in a diverse set of industries—manage their own websites. In time, Evolve Systems also began offering credit card merchant services to those business customers. Partnerships with selected graphic designers and marketing firms allow the Raleigh family to provide tailored, single-source services to its clients.