Craig Stephenson represents generational change in business leadership, both literally and figuratively. As CEO of COC Properties, he was the first member of the second generation of the Stephenson family to join and eventually lead the parent company of Cary Oil and the Breeze Thru Markets convenience store chain. As such, he’s a textbook example of a leader who worked his way up through the ranks of the family business, from part-time work during summers in high school to the lead role of the company.

At the same time, he represents a generation who had to bridge the gap between first-generation leadership—a father, Harry Stephenson, who very much led with his gut—and modern progeny who study and understand the language of business and employment.

“[My father] would make the decisions, and it was not a particularly collaborative style,” Craig Stephenson said. “Not that it was combative, but he was going to make the decisions, as is typical of most founders and entrepreneurs. [Founders] are not people generally wracked by doubt and uncertainty.”

Such leadership by declaration is largely frowned upon today. As part of the generation who lived through that evolution, Stephenson has led the company through the transition, one that focuses on company culture, a succession plan and training in every step of advancement for both family members and others.

“As in many family businesses, you join at the kitchen table. And that was true for me,” Stephenson said. “I was the first ‘gen two’ family member to come back. ... You [would] learn by observing and watching and making mistakes. No one would sit me down and say, ‘OK, son, this is what you do. This is how you act.’”

Today, the modernization of business strategy requires a willingness to learn and adapt to remain relevant. Operators who have lived through the challenges of managing a family business firsthand offer best practices that can make it work—generation after generation.

Earn Your Spot

This summer, Nikki Earp advanced from chief financial officer to CEO of Good Oil Co. when her father, Don Good, retired to a chairmanship role.

Earp’s grandfather, Don Sr., started the company in 1941 as a bulk petroleum supplier to farmhouses in Winamac, Indiana. The company opened its first c-store 30 years later. Today, it owns and operates 20 Good To Go stores in three states.

“From an early age, my dad knew that I was very interested in the business,” Earp said. “It’s always been what I wanted to do. I never wanted to be a teacher or a doctor.”

She and a cousin, Wyatt Good, who also showed interest, structured their college educations around preparing for succession planning and taking over the business. Today, Wyatt Good is vice president of the company’s transportation arm, Good Transportation LLC.

The Goods’ efforts while growing up illustrate a constant among the operators interviewed for this report: The younger generation couldn’t assume they would be allowed to take on leadership roles without getting an appropriate education, putting in hard work and proving themselves ready and able through hands-on experience.

“There is no free ride,” said Gus Olympidis, who founded Family Express in the mid-1970s. Today, his three sons hold leadership roles in the Valparaiso, Indiana-based chain of more than 80 stores. “This wasn’t handed to them. They truly earned it over time.”

Roy Strasburger had no expectation of joining his family’s business, until he did. His great-grandfather got into the grocery business in the late 1800s. Strasburger’s father would eventually take over the business and transition it to convenience stores in the 1960s. At its peak, Strasburger Enterprises operated 150 c-stores in Texas and was responsible for almost 6,000 stores in 33 countries as a third-party operator. 

“When I was in high school, my father told all of his children that we would not work in the family business,” Strasburger said. 

After Strasburger earned a law degree and relocated to the U.K. to start a publishing business, his father, Tommy Strasburger (who died in April at age 92), rethought that decision. 

“I was always interested in the company but didn’t think I was going to be a part of it,” Strasburger said. “It wasn’t until the business started to expand internationally that I was asked to join the company. My father thought that my legal training and interest in international travel were a big advantage.”

He joined as general counsel. A brother and brother-in-law also eventually joined, with the three becoming the fourth generation in the family business. Strasburger negotiated international agreements and eventually took over international operations. “I became responsible for all retail operations of the company,” he said.

And as with the other retailers, familiar surnames did not guarantee upward mobility in the company. “There was no timeline for the position changes,” Strasburger said. “It depended upon when I was ready for promotion or change in position, and an opportunity opened up either through a new business development or attrition as someone retired. My father was very much in control of the company and advanced us within the organization according to our talents.”

Strasburger, who is now CEO of retail management company StrasGlobal, said his father instilled in him “a deep sense of responsibility and duty for taking care of our employees and their families.”  

“We had to work hard to make sure the business was a success, not just for the owners’ sake but because hundreds of people relied on us for their livelihood. That felt like a huge responsibility,” he said. “If we were having a lean year, it was family members’ salaries that were cut or [there were] no bonuses taken by us [because] we had ‘sweat equity,’ rather than our employees.”

Strasburger also felt a need to prove himself, not just to his father but also the entire company.

“I felt that I had to be seen doing more than my share so as to not be seen as a ‘nepo baby,’ a term that was not in existence at the time,” he said. “I worked long hours and traveled constantly, internationally as well as domestically, sometimes being away from home for up to three weeks at a time. And family gatherings often resulted in work sessions—some fun, as we bandied ideas and strategies around, but other less so if you were exhausted and needed a break from work.”

Earp said her family goes out of its way to separate work and home life.

“We try not to talk business at the table. Business stays business,” she said. “At the dinner table, let’s enjoy each other’s company, and when we go back to the office the next day, we’ll pick up where business left off.”

She also cites distinct advantages of working with family.

“It’s nice to be able to feel comfortable having the discussions you need to have that you might feel uncomfortable about if you weren’t family,” Earp said. “My father, my uncle, my cousin, they’re going to be OK with me if our opinions differ. At the end of the day, we’re still family.”

Plan for Succession

Nearly 50 years after opening their first c-store—and about 25 years since Roy Strasburger joined the family business—he and his father concluded in 2012 that it was time to sell the retail assets of the company and focus on its other business arms, including third-party c-store operation, c-store design, travel, agribusiness and banking.

“The sale allows us to focus on the provision of our convenience management services to property owners,” Straburger said at the time.

But the other reason to sell came down to a common problem in family businesses. “The next generation was not interested in continuing with the business,” he said, “and we received a good offer.”

The lack of an interested heir echoes through family business sell-offs. However, the decision to sell COC Properties’ retail business was based on strategy and finances, Stephenson said.

“Like a lot of distributorships, you’ve got different parts and different pieces, and they’ve grown at different paces. They’ve been capitalized at different amounts over the years,” he said. “And so just in the process of thinking about where we’re going to be in the future, where we had particular passion and creativity, where we wanted to deploy capital, it was a fairly quick decision to think more carefully about a strategic decision around our convenience stores.”

Today, there are two third-generation Stephenson family members in the company, one of whom will move from the convenience side into the oil business. Craig Stephenson, meanwhile, is planning his exit from management of the company; he intends to transition to a role of governance as a board member by fall. He said it’s bittersweet to say goodbye to convenience retailing.

“It’s a marvelous business. ... It’s a very difficult business. It’s operations-intensive. It’s labor-intensive,” he said. “I can say I certainly will miss the people side. Being able to provide meaningful work to folks and watch them grow and thrive and take on new positions of leadership is something that I will miss. [That] was very instrumental in our decision, our principal decision for how to sell and to whom to sell.”

COC Properties sold its 15 Breeze Thru Market c-stores to Sampson-Bladen Oil in June.

“We’ve known them for years,” Stephenson said, “and I’m very excited about their management of these assets and these people.”

Still Growing

Back over at Good Oil, Earp said the company is not selling but growing. In May, the company acquired five Big Mike’s Gas N Go convenience stores in Ohio, expanding to 20 locations in central Indiana, Illinois and now Ohio. It plans additional growth across the Midwest. 

The company also appears to be set for at least one more generation of the Good family, Earp said. Her oldest daughter “has wanted to join the business since she was probably in kindergarten,” she said. “She would play a game with us called ‘Interview Me,’ where she liked to be interviewed like she was going to be hired onto the job.”

Now in high school, the fourth-generation daughter got her first taste of the job this summer.

“She gets to start where I started, [on the] paint crew,” Earp said. “She gets to paint curbs just like I did.”