Sibling Rivalry
Like Jeff, children of successful entrepreneurs often feel trapped—either because the founder is unwilling to cede control or because they themselves are ambivalent about their role in the family business. Family business counselors say that before heirs such as Jeff and Jay Sullivan can confront a parent about issues such as succession, they must recognize the role that the business has played in their families, and how they feel about it.

“For most founders, the business they create is their favorite child,” says Bill Provett, facilitator at the Family Business Institute in Raleigh, N.C. “The kids have seen dad taking care of the favorite child, spending all of his time and all of his energy on it.” Provett says that children internalize the sacred status of the business as a result. They may also come to loath the idea of joining the business, because they see how much their father has to work, and how the business consumes him.

“The business literally takes a seat at the dinner table, and the kids either hate it or love it from early on,” says Fredda Herz Brown, managing partner at the Metropolitan Group in Cresskill, N.J., a consulting company that counsels entrepreneurial families on generational conflicts. “The parent’s emotional need to perpetuate the business gets introduced early on.” Members of the second generation can see their role in the family as contingent upon their role in the business. Jeff found this to be the case. “I didn’t think I could leave the company. It wasn’t even an issue of loyalty. You just don’t stop being someone’s son.”

Jeff and his brother felt trapped and increasingly unhappy. When the economy was shaken in September 2001, the company’s sales plummeted. The crisis forced the family to reconsider the company’s future and allowed Jeff, for the first time, to begin to envision a path for himself that did not include the family business. “The day I realized that I could go do something else—sell bananas, or anything else for that matter—that was a real shift for me. I could say to my dad: ‘We’re going to solve this or I’m out of here.’ ”

Ultimately, the Sullivans hired consultant Jim Hutcheson of Regeneration Partners in Dallas to broker a succession plan, which relieved tension on all sides. Hutcheson had worked with other clients on succession issues like those that bedeviled the Sullivans. The founder who refuses to exit gracefully is a common problem, he says. “Work gives them a reason to get out of bed in the morning.”

Looking back on the experience now, Jeff wishes he had taken control of his destiny earlier. He could have worked elsewhere for a while to gain experience and confidence. He could have challenged his father earlier and threatened to quit if he was not free to make his own decisions and mistakes. He could have given himself permission to leave.

In the Wake of a Titan
Often, it takes a crisis of some kind to bring the issues to a head and to force the founder to recognize that the time to leave center stage is nearing. However, a family business succession is not the product of dispassionate corporate executives considering tactics with professional sangfroid. The architects of these plans have both a professional and emotional stake in their success.

They are also, typically, strong-willed individuals. Builders of successful businesses are often absentee parents who have taken enormous financial risks—and won. Their children do not just know the story of the family’s success, they have watched it unfold. Like Jeff, they may feel unable to challenge their larger-than-life parents on anything. “The children of entrepreneurs have enormous admiration for their fathers, because they sat right there and have seen what was sacrificed to create the business,” explains Leslie Mayer, CEO of Mayer Leadership Group, a consulting firm in Wayne, Pa., that advises CEOs on leadership issues. They admire their parent’s sacrifice, even if that included their relationship with their children and any possibility of a normal home life, Mayer adds. “They are not allowed to feel disappointment for what they didn’t get. They get the message that they should feel part of the sacrifice that made the business possible.”

Successful entrepreneurs are winners, Hutcheson notes. “They have organized their lives so that they succeed in spite of everything.” Rarely do their children have, or need, that drive. When the child of a successful entrepreneur enters the family business and prepares to take charge, he or she can feel inadequate to the task, even if better educated than the founder.

Members of the second generation can see their role in the family as contingent upon their role in the business.

“They try and emulate dad, but they can’t,” Provett notes. “If they entered the business at age 30, well, he entered the business before they were born. They can’t know everything he knows and everyone he knows. When they try, they are doomed to failure.”

For Richard, the son of a newspaper publisher in the Southwest, the feeling of inadequacy was reinforced everywhere he looked. “My father was tremendously popular with his employees,” he says. “I was Little Richie, who used to get stuck in the doors when I came to visit the office because I wasn’t strong enough to open them. I was an adopted son in a family of extremely smart people. My dad was Phi Beta Kappa in college and an extremely dynamic person. I was a good athlete but a poor student, and couldn’t compete with him intellectually.”

Richard did not feel up to the job of running a newspaper and overseeing the other family properties. He was also afraid the company’s employees would sense his fear and lose what little respect they had for him. When Richard joined the paper, his father devised a training program that rotated him every six months through a series of departments. “I knew I was in the spotlight with everyone watching what I did. Some people saw me as a way to get messages to my dad. Others felt that they needed to make me learn the hard way,” he recalls.

A few years after he joined the family business, Richard’s father fell ill, which caused him to rely more heavily on his son. “He promoted me to associate publisher and was complimentary to me on my work, but, really, I didn’t even report to him anymore. I had my own budget and full authority,” Richard remembers. His father died soon after, but his son continued to feel inadequate, even years later. Employees continued to talk about his father, and some even claimed that they had seen and spoken with his ghost. Richard laughs about it now, and sees it as a testament to his father’s charisma, but for years it was an unwelcome reminder of the differences between the two men. 

Harvard vs. Hard Knocks
Members of the second generation often attempt to offset their lack of real-world experience with knowledge and perspective. The heirs of entrepreneurs may have studied business in college or even graduate school, while the founder often learned everything he knows in the marketplace. “The second generation is the first to get some formal education related to business processes and strategy. In some situations the business founder is beaming, saying, ‘Here is my son who is going to teach us,’ ” says Leslie Mayer, CEO of Mayer Leadership Group. “But in many cases the founder will be incredibly threatened, and will put down any ideas coming from academia. This is very frustrating to the second generation, having gone out into the world to gather resources, not being able to use them to influence the founder. It’s fertile territory for power issues in the business, entrepreneurial superiority versus educational superiority.”

Illustration by Jonathan Barkat.

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Additional Information
 The Big Picture
 The Daughter's Dilemma