May-December alliances can make sweet music

Dorsey described a friend, now 28, who was able to raise considerable money for a business that subsequently imploded, and who decided to do things differently when he started his new business. Dorsey says his buddy gave up equity in the new company to bring on more seasoned entrepreneurs, including his former college professor. “They got him his biggest customers through their relationships, yet he has the energy and creativity and puts in a lot more hours than they do,” says Dorsey. “That’s his contribution.”

“He recognized from his previous failure, where everybody was young, that there was a real value-add having a partner who’d been down the road and had been successful,” says Dorsey. “Before that, he thought he knew it all.”

Dorsey says young people can “short cut their learning curve dramatically” by bringing on someone who’s done it before. The time factor is especially critical for technology-heavy businesses, he says. “To grow fast, you often need money and contacts and experience which, many times, the younger person doesn’t have,” he says.

If the benefits are ample for the younger person, there are advantages for the more senior member of the business, as well. Dorsey says an older person often wants “to leave a legacy that’s more than financial,” and sometimes teaming up with younger blood is the way to do it.

Despite his enthusiasm for these types of businesses, Dorsey has caveats. “Check every reference and do due diligence,” he says. “Just because they have a good title, it doesn’t mean they’ll bring what you need to the table.” He also suggests doing a project or research together, which “helps you see how they think, and how they view the market and the opportunity.” Making sure your time lines are similar is important too. A young person may want a win, but is willing to spend ten years to build it. In contrast, an older person may not want more than a three- to five-year commitment. “The older person may want a ‘second act’ but not a long second act,” says Dorsey.

Psychological issues also need to be examined.

Tom Gegax, a management consultant with offices in Minneapolis and San Diego, says it’s not so bad for the more senior person to be fatherly or motherly. “It can be protective caring,” says Gegax, author of “The Big Book of Small Business: You Don’t Have to Run Your Business by the Seat of Your Pants” (Collins, 2007).

But Gegax says there can be a downside. You can revert to what occurs in your family of origin, he says, where mother and father issues may have been the source of dysfunction. “Some emotional components don’t go away,” cautions Gegax, underscoring that partners need to report to each other as equals.

And what about that all important notion of branding a company when the partners are of sometimes vastly different ages?

“Brands are a kind of short hand for what a company does, how it works and where it has been,” says Ira Matathia, a partner in the brand consultancy NoFormula and co-author of “Next Now: Trends for the Future” (Palgrave Macmillan, 2006). Whether such a pairing of young and old can make for a good brand, he says, “depends on the nature of the pairing, whether they are effective or ineffective at what they do.”

“I don’t think age is significantly relevant,” says Matathia. “The culture moves so quickly now. An average 24-year-old person probably knows more and has done more things than a 60-year-old person a generation ago.” 

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