Bridging The Gap

Ol' Will Shakespeare said it centuries ago: ''Crabbed age and youth cannot live together.'' Maybe not. But they can incorporate.
Magazine Contributor
10 min read

This story appears in the September 2000 issue of . Subscribe »

Somewhere in the middle of New York City, in a small art auction house, there's a crack in the foundation. Even the best building inspector on the block wouldn't find the crack in the walls of Swann Galleries, because the crack is a chasm. A gap, really. A generation gap.

And the entrepreneurs are the foundation. Nicholas and George Lowry own Swann Galleries. Nicholas is 32; his dad, George, is 69. Sometimes they disagree on how to run their business. "Whenever there's an age gap between business owners, there are points of contention," says Nicholas.

For instance, Nicholas recalls the arguments with his father when they were updating their offices and corporate logo: "We are now a 21st century company," Nicholas had argued. "We can't have a 17th century look!" So the offices as well as the logo finally changed, "radically." And the business is still thriving.

Partner with a person just 10 years your senior, and you may feel like you've teamed up with your older brother. Which could be a problem, if your brother would give you a wedgie in a room of VCs.

Then there are questions you're likely to ask when your partner is 20 years older: Will I be sent to my office after a disagreement? Can I borrow the company car? Is Dad going to apologize for the Christmas Eve I saw Santa making out with Mom?

Er, um, anyway, Gen X is bridging the generation gap every day with stunning success. In 1997, Jaye Muller was 24 when he hired then 38-year-old Richard Ressler to take the role of CEO and run his then-stalled New York City company, JFAX.COM, a high-tech fax delivery system. Together, Muller and Ressler forged a powerhouse that has clients in 200 countries and brought in $7 million last year. It's a firm so successful, it's allowed Muller to get back to the thing that fires him up the most: making music.

A CEO With Experience

Muller really is a musician. In fact, he did this interview from the studio, where he's recording his second CD. The story goes that in 1994, Muller was touring in the United Kingdom, when he was so sick of missing faxes, he had a brainstorm. JFAX was a hit.

But three years later, when the firm was solid, with a staff of 15 and sales trickling in, he felt he needed an older, wiser partner who could "take the company to the next level," says Muller. He hired Ressler, one of his major investors, as his CEO.

Ressler was then 38, a man who had been in business for his entire adult life and owned an investment and consulting firm. Ressler usually would invest millions in a company, take it over for a few months, and then, with his wallet fat and the firm a success, he'd move on. In Old West terms, Ressler was the sheriff that showed up, chased the bad guys out of town and rode off into the sunset with the girl.

At JFAX.COM, Ressler stayed longer than usual: He was the CEO for almost four years, and earlier this year, he stepped down but is staying on as the company chairman. Ressler and Muller's relationship was simple. Ressler worked on the day-to-day operations, like any CEO, while Muller was the frontman, handling the press and hunting for venture capital.

Weed out the rest to find the best. Gone Fishin' will show you how to lure a head honcho with a good reputation.

Muller didn't immediately hand the reigns to Ressler. It was a six-month transition period in which the two talked for hours, not only about the company, but also about politics, current events and music. "You have to have something in common other than just the business, and you have to like each other," warns Muller. "Otherwise, it just won't work."

Ressler agrees, cautioning younger entrepreneurs not to be too enchanted by an older entrepreneur's experience: "Make sure you have a partner who has the skills you need. Being older doesn't automatically mean they have the right experience."

In fact, both men say the 13-year age gap never really mattered. "Well, he's younger, thinner and better-looking," laughs Ressler, "but, otherwise, no. I don't think age really comes into play-at least not in our business. We brought different experiences to JFAX."


Learning From Other Generations

When people of different ages work together, however, problems can arise. If they didn't, Lynne Lancaster, 42, and David Stillman, 31, wouldn't own BridgeWorks LLC, a San Francisco and Minneapolis-based consulting firm that specializes in explaining to large enterprises, crammed with different generations, how we can all just get along.

Lancaster initially was a career counselor for Stillman, who previously worked in the high-tech field. They started becoming friends and learning something about each other's age groups along the way. Stillman believed that baby boomers were workaholics at the expense of everything else; Lancaster thought Gen Xers were lazy, impatient and unable to hold a job.

But as they talked, Stillman learned why Lancaster--and boomers--appeared to be workaholics. They had grown up in a different era. A scary era. Lancaster had grown up being promised the world; her own father, who graduated from college in the 1950s, had six or seven job offers almost immediately. But when Lancaster graduated in the late 1970s, there was a recession. "Just as this humongous force entered the job market," she muses.

Meanwhile, Stillman vividly remembers watching his parents' generation being downsized out of jobs left and right. He wasn't promised the world; actually, he was told, "Your generation is going to be the first generation ever to do worse than your parents."

Lancaster applied for jobs that had 400 other applicants going for them, so when she found her first job, like a goldfish pulled out of a piranha tank, she was going to do everything she could do to stay with the company. Stillman, on the other hand, conditioned himself not to allow his career to thrive at the expense of his life.

Man must choose wisely when choosing a partner. A business partner, that is. Take some advice on how to do it in Partners Are From Mars.

Fascinated by their generational differences, the two went into business together. And even as they host seminars and advise entrepreneurs and employees, Lancaster and Stillman still struggle with their generation gap.

Lancaster recalls an instance when Stillman was scheduled to be interviewed by a national magazine. When Lancaster called Stillman at home to see how it went, he said, "Oh, yeah. I had to blow her off." Fresh from a two-day business trip and unwilling to give up putting his kids to bed, Stillman rescheduled for the following Monday morning when the writer called later than they had planned.

"I would have called my husband, skipped dinner and stayed at my desk to get the job done," says Lancaster. But when she called the editor the next week to see if she had all the necessary information for the article, "the first words out of her mouth were, 'Oh, I just love your Generation X partner. He has the best values.' "

Stillman notes that when his partner was his age, competition was so stiff that "if she hadn't done the interview, there would have been 80 million people willing to do it."

Lancaster answers her own question of who has the better values: "Neither one of us. They're just different."

A Wise CEO For A Start-Up

Dennis M. Lynch is the founder of, an Edgewood, New York, business-to-business auction site that specializes in the asset recovery of pre-owned and off-lease technology.

Lynch, 31, hired Wade Clowes, 46, to be his COO, and then asked him to be the CEO four weeks later. The two men have an obvious generation gap, in both ages and experiences. As Lynch puts it: "Wade wears khaki pants and a nice, white, collared shirt--everything ironed, nicely shaven, and his hair looks great! I wear the same pair of jeans that I wore yesterday, a New York Yankees sweatshirt, sneakers--I haven't shaved for two days, and I need a haircut."

Wade is on time; Dennis isn't. ("I'll be late to my own funeral," he promises.) Wade is mature; Dennis has a "wild" streak. Wade listens to their staff; Dennis needs to learn to delegate. Wade is patient; Dennis-well, you get the idea. "But at the end of the day," concludes Lynch, "we both love margin, we both drive revenue, and we both love to work hard."

As indispensable as Clowes is, Lynch advises his peers: "Never hire an older corporate guy to start your start-up. It will never get going. You have to be the CEO and get it going. You'll know if you've been a success-your business will have grown beyond your wildest dreams."

You don't get just one, but a variety of partnerships to choose from! Read Partnership to pick out the one that fits you best.

And when that happens? Lynch says it's important to realize when it's time to hire an older, wiser CEO. If he had hired someone his own age to be the CEO? "We would be brawling in the parking lot every day," says Lynch. "I needed maturity and experience, not another ego."

Lynch, who runs the technical side of, performed ably: "I got us far, real fast," he says. "[But it's Clowes] who will use his skills and maturity to bring us to the next level. I have no experience with that. But that's OK, because when I am 40, I will know both ends of this game. I will know what I taught myself as a start-up, and I will know how to run a big ship--what I've learned from Wade."

Opposites Attract

His knees give out on him sometimes when he plays softball. He listens to older music, not "that '80s stuff." But at age 46, Wade Clowes may be the youngest guy on the block. After all, if you're in your 20s and just starting a business, how much do you really stand to lose, other than your dignity and priority-registration on that new MasterCard in the mail? However, Clowes left a top-level job at Hewlett-Packard to work at a dotcom, a hip, happening but hardly guaranteed-to-succeed way to make a living.

But just because Clowes has a sense of derring-do doesn't mean it's easy to work with a younger entrepreneur. "There are natural tensions," admits Clowes, who surmises that people like Lynch seek people like himself because "they want somebody who thinks in a processed fashion, yet somebody who moves quickly. I think if you have one or the other personality type, you're in trouble. So I would expect that the kind of interaction we have is pretty typical."

In fact, when he goes to meetings in his suit and Lynch wears jeans, the investors don't blink an eye. Says Clowes, "Dennis is the young entrepreneur. They almost expect a different, or relaxed, look. I think a lot of investors come aboard because they know that that kind of natural tension is healthy."

Lest he create a generation gap in his easily embarrassed family, Geoff Williams wants to make clear that he didn't really come down the stairs one Christmas Eve to find his mom making out with Santa.

Contact Sources

BridgeWorks LLC, (888) 519-1187,

Swann Galeries, (212) 254-4710, fax: (212) 979-1017.

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