Drawing a Life

Stern spent the early part of his career in the brutal world of stand-up, first as a comedian, then as a manager. He made connections with such giants as Seinfeld and Jay Leno, but as with so many others in the biz, his act never quite caught on. (As one comedian friend of Stern's put it, "It was hard for a room full of plumbers to laugh at jokes about the problems of growing up superrich.")

Abandoning the impecunious life of a struggling comic, Stern turned to executive recruiting. By the mid-1990s, he was racking up commissions as an independent recruiter, courtesy of one of the most severe labor shortages the United States has ever faced.

When the economy tanked in 2001, Stern had already pocketed plenty of money and was ready for a new challenge that would allow him to spend more time with his family. The idea for the strip hit him one night at a dinner party he threw for several friends. Someone asked what his father was like, and Stern blurted out, "Well, he's kind of a CEO Dad." The quip got some laughs, so he tried it out on other people who reacted the same way.

His original notion was to create a cartoon as marketing collateral for his executive-search business. He hired an artist to draw panels for all the gags he'd come up with, such as the kids having to vie for a corner bedroom, making allowance requests with PowerPoint, and listening to LBO-themed bedtime stories. Before long, though, CEO Dad evolved beyond marketing material into the new adventure Stern had been seeking.

But to have any shot at becoming the next Scott Adams, Stern needed more than just a knack for promotion and an ironic take on growing up with his distant father. John Newcombe,

Creators' director of comic development who picked CEO Dad from a pile of unsolicited submissions, told Stern that to get a syndication deal, he'd have to fix the strip's lousy artwork.

Using his family's friendship with the famous photographer Richard Avedon, Stern found his way into the stable of cartoonists at The New Yorker. From there, he was introduced to C. Covert Darbyshire, a young artist and aspiring comedy writer. As a bonus, Darbyshire had also served a tour of duty in pharmaceutical sales, so he had a good eye for business humor. After some wining and dining (not to mention guaranteed minimum payments and a cut of future profits), Stern hired Darbyshire to draw CEO Dad from his home in Austin, Texas.

"I'd say he's like Larry David, and I'm like Jerry Seinfeld," Darbyshire says, alluding to one of the duo's favorite cultural references, Seinfeld. "Tom comes up with the big ideas, like Larry did, while I execute and add a little bit of polish like Jerry."

Once Creators saw Darbyshire's art paired with Stern's words, the syndication deal was clinched. But even syndication is only one small step in a much longer, grueling process. Dilbert creator Adams says that anyone with above-par material can get a syndication deal; it's what happens after a strip launches that really matters. "I had a hunch about what was happening in the early 1990s, like with downsizing," Adams says. "Luckily for me, I created Dilbert at right about the same time the media wanted to put a face on what was happening in the office."

Could CEO Dad's timing be right, too? Cynthia Nash, The Seattle Times' director of content development who was one of the first to pick up the strip as a test comic, says the trick to having a good comics page is getting the right mix of topics. "I think CEO Dad has a huge resonance with modern families," she says. "There are lots of people, both men and women, who are fully engaged with work but who still want to play an important role in the family. I think this strip tackles those issues in a very charming way."

Newcombe offers a bit more caution in his assessment of CEO Dad's chances. "It's typical that we don't recoup any money on a comic strip for five years or so," he says, adding that Charles Schulz's Peanuts, the gold standard for comic strips, took many years to get off the ground and might not have lasted long enough to make it in today's market.

For his part, Stern remains confidently undaunted. "I'll go down swinging till there's no more bat in my hand!" he booms, startling the other patrons enjoying their meals at a small trattoria near his house in Woodland Hills, California. Of course, there's just one caveat to that vow: Unlike CEO Dad, he'll call it quits early if his family asks him to.

Ryan Underwood is a Fast Company staff writer.