What It’s Like To Be An Entrepreneur With OCD

Some creative behavioral solutions helped David Schottenstein, cofounder of Viewabill, turn a challenge into an asset.

What It’s Like To Be An Entrepreneur With OCD
[Buses: American Spirit via Shutterstock]

Lots of people joke about “being OCD,” but for some entrepreneurs, it’s literal.


David Schottenstein doesn’t remember a time when he didn’t have obsessive-compulsive disorder. As a young child, on the bus home from school, he was so obsessed with his homework that he would occupy an entire seat, spread out his books, and not let anyone talk to him. When he wanted to arrange a sleepover with a friend, he would schedule it three weeks in advance, calling the friend regularly to re-confirm.

David Schottenstein

He knows he could be less fortunate–a cousin has the disorder so bad that he slathers himself in Purell simply when someone passes near him. Schottenstein doesn’t have the germaphobic variant. “Mine was always centered around tasks,” he says. “I would obsess about making lists of tasks and checking each box off to make sure I was on track–whether I was seven years old, or I was 30 years old and running a business.”

As an entrepreneur, having OCD has been both a blessing and a curse (as anyone who claims it–jokingly or not–probably already knows). Schottenstein founded and sold a menswear company, Astor & Black, and then, with Alan Dershowitz, (created a billable hours tracker), Viewabill. OCD evidently didn’t prevent success, but in recent years, Schottenstein began to feel it getting in the way. When he owned Astor & Black, he often sent his sales associates text messages reading “???” if they didn’t respond right away, something he insists they eventually found “endearing.” But now that Schottenstein was taking on a more sensitive endeavor–pitching law firms on the idea that they should adopt a piece of software that tracks their billable hours–this “endearing” persistence was wearing thin. Some firms started telling Schottenstein’s cofounder, Robbie Friedman, that they were sick of hearing from Schottenstein.

“They hate you,” he recalls Friedman telling him. “They really hate you.”

Meanwhile, Schottenstein was having trouble at home. After selling Astor & Black, Schottenstein treated himself and his family to a two-week vacation in Israel. But the whole time, he wasn’t able to stop looking at his phone. An Orthodox Jew who is supposed to set aside electronics on the Sabbath, he got in the habit of asking the family’s non-Jewish nanny to check his phone for him every hour. (“She wanted to murder me,” he says.) Finally, one night, as he and his wife were getting ready to put their children to sleep, his daughter said, “Could Mommy put me to sleep?” Schottenstein asked his daughter why. “You’re always pulling out your phone,” she said.

“I thought, ‘Something’s wrong. This is not the way we’re supposed to live life.’”


A less obsessive person might have tried any local therapist in Columbus, Ohio, where he lives. But Schottenstein didn’t want to waste time wondering if he was getting the best possible treatment. So Schottenstein called his cousin–yes, the one with the Purell. His cousin recommended Dr. Michael Jenike, a famed Harvard psychiatrist who specializes in OCD. “If I’m gonna do it, I’m gonna do it right away 100%,” he says. “I wanted to start from the top.”

Schottenstein and his wife visited the doctor in the fall of 2011. Schottenstein recalls that the doctor explained to him that his phone addiction was similar to any other–“I was just shooting up in a different way.” And the doctor was able to tap into something that Schottenstein prides himself on: “One thing I have a lot of is self-control,” he says. The doctor challenged Schottenstein to hand his wife his phone for two hours upon leaving the office, then to email him at the end of the ordeal.

“He told me the first 15, 20, or 30 minutes, I’d feel miserable, but the last hour and a half I’d feel fine,” recalls Schottenstein. In truth, he recalls feeling miserable for 45 minutes. “But then my wife and I got talking, and I got engrossed in our conversation, and I didn’t think about the phone until the alarm went off.” Now, whenever Schottenstein and his wife go to dinner with friends, he wordlessly hands the phone off to her.

The trick, Schottenstein has found, is to leverage the parts of your OCD that help you stay on task, while discarding the others, he says. “You have to be OCD about dealing with your OCD.”

As Schottenstein got better about managing his OCD, he was more able to let go of aspects of Viewabill, when it was for the good of the business. “I had to recognize that it was not good for the company to have me interfacing with the law firms,” he admits. “So I took a big step down, and I decided to channel my energies in ways that are more helpful–on the client side of things.” Now, a year and a half after that decision, Schottenstein says that nearly 100 law firms are connected on Viewabill. Some of them are even taking an active hand in suggesting ways Viewabill might improve the product to make it more appealing to firms, by enabling them to track their own attorneys’ time internally, for instance.

“All of that only happened because I recognized that my OCD was leading me to drive these people crazy,” he says. “The relationships have gotten so much better now–because I’m not allowed to talk to them!”

About the author

David Zax is a contributing writer for Fast Company. His writing has appeared in many publications, including Smithsonian, Slate, Wired, and The Wall Street Journal.