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A Founder Is A Staff Of One: How To Delegate To Yourself

CEO, CFO, CTO . . . how does a solo founder juggle those roles? Olga Vidisheva of Shoptiques, who’s done it, has useful, color-coded ideas.

A Founder Is A Staff Of One: How To Delegate To Yourself
Shoptiques CEO Olga Vidishevas used some intensive compartmentalization techniques to help get her company off the ground all by herself. [Photos: Jeff Mikkelson]

Walk into the lower Manhattan offices of Shoptiques, a boutique shopping website, and you’re confronted with dozens of stylish employees clustered at desks representing different departments: technology, customer service, sales, and so on. Each Monday, Olga Vidisheva, Shoptiques’s CEO, meets with the leaders of those departments, setting goals for them through the week. But just a few years ago, all of those departments–and each of those leaders, in a sense–had to exist in just one brain: that of Vidisheva herself, who founded Shoptiques on her own.

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Olga Vidisheva (left) in the officePhoto: Bridget Badore

When Vidisheva first founded the company, she drew a diagram that looked sort of like a family tree. At the top was the word “Shoptiques.” Then three branches representing the three pillars of the business she envisioned: boutiques, customers, and the platform. Then, beneath those, branches representing roles related to each of those pillars. She had created a taxonomy of jobs she would like to hire for, but she had no money to hire. Instead, she realized, there would have to be seven or eight Olga Vidishevas: CEO, CFO, CTO, salesperson, data person, and so on.

A less organized person might simply have listed tasks she needed to achieve, and gone down the tasks one by one, or worse, have attempted to address tasks as they arose, pell-mell. But Vidisheva remembered something someone had told her about engineers: “They said they’re like jugglers juggling these little balls. If you interrupt them, the balls will fall down, and you’ll have to start juggling again, and that might take 15 to 20 minutes.” Vidisheva realized that as a CEO/CFO/CTO/etc., all in one, she too was a juggler. “I had to juggle roles.” And it was important not to interrupt herself.

A look inside Vidishevas’s notebookPhoto: Bridget Badore

She realized that in order to achieve peak efficiency, she would need to essentially schedule blocks of time for her to be a different, specific person. For a four-hour block on Saturdays, she might be a CEO in blue-sky mode, thinking exclusively about long-term strategy. Tuesday morning she might have blocked out for media relations, Wednesday morning for customer service, and so on. “I was putting different hats on,” she recalls now. And once a hat was on, it stayed on. If CEO Olga got an idea that was best delegated to sales manager Olga, then the former sent the latter an email, to be addressed later. “I would walk into a store and think, ‘I need to be thinking about this–but I’m not thinking about it now.’”

She recalls those early days that the minimum useful unit of time to wear a certain hat was two hours, but that it was preferable to wear no more than two hats in one day. A well-scheduled day might have half the day in one role, half the day in another. There was strategy behind the schedule of hat wearing, too: Sales made most sense for weekdays in the late mornings, when boutiques just opened. Mission-critical financial stuff was best done on weekends, when the coworking space she worked in at the time was quiet and empty, allowing laser focus.

She became expert at labeling emails, using different colored flags in Apple’s Mail program. Finance-related emails were labeled one color, sales-related emails another, and so on, and she would turn to them when the schedule called for it. Her inbox to this day is essentially a multicolored to-do list. “People who are not efficient try to do things as they come,” she says. She’s noticed the staff members who respond to her emails right away; to help them be more efficient, she instead sends them fewer, longer emails that group multiple directives together.

The Shoptiques team today

It takes a preternatural degree of focus to do what Vidisheva did, as well as a real passion for her business (in the early days, she says, she worked about 18 hours a day). But even those lacking that degree of focus or drive can experiment with Vidisheva’s technique, she says, simply by getting a little more aggressive with Google Calendar, perhaps with just a fraction of your days to start. Her sister is applying to medical school, for instance, and Vidisheva has coached her into scheduling discrete units of time through the week to focus on her essay. “When you separate your schedule, you know ahead of time when you’ll get everything done. You’re never surprised. There’s never, like: ‘Oops! I never got to that!’”

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The job of a solo founder can be daunting, says Vidisheva. “You’re trying to get so much done, you don’t know where to start, but unless you start somewhere nothing will get done,” she says. “I’ve seen people paralyzed by that.”

If you’re founding a company, and staring down a list that seems like the work of 10 people, be reassured that it probably is the work of 10 people. All you need to do is realize that those 10 people are you.

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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

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