Living (And Running A Start-up) Without Fear

On paper Dina Kaplan had it all: a co-founder of, a successful platform for original web series which raised more than $20 million in venture capital, Kaplan was at the heart of the New York tech scene, heading up both the networking group The Founders Club, which became a quarterly invitation-only networking event that’s a must-attend for the city’s movers and shakers such as media mogul Rupert Murdoch and Mayor Michael Bloomberg, as well as the Calliope Group, an organization that gathers women founders of tech companies such as Gilt Group, Rent The Runway and Paperless Post as well as senior executives from Google, Entertainment Weekly and Conde Nast.

Kaplan was invited to a World Economic Forum meeting in China and was named one of Fortune Magazine’s most powerful women entrepreneurs. She spoke at Fortune’s Most Powerful Women Summit, along with Hillary Clinton (then U.S. Secretary of State) and American fashion designer Tory Birch. She was also named, along with Huffington Post founder Arianna Huffington, one of Fast Company’s Most Influential Women of Web 2.0.

“From the outside my life looked perfect,” says Kaplan, a scheduled speaker at LeWeb, an Internet conference in Paris taking place from December 10th to 12th. “But what I felt on the inside was the exact opposite. All of these accolades and huge opportunities to support women in tech were really important to me and my company was doing great. But all this fear made it not worth it in the end.”

After seven and a half years of working 24/7 in start-up mode Kaplan was suffering from severe burnout and — although she hid it well — felt crippled by fear.

“In a company of 75 people I was running six departments by myself which was absolutely crazy,” says Kaplan. “I was in charge of finance, business development, PR, the marketing, HR and investor relations and all without even one full-time direct report. I was afraid to be vulnerable and ask for help, afraid I wasn’t good enough to deserve a staff and equally afraid that I wouldn’t be a good enough boss.”

There were no women role models for women to look up to,” says Kaplan. “I kept asking myself, ‘What would Mark Zuckerberg or Jeff Bezos do?’ And the answer I told myself was, ‘Work harder — work more hours.’ I had this image of [Google founders] Larry and Sergey sleeping in sleeping bags in the hallway of their offices and I thought that is what I should do — that everything I did should be in service to the company. I was working every night, every weekend, through vacations.”

Kaplan recalls one vacation with her family in Italy. “We went cycling. When we stopped at each red light I would respond to each and every email, including checking things with lawyers, then I would have to race to catch up with everyone and then, at the next red light, do it all over again. That was my idea of a vacation.”

Finally, she decided she had had enough. In early November 2011 she told her surprised family that she was going to leave the company that she had worked so hard and so long to build. She bought a one-way ticket to Indonesia and left on December 21st, 2011, the start of a year-and-a-half-long trip around the globe. “I wanted to live an opposite life on an opposite side of the world,” says Kaplan.

She took to heart the advice of a man she met on the first leg of her journey who told her “use the time given you to conquer all your fears.”

Kaplan did just that, forcing herself to do things that scared her, including scuba diving (because she watched someone she knew die during a scuba trip when she was young); zip-lining at 40 meters; and bungee-jumping.

The bungee-jumping in New Zealand was the toughest. After much hesitation she says she looked down and thought, “I am not doing this for the peer pressure. I am doing this because I need to change my life. And then I jumped. I felt tingles in my whole body from the tips of my fingers to my toes. I had made the leap. I had moved into my new world. I was now going to live without fear because I had conquered every physical fear I had.”

Kaplan is currently living in the U.S., preparing to launch a new start-up. But this time will be different, she says.

“I’ve been back since the beginning of September and life is really different, both personally and professionally,” says Kaplan. She now makes time to meditate twice daily. “The message I am going to give at LeWeb is the importance of mindfulness for entrepreneurs, to be aware of what you need and be aware of your emotions. You can calibrate your life to suit what is good for you and you can do a much better job running your company or investing if you live a mindful life.”

At, Kaplan says she would not allow employees to work from home. In her new company she will not only be more flexible about where people work but about how they work. Some people work well in 90-minute spurts, she says, and then need to take a break and do yoga or something else. “Different people have different styles so we will adapt to have happy, productive employees,” says Kaplan. That approach will also be good for the productivity of the company, she says. “If you are knee-deep in operations and working nonstop you can lose sight of the strategy of the company and the market. You need to leave some white space in your day to think big-picture thoughts or to find creative solutions to a problem.”

In her new company, she says, “I will focus a lot more on people and encourage those I work with to maintain great relations with their families and loved ones instead of thinking of that as a distraction. I am going to get angry with people if they are sending out too many emails on weekends or late at night instead of spending time with family and friends because these are important relationships that feed happiness.”

One of the biggest lessons learned over the last year and a half was that “there are three types of currencies,” says Kaplan. “Money, peace of mind and freedom, and if you have the last two you are actually doing pretty well.”

And as Kaplan herself as learned, when it comes to running start-ups, it also helps to be fearless. “I heartily recommend it,” she says. “It makes you happier, better at your job and better with people — personally and professionally.”