The Definitive Guide to Business

Ex-Google employees turned start-up CEOs: Master this skill to be successful

Founder and CEO of Vida Health Stephanie Tilenius (L) and Founder and CEO of Drawbridge Kamakshi Sivaramakrishnan.
Photo by Andrew Toth
Founder and CEO of Vida Health Stephanie Tilenius (L) and Founder and CEO of Drawbridge Kamakshi Sivaramakrishnan.

The most critical part of launching a successful start-up can also be the hardest — learning how to navigate calmly forward in a fast-moving, ever-changing environment.

"I have learned, as an entrepreneur, the most important skill you have to have is you have to be an optimist and pessimist at the same time," said Stephanie Tilenius, former Google VP and founder of Vida, an app that pairs you with 24/7 access to a health coach.

"The hardest thing is the psychology of it," she said.

Tilenius said she has to be both relentlessly optimistic about her long-term goals for the company and brutally honest about what's not working in the day-to-day operations.

"You have got this 10-year vision and you know where you want to go ... that's why you started a company," said Tilenius, speaking at the Vanity Fair Founders Fair in New York City recently. But "you have got to be really pessimistic about things that you are doing that may not work" to actually get there, she said.

Because in a start-up environment, mistakes must be immediately addressed for the start-up to survive. "You have got to move fast," she said.

"Playing that optimist and that pessimist and knowing that right balance at all times is really hard," says Tilenius.

Indeed, it's "a constant game of risk management," says founder Kamakshi Sivaramakrishnan, who also worked at Google but left in 2010 to launch Drawbridge, a company that builds technology to connect users' screens and devices without relying on their personal security information. The company has raised $45.5 million in venture capital and its tech reaches more than 1.3 billion consumers across more than 3.3 billion devices globally.

"You have to really get comfortable with being uncomfortable." -Kamakshi Sivaramakrishnan, founder of Drawbridge

"The high is high, and the low is low, and it will happen in a matter of minutes," Sivaramakrishnan said at Founders Fair.

"You have to really get comfortable with being uncomfortable," she said. "[It's] a self-training that you have got to go through."

See also:

Entrepreneurs reveal 5 things they learned from working at Google that helped them get ahead

Why one exec passed up the chance to be president of this $127 billion company

What this entrepreneur learned co-founding a company with billionaire VC Marc Andreessen