Some founders learn to build a business by going to business school or climbing the corporate ladder, others seem to be born with the knack and manage nothing bigger than a lemonade stand before starting up.

But Diane Greene, co-founder of billion-dollar software company VMWare, attended a far more unusual startup school--the sea.

"Building a company is so much like racing a sailboat."

In a fascinating recent interview at Y Combinator's Female Founders Conference, the three-time entrepreneur turned Google executive explained how she grew up on the Chesapeake Bay and learned to sail at a young age.

"I soon found myself taking off on long sails in my little sailing dinghy, and this was formative," she told the audience. Later, Greene raced sailboats competitively and became an avid windsurfer.

The lessons she learned weren't all nautical in nature. Sailing, she explained, was what taught her the skills she would later use to lead VMWare to a $19 billion IPO.

"Building a company is so much like racing a sailboat," Greene said. "More than anything, I think my connection to the sea has really helped me develop my independence and a sense of the importance and value of my own vision." What specific lessons did she learn?

  1. Observe carefully. "To sail successfully, you need to observe with great care. You need to identify what the wind and the water are telling you and then find a way to execute, to reach whatever goal you've set, be that simply making it home or winning a race," Greene said. Entrepreneurship requires a similar dedication to keeping an eye out for the first ripple of change or trouble.
  2. React quickly. Once something does change, you need to respond fast. "You need a plan and then the ability to reevaluate the plan in real time as new information is acquired.... When it's time to make a decision, a competitor's come upon you, or the wind shifted, you make it. The race won't wait for you," Greene explained.
  3. Jettison self-doubt. Successful sailors strike a delicate balance between healthy self-evaluation and paralyzing self-doubt. So do founders. "When you campaign a sailboat, you need to be in the moment. You need to let go of your self-doubt, and yet you can't lose the ability to question your decisions," noted Greene.
  4. The right team is all important. "When you race a sailboat, the selection of your crew is just completely paramount. It's impossible to be an effective skipper if you don't have the right people working harmoniously in the right roles," Greene said. The same is true of startups.
  5. Enjoy the process. "The bottom line in sailing a boat or building a company is that you give it your all. You give it your all, not because you're supposed to, not because that's what makes you win, but because you have respect for your goal and you enjoy the process. As a company founder, enjoy building things. Enjoy creating value," Greene concluded.

The undersung value of hobbies for entrepreneurs.

Check out the complete talk below for lots more insights, but perhaps the biggest, most actionable takeaway of Greene's talk isn't anything specific to sailing at all (most of you probably can't run out and start racing dinghies, after all). Instead, it's the value of any hobby at all for entrepreneurs.

While Greene's passion may be unique, other successful founders have come out to say how their hobbies--from horseback riding and surfing to long-distance running and mountain climbing--have been instrumental in instilling the grit, clarity, and fearlessness required to grow their businesses. Plus, studies and personal accountants say the mental break provided by these pastimes boosts both creativity and work performance.

So if you're a bit of a couch potato during your off hours, let Greene and other active founders inspire you to consider taking up a mind-clearing, resilience-boosting hobby.

Published on: Aug 14, 2017