12: Growing oDesk to Become The Market Leader in Online Work

Execepreneur: From Executive to Entrepreneur

Gary Swart joined oDesk in 2005 as CEO and led the company for over 8 years, turning into the market leader in the online work industry. It was the first workplace to reach $1 billion in work, and has over 5 million freelancers and thousands of jobs posted daily. Gary led the company through a merger with #2 player eLance before leaving to join Polaris.

In this episode, part II of our conversation, he shares with us the importance of focus in a company, iterating quickly, why he thinks being an execepreneur is a good idea – and why he’s ok being hit by a pitch.

My question for Gary this week: Having been involved with large corporations like IBM, and a number of startups, what motivates you to help grow small to large and what’s your advice for execepreneurs?

“I remember flying home from Seattle in a small Alaska Airlines plane and I got claustrophobic… I said I don’t want to wake up 15 years from now saying I didn’t step up to the plate. That wasn’t going to be good enough for me. Even if I didn’t hit the ball I wanted to stand at the plate”

Questions:

1. You started to discuss focus last week and how that was critical for oDesk - can you give us examples of tradeoffs you had to make?
2. What are your thoughts about Executives taking the leap to entrepreneurship, similar to your situation?
3. What’s the one thing you’d leave our Execepreneur audience with?