
13: The Path to 1 Million Users. Twice.
08/19/15 • 29 min
Previous Episode

12: Growing oDesk to Become The Market Leader in Online Work
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:
- 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?
- What are your thoughts about Executives taking the leap to entrepreneurship, similar to your situation?
- What’s the one thing you’d leave our Execepreneur audience with?
Next Episode

14: How Did Engineers Create a New Fashion Category?
Aman Advani co-founded Ministry of Supply while at business school at MIT. They have created the performance professional category - business professional attire that's actually comfortable.
You can see from the way they run themselves that they’re engineers solving problems in the fashion space. A Fast Company piece on them put it this way “its conception, its design process, and how it interacts with customers, Ministry of Supply arguably has more in common with the likes of Apple and Google than with J. Crew “
So that's why we wanted to Amam - to understand how they've applied that hypothesis driven testing approach to the fashion space, and how you can leverage testing to benefit your business.
How have engineers created a new clothing category?
"We think with our engineering hats on more than we do with our fashion opinions or ideas. It's a deeply rooted customer insight-based focus on how can we create a new category that is not just creating a slightly better pair of socks - but a truly rethought pair of socks or rethought undershirt"
My questions this week?
- How did he wind up launching this particular business?
- How did he and his co-founders launch the then highest grossing kickstarter fashion campaign?
- How did they use their engineering background to create a new fashion category?
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