Six Entrepreneurs, One Question: ‘What Inspires You?’

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Boston tech influencers have at least one thing in common: a commitment to creating successful outcomes for our community through the businesses they build and the talented people they employ and mentor. They are passionate about our city and are actively cultivating and expanding our ecosystem while constantly seeking ways to improve it. The work they are doing every day is both fascinating and noteworthy, so I asked a few of them to spend an hour with me to discuss success, challenges and their approach to managing their businesses and themselves. We talked about their paths to leadership, pivotal moments of learning, their habits, as well as the awesome things they are building, seeing and seeking. Each was generous with their time and candor. To follow, are answers to one question I asked of all six of these successful Boston tech leaders.

What inspires you?

Lou Shipley, CEO, BlackDuck Software

“Winning. Not losing is probably right up there next to winning.”

Kirk Arnold, CEO, Datagravity

“Great leadership.  I’m a bit of a student of leadership. I’m still learning and I am ever more convinced that successful business is about talent. I was mentored at one point by Jim Collins and the big take away that he was working on with me as part of my leadership experience was that teams come before strategy. That was totally counterintuitive to me at the time, but it proved to be the best counsel I have ever got and also the hardest thing to do. I am inspired by great leadership every day at every level and a huge believer in leadership team building -- it’s a team sport. When I see it done well, and there are a lot of folks here who do it very well, putting great teams together, it causes me to really reflect and extend and think about how I can do it better. Great teams build great businesses.”

Brian Shin, Founder and CEO, Visible Measures

“Two things: I think just to see something created from nothing is the ultimate excitement and high. The other that really motivates me is that I have the dream to create value for people.  That’s why I still do this. If a young person here can potentially make enough money where they can take a year off to start a company of their own, that would be amazing.”

Diane Hessan, Entrepreneur, Marketer, Investor

“I love walking all over Boston -- especially along Fort Port Channel and in Seaport.  When C Space moved to that area in 2010, it was a dead neighborhood, with mostly parking lots, and a bit of construction.  Over the years, when I needed to think, I would stand in my office, stare out the window, and watch the buildings go up, like magic.  Now, it is transformed -- full of energy and creativity.  It symbolizes how something amazing can arise from nothing.  And, it puts everything into perspective because you know you have all these problems, but it’s a really big world out there -- you aren’t the center of the universe.”

Ellen Rubin, CEO and Co-founder, ClearSky Data

“I really, really enjoy hanging out with smart, talented engineers. I am a sales person at heart. I love marketing and talking to customers, but when you hang out with someone who is a brilliant technical idea person, they just see the world in a different way. They see it as, 'How do I fix that? How do I make it better? What's a cool thing that I could create that would dramatically change things for those who are going to use it?' My job is to shepherd those ideas and figure out how to build businesses around them. I get very inspired by that."

David Cancel, Founder & CEO, Drift

“Getting better, learning, progressing. Family inspires me, teams inspire me. A lot of stuff inspires me… I think about it everyday. I don’t wait for inspiration.  You need to create your own.”

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