First, I want to make one thing clear: I am not a runner. Before I committed to running this year’s Boston Marathon, I ran very rarely, and never went beyond 5 miles. Even now that I’ve been training for months, the team here at InsightSquared has compiled a very unflattering list of things that they can do faster than I can run a marathon.

No, I’m not running to check the Boston Marathon off my bucket list, or because I want to improve my health, or because I got caught up in the buzz that hits Boston on Patriot’s Day every year.

I’m running because one of our investors told me I should.

How it all started

Back in January, Jeff Fagnan (who, for the record, is also a good friend of mine) of FKA Atlas asked me to run as part of a group of CEOs from tech startups around Boston in support of TUGG (Technology Underwriting Greater Good), a non-profit that he co-founded in 2009.

TUGG’s mission is compelling because it is fundamentally about supporting the underdog.

It takes a venture capital approach to find risky social innovation projects that have the most potential to catalyze social change, and then helps them to expand their impact by connecting them with resources from New England’s tech community.

InsightSquared partners with TUGG and has also worked closely with a number of nonprofits in TUGG’s portfolio over the years, most notably InnerCity WeightLifting (ICW), which just opened a new location by our office in Kendall Square.

Given that we’re now next door neighbors with one of the non-profits we support, we’ve seen firsthand just how big of an impact these organizations have on the lives of young people around Boston.

Still, when Jeff proposed that I run the marathon to help support TUGG’s efforts, my first thought was, “There’s no f***-ing way I’m running 26 miles.”

However, Jeff is one of InsightSquared’s most ardent supporters, and has been throughout the past four years that we’ve grown the company. After thinking more on his offer, I couldn’t show weakness to someone who has given me so much strength, and I couldn’t let my own reservations stop me from supporting a good cause.

I have to say that I’ve taken quite a few lessons from my preparation over the past three and a half months. These three are the most important:

1. You need your team to pull you through the rough spots.

This is a lesson that is a core belief we have at InsightSquared, but my experience running has reinforced it for me.

Without Michal Schmidt, Brent Grinna, and Matthew Bellows, the three other guys running with me on Team TUGG, I would not have made it through the cold, snowy loops up and down heartbreak hill, and I probably wouldn’t show up at the start line for the marathon.

At the end of the day, no matter how much you love your work or love your sport, you will be stronger if you care about the other people that are in the fight with you.

2. It doesn’t matter where you start

I honestly didn’t think there was any way that I’d be ready to get through a marathon in just three and a half months, but our coach, Erik Hajer, convinced me otherwise.

In spite of the doubts I had going into training, the nagging injuries, and the worst winter that Boston has ever seen, Erik got us to the point where we can comfortably run 18 miles in one stretch.

Now that we’re tapering, part of me actually misses running the longer distances.

That served as a good reminder that no matter what shape you’re in when you start off, either as a business owner or as a runner, there are people out there with the knowledge and the energy to help you get to where you want to be.

3. It gets easier after the first three miles

This final lesson is especially pertinent to TUGG, and to small and medium sized businesses more generally. Having never run on a regular basis prior to committing to the marathon, I never quite understood what people meant by “runner’s high”. I get it now.

Before, I never went beyond five miles because I just couldn’t get to a point where I felt comfortable. What I never expected was that as we increased our mileage in training, I actually loosened up more the longer we went.

In fact, I’ve found that I run faster after going for an hour, and the fastest miles I’ve ever run came at the end of a half-marathon we did in training. I needed the spark from my coach and from my teammates to get started, but I get stronger the longer I go.

For companies that are just trying to get off the ground and break through in new and innovative ways, getting started is tough, and you need help to do it. For runners, that’s what having a coach and a team is all about. When it comes to social innovation, that’s what TUGG is all about.

So, to sum all that up, I’m running because I believe that the tech community can come together to solve society’s most endemic problems, and because, having trained with the TUGG team over the past three and a half months, I think I might actually enjoy it.

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Fred Shilmover
Fred is the CEO and Founder of InsightSquared.
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