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Rob Ramsdell Talks Head of the Charles with Kevin “Mr. Wonderful” O'Leary

Each year in October, rowers from all over the globe descend on Cambridge, Massachusetts for the world’s largest rowing competition: The Head of the Charles Regatta. Real estate advisor Rob Ramsdell, of Gibson Sotheby’s International Realty’s Cambridge office at 1762 Massachusetts Avenue, has been deeply involved in the sport of rowing and this historic regatta for years. Watch below as he catches up with Shark Tank’s Kevin O’Leary, and read on to hear more from Rob about his role as Chair of the House Committee at the Cambridge Boat Club  and what HOCR means to Cambridge. 


Tell us a bit about the Head of the Charles and the significance of the Regatta. 


The Head of the Charles was started in 1965 and was initially a small event. Over the years it's grown into the largest rowing event in the world. Over 9000 athletes travel from across the globe to participate in the 3 mile race on the Charles River. In addition to the racing, the course is also lined with vendors and sponsors, creating a festive atmosphere. Good weather is a big plus and the forecast looks great for this weekend!

How did you first get involved in rowing?  

I played basketball, soccer, and baseball at my tiny high school in rural northern Vermont. When I got to Brown University for college, I heard rowing was a sport that embraced walk-on athletes. I went out for the team, and it was a major part of my experience in college. Most of my enduring friendships are former teammates, and the challenge and excitement of competing at the collegiate level in a new sport was incredibly rewarding. I took a 25 year break from the sport and returned when my son started rowing in high school. Watching him made me realize how much I missed it. I now row at the Cambridge Boat Club (CBC) which is the boathouse with the blue shutters at the Eliot Bridge. It's an amazing community of people, and I'm so fortunate to have incredible access to the Charles River. I'm Chair of the House Committee at CBC, which means I get to help coordinate the ongoing efforts to maintain and improve this historic boathouse.

What aspects of your experiences as a rower and leader carry over to your “day job” as a real estate agent?

Moving a boat smoothly and quickly through the water is incredibly satisfying and rewarding. Doing it well requires focus, persistence, and a competitive drive. It's also important to have a keen awareness of your surroundings, and when in team boats, the ability to work well together is essential. All of these characteristics of the sport transfer to other aspects of life and certainly to my work as a real estate agent. Keeping everything moving smoothly towards a shared goal and partnering closely with my clients to achieve a desirable outcome is the "work" and a great source of satisfaction.

Any can’t-miss races during this year's HOCR?

There are over 72 events across the 3 days of the Head of The Charles. There are athletes from their teens to eighties competing in every configuration of boat — singles, doubles, pairs, fours, quads, and eights. There are world champions, high school and collegiate teams, and people who row on their own. Check out the list of events here. I will be racing in the Senior Masters Double event at 10:10am on Friday and also in the Director's Challenge Mixed Eight event on Sunday at 3:38pm. 

The Head of the Charles Regatta is just one of Cambridge's rich historic traditions. What else do you love about this city? 

My four kids have all attended the Cambridge Public Schools and my wife, Meg, is the Executive Director of Cambridge School Volunteers, which places over 900 volunteers across the public schools. Our family has greatly benefited from all of the opportunities the city offers. There are incredible universities and businesses, amazing cultural opportunities, and a wonderful mix of people. We are very lucky to be a part of such a vibrant community. 

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