VC McDermott Rocks to Cleantech

Our latest Who Knew? list of quirky details on prominent members of the Boston-area innovation community included this one: “Chuck McDermott, general partner at RockPort Capital Partners, dropped out of Yale University to pursue a career as a singer, songwriter, and guitarist. McDermott led a country rock band, Chuck McDermott and Wheatstraw, which drew huge crowds in Harvard Square in the 70s and cut two albums praised by Rolling Stone and Billboard, among others.”

Today, we noticed a nice little profile of McDermott in the Boston Herald that tells the more complete story of his unlikely odyssey from country rocker to energy investor.

McDermott grew up in Iowa, and he started playing guitar at age 9, so perhaps it wasn’t surprising that he fell in love with country music—it was only surprising that it took him until his second year at Yale when, according to the Herald, he heard Stand By Your Man by Tammy Wynette and got so hooked on country that he dropped out and formed Wheatstraw in 1971.

The Boston-based band toured the East Coast, including memorable stints at the Lone Star Cafe in New York, where the likes of Andy Warhol and Johnny Cash were in the crowd and Willie Nelson once joined them on stage, the story goes on to say. When Wheatstraw disbanded, McDermott moved to LA and formed a close working friendship with John Stewart, ex of the Kingston Trio. “We played all over the States. We toured Europe and Canada, and did these wonderful duos with people like Bonnie Raitt, John Prine and Roger McGuinn from the Byrds,” McDermott told the Herald.

Then, in 1984, married and with a child on the way, McDermott moved into a more mainstream business trajectory by joining Joe Kennedy’s Citizens Energy, a now Boston-based nonprofit. He led Kennedy’s 1986 bid for the U.S. Congress as campaign manager, and then joined the newly elected Congressman in Washington, ultimately spending four years in DC. Next up was a stint at Waste Management, which he helped build into a large environmental services enterprise.

McDermott’s longtime friend Wilbur James asked him to join RockPort when it was founded in 1998, and he has been there ever since. RockPort was initially a merchant bank, but when it started its first venture fund three years later, McDermott helped get it into energy and the environment. “The best advice you get from people who’ve been in the venture world for a long time is invest around what you know,” McDermott told the Herald. “What we did know about was energy and environment.” (You can check out RockPort’s portfolio here.)

Apparently, McDermott is still playing music as well. We’ll have to see if he will make an appearance at the next Xconomy Battle of the Tech Bands.

Bob is Xconomy's founder and chairman. You can email him at [email protected] Follow @bbuderi

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