You might know Diane Hessan as an accomplished entrepreneur, marketer and author. She’s currently CEO of Startup Institute, but she also co-wrote the book “Customer-Centered Growth: Five Strategies for Building Competitive Advantage,” a BusinessWeek best-seller, and until last year, she was founder and CEO of the fast-growing social networking company Communispace (of which she's still a chairman). She’s also an angel investor, backing startups like Tablelist and Grapevine, and serves on the boards for Panera and Tufts University. And June 16, she'll be a keynote speaker at BostInno's annual State of Innovation event. But somehow, she finds time in her busy professional life to pursue her longtime passion for music.
“Let me be clear here,” she tells me on our phone interview. “I’m not a great singer. I could never quit my day job.”
Still, Hessan began playing the piano and singing from a very early age. And she describes herself as a strong team player. Which is what sparked an idea she got about 15 years ago for an a cappella group that sang songs about business. She admits that, in fact, she became totally obsessed with making it happen. So around 1998, Hessan and a friend formed The Sound Bytes, a group of eight local entrepreneurs who also happened to be pretty talented singers. The group included PR pro Patrick Rafter and CL-Media Relations co-founder Sarah Lazarus. Essentially, they took popular songs from all genres and modified the lyrics to be relevant to the tech world.
The Sound Bytes ended up landing a stint at the TechLearn Conference, performing before every general session. And the group was so well received that they were invited back four years in a row. In that span of time, The Sound Bytes sang to everyone from former General Electric CEO Jack Welch to business writer Tom Peters. Naturally, for Peters, the group tweaked the lyrics of “Wild Thing.” Just take a minute to picture that.
“It was so much fun that I started thinking about ways to integrate music into my professional life,” said Hessan.
That inspired CommuniJam—a biannual massive jam session with Communispace employees who played instruments. And when a new employee would start, it became a tradition for everyone in the company to sing them a song.
In 2012, Hessan took the opportunity to MC the MassChallenge launch. And when Communispace CTO Howard Kogan dared her to show off her pipes, she decided to take him up on it.
“He said to me: If you had any guts, you’d do something really memorable—like sing.”
(Check out the video below—she breaks into song at 1:38).
When Jeff Glass, who at the time was CEO of Skyhook Wireless, told her he played the lead role in “The Music Man” in high school, she knew they had to partner up. And soon after, the duo decided to perform at a TUGG event.
Now, Hessan is working on planning a variety show modeled after "Saturday Night Live" for charity, which will likely happen either this fall or next spring. The idea is to encourage people from the local community to showcase skills no one knew they had—whether they’re singers, actors, comedians or dancers. And remarkably, Hessan says Boston entrepreneurs have been coming out of the woodwork with their hidden talents. Like MassChallenge Managing Director Scott Bailey, for instance—who happens to be a good tap dancer. (Secret’s out, Scott. Deal with it.)
“Basically, it’s going to be the who’s who of Boston tech—making fools out of themselves,” added Hessan with a laugh.
As for Hessan, these days she says she’s usually on breaking out into song around family or—more typically—alone.
“I still sing…” she says, “...in the shower.”
