Growing up, Dan Gregory would watch his father return home from work “totally romanticized” by this idea of the entrepreneur. His father was the co-founder of Boston’s Greylock Partners—one of the oldest venture capital firms—and Gregory was inspired to become a builder, spending his career repeatedly starting something new before becoming Northeastern’s Co-Director of the Center for Entrepreneurship Education.

When Gregory’s father helped found Greylock in 1965, “it was a very different era of venture capital,” according to Gregory, who claims, “It was all about the entrepreneur and what the entrepreneur was creating. It was about facilitating what entrepreneurs were able to accomplish both with resources and contacts.”

Gregory’s home environment fueled his entrepreneurial career. After graduating from Wesleyan, he moved to New York City and was quickly recruited to launch a set of magazines for Scholastic. “I was assigned from the outset to start stuff,” Gregory says. “I always dealt with situations where nothing existed—no businesses, no customers.”

As Gregory’s responsibility started growing at Scholastic, and he had more people reporting to him, he decided he needed to enroll at Harvard Business School. When he graduated in the mid-1980s, Gregory started working at New England Business Service—which has since been acquired by Deluxe Corporation—creating a publishing company for them. Eventually, NEBS asked Gregory to run their core, over $125 million division, but having to report to the board and justify every step he was taking didn’t feel true to his entrepreneurial instincts.

Gregory joined a startup video company, and later worked for Vertigo Development Group, all before deciding to start a publishing company of his own, called Turnstone Publishing. He became one of the first to give major publishers the opportunity to integrate online curriculum with textbooks. Despite making “a tremendous amount of progress,” however, the country hit the 90’s Internet meltdown and Gregory opted to sell his company to Houghton Mifflin Harcourt.

He moved on, creating his own consulting firm, called The Launch Group, where he worked with companies and universities to develop new products, eventually finding himself working at a local university.

“I absolutely never would have predicted I’d be on the faculty at a large university anywhere,” Gregory admits, who’s currently an advisor to Northeastern’s student-run venture accelerator IDEA, on top of his role as co-director of the Center for Entrepreneurship Education. “When I started at Northeastern five years ago, no one knew IDEA could have existed.”

Gregory admits his career has started to come full circle. After being inspired by his father’s love for the entrepreneur, he became one himself and is now fostering other entrepreneurs and helping their ventures grow. “My total focus is now on the entrepreneur,” he says. “Working with entrepreneurs, it’s never easy, but I know what they’re going through. They just don’t know what they’re going through.”

When he’s talking with student entrepreneurs, Gregory tells them they need to accept they won’t always be right. He says:

Always investigate whether you are on the right path and are doing the right thing. You do that by talking, and listening and networking. The people that aren’t successful entrepreneurs are the ones that get so passionate about their idea they can’t hear the input. … Don’t be stubborn. Be open, and accept mistakes. Embrace your mistakes. A lot of entrepreneurship is knowing you can be wrong and recovering from being wrong. If you can do that, you’re going to be a much stronger entrepreneur.

Throughout Gregory’s journey, he’s continued to take the chance and throw himself into new projects. He’s sure to emphasize, however, it was never because he was bored. “I don’t believe in ‘getting bored,’” Gregory admits. “That’s the shortcoming. It’s always been more the desire to start something new.”


Featured Photo Courtesy of Northeastern