Grant Easterbook started his first job after Bowdoin at Corporate Insight, a small family-owned consulting firm in New York City. In his free time he began looking around for a topic or field in which he could become an expert.
“I was looking for a topic that hadn’t blown up yet, but was something that would become hot within a few years time,” he said. “And I thought I’d become the expert in that space before the big firms like McKinsey, Oliver Wyman, and Bain started covering it.”
He settled on financial services technology, or “fintech,” which refers to the automation of the financial services industry, with tools like online robo-advisors offering algorithm-based advice to investors. “I picked this area, and sunk my free time into it to become an expert. I then started persistently pestering every reporter I could find via LinkedIn and email. When the topic did start to blew up, I was already well established and I rode the wave.”
Easterbook became the go-to person in this space, and he has been quoted in the media over 100 times.
He was also beginning to think more seriously about starting up his own business. He said when he was ready, he left Corporate Insight to launch, with two friends, a new financial company called Dream Forward.
Easterbrook explains the premise of his company this way: “My great-grandfather and grandfather had pensions, but that is going away. Now, everyone has 401(k)s. But the problem with that switch is in the past, your employer handled saved for you. Now, it’s all on you.” He continued, “And people aren’t saving. We’re short-term animals, and it’s hard for people to save for something that is 20, 30, 40 years away.”
Dream Forward Financial offers 401(k) retirement accounts with new technology that “holds your hand and keeps people on track and doing the right thing,” Easterbook said. The technology can address a range of concerns—from feeling like you don’t make enough money to wanting to save for your child’s college education as your first priority.
The company’s virtual advisors will be available at any hour. “People start to panic late at night, in odd hours, when you can’t get a real human in front of them, and they’re going to make a bad decision,” Easterbook said. He hopes Dream Forward Financial, based in New York City, can steer them from going astray. “I thought it was a good business idea and it does some social good at the same time,” he said.
At Bowdoin, Easterbrook majored in government and legal studies and minored in history. He was the president of the class of 2011, played on the Bowdoin College football team, did leadership training at the outing club, and was co-leader of the campus blood drives.
He said that his Bowdoin education gave him two very important gifts: an ability to write well and a close-knit alumni circle. “When you graduate, you realize how valuable the alumni network is,” he added. “You can reach out to Bowdoin alums in your industry and they are almost always happy to help.”

Easterbrook advises current students to sign up for many different classes, clubs, and activities at college. “Get the most out of Bowdoin, and always be trying new things,” he counseled. For those who are thinking about founding a new business someday, he added, “Always be thinking about what you could do differently. Even just going about your daily life you’d be surprised how many ideas you’ll start having. Eventually, you’ll find something that really excites you.”
(Easterbrook, who is also currently president of the Bowdoin Club of New York, also extended an invitation to alums in the NY area to come to events.)
