Too often ‘opportunity’ is exclusively synonymous with privilege. Brian Hamilton is determined to change that.
Brian Hamilton doesn’t know what he’s going to do.
He’s a man of action, certainly. The 1987 Sacred Heart alum, entrepreneur, philanthropist and former University trustee has been working essentially every day of his adult life, and then some. With humble Bridgeport beginnings, Hamilton has recalled in other interviews selling soap and Christmas wrapping door-to-door as a young boy. An undergraduate in the early days of the school, when Sacred Heart was still a commuter college and most of the students had a least some side hustle, Hamilton started a landscaping business to make ends meet and would carry his earnings in cash to the bursar’s office to pay his tuition. He went on to grad school, earning his MBA at Duke and eventually becoming a professor there in addition to serving as the minority business consultant for the North Carolina SBA.
Expanding his work into volunteerism, Hamilton joined his friend, the Reverend Robert Harris, in his prison ministry, helping convicts find gainful legal employment on the outside. Their work led the two to launch Inmates to Entrepreneurs, a nonprofit aimed at helping the incarcerated learn the skills necessary to start their own busi nesses once they are released from prison. At the same time, Hamilton and a student of his at Duke, computer programmer Sarah Tourville, cofounded Sageworks, the nation’s first financial technology company. Over the next 20 years, Hamilton grew Sageworks to employ more than 400 people and become the largest provider of software to financial institutions across the U.S.
So you can say he’s kept himself busy.
But in 2018, Hamilton sold Sageworks and his interest in it to the private equity firm Accel-KKR. And so now, as one might say, “unemployed” for essentially the first time in his life, Brian Hamilton admits, “I don’t know what I’m going to do.”
There’s a tell in that sentence, however. He doesn’t wonder what to do; he wonders what he is going to do. The difference is subtle, but important. Both phrases address uncertainty. But the first—wondering what to do—implies bewilderment, befuddlement, a sense of being overtaken to the extent that there even exists the option of doing nothing. The second phrase, however, the phrase Hamilton actually uses— casually, instinctively, it should be noted—takes a different path. It assumes not only action but personal responsibility for that action in one breath.
Such is the mind of an entrepreneur. Circumstances are data points: some are advantageous, some are not; some you can control, some you cannot. Sometimes there is uncertainty. See it all, recognize it for what it is and act, never allowing yourself to become distracted from the fact that your actions are your own.
So Brian Hamilton doesn’t know what he’s going to do; but something will be done, and he will be the one doing it.
“When you’re in Brian’s presence, you’re in the presence of a top-flight CEO,” says Professor Gary Rose. Rose taught Hamilton as a freshman, coached him as a college debater and remains a friend still. “There are just some people who are very directional, very goal oriented. There was never any sense of entitlement with Brian. He’s not a man with aristocratic tendencies. Success has always been about performance. It doesn’t surprise me that he can work with inmates.”
Indeed, Hamilton works very well with inmates: something of a feat, given that the tall, trim, well-spoken, gray-haired white gentleman of a certain age is the absolute picture of The Man, that eponymous personification of the Establishment. What that picture doesn’t tell you is that Hamilton is also the first of his family to go to college, that his father didn’t even complete high school (opting instead for the Marines, the elder Hamilton later did earn his GED). So when he walks into a prison, as he has done these last 27 (and counting) years, seeking to help convicts (arguably the most anti of anti-Establishment) not only find a way back into society, but to become some of its most valuable members—Main Street business owners and entrepreneurs—Hamilton brings with him the one thing that cannot be denied: the grit of experience.
“In prison, they can sniff out a phony in 10 seconds,” Hamilton says, “so you focus on the content. How do you start a lawn service? How are you going to mow your first lawn? “We all have dreams,” he continues. “Let’s not get wrapped up in expectations. Let’s focus on the content and help people where they are.” His mission, many have noted (including Hamilton himself), bears a striking resemblance to that of his alma mater. “It started as a working-class school, one hundred percent,” he says. “Sacred Heart was founded to give people a chance who might not [otherwise] have it. It was started by strivers, and they gave a culture to the University so that even as the University changes, that culture remains.
“What that school has managed to achieve,” he adds, “represents America to me.” It’s the belief that cause and effect can be more powerful than circumstance, that there is a sense of order that ties hard work to reward. You know: the American Dream.
What Hamilton did not realize until well into his 40s was that the order he’d always assumed was natural was, in fact, learned from experience. Growing up, the Hamilton family may not have been born with silver spoons in their mouths, but Brian’s father, the former Marine, certainly understood the benefits of perseverance and determination: if you want to play the game, you practice; if you want to pass the test, you study; if you want to earn the money, you work. It always seemed obvious.
Like most things, however, it’s only obvious if it’s what you know. But what if, for whatever reason, you’ve never known it? What if you’ve never experienced that relationship between effort and result? Then the world would seem a cruelly random place.v
In a public school system where local taxes support local schools, “Education is fundamentally skewed against the poor and minorities,” Hamilton notes. “Four out of five people in the U.S. cannot read at grade level.” How can individuals be held fully responsible for their decisions when those decisions—fundamentally—cannot be fully informed?
And so it was that Inmates to Entrepreneurs was rebranded as the Brian Hamilton Foundation, seeking to help not only the formerly incarcerated but all socioeconomic outliers, like minorities, veterans and those lacking education—anyone “with the odds stacked against them” as its website states—people much like those working-class and first- and second-generation Americans who were the foundation of Sacred Heart.
v“There is intellectual property people have that they don’t know they have,” Hamilton says. “Experiences and resourcefulness that they don’t realize are relevant. We want to change that. We want to redefine the advantage.”
To do that, Hamilton again turns to his experiences at SHU.
“The best course I had was a class called Religious and Philosophical History.” That, Hamilton says, was the class that opened him up to thinking about Thinking. “More than anything, the liberal arts teach you how to think. They exercise that capacity to critically analyze. And I remember in that class realizing that everything, from theological beliefs to economic models to assembly lines, all of it can be broken down and studied as systems.” That realization not only became the foundation for his own vocation as an entrepreneur, but it informs everything the Foundation does to improve the lives of their clients.v
“We teach them the technical stuff,” he says. “The nuts and bolts of how to start a business.” But those nuts and bolts foundationally change their clients’ thought processes. They build connections and give them practice at critical, lateral thinking, showing them multiple effects from any single cause, giving them options so that obstacles are no longer the end of the road but rather merely circumstances to be considered, assessed and managed—as they would be for any entrepreneur.
Indeed, as they would be for Hamilton himself, whose current circumstance is that uncertainty with which we began. Between speaking engagements, the Foundation and his family, there is certainly plenty to keep the man busy. But for someone like Brian Hamilton, “busy” is not enough. “I want to add value,” he says, looking at the world around him, assessing it and his place in it with the systems he knows best. “I’m just not sure how yet. So I go day by day and I make a list. “I don’t know any other way.”