Winslow Sargeant: Stepping onto the train called Wisconsin – Part 2

Winslow Sargeant: Stepping onto the train called Wisconsin – Part 2

This is Part 2 of a two part interview. Read Part 1.

Winslow Sargeant’s combination of academic, commercial and government experience gives him rare insight into the world of entrepreneurship and risk. His memories of growing up in Dorchester remind him that to succeed at anything, tenacity is essential.

Winslow Sargeant

Madison is far removed from the place Sargeant knew as a child. In June, 1974, U.S. District Court Judge W. Arthur Garrity, Jr. ordered massive busing throughout the city of Boston as a supposed solution to the fact of racial segregation. Fierce riots between blacks and whites ensued, and Winslow and his siblings were caught in the crossfire.
It was a tough time, he said.
“You’re riding a bus and you have police cars following, and people are throwing rocks at your busses, and some of us”-not him, he assures me—“older kids would carry eggs, [and] throw eggs at some of the protestors.” His voice faded.
“No one was innocent,” he continued. “I don’t think that we knew how dangerous this was.” One boy from Charlestown High School was shot and remains paralyzed, Sargeant said.
Most people now say that forced busing did not help alleviate racial segregation, but made matters worse, a sentiment shared by Sargeant. “White flight to the suburbs due to busing helped to create a public school system that is made up of kids from the economic lower class,” he told me later in an email.
As a kid, the only professional black adults he saw were teachers, Sargeant said. His father, a former mason in Barbados turned custodian, and his mother, a nurse’s aide, strongly pushed education as the key to a good future. Winslow listened to them, and later, despite being encouraged to consider joining a basketball team after being accepted to Northeastern University on an academic scholarship, he decided against it. “I knew that I wasn’t as good as the professional recruiters were telling me,” he said.
So, after graduating, he went to graduate school in, of all places, Iowa State University in Ames. After he located the state on a map and started school, he realized that he loved it there.
“I didn’t know much about the Midwest,” Sargeant said. “My friends told me there’s nothing out there but corn and dirt roads. And that all they do out there is ‘cow-tipping.’” He laughed.
Cow-tipping is two myths rolled into one: the first, that cows sleep standing up, and two, that wise guys try to push them over.
Sargeant asked a farmwoman if cow-tipping really existed. “She gently slapped my hand and said there’s no such thing as cow-tipping. A cow weighs 600 pounds or more. There’s no way that one person could push one over,” he chuckled.
After Iowa, Sargeant came to Madison in 1988 after meeting John Wiley, now chancellor and then an associate dean in the engineering school. Sargeant had seen an ad in the magazine of the National Society of Black Engineers recruiting for black engineering graduate students, and Wiley was the contact person. What Wiley remembers best about Sargeant was his intensity. “I saw intense focus,” he said. “He knew what he wanted. He thought it through.”
Sargeant enrolled in graduate school in Madison in 1988, where he also met his wife, and then left in 1992 to work at IBM in Rochester, Minnesota. He received his Ph.D in 1995, and then took a job with ATT/Bell Labs in Allentown, Pennsylvania. There, he and his partners saw the potential of a computer chip they were designing, and so spun off Aanetcom. Cisco Systems provided the financing and bought their chips, too.
The rest is history.

Nowadays, Sargeant has more in common with the world of moneyed finance than with his old Dorchester stomping grounds, though his parents still live there. The neighborhood is still segregated, and few kids attend college. Most have no idea what opportunities lie beyond the place they call home.
Once, years ago while still at Northeastern and living at home, he told some young friends that he was pursuing a degree in engineering. “And I can remember one of the guys, who might have been 12 or 14 at the time, who said, ‘Oh, Winslow, you’re going to drive a train!’ ”
“All he knew was that an engineer drove a train,” Sargeant said, sounding pensive. “And I looked at him and said, Yeah, I’m gonna drive a MBTA train.”
After so many years, Sargeant does intend to be on a train, but this one is called Wisconsin.
Something’s happening here, he says. The right mix of people and ideas is converging: at Venture Investors, his new job will be to help bring in some new money. “That’s why I’m coming back,” he said. “I can see that the train is starting to leave the station, and I want to be on that train.”
He genuinely likes Madison, he told me. “Wisconsin is a welcoming place,” he said. “That’s why I would move my family here. I don’t find it as racial as some other places I’ve been. People here really try to look at what you bring to the table.”
His message to entrepreneurs here? It’s similar to what he’d tell those black kids back in Dorchester: Keep your eyes on the prize. And—speaking specifically to Midwesterners—don’t be afraid to fail.
“I think that the Midwestern attitude is very conservative. People are worried about the scarlet letter,” he said. “Whereas on the coasts, people fail many times. Failure sometimes can be a badge of honor because it means you have experience.”
“I’ve learned that in everything you do, there’s a chance you’re going to fail. But If you let that be the driving force in your life, you’ll play it safe,” he said. “You just have to launch out once in a while.”

Katherine Esposito is the senior staff writer for WTN in Madison. She can be reached at