Seaford grad, Air Force vet involved in schools, housing, politics

When Jeffrey Benson Jr., graduated from Seaford High School in 2002, he wanted to get as far away from home as possible. He joined the Air Force and made it as far as Ramstein, Germany.

“It’s a big world out there,” Benson said. “And it’s okay to leave [home.] But there are things that we have here that other people don’t.”

When he finished his time in the military, Benson saw an opportunity and returned to Seaford. He was 22 and excited to take over his grandfather’s drywall business. Quickly, though, the housing bubble that had contributed to the business’s success popped.

“I found myself unemployed, which was scary. I didn’t have any skills to get a job that would pay a living wage,” Benson said.

A friend got him a job selling cars and he quickly excelled. He had a talent for sales, averaging about 10 cars a month. When an insurance salesman encouraged Benson to get his license in 2007, he went for it. He started his own company, One Direction, in 2016, later merging with Prominent Insurance. The business continues to grow.

While working, Benson started the Wilmington University MBA program, graduating in May. Now he’s working toward his doctorate.

“I thought I would be done. I’ve never been a school type of guy, always been more a hustler,” he said. “But at graduation I saw the doctoral students walking by, with their robes and caps, and I knew right then that I was going back.”

Benson’s eagerness to learn earned him some bonus opportunities along the way. In 2013, he was selected for Leadership Delaware, an intense 10-month leadership mentoring program. In 2019, Rep. Lisa Blunt Rochester sponsored him for a Congressional Black Caucus Fellowship, a weeklong leadership seminar that teaches the basics of running for office, and he became chair of the 39th Democratic District.

“I serve on the Seaford school board. My next run will be city council and then wherever else God takes me,” Benson said.

Quickly becoming a successful figure in his hometown, Benson wanted to help others achieve their goals.

“When DuPont left it was a vacuum, and we’re still feeling those effects, but we’re working to make Seaford better,” he said. “You’re gonna see a lot of good things happening over the next couple years. You’re gonna see the old community come together.”

Serving Seaford schools

On the Seaford Board of Education for about five years, he plans to run for another term.

Initially, Benson ran (and won) on “bringing the community together.” He’s doing a lot to make that happen.

“Every year, we do an annual welcome back, where we have stakeholders in the community – policemen, firemen, businessmen, anyone you can name – high-five the kids coming back. The kids look forward to it every year. We do each of the six schools. State representatives, county representatives – it’s just a highlight,” he said.

Benson also helped pilot “Donuts With Dudes” in 2019, a breakfast for dads and father figures and their students. Over 400 people attended at Central Elementary School. In 2020, “Donuts With Dudes” will expand to other district schools.

Benson started the Gentleman’s Club at Seaford Middle School in 2016 and later expanded to the high school, in partnership with nonprofit Pathways to Success. The group meets weekly and focuses on self, value, consequence, power and respect, what Benson calls “the five senses of leadership.”

He’s most proud of a project he helped spearhead in 2019, a youth shareholder initiative. With La Mar Gunn Sr., of Gunn Wealth Management in Dover, and Wilmington City Treasurer Velda Jones-Potter, he partnered with WSFS Bank to introduce kids to finance. Ten students from each county, some of them part of the Gentleman’s Club, went to a WSFS shareholders’ meeting and had the opportunity to ask questions. They were each given five shares of stock worth about $200.

“This is huge, it’s historic. I don’t know of any other companies doing this,” Benson said.

Several of the students were selected as junior board members and will have their first board meeting in February.

“Our goal is to work with other … corporations here, like Amazon or Disney, and duplicate what we did with WSFS. Maybe even start thinking nationwide,” Benson said.

Future prospects

The always business-minded Benson noticed an opportunity in Sussex County, in a market that’s woefully underserved.

“Right now, what you have in eastern Sussex is an abundance of homes being built with, in my opinion, inflated prices. But there’s a demand for it, these $280,000 to $400,000 homes,” he said. “But there’s another price point that’s needed throughout Sussex County, which is $170,000 to $220,000. There are a lot of people qualified for these homes but not a lot of inventory available, so we’re trying to fill that need.”

Benson is working as something of a broker between landowners and builders to develop a 21 acre lot in Milton into about 30 single-family homes.

“We want to provide individuals that work in the area with decent homes. Rather than paying $900 to $1,300 on rent, they can actually have a mortgage for that,” Benson said.

He hopes the project will break ground no later than March, and should all go well, wants to continue building similarly-priced housing developments.