Virginia Beach Entrepreneur Networking Happy Hour Makes Connections – Daily Press

VIRGINIA BEACH — While many local millennials choose to pursue careers outside of Hampton Roads, Jake Maines has done the exact opposite.

The Northern Virginia native has not only mingled with the community, but is doing what he can to improve it and help other ambitious people develop regional roots. A beach lover, Maines said he had no qualms about making Virginia Beach his new home.

He came to Norfolk to attend Old Dominion University in 2011 and graduated with a bachelor’s degree in marketing in 2015.

“I knew I wanted to open my own business eventually, and I figured any business I eventually opened would need some marketing,” Maines, 29, said.

After internships in his field and a month-long sabbatical in Europe, Maines started as a marketing manager at Array Digital in Chesapeake in 2017. Originally a software development company, the company expanded into turned to Internet marketing a year and a half after joining the team. , says Maines.

“We transitioned the business and restructured it around my department,” he said. The company has grown from little recurring revenue to a lucrative digital marketing agency, he added.

Maines said his 4.5 years with Array Digital have been a great ride. He said he honed his skills in the industry and learned how to run a business from owners Erik J. Olson and Kevin Daisey.

Olson has long called Maines his right arm: “He was the perfect guy at the perfect time and very ambitious.”

Ready to dive into his entrepreneurial side, Maines decided to get his real estate license during the pandemic. Soaking up the change of pace that included being behind a desk, breaking free from the 9-to-5 workday and networking in the community, Maines changed careers last year. Under contract with Iron Valley Real Estate Hampton Roads, Maines said it was well positioned to sell under Jake Maines Realty.

“Seeing the smiles on people’s faces when I’m able to help them access their dream home and invest in real estate is a great feeling,” he said.

Beyond the new gig, Maines said he found a lot of fulfillment in community interaction through the Networking Happy Hour he launched in August.

Open to all business owners, professionals and anyone looking to connect, the free events take place on the first Wednesday of each month at local bars and restaurants. They have no other agenda than to meet and mingle.

“I was able to help people generate a lot of business from it,” Maines said. “It’s been really satisfying.”

Maines, who volunteers with the Foodbank of Southeastern Virginia and the Eastern Shore, Lynnhaven River NOW and The Noblemen, has incorporated quarterly partnerships with local nonprofits into the events. Last month, he raised enough money to buy 500 pounds of dog food for Hope for Life, a Virginia Beach animal shelter.

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Maines said his five-year plan includes the even greater growth of Networking Happy Hour, helping more people grow their businesses and giving back to the community on a larger scale.

“You never know when you meet more people what can happen,” he said.

Sarah Dodson, from Norfolk, is one of many Networking Happy Hour attendees.

She works in business development. As soon as she heard about the monthly Maines event, she did her best to clear her calendar on the first Wednesday for the foreseeable future.

“It’s a great networking opportunity,” Dodson said. “Jake is a really genuine person who just wants to be the connector for others, and he does such a great job.”

For more information on Networking Happy Hour, visit

Sandra J. Pennecke, 757-652-5836,