1 family, 2 brothers, 3 businesses and Five Guys

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Hospitality is a family affair for the Prentices of Portland, Yarmouth and Florida

YARMOUTH — The Prentice family is tight. They work together, live together and between them run three businesses.

Brothers Dick and Miles Prentice and their families own and operate the Chebeague Inn, Diamond’s Edge restaurant on Great Diamond Island and the Five Guys Burgers and Fries franchises in Maine, Boston and Rhode Island.

Yarmouth residents Dick and Gerri Prentice bought the Chebeague Inn about a year and a half ago. Dick, an attorney, is a partner at Pierce Atwood in Portland; Gerri and their son Casey manage the inn. A daughter, Caitlin, is joining the family business and will help with marketing, public relations and event planning for Diamond’s Edge.

Miles and Katie Prentice, meanwhile, live in Florida and have a summer home in Sebago. Miles is also an attorney, but he and his son, Gene, and their operating partner Jamal Bourote own the territorial rights to five Five Guys restaurants in Maine, 18 in the Boston area and 10 in Rhode Island. After opening two in Rhode Island, the first Maine store opened April 11 on Fore Street in Portland’s Old Port.

Gene Prentice, 26, is the senior vice president. He said the Portland restaurant is his first restaurant experience and it has been a lot of fun.

“This city has a great feel,” he said. “It’s been great hearing all the feedback from customers and getting to know the area.”

Bourote, president and chief operating officer, has 23 years of restaurant experience. He said the Portland Five Guys has been very busy since its opening. 

“This is our passion,” Bourote said. “If you don’t love food, love people and love the restaurant industry, this is not the profession for you. We care, we are passionate and we are looking forward to opening other restaurant locations.”

Prentice did not specify where or when the other Maine locations would open, but said they are narrowing their options.

“There is a lot of promise from Kittery to Bangor,” he said.

While the families are close, the cousins are even closer: Casey, Gene and Caitlin share an apartment in Portland.

“It really is great living together,” Caitlin said. “Our kitchen table is like an office 24 hours a day.”

For the past five years Caitlin has worked in New York as a global marketing manager for the Edelman public relations firm. After numerous trips to Maine to help out at the inn, her family asked if she wanted to take a more active role in the business.

“As a family we talked about the logistics of a move and how I would fit in to the plan,” she said. “It sounded great, and I decided I was in.”

Caitlin will be in charge of the marketing, public relations, event planning and social media for Diamond’s Edge. The family has a lease with an option to buy the 250-seat restaurant and plans to open May 21.

Casey Prentice runs the business side of operations for Prentice Hospitality Group. He said guests at the Diamond’s Edge restaurant will have access to the art gallery, the 40-slip marina and the 500-person event area, which is suitable for large gatherings, weddings or business meetings.

As owners of the Chebeague Inn, Prentice and his mother Gerri said they have a few improvements in mind for the coming season. They plan to open on May 14 and are excited about sustainable tourism on Chebeague this summer.

In addition to biking, exploring and relaxing, guests will be able to participate in interactive activities when they visit, he said. They will be able to go lobstering with local fishermen, clam digging on the flats or sea kayaking in Casco Bay.

“We’d like to incorporate sustainable tourism into this season,” Prentice said. “We want people to experience Casco Bay and all it has to offer.”

The family is making improvements to the inn and planning a Fourth of July celebration with a pig roast, live bands and fireworks, Prentice said.

“We are looking forward to a great season,” he said.

Amy Anderson can be reached at 781-3661 ext. 110 or aanderson@theforecaster.net. Follow her on Twitter: @amy_k_anderson.

Sidebar Elements

Gene Prentice, left, and Jamal Bourote own 33 Five Guys Burgers and Fries franchises in Maine, Massachusetts and Rhode Island. The Portland restaurant on Fore Street is the first in the state.

This side of the Prentice family owns the Chebeague Inn on Chebeague Island and the Diamond’s Edge restaurant on Great Diamond Island in Portland. Caitlin Prentice,left, is in charge of marketing and event planning for the Diamond’s Edge restaurant. Gerri Prentice and her son Casey run the Chebeague Inn. Cody the family dog joins them.