Keeping busy with Ken and JD Chester

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By Debbie Flessner

If it’s true that “idle hands are the devil’s workshop,” then Ken and JD Chester should never have to worry about getting themselves into trouble.

Ken and JD Chester
Sarasota residents Ken and JD Chester own the Munchies 4:20 Café, as well as a stable of other businesses. Photo by Debbie Flessner
This dynamic father and son team currently own and run no less than eight successful businesses, and though Ken is preparing to phase out his side of the operation, JD is actually looking for ways to expand their Florida holdings. Hard to believe that less than two decades ago, they were both living in New Jersey and working for other people.

When JD was a student at Monmouth University and Ken was a pharmaceutical sales and marketing representative for national companies, they had probably not fully envisioned what they were going to create years later in Florida. But when he reached the age of 52, after having helped propel a generic pharmaceutical company he was working for to number one in the marketplace, Ken experienced an epiphany—he needed to make a change.

“I just hit the wall and announced my retirement,” Ken said. “I had no intention when I left home to go to work, but I just said, ‘I’m done.’ I went home and told my wife Sara that I had retired and three weeks later, we moved to Sarasota.”

After arriving on the Suncoast, Ken settled into a relaxed life of playing golf and catching up on his reading. That lasted all of 30 days. After a life spent constantly on the go, he knew he was not well-suited to a complete retirement, so he began looking around for something he could do.

He thought he would give real estate a try. “Every day I kept looking at this vacant lot on Stickney Point Road, and I thought, ‘Someone should develop that,’” Ken said. “I contacted the owner and purchased the lot, which is now the shopping center where the Stonewood Grill and New Balance are.”

Though he had no prior development experience, the project was a success. After the shopping center was completed, Ken sold it to an investment group.

Shortly afterwards, his son JD decided to move down to Sarasota as well. Before long, he ran into an issue that quite a few young people visiting and living here have called attention to in the past—there are just no late night dining establishments.

As is the case with many successful concepts, JD’s business, Munchies 4:20 Cafe, was developed out of necessity.

“I was 23 years old and had gone out drinking with a buddy,” JD said. “After I got home, I was hungry, but I couldn’t drive, so I started flipping through the phone book to see what I could find.” What he found at that late time of the night was restaurant after restaurant that had been closed for the evening for hours.

JD didn’t have any money of his own to open up a restaurant, but he had some friends who owned Fandango’s, which at that time, was on Old Stickney Point Road. They allowed him to come into their kitchen after the restaurant was closed for the evening and run a late-night food delivery service from there.

He called it Munchies 4:20 Café, because he actually prepared and delivered food until 4:20 a.m. Business was so good that JD soon began looking for a small storefront to use and he found it, right on the corner of Gulf Gate Drive and Superior Avenue—an area that is saturated with bars and restaurants of all types.

At the time, Munchies had 22 seats. Since then, JD has also taken over the two spaces next to his original location and expanded to include seating for 178 people and a beautiful covered tiki bar area outside.

Meanwhile, having sold the shopping center, Ken was again getting restless. He decided to set his sights on another Gulf Gate area business.

“I bought a bar called the Boar’s Head Lounge,” he said. “I upgraded everything in it, and put a tiki bar inside it, which made it look very Key West-like. I named it Chester’s Reef.”

Capitalizing on Munchies 4:20 Café’s success, JD began looking into additional business opportunities. He figured his late-night restaurant/bar concept would work well in a college setting, so he opened up two establishments in one of the best-known college towns in Florida, Gainesville.

Both Fat Daddy’s and the Rowdy Reptile are located in the Midtown area of town, adjacent to the University of Florida, and are consistently reviewed as two of the top bars in Gainesville.

JD said that he frequently makes the two-and-a-half-hour trip from Sarasota to check on and work at his businesses. Sometimes that means that he closes the bar in Gainesville, then drives back to Sarasota to grab a couple of hours of sleep in a back room at Munchies, before opening the doors for the day.

“I’m very hands-on with the bars in Gainesville,” he said. “It’s big business up there.”

For the Chesters, it’s also big business here in Sarasota. Ken has added Cannon’s Steakhouse and Tavern, which features live music, as well as Cruise Car, a custom golf cart shop. JD introduced Pride of the South, a BBQ restaurant, and Sarasota Performance Auto Repair.

Clearly, the two have a knack for running a successful business, but Ken has finally decided it’s time for him to phase himself out of the day-to-day operations. He is selling the golf cart business and has taken on a partner at Chester’s who has big renovation plans and a name change in store for a new night club. It will be called SRQ Live, and will feature live music five nights a week.

JD, like his father for so many years, has no intention of slowing down. A classic car collector himself, he is in the process of obtaining his car dealer’s license and will be opening a dealership of his own in the new year.

“I also plan to open up more bars in college towns,” he said.

Never one to sit still for very long, Ken has big plans of his own. “I want to travel,” he said. “I have a girlfriend now, so I’m waiting for her to retire.”

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