With the Beantown Jazz Festival coming up next week, I though it appropriate to post a profile I did about a year ago on Darryl Settles, a Boston restaurateur and the man who created the festival we in the South End have come to enjoy…
Once a year, the rather tucked back street of Columbus Avenue is transformed into a sanctuary for lovers of jazz. Floating saxophone, smooth trumpet, and a chorus of silky voices come together in a celebration called the Beantown Jazz Festival. And it’s all thanks to the genius and generosity of a man named Darryl Settles.
There are, perhaps, only a few more well known men on the Boston social and music scene than Darryl Settles. A grinding business man with a heart for philanthropy, his interests have developed into many ventures over the years, but they all converge on one: jazz.
Settles, the tall and lean 50 year old African American business man and the owner of Darryl’s Corner Bar and Kitchen on Columbus Avenue, in the South End, is a man that has woven a rather intricate web of connections and business ventures over the years.
“He’s an entrepreneur of the highest level, I think,” said Rob Ross, a Berklee College of Music professor. Ross is also the director of Settles’ brain child, the annual Beantown Jazz Festival. “He’s very good at what he does. In business, he’s always looking for new ways to bring people what they want. I think of Darryl as an entertainer, really.”
In addition to Darryl’s Corner Bar and the Beantown Jazz Festival, Settles has and remains involved in real estate ventures and businesses across the city of Boston. He is a man who has seen both sides of business, the ruthless and the caring side, and come out on top.
Born to Rebecca and David Settles in Aiken, South Carolina in 1962, Settles grew up around music. His father, who owned nightclubs with live music, introduced him at an early age.
“I’ve always loved music,” he said. “I would say I was probably an older soul. I was very mature for my age.”
Settles stayed in South Carolina through high school, working on his grandfathers farm, then went to the University of Tennessee, Knoxville to study engineering. After graduation, he attended graduate school at Virginia Tech, then went to pursue a career in Boston.
Settles came to the city with Digital Equipment Corporation, hired as a salesperson, which he did for a year and a half, before moving to marketing. In marketing, Settles began to see the true side of business.
“I think every business has a niche..I have always said that Boston is a great area for college age kids, because you could literally go to a different bar every night of a school year if you wanted to, and you would only see people, forget the underage kids, between the ages of 21 to 35. Very rarely do you see people in their forties. You might see them in the restaurant but we don’t have any lounges or bars that cater to them, and that’s a market that was wide open for someone to take advantage of.”
That’s exactly what Settles did. He was striving for more, more money and more success, so he started doing development with a partner, developing condos, and the broker told him that a restaurant that had gone into bankruptcy was available as a steal.
“I got into it by accident,” he said. “It wasn’t a plan, it was an opportunity that presented itself that I latched onto.”
The building, located on Columbus Avenue right off of Massachusetts Avenue, was the perfect place for Settles to develop the niche market he had seen available. Bob the Chef’s emerged, and it was where Settles would remain for 18 years. The name would change over the years, to Bob the Chef’s Jazz Café, then to Bob’s Southern Bistro, but the concept did not.
“When I worked with Digital as a sales person for seven years, I did a lot of entertaining with clients, and I used to take them out all the time, taking them to jazz clubs. There was this hotel called Turner Fisheries and, I just fell in love with it. And around the same time, or the year after, I bought Bob the Chef’s in 1990, a new general manager took over the hotel and got rid of the live entertainment. And that was the really the only place in the city that was jam packed, every night of the week with a mature audience, older people in their mid-thirties and up, and so I wanted to create that, and I did.”
After remaining on Columbus for a long while, Settles decided to move forward. He developed The Beehive, another live entertainment restaurant, with two partners, on one of the busiest blocks of the city.
“Beehive was really the concept of Bob the Chef’s or Bob’s southern Bistro but more of a bar scene,” Settles said. The building, located on the Boston Center for the Arts property, was “prime property for a boston night life,” as Settles told the BCA’s executive director.
“BCA was really at the heart of the city, it’s like right in the center of everything. And that notion turned out to be very true,” Settles said. “It is one block, the busiest block in the South End and probably one of the busiest in the Back Bay also. It’s a very very busy block.”
The Beehive thrived for several years, until the partnership went south. Settles and another partner, Jack Bardy, butted heads, effectively ending the relationship and Settles’ involvement with the restaurant he had helped to create.
“It was my concept,” Settles said, “and at the end of the day, I was bought out. I will say that I’ve been involved in a lot of partnerships, and it’s the only one that did not go well. And the lesson learned is that the people in this world are bad people; and my ex-partners are bad people.”
Bardy, had no comment other than “I’m not really interested in having this discussion. I really don’t have any comment.”
“After working with them for a while, he started to realize they were not the people that he thought they were. They were not people of integrity, they were just not who he thought they were. He would try his hardest to have meetings with them to work things out, as far as what he saw that was going on with the restaurant and what they were doing,” Settles’ close friend and bookkeeper Liz Falzone said, describing how Settles was pushed and eventually bought out. “It was very hard on him, he tried really hard to take it in stride, you know In some ways it made him a little more cynical of people, and then in other ways it made him stronger as a person. Sometimes you go through things like that and you come out stronger. But it was very unfair.”
Settles had sold Bob the Chef’s when he opened Beehive, but still owned the building, and when two other restaurants faltered and vacated the building, Settles decided to try again. He opened Darryl’s Corner Bar and Kitchen, a restaurant that would make Settles the institution he is today in the South End.
“It’s more upscale now, it’s more of a bar scene, and this place is open for dinner only where bobs was lunch and dinner,” Settles said. “We’re aiming towards more money, more revenue, more profits.”
Darryl’s turned Settles into the true entrepreneur and socialite he has become. Described by his friends as a caring generous guy who loves to entertain, Settles makes an impression.
“He is a very loyal friend. He’s somebody who would do anything for you. He would have your back, he would come to your rescue, and he loves to get people together,” Falzone said. “He would invite ten couples to go for dinner, he just calls you up and says we’re doing this, can you come and he loves to get people together, he loves to be around his friends.”
“I like to have fun,” Settles said.
With a successful restaurant and a other successful business opportunities in real estate under his belt under his self-owned managing company, D’Ventures Limited, Settles decided to give back to the community. He began the Beantown Jazz Festival, an annual all day event for all ages along Columbus that highlights jazz and local music scenes.
“I used to travel a lot to the New Orleans jazz festival, and then I got hipped into the Montreal jazz festival about 15 years ago. The first year, coming from there I said wow, why can’t we do that in the city of Boston? I went to the mayor had a conversation and he said sure why not? But it wasn’t that simple.” He said with a laugh. “It literally took about a year of planning, and then in a year and a half to raise the money to do it, because it’s not an inexpensive proposition to operate. In the first year, it was successful, but it just continued to grow.”
The festival was taken over by the Berklee College of Music at the end of 2007, and Settles is pleased with the work they’ve done.
“It was a concept Darryl had had, and he wanted to bring that as a give back and a thank you to the entire South End neighborhood,” Berklee director Rob Ross said. “He’s a very interesting guy. He’s a very creative guy and even though music is a very creative business, there are parts of the business that aren’t so creative, but I think Darryl does his best to put creativity and be creative in those aspects.”
“One of the good things about Boston is we have so many music schools around here. And there are so many musicians…you know it’s hard to make money in music. So a lot of people go to music school, and a large percent don’t graduate, and those who do graduate actually can’t make money so they stay in the city because they love Boston and they develop groups here,” Settles said. “We’re fortunate enough to have a lot of musicians that live here.”
In addition to the festival, Settles has found other ways to give back. In coalition with the Winn Real Estate Company, Settles created WiSe Urban Development in 2010, devising ways to make more affordable housing in urban areas, particularly low-income.
“He cares deeply about his community,” Falzone said. He does a lot, feeds homeless with food from the restaurant, and is always trying to figure out how to make things better for people. He’s very well liked and very well known.”
Falzone and Ross, both who have known Settles for at least 15 years, agree with his self-label as an old soul, but say he is also an great family man, and a great friend. Settles married in 2003, and has a daughter who is seven and a son who is five.
“He’s somebody that’s maybe a little more old fashioned, in his morals and values, and I see that in his children, he’s very loving, he’s very caring and he’s very hands on, but he also expects certain things of them,” Falzone said. “They’re just these cute little kids but they need to say excuse me when they leave the table, things like that. He’s very traditional.”
“Darryl’s a very outgoing personality. He cares a lot about what he does and the people he works with and the people he affects. I have a great respect for how he approaches business and a lot of things in life,” Ross said. “Darryl likes the best. He likes to offer the best to people. It’s very important to what Darryl does and who he is. It’s part of him being an entertainer.”