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Darryl Settles is unsettling. No, not in a bad way. It’s just that if you spend time talking to this urbane, friendly and intelligent man, you just wind up not quite sure that you haven’t missed something in your past business life. Perhaps you should have bought those condos, looked for a broken down restaurant or two, or started a music festival. Blithely, Darryl describes these activities as if they are things that you do before breakfast as you move onto more important happenings in your business day. He has little or no ego about his successes and a disarming way of challenging everything from the way you do business to the future of the hospitality industry in general.
Born in the South, Darryl drifted gently north, winding up as a young sales engineer working for Digital. This was presumably a good job for him, as his only expressed regret was not working for IBM instead.
Dabbling in some side investments, he graduated from condos, to looking for an investment business and wound up owning (the then broken down) Bob the Chefs in 1989. Not a very smart move many would say. He tells of hiring two consultants to look over the new business before he finalized the deal. One of them walked off the job telling Darryl that he could not take the money of someone dumb enough to go ahead with such a purchase.
That dissenter may well have been right. What happened next was hardly pretty. Darryl managed to apply some good business sense to promotion. Leveraging his connections at the Globe and elsewhere he soon filled the place with curious diners, interested to experience southern style food, presented by this energetic young African American business executive who had stepped in to save a Boston institution. Within weeks he had a busy restaurant, a bunch of new staff and rapidly diminishing cash reserves. Not exactly the way he envisaged his investment turning out.
Somehow, he survived this period. Maybe it was taking his accountant’s advice and spending time in the kitchen with a notebook finding out what his many employees were actually doing. Whatever, he ordered the chaos and eventually set Bob’s on the road to recovery and a prosperous future.
Just staying in business from 1989 to 2007 was no mean feat. There are not a lot of southern style restaurants in New England. Many have tried and many failed as they realized that great fried chicken and collard greens were not quite enough to win the hearts and cash of the stoic New England crowd. It speaks to a pretty high level of restaurant management skills that Darryl and Bob’s have prospered through changing times and food fashions.
Fast forward 18 years and we arrive at a very different place. Bob the Chef’s has recently become Bob’s Southern Bistro. A much improved place after four renovations over the years. It is back in its role as an institution, this time as a great place for jazz, southern food, good drinks and friendly service combined with an electric energy among the many regular and ethnically varied diners. Who would have guessed on such an outcome given its humble beginnings? Fewer and fewer people call Darryl “Bob” these days and his stock as a local entrepreneur is at an all time high.
Recently he teamed up with three new partners. Jack Bardy owner of Pho Republique in Cambridge Square, William Keravuori of the Abbey Group and William’s wife Jennifer Epstein a corporate attorney in private practice. Together they started to look around Boston for a new venue for Darryl’s most ambitious project yet. Beehive is an adult entertainment complex with food and music designed to appeal to the many people who love good music, good food and a late night venue to enjoy them all in.
Offering rustic comfort foods, the menu will be reflective of Mediterranean, American and Middle Eastern cuisines. This uniquely designed underground bistro will present entertainment daily, including cabaret, burlesque and live jazz with weekly appearances by Berklee College of Music students, alumni and members of the faculty.
There is something different about Darryl. As we debated another business topic, it suddenly struck me - he doesn’t quite think of the hospitality business in the same way that most of us do. He sees it as a real industry complete with political and economic dynamics that affect it as a whole and he tries to understand it as such. Not drawn by flights of fashion, food or fancy he intellectualizes things and applies some good old fashion business thinking, rather than ego-driven emotion. That is the essence of Darryl, not so much that he is the driving force behind his success, more that the ideas ebb and flow around him and he embraces only the ones that he feels will work. An interesting twist on the norm and something that seems to enable him to succeed where many fail.
He may be unsettling, but if you have a project or idea that you think will rock the Boston hospitality scene then this may well be the impresario for you.
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Industry Luminary 
