What I've Learned

Getting to Know Dan Flannery, CEO of Cape Resorts


I went to University of Maryland, College Park as an English major, intending to go to law school. Early in my freshman year, I was hired by a hotel. I waited tables in their casual restaurant and bussed tables in the fine dining restaurant.
A year later, I changed my major to Business and decided it was the hospitality business for me.
Last summer, I left Marriott after 37 years. They held a retirement party at The Times Square EDITION hotel in Manhattan, hosted by my mentor and great friend. There were so many people who were important at various stages of my career. My wife Jessica told me how lucky I was to be able to hear the impact I made on some people’s lives. She said, “Most people only have things like that said about them at their funeral.”
Having children is amazing— am I allowed to say that having grandchildren is even better?
Work ethic was everything in our family. I cut lawns and delivered newspapers, but my first “real” job was flipping hamburgers at McDonald’s in my home town of Gaithersburg, Maryland.

Images depicting Dan Flannery in his youth

Left: Dan Flannery with his two best friends in High School, Steve Ferra and Bob Haislip, who, coincidentally, both now live in Cape May. Bob is Congress Hall’s General Manager
Right: Dan Flannery at his High School graduation day with his late mother and grandmother

Marriott signed a deal with Ian Schrager to lead the development of a new luxury brand for Marriott called EDITION. They asked me if I wanted to become the Managing Director and build a team out of his office. He is as brilliant and driven as anyone I have ever known and was relentless about creating something exceptional every single day. It was exhilarating— and exhausting. I wouldn’t have had it any other way.
If I could go back in time, I would visit Studio 54, the nightclub Ian Schrager and Steve Rubell opened in New York in 1977. Having worked so long in the hospitality business and having worked with Ian, it would be incredible to experience that phenomenon.
I heard a great phrase once that leadership in the service industry requires “constant, gentle pressure.” Without pressure, you have no standards. If it isn’t constant, then it’s unfair to your team because you aren’t consistent. If it isn’t gentle, then people think you’re a jerk and tune you out. That captures what I aspire to.
On our tenth wedding anniversary, Jessica and I stayed at the original Ritz-Carlton in New York, which is now closed. My old boss was the GM and she put us in a suite overlooking Central Park that was bigger than our house. It had six balconies and the largest bathroom I have ever seen.
Bodrum, Turkey is my favorite beach town in the world. The landscaping was stunning, the beaches and water were pristine, the food was delicious, and the people and culture were wonderful. They could really use our help right now.
I finally went to The French Laundry with Jessica and another couple. It’s typically a nine-course meal, but the owner, Thomas Keller, was a regular at our hotels, so they sent out so many extras we ended up with 21. We started getting tired around course sixteen, but, hey, we made it in the end.
That would be my Death Row meal. Twenty-one courses at The French Laundry would buy me another four hours or so.
I love to binge watch – but we hold off until a show has been out for a few years. That way we can get through it all without any delays. We just got finished with Yellowstone.
A great Pinot Noir is how I’d start off the perfect evening.
When I was a college sophomore, Nike Air Force 1 came out. I wore them constantly. They recently made a revival – I’m still wondering if a 60-year-old can get away with wearing them today.
I stopped using shoe polish a long time ago, but I do love a good shoeshine when I come across one.
My dream car is a Lamborghini. My five-year-old grandson is with me on this one.
I still tear up watching Field of Dreams. I love baseball movies and I lost my father at a very young age. Being able to play catch with him as an adult… that would be amazing.
I coached all of my kids’ basketball teams. My daughter Lauren and I always said our dream was to own an arena and run an AAU basketball program.

A young Dan Flannery posing next to his family and Kareem Abdul-Jabbar

Dan Flannery with his family and Kareem Abdul-Jabbar, a regular guest he got to know. Kareem visited Lauren’s middle school during Black History Month

Growing up, I wanted to be a hockey player. Wayne Gretzky is the greatest of all time, but my heroes were Derek Sanderson and Bobby Orr on the Bruins. I was pretty good, but I had to quit during the gas crisis in the early ‘70s, so I started swimming, and I made the University of Maryland Division 1 team in my freshman year.
There are some tough days in this business. When that happens, I jump on the boat with my dogs and hit the ocean. We caught a seven-foot thresher a few years ago off of Asbury Park. He is known today in our family as the Asbury Shark.
I should have taken Spanish classes instead of German. A lot of our team speaks Spanish—not once has German come in handy.
I love to cook when I’m off. I favor the classics I was taught early in my career. Caesar salad with dressing and croutons made from scratch. And Steak Diane every Christmas Day – my family demands it.
I love the beach, but I need to be doing something. Sandcastles with the grandchildren or bocce ball.
But if I ever DID sit still long enough to crack open a beach read, it would be “The Five People You Meet in Heaven.” I’ll get to it one day.
I wish everyone knew how hard a housekeeper works. Try cleaning and making up 12-14 rooms a day and I bet it would give you a new appreciation. I try to leave time in the morning to strip my bed linens, consolidate trash, leave a tip and a nice thank-you note.
Don’t do what you love… do what you’re good at. You’re much more likely to enjoy it.

“Leadership in the service industry requires constant, gentle pressure. Anything else is unfair to your team.”

CEO of Cape Resorts, Dan Flannery posing for a picture

Dan Flannery joined Cape Resorts in June 2022 after 37 years at Marriott