His road to retiring in Hawaii is now working in Chicago, with a memory of days in Key West, Fla.
Robbie Baldwin was 18 when he went to Key West on vacation, and immediately fell in love with its laid-back lifestyle.
"I went back [home], packed up my stuff and moved," to Key West, he said. "When I got there, I realized how expensive it was to live there. I figured out the best money was in bartending and convinced a bar owner to give me a shot, [even] with zero experience and without ever having been in a bar being so young."
Still, he got the job and was hooked on the industry.
"There's no better feeling than coming up with a concept/event and working on it, and then seeing it all come together," said Baldwin, who now works his bar magic on Halsted Street, in the heart of Boystown.
"I really love what I do. It's great. I feed of the energy of the customers. I love when I look around and everyone is having a great time and dancing. It means I've done my job."
What's the most difficult/challenging part of the job?
"There's a fine line between throwing a party and being part of the party. It was hard learning how to do this when becoming a manager," he said.
Job title: General manager at Scarlet
Favorite movie: "Tough one; the last movie that I loved was Ted."
Favorite TV show: "As terrible as it is, I love The Real Housewives of Beverly Hills."
Four people (living or dead) who you'd like to have dinner with: "My grandpa, Brandi Glanville, Robert the Bruce and Hillary Clinton"
Biggest tip ever received: $100, a few different times
Tattoos: Has a Foo Dog on the back of his neck and a Nautical star on his right calf
Little-known fact: "I'm kind of obsessed with penguins."