Bootsie was crushed when he had to close the doors to his club four years ago.

He’s now back on the scene with The Grand, the live music and comedy club he opened on Church Street last month.

“I’ve learnt a lot of lessons over the past few years, so now it’s about giving people something different and finding a different angle for them to enjoy,” said the comedian, who joined Magic 102.7FM as a host after his comedy club went out of business in 2011.

He quit that job in September to follow his dream.

“I made a decision, a tough decision, to put radio down and just begin to attack this idea 100 per cent and give it my all,” said the 49-year-old, whose real name is Earlwin Wolffe.

“My idea for the club is to offer a venue for folks who need a space to have their birthday party or event. There aren’t many places to go for that, which are affordable, so we are catering to all kinds of parties — birthdays, anniversaries, divorce parties, whatever.”

Live music and comedy will take centre stage whenever there isn’t a private function booked.

“Instead of just opening as a drinking hole, I want it to be a space where people can enjoy quality entertainment,” he said. “The restaurant portion will eventually come on board as well.”

Bootsie was a college freshman studying marketing management when he decided a career in entertainment was a better fit.

“I’ll never forget it, I just finished an economics exam and was beat. A group of us decided to go rent some videos and one was Whoopi Goldberg in concert, where she does all these funny skits. I was watching this stuff and thought, ‘I could do that’.”

He returned to Bermuda and told his family he was done with school.

“They asked me what I wanted to do instead and I said, ‘I want to tell jokes’. They were like, ‘Okay ... ’.”

He started off performing skits. His first show in 1990 sold out. “It was three shows and that room held 650 people,” he said. “I was like, ‘Wow’.”

In the years since, he’s emceed at comedy clubs and events, and worked as an educational therapist’s assistant and radio host for Hott 107.5 and Magic 102.7FM.

“My first radio show was called Bootsie and Company and that did extremely well, but they fired me in 2003 or 2004,” he said.

“I was devastated. That’s when my old buddy Chris Trott told me about a building he had that was just sitting there on Front Street. He said, ‘Do you think you can do something with it?’

“I always wanted to have my own comedy club so I ventured into that.”

He opened the club and then decided to renovate. According to Bootsie, that was a big mistake. The project was supposed to take six weeks; it wasn’t completed for six months.

“When we reopened, the recession hit and that’s when all the violence started coming,” he said. “I wasn’t making money and it was developing a stigma that it was a rough spot. The best thing to do was to get away from it and close.”

The experience taught him the importance of staying true to himself.

“A lot of times we go through life and we’re not honest with ourselves so we stay in situations for too long. We’re afraid of failing or what other people might say or think. We’re afraid of change. But I think once you’re honest with yourself, then you feel free. A lot of my pitfalls happened because I wasn’t honest with myself. With the building on Front Street, I saw trouble but I tried to ignore it.”

The comedian admitted to feeling a bit afraid about starting another business.

“When I started this venture I had some people say, ‘I hope you make the right decision because you failed on the other one’. I don’t see it as failing, I look at it as learning.

“You only fail if you haven’t learnt anything or go back and make the same mistakes.”

Bootsie will open for comedian Don Spencer, billed as the world’s fastest hypnotist. The show takes place at Hamilton Princess on Saturday. An after-party will be held at The Grand.

Tickets, $50, are available at 27th Century Boutique and The Grand. Mr Spencer is also offering private sessions for anyone looking to break a habit or cycle. Sign up on Facebook: Bootsie @ The Grand.