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Retirement isn’t slowing Johnny Winston down

Johnny Winston, Jr. Photo supplied.

Retirement is supposed to be a time to slow down, relax, maybe travel, maybe take up a hobby.

For Johnny Winston, not so much.

Winston, 54, retired from a multi-decade career with the Madison Fire Department last year, and has since launched not one but three business ventures – and has his eye on a fourth.

“I was on that big red fire truck for a long time,” Winston tells Blueprint365. “Being in business has been different. It’s a lot harder than I thought. But it’s a great challenge, though. Which is kind of what you need at my age when you’re retired.”

One of those ventures actually overlaps with his firefighting service: teaching CPR. Under the banner Johnny Winston CARES (Community Action Resource Education Services), he’s been a certified CPR instructor since 2016. He said that business ramped up considerably after Buffalo Bills safety Damar Hamlin went into cardiac arrest during a game on live television, only to have his life saved by the fast actions of medical personnel, including the administration of CPR. 

Another venture grew out of his own need to improve his own health.

“During the pandemic, I had gotten up to 235 pounds. I was having some health issues,” he says. “I’ve never been that big before. Like everyone else, I wasn’t going outside, I wasn’t going to the gym, wasn’t eating very properly. And so I kind of let myself balloon up. And when I started having some health problems, I decided, hey, maybe I need to do something about it.”

He signed on with a personal trainer, and that first session was a tough one.

“First session, I almost quit,” he says with a laugh. “I just was like, oh my God, I thought I was in good shape. I found out I wasn’t, and I needed to pick it up a notch.” 

He did just that with a second trainer, then decided to step into the role of trainer himself, taking on a small cadre of clients looking to get healthy.

The third business venture came about organically as well, owing a great deal to Winston’s long history of community involvement. He served two terms on the Madison school board, organized a streetball tournament and block party for many years and put a lot of time in with organizations like 100 Black Men of Madison and the Sable Flames. When Vera Court Neighborhood Center was looking for a new executive director, board members asked Winston to use his local network to find some candidates. Four of the five finalists were people he recruited.

“In the fire department, I did a lot of recruiting as a part of the hiring processes. Could I continue to do something like that for nonprofit organizations, or for profit organizations, helping in their recruitment efforts?” he says. “Just trying to help people. I don’t have a big red fire truck anymore, and people don’t have to call 911. They can just call me and say, ‘Hey, Johnny, I’ve got a challenge, can you help?’”

Now, he helps organizations address those challenges under the banner of Johnny Winston CARES Leadership Solutions.

The fourth venture Winston is looking to get off the ground is to pool some money with some other local Black investors and buy some income property.

“I would like to buy one (small apartment building),” he said. “If I buy one, I’d like two. If I got two, how about three? But why not try to share the wealth? Why not bring some other people on with me? I’ve never thought about life like this. The goal is to do it. We can talk about it all day long. Three businesses that I have going are aimed at providing the income needed to start the fourth, which is future assets. And if you had more people along with me, we could buy more assets.”

What does starting a business have in common with his old gig as a firefighter?

“It’s still helping people,” he says. “I’m just trying to help people without the big red firetruck.”

He said with more people of color in positions of power than ever, Madison is ready for more people of color to go into business.

“I think this is the perfect time. I think the pandemic kind of showed us (we) can’t just do nine to five anymore. There’s other ways that we can make our economics grow,” he says. “The challenging part of this whole thing is that we’re all human beings, and different people have different ideas of what a partnership looks like. And I learn something about myself every day, and I learn something about people every day. I have to learn, to work through challenges, and come up with solutions. And I think that’s what everybody does every day. That’s what business owners do. Every day.”