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Western Mass. CEOs, business leaders tell young podcaster what it takes to be a 'Realistic CEO'

Every episode of the podcast begins with Mychal Connolly Jr. relaying the basics of how it got started.

“During a high class project, my teacher told me 'it's unrealistic being a CEO.' It's been my dream since I was 10, so I told her, ‘it is realistic.’"

Then Mikey, as his family calls him, invites listeners to follow him on his journey to learn what it takes to lead a company, a business or a community organization.

The podcast began about a year ago, when Mikey was still a senior in high school — after his teacher in a business class asked students to pick a car based on the income of the career they wanted.

Mikey said — he wanted a really nice car, so he was going to be a CEO.

When his teacher told him it wasn't realistic for him to be a CEO he said he pushed back.

“I defended my dream and I ended up becoming a CEO for that project,” Connolly said.

Mikey is now finishing his first year at Holyoke Community College, and simultaneously over the last 12 months he's interviewed about 60 CEOs and CEO types around western Massachusetts — bank presidents, restaurant owners, community organizations directors, lawmakers and truck drivers.

During a 30 minute interview, he asks a series of questions that eventually get to the nugget—what does it take to be a successful leader?

Jill Kaufman
/
NEPM

A series of questions and some consistent answers

Top tips Mikey has learned and shared through the podcast — develop confidence in yourself and your ideas.

“You just got to believe in yourself. I did not realize how simple it really was," he said.

Even as simple as just slowing down Mikey said, getting out of your head and sometimes taking a leap of faith.

Another CEO trait, listen to people.

"As a leader, your biggest quality is to be able to listen to the others around you," Mikey said, "not only your team members, but also your customers, so that you can learn how to improve.”

Several people on podcast episodes shared this advice, including Holyoke Community College President George Timmons.

"As a leader, you got to be humble enough to say, hey, what's the greater good?," Timmons said during Episode 28. "Is it because [the idea] is my way? Because I'm the president and it has to be my way? Or you know 'so and so introduced Option B' and it's going to still get me there and it's going to create better buy in," Timmons told Mikey.

Since few start off their adult lives as CEOs, finding out how they arrived at this point is a key part of the conversations.

When Mikey asked Diana Szynal how she became president of the Springfield Regional Chamber, she was strikingly candid about the hurdles.

“So one was I didn't finish college," Szynal said in Episode 16. "I was going to UMass to be a kindergarten teacher and, you know, basically ran out of money. I was supporting myself [in my] early 20s. It was actually at that time that I started working for the town of Hatfield. And... I just fell in love with local government.”

Reaching a TikTok generation

The intended audience for Realistic CEO videos are people around Mike's age, late teens, early 20s. But with each video episode originally a half-hour long, will they watch?

“Honestly, TikTok brain has kind of messed up the kids — and my — attention span," he said.

So Mikey and team package the long interviews also into shorter YouTube clips.

Mychal Connolly Jr. and Sr., in a studio after filming another episode of the Realistic CEO podcast.
Jill Kaufman
/
NEPM
Mychal Connolly Jr. and Sr., in a studio after filming another episode of the Realistic CEO podcast.

That team includes Mikey’s father, Mychal Connolly Sr., a marketing and content creator, and CEO of a digital billboard business.

In the job of parent, Connolly said he is mentoring his son.

“He's learning to become a CEO. He's learning how to make the decisions. Sometimes he listens to me, sometimes he doesn't,” Connolly said.

With Realistic CEO, Connolly has been connecting him to business contacts around the region, working with him on speaking with adults and getting projects done.

A children's book too, and the "LBW"

Realistic CEO began as a children’s book, written by both Connollys.

It features a little boy named Tony who lives in Dreamville. Like Mikey he sets out to prove that no dream is too big—especially becoming a CEO.

The class project for Tony is a lemonade stand.

“And then as he grows older, he turns the lemonade stand into a lemonade company,” Mikey explained.

The book – colorful and short – highlights qualities a CEO wannabee might need to know about, including the "LBW," the long or lonely boring work that is part of the job.

In the podcast, Charles Evans spoke about that. Evans was an aspiring NBA player, who now owns a team in the American Basketball Association

“As far as anybody wanting to own a team, it's a lot of hard work, a lot of grit, a lot of grind, a lot of dog days, a lot of tired days, a lot of heartbreak," Evans said. "But for the most part, you know, it's worth it."

The "LBW" for Mikey is booking interviews, he said, waiting for people to get back to him and booking speaking gigs at schools — which is happening more and more, to his surprise.

“I'm naturally super introverted. So this is out of my comfort zone," Mikey said, adding that over the last year, he's definitely become more comfortable.

Mikey has also demonstrated to himself and others — he has the markers of a Realistic CEO, especially determination.

Jill Kaufman has been a reporter and host at NEPM since 2005. Before that she spent 10 years at WBUR in Boston, producing The Connection with Christopher Lydon, and reporting and hosting. Jill was also a host of NHPR's daily talk show The Exchange and an editor at PRX's The World.

The independent journalism and non-commercial programming you rely on every day is in danger.

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SOMOS CONNECTICUT is an initiative from ǻ, the state’s local NPR and PBS station, to elevate Latino stories and expand programming that uplifts and informs our Latino communities. Visit CTPublic.org/latino for more stories and resources. For updates, sign up for the SOMOS CONNECTICUT newsletter at ctpublic.org/newsletters.

SOMOS CONNECTICUT es una iniciativa de ǻ, la emisora local de NPR y PBS del estado, que busca elevar nuestras historias latinas y expandir programación que alza y informa nuestras comunidades latinas locales. Visita CTPublic.org/latino para más reportajes y recursos. Para noticias, suscríbase a nuestro boletín informativo en ctpublic.org/newsletters.

The independent journalism and non-commercial programming you rely on every day is in danger.

If you’re reading this, you believe in trusted journalism and in learning without paywalls. You value access to educational content kids love and enriching cultural programming.

Now all of that is at risk.

Federal funding for public media is under threat and if it goes, the impact to our communities will be devastating.

Together, we can defend it. It’s time to protect what matters.

Your voice has protected public media before. Now, it’s needed again. Learn how you can protect the news and programming you depend on.

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