Page 37 - BusinessWest April 27, 2026

Darryl Cole
Global Cyber Product Consultant,
Liberty Mutual: Age 39
Cyber insurance is one of the more dynamic corners of
today’s business world. Just ask Darryl Cole.
“I would say the cyber insurance marketplace is
evolving as rapidly as technology itself,” he said. “When
I first started in underwriting, we were looking at theft
of credit card data as the biggest exposure company
could have, and we were looking at retail and hospitality
operations — restaurants and hotels, things like that
— as the most risky businesses. Now it’s a lot more
generalized.”
Cole was an underwriter for a decade before taking on his
latest expansive role at Liberty Mutual.
“What I’m doing now is helping other underwriters do
their job. I’m responsible for helping to set global strategies; set
strategies for marketing materials, presentations, and content for
our underwriters; and helping underwriters learn and develop,
helping them understand what’s happening in the cyber market
from an insurance perspective and a risk perspective. To be able to
do that globally is pretty cool.”
Active in the community, Cole has been PTO president at his
children’s school, served in his church’s youth ministry, volunteered
for Junior Achievement and the United Way, and helped coordinate
local efforts for Convoy of Hope.
And last year, he was elected president of Wilshire Athletic
Assoc., one of the most venerable youth sports nonprofits in
Western Mass., bringing his business acumen and ability
to connect with people to the organization’s leadership.
“Because I have a business and insurance
background, I noticed a few opportunities and I was
really eager to bring Wilshire forward,” he said. “And
we’ve hit this year running - we’ve increased our
social media presence, brought in guest speakers
for banquets, and put on a basketball showcase to
celebrate our players. We have amazing volunteers
- from our board of directors to coaches - and we’ve
been able to accomplish a lot.”
Much of his volunteer work stems from his heart for
children.
“I want to make sure kids are supported and cared for,”
Cole said. “At my core, I just care about helping people in
whatever way I can — particularly children, but anybody,
really.
“As humans, we all deserve security and respect and care
and support,” he went on. “And I’m always looking for ways
to live up to those ideals, whether it’s an informal setting,
offering whatever I can, or more formal opportunities like
partnering with community organizations. I think it should be
a way bigger part of the human experience to make sure our
fellow humans have everything they need.”
—Joseph Bednar
Mychal Connolly Jr.
CEO, Realistic CEO: Age 19
One of the intriguing aspects of 40 Under Forty turning 20
is the opportunity to welcome multiple generations into
the club. But while Mychal Connolly Jr.’s father, the
creator of entrepreneurial enterprises like Stinky Cakes,
Stand Out Truck, and Marketing and Cupcakes, was
inducted into the class of 2009, this 19-year-old —
one of the youngest honorees ever — has created
his own very different, and very impactful, niche.
It’s called Realistic CEO — an enterprise inspired
by a school project during which a teacher told
Mikey that his dreams of being a CEO were, well,
unrealistic.
Connolly has turned that motivation into a
leadership and success platform serving young
people from elementary school through college
through books — including a much-distributed
illustrated book that tells his own story —
as well as curriculum, workshops, media
platforms, and speaking engagements.
“The last couple of years, we’ve impacted
about 17,000 students through our books, our
curriculum, and our programs, and we’ve been
working on expanding our reach from the local
area — Springfield and surrounding towns and
cities — to going a little farther, to the Boston
area and Worcester,” he explained.
“Our goal is to be able to impact 500,000
students. The whole goal behind Realistic CEO is to help
students with career readiness, workforce readiness, and
financial literacy,” he went on. “My goal is to help students
prepare for careers — and we do it in a way that we want
every single student to feel like they’re worthy enough
to be an executive.”
Connolly also hosts the Realistic CEO podcast, now
topping 100 episodes, in which he interviews local
business leaders about their journey and how they
seek to inspire others. And he also launched Realistic
Lemonade, a nonprofit that raises money and seeks
sponsorships to enable him to go into more schools.
Oh, and he’s doing all this as a full-time honor roll
student at Holyoke Community College.
“My favorite part is seeing the difference in the
way students light up,” he said of those visits and
speaking engagements. “Maybe the lightbulb needs
to be twisted a little more to be totally turned on.
And you see the light is fully on after we speak.
That’s my favorite thing — to see the students
believe in themselves, to hear them after we’re
done, saying, ‘thank you, I needed this.’
“We know how bright and smart the students
in the community really truly are,” he added, “and
we’re able to create a bridge that allows them to
cross.”
—Joseph Bednar
Business W est 2026
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