Page 5 - BusinessWest August 18, 2025

Tony and Jenna Gleason at their self-storage facility in Easthampton,
part of a portfolio that now includes more than 2,200 units.
Staff Photo
comparing the offers that were presented and looking at both paths,
it was going to be easier, and bring me more joy, to go down the path
of real estate growth and expansion and moving our self-storage busi-
ness forward than to try take our landscape and snow removal business
regional.”
Thus, he sold the business to Yellowstone Landscape, the second-
largest landscaping firm in the country, in May 2023, thus beginning
what we’ll call the next chapter of his entrepreneurial exploits. It
includes the formation of the Gleason Realty Group and that inward
growth of the real estate and self-storage divisions that he mentioned.
With the former, the company has acquired what would be consid-
ered downtown Northampton landmarks — the historic Coolidge build-
ing, also known as the old Post Office on Pleasant Street, as well as
what Gleason calls a three-part purchase of the Fitzwilly’s building on
Main Street and the Fitzwilly’s and Toasted Owl operating businesses.
The portfolio also includes 179 Northampton St. in Easthampton,
a mixed-use campus, as well as the Gleason complex on Pearl Street,
where the family has done business for more
than a century, and where other tenants, from a
brewery to the Registry of Deeds, reside. And it
will continue to grow in controlled fashion, said
Gleason, adding that the real estate market is in
an intriguing state of flux where both opportuni-
ties and challenges abound (more on this later).
With the self-storage division ... it has
become the purview of Gleason’s wife, Jenna,
who left a job working in marketing and brand
strategy for Baystate Health to assume this
challenge. The two are both BusinessWest 40
Under Forty winners, Tony in 2010 and Jenna
in 2017; Tony also won the Alumni Achieve-
ment Award in 2022.
“It was a big jump and a big risk, but it’s one that we believed in, so I
totally pivoted my career,” said Jenna, while offering a primer on the self-
storage business and acknowledging that she had to learn it herself, and
is still learning.
“I had limited exposure to the storage industry — Tony had some
experience in that he owned a facility in Hatfield for three or four years
— but it was really my baptism-by-fire learning experience,” she went on.
“I looked at everything from different software programs we wanted to
use to how to brand ourselves and differentiate ourselves; we really got
to create it from the ground up.”
This side of the venture, called GiGi’s Self Storage, started with the
acquisition of property in Easthampton that included 46 units of self-
storage, a site that has been further developed, bringing the number
to 200 units. Since then, there have been additions to the portfolio in
Greenfield, Northampton, and, more recently, Sunderland, Pittsfield,
Palmer, Leicester, and Stafford Springs, Conn., bringing the totals to
nine locations and 2,200 units.
These investments include a mix of existing businesses and new
developments, including the conversion of older properties into self-stor-
age, as happened with the Dumont factory building in Greenfield, and in
Julie M. Quink, CPA and Deborah J. Penzias, CPA
Richard F. Burkhart, CPA and Salvatore J. Pizzanelli, CPA, JD, PFS
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“It was a big jump
and a big risk, but
it’s one that we
believed in, so I
totally pivoted my
career.”
Business W est << FEATURE >>
AUGUST 18, 2025
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