Moving Story

Jackie Janulewicz (left) and Tony and Jenna Gleason
Tony Gleason recalls that the landscaping business he started when he was 16 and had grown into one of the 100 largest such ventures in the country was at a critical crossroads.
“We had substantial, profitable, high-end accounts, and we thought we had achieved optimal growth,” he explained. “Our future paths would have been an outward geographic expansion or inward expansion through our real estate and self-storage portfolios, and I felt that, when 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 business 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 considered downtown Northampton landmarks — the historic Coolidge building, 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 opportunities and challenges abound (more on this later).
“Storage can be extremely profitable or stagnant, depending on how you enter the market. You have to take a lot of time to invest in the diligence process and look at the metrics — there’s square-footage-per-capita metrics that tell the story of the demand, and you have to remain true to those metrics.”
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 Achievement 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.

Tony and Jenna Gleason at their self-storage facility in Easthampton, part of a portfolio that now includes more than 2,200 units.
“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-storage, as happened with the Dumont factory building in Greenfield, and in Pittsfield, where a three-decade-old warehouse and, more recently, a cannabis facility is being similarly converted.
As with the real estate arm, the plan for the self-storage division is controlled growth but eventually becoming one of the largest self-storage operators in the country, Jenna said, noting that the goal for the next several years is to continue filling in the spaces between the pinpoints already on the map.
Tony agreed, while noting that there is still room for considerable growth in this still relatively young business, with many communities in this region far from saturated — although some, like Springfield, have likely reached that point.
“Storage can be extremely profitable or stagnant, depending on how you enter the market,” he explained. “You have to take a lot of time to invest in the diligence process and look at the metrics — there’s square-footage-per-capita metrics that tell the story of the demand, and you have to remain true to those metrics.”
For this issue, we take an in-depth look at the Gleason Realty Group, now with a portfolio value approaching $70 million; its recent investments, totaling more than $30 million; and its plans for continued expansion.
Space Exploration
Tony Gleason told BusinessWest that his family has a long business history in Northampton — his great-grandfather operated a moving and storage company in what is now the Gleason complex — and with its most famous resident, the country’s 30th president.
Gleason said his great-grandfather’s company moved Calvin Coolidge into the White House when he assumed the office after the death of Warren Harding in 1923, and also helped move his items back to Northampton and into his presidential library. Meanwhile, Gleason Realty now owns and manages the Coolidge building, and the Fitzwilly’s building is home to Coolidge’s old law office. It’s on the second floor and is now occupied by a researcher.

The old Post Office in Northampton is one of several recent additions to the Gleason Realty portfolio.
But enough about Silent Cal. His former office is a small part (250 square feet) of a much larger picture, with the Gleasons and their team still filling in the canvas.
On the real estate side of the equation, there have been several additions over the past several years, including the mixed-use campus in Easthampton, which houses a diverse mix of tenants, including a doctor’s office, a tattoo parlor, a chiropractor, and other small businesses, said Jackie Janulewicz, a former school librarian (who also worked for Gleason’s landscaping company while earning her master’s degree in education) who joined Gleason Realty in 2024 and serves as director of Operations and Development and wears many hats, including property manager.
But much of the recent activity has been in downtown Northampton. The Coolidge building was acquired at auction in late 2023 when it was only half-occupied, said Tony, adding that it is now 100% occupied, with a mix of medical, office, and special-use tenants.
Meanwhile, the Fitzwilly’s building and the Fitzwilly’s and Toasted Owl businesses were acquired over the past few months. (The acquisition also includes a separate building off Route 9 in Hadley that will be separately marketed for sale or lease.)
“My first thought is always that we’re helping our customers, which are, ultimately, also our neighbors.”
The Fitzwilly’s building, also known as the Masonic building, was broken up into six different condo units with separate ownership, said Janulewicz, adding that the property is nearly full. “I only have two small spaces left, and I have bites on both. I don’t imagine them being vacant much longer.”
Moving forward, Tony said the real estate division will continue to grow and add to its portfolio, but in a smart, controlled fashion.
“We’re always looking for new opportunities, but the deal has to be right, and we have to be cautious and conservative in all of our decisions related to the commercial real estate business, because there are ebbs and flows to occupancy and varying levels of risk factors that tie into different types of tenants that may into a building,” he explained. “Our primary focus is on our self-storage business growth, but we are always going to look at Western Mass. real estate opportunities as they come around.”
Elaborating, he said the trend toward remote work continues to impact the commercial real estate industry, with many larger buildings in different markets seeing higher rates of vacancy as businesses continue to downsize. There is interest in smaller spaces, 5,000 square feet and under, he noted, adding that his company will continue to look for opportunities that provide those footprints.
“One of the reasons we did these last two deals is that a lot of these spaces are smaller in nature, and it’s easier to grow occupancy,” he explained, adding that there are many properties now coming onto the market, and the company will be diligent and cautious as it seeks to grow the portfolio.
“I think I look at 10 or so deals a week,” he explained. “Some advance five minutes, some advance 20 or 30, and some four to six months through a due-diligence process that ends up in an actual acquisition. What sets us apart is trying to remove emotion from the decision, as well as not going after everything that’s available; 95% of what’s out there is not going to work, and that’s OK.”
What’s in Store
Jenna Gleason remembers telling friends and colleagues at Baystate of her decision to leave her role in marketing, shift to the family business, and focus most of her energies on growing its self-storage portfolio.
“Some of them were like, ‘what are you thinking … you’re getting into self-storage?’” she recalled with a laugh, adding quickly that this is serious business, one that has grown steadily over the past half-century or so and still has enormous growth potential.
But before getting into it, she had to learn it, as she acknowledged earlier. And there was a lot to learn.

The Fitzwilly’s building, another addition to the Gleason Realty portfolio, is now at nearly 100% occupancy.
“I listened to a lot of podcasts on storage and tried to read as much as a I could on the business and the industry — any article I could find — and we worked together to figure out how we were going to leave a footprint,” she recalled, adding that she got involved as Tony was fully engaged with selling the landscaping business. If she had a problem, she said, he would usually reply, ‘figure it out.’ And she did, learning while doing.
From the beginning, the goal has been to stand out in a field that was crowded with players of all sizes and has become more crowded since, she went on, adding that she believes the company differentiates itself through a personal approach defined by building relationships with customers.
“My first thought is always that we’re helping our customers, which are, ultimately, also our neighbors,” she explained. “When someone’s in need of storage, typically it’s a stressful time in their life; they’ve lost a loved one, it might be a change in a professional career, a change in a relationship or home life — there’s usually a quick, dire need for storage. So we want to be there for them and make this less of a hassle and more easy.”
As for the name, Gigi is a family nickname for Jenna, and GiGi’s Self Storage gives the venture a less corporate feel, they said, adding that, as with the real estate division, the goal with this side of the business is controlled growth.
There are plenty of existing facilities that come onto the market, said Tony, adding that the company is continuously looking for opportunities that make sense, knowing that size brings obvious efficiencies and economies of scale.
And there is room for new development as well, they said, noting that, unlike with the banking and cannabis sectors, most area communities are not yet saturated or oversaturated with self-storage facilities.
Still, there are risks involved with such developments, and due diligence, in the form of understanding a market and its needs, is necessary.
“When you’re building from the ground up, you have to be very confident in the market — that you can lease out the spaces,” Tony said. “You want to make sure the demand is there. The worst possible scenario would be to build or overbuild a facility and look back three or four years later and not be able to fill it.”
And for the first time in the history of the industry, there are signs of oversaturation in some markets, he went on, adding that smart growth will be the course with GiGi’s, which is still a tiny player within the market, but has plans to become one of the 100 largest in the country, and can get there by growing four or fivefold.
That’s the plan for the next five to 10 years, anyway, and based on the success of Gleason’s landscaping business, there is little doubt that these driven entrepreneurs can get there.
















