Smart Move: Guy Middlebrooks’ Journey From Winn-Dixie To CubeSmart

Picking up a part-time job in high school used to be a rite of passage for teenagers. It was how you earned money for dates, a new record, and maybe even a used set of wheels. But most people aren’t still talking about that high school job 40 years later. Guy Middlebrooks is an exception. He took a part-time gig at Winn-Dixie supermarkets and turned it into a career. While he eventually pivoted to self-storage, the lessons he learned stocking shelves and managing stores still resonate today. 

A Winning Job 

To share his story, Middlebrooks is calling in from CubeSmart’s headquarters in Malvern, Pa. At 6’4”, he’s a commanding presence, even on Zoom, but as he reflects on his early years in Tallahassee, Fla., he reveals the thoughtful, down-to-earth personality behind the tall frame. 

He takes us back to 1983, when a 16-year-old kid from Florida was just looking to make a few extra bucks. Winn-Dixie, the well-known Sunshine State supermarket, was hiring clerks, so Middlebrooks signed on—without the slightest idea how long he’d stay there. “You don’t expect to stick with your high school job into your 40s,” he says with a laugh. “But that’s how it went. I worked my way up—started on the floor, then became a store manager.” 

Winn-Dixie recognized his potential early. They invested in him, sending him to meat cutting and produce schools, then off to Jacksonville for a two-week certification course that opened doors to corporate positions. “After that, I became a district manager, then regional manager.” 

At every level, Middlebrooks absorbed the lessons. “Early on, it was all about customer service, store conditions, cleanliness, managing employees and schedules. Later, it was budgets, financials, and P & L reports. That all carried over when I transitioned into CubeSmart.” 

Opportunity Knocks 

Winn-Dixie had been good to Middlebrooks, but the grind of retail was starting to take its toll. “The holidays were brutal, weekends didn’t exist, one store had just been robbed, and someone fell at another and was getting litigious. I needed a change.” 

In 2006, his résumé landed on the desk of a recruiter for U-Store-It. “That was our brand before we became CubeSmart,” Middlebrooks says. “It had gone public two years earlier, but we didn’t rebrand until 2011.” 

Middlebrooks remembers the phone call like it was yesterday. “The recruiter says he’s calling on behalf of a self-storage company that had recently gone public, raised a lot of capital, and was growing fast, and they were looking for operations people to run properties.” 

At the time, Middlebrooks had no real knowledge of the self-storage industry, so he politely declined. But the recruiter anticipated that. “He says, ‘No, Guy. They want people like you—your skill set, your experience in retail. They think you’ll fit in well with their industry.’” 

Despite some hesitation, Middlebrooks made the leap, leaving behind the familiar comfort and occasional chaos of Winn-Dixie to manage a Florida district for U-Store-It, a territory that stretched from Jacksonville to St. Augustine. He quickly found his footing, applying lessons from retail through a self-storage lens and spotting connections others might miss. 

“In retail, you have your everyday grocery shoppers,” Middlebrooks says. “But as a store manager, you begin to recognize life events—weddings, funerals, birthdays, graduations. Customers need your help, whether it’s a catering tray, a cake, or a bundle of balloons.” 

Drawing the parallel, he adds, “And what’s the primary driver in this business? Life events.” He counts them off on his fingers—death, divorce, downsizing, displacement, deployment—and continues, “When someone passes away or a couple splits, sentimental items or furniture gets placed in storage. Someone loses a job and downsizes, they turn to storage. Conversely, your career is booming, so you’re spending money and you need a place for your toys—the boat, motorcycle, or convertible. That’s the self-storage cycle.” 

With this understanding, Middlebrooks made customer care a focus, just as he had done at Winn-Dixie. “When someone walks in or calls t 

‘.o rent a unit, our teammates need to understand their situation and be empathetic. The personal interactions we have with our customers really sets us apart from the competition.” 

Putting this perspective into action made his district very successful, and it didn’t go unnoticed. Not long after, he received a call—not from a recruiter but from the CEO himself. “Dean Jernigan, the CEO at the time, asked me to take over Atlanta as well,” recalls Middlebrooks. Jernigan told him, “We need you to duplicate what you did in Florida—Atlanta’s struggling.” 

Not long after that, Jernigan asked Middlebrooks to take on the director of operations role. Middlebrooks was game, but there was a catch. The Florida native would have to uproot his family and move to Malvern, Pa. 

“There was a lot of discussion about that,” Middlebrooks says with a laugh. “We lived eight blocks from the ocean in Neptune Beach, and our kids, Matthew and Hannah, loved it there. Giving that up wasn’t easy. But Dean was persuasive, telling me I’d have a really bright future with the company if I did it—he even got my wife in his corner!” 

Once she was on board, it was decided. The family moved to Malvern—and Jernigan kept his word. Middlebrooks moved up quickly, from director of operations to vice president of operations. In 2010, the company acquired United Stor-All Management, bringing 80 properties into its third-party management portfolio. Several years later, Middlebrooks was tapped to lead that department as senior vice president of third-party management.

New Relationships 

As senior vice president of third-party management, Middlebrooks forged connections across the industry. “Large and small operators, buyers, brokers, suppliers—you name it. I met so many people in this role. I was attending all the conferences, speaking on panels, delivering presentations and keynotes. It was a tremendous time of growth and success.” 

He’s not exaggerating. Middlebrooks and his team grew the original 80 stores acquired through United Stor-All to an impressive 850 third-party-managed locations. 

But there was still another rung on the ladder left to climb. Today, Middlebrooks serves as executive vice president of operations, overseeing store operations, facility services, real estate development, and store transitions. Although Middlebrooks has taken on a lot of responsibility, he says the secret to his success is having a good team. “I work with some really good folks,” he says with a bit of his Southern drawl shining through. “I only have four direct reports, but there are many other layers of people helping out.” 

That’s what has allowed him to keep a finger in the third-party management pie. “I didn’t want to give it up completely—I enjoy it too much,” he says. “So, along with everything else, I’m still involved, but I promoted Devin Crow to run the day-to-day, and I’m lucky to have him.” 

Middlebrooks also made a lot of connections during his three-year stint with the Self Storage Association (SSA). “I was on the board of the SSA as their first-ever REIT representative,” says Middlebrooks. “In 2010 or so, it got to a point where the REITs were getting so big that the SSA wanted a voice from them on the board. And that was me.” 

There wasn’t any tension between himself and smaller operators; rather, being there helped open the lines of communication to make business better for everyone, regardless of size. 

His involvement with the associations didn’t stop there. Middlebrooks has gone on to speak at numerous events for the Texas, Arizona, Colorado, and New York SSA chapters; he even joined the latter two years ago. “We have a big presence in New York City as a company, so I'm able to stay close to what’s going on there, offer support to the association and the board, even help out from a political perspective.” 

Hot Topics 

Many industry hot topics are inescapable, discussed on socials, podcasts, and at every tradeshow. But when asked about them, Middlebrooks holds up a big hand. “You know, I think a lot of it has already been said, and I don’t know that I have much to add … there’ll probably be a story in this issue on one of those topics anyhow.” 

He’s not wrong, but he does agree to field a couple of questions before moving on. 

On the topic of existing customer rate increases, particularly the strategy of offering low rates followed by high rent increases a few months later, he is firm that CubeSmart has not taken that approach. “Our strategy is to take really good care of our customers and to maximize revenue for our shareholders. Sure, there is some pushing and pulling in different areas to improve revenue, but we’re not engaging in that.” 

Still, he respects what other operators are doing. “Our peers are smart—really smart. They know that pricing makes an immediate impact and they’re doing what works best for their company or property.” 

Next up is remote management, which grew in popularity during the pandemic and continues to grow today–not that everyone is on board. “CubeSmart has 75 to 100 remotely run properties,” he says, “but it’s more of a hub-and-spoke model.” 

The hub-and-spoke model simply means that a large, fully staffed property with a strong general manager supports smaller, remotely managed sites nearby. “That’s the way to do remote management,” he says. “Otherwise, I like the customer care aspect of having someone on site.” 

Middlebrooks notes that customer preferences vary. “We’ve done surveys and worked with consultants, and we’ve determined that there are basically three types of customers: those happy never to speak with anyone and do everything online; those who want to see a manager, tour the facility, and review leases in person; and a middle group that can use technology but still likes to visit the office and pay in person.” 

His goal is to serve them all. “If there’s a manager there, people can choose whether or not to interact. I think that’s important because technology can fail. We’ve all experienced hiccups.” 

One tech hiccup he recalls happened when he was attending a conference shortly after the hotel implemented Bluetooth-enabled locks on the rooms. “I did the pre-check, went straight to my room, and it didn’t work, so then I’m having to drag my luggage back down to the check-in desk anyhow. It’s like, ‘Just give me a key I can put in my wallet, please,’” he says with a laugh. 

Lastly, Middlebrooks shares the biggest headwind in the industry today: “New supply,” he says matter-of-factly. “That can have a dramatic effect on local market pricing, occupancy, and financial results. It’s fine when there's a lack of supply or a fast-growing population, but not when a market is already oversaturated. We get worked up about legislative issues and such, and those are important to keep an eye on too, but ultimately oversupply is our biggest challenge.” 

His Greatest Successes 

Today, Middlebrooks couldn’t be more pleased with how things have turned out for both CubeSmart and himself. “We knew 15 years ago that CubeSmart could be a major force in the industry, and that’s why we rebranded,” says Middlebrooks. “U-Store-It just felt like a low-price, do-it-yourself brand, which didn’t fit with our vision. Now we buy some of the nicest properties nationally while selling off older, lesser-quality first-gen stores.” 

He continues to highlight the cooperative spirit in self-storage. “There’s mutual respect among operators. When one company or property does well, it lifts neighboring ones too. There’s a ‘we’re all in this together’ attitude, which is wonderful.” 

Mentorship is also something close to Middlebrooks’ heart. “I’ve mentored many teammates who started right out of college or whom we brought in with no industry experience. Over 17 years, I’ve watched them grow in their career, get married, have kids, and even attend some of their weddings. It’s been a joy to help them on their journeys. It’s all about our company culture and our values ... and the leaders who genuinely care about developing their teams and role model what it means to be a CubeSmart teammate. Those are the things I’m most proud of. Their stories are my greatest successes.” 

The Long Haul 

When Middlebrooks visits his now-grown children in Florida and steps back into a Winn-Dixie, he’s reminded of his roots. “I figured I’d retire from Winn-Dixie,” Middlebrooks says thoughtfully. “We had a great little life in Florida, just off the beach. I had no idea that almost 20 years later, I’d be an executive vice president of a publicly traded company, living in the Northeast, ringing the opening bell on the New York Stock Exchange, and overseeing 3,000 teammates.” 

Middlebrooks shakes his head, as if he still doesn’t believe it. “I mean, that’s a big deal!” 

When he gets back to the Sunshine State, does he ever think about staying? “We’ll probably retire there one day, but there are no plans in the immediate future! I’m continuing to take on new responsibilities, so I’m in this for the long haul.” 

Middlebrooks pauses for a moment, then smiles. “I’ll put it this way: Your story may be my first cover, but I don’t plan on it being my last.” 

Brad Hadfield is MSM’s website manager and a staff writer.