Combining Personality & Passion Into Life & Business | Jonathan Wasserstrum, CEO of SquareFoot

Combining Personality & Passion Into Life & Business | Jonathan Wasserstrum, CEO of SquareFoot

A lot has been made about Jonathan Wasserstrum sitting in the middle of the open offices at SquareFoot, his commercial real estate company, instead of in a corner office secluded from his employees.

But when you consider how his company is disrupting the office space game it doesn’t really come as that much of a surprise that he’s mixing things up in the office as well. Co-founded by Wasserstrum in 2011 in Houston, Texas where he grew up, SquareFoot helps growing businesses find flexible location options – so as they continue to scale up they either have room to grow or the option to find another space.

As you’d expect, SquareFoot, now based in New York City, uses all manner of technical tools and algorithms to source spaces and determine how a company will fit into a space, but they also rely on brokers to understand clients’ needs, show them available locations and walk them through the lease process.

This combination of advanced analytics and human guidance has made the company popular with clients like mattress giant Casper, food deliverer Instacart and Breather, the Airbnb of workspaces. It’s also made them a focus of investors—a recent $16 million in Series B funding means SquareFoot has nearly $30 million in backing.

Not bad for a company that offers a free service (SquareFoot gets paid transaction fees by landlords). In February 2019, SquareFoot acquired PivotDesk, which helps companies with tenants for their unused office space. Again, they get paid on commission so there are no upfront costs.

In June 2019, Wasserstrum and crew created FLEX by SquareFoot, which sees the company leasing directly from landlords and then re-leasing that space to clients at much-shorter-more-flexible-than-normal lease agreements. The company has also come full circle, as they’ve just launched in Houston, looking to tap into the area’s small business and startup growth.

We connected with Wasserstrum to hear about how SquareFoot came to be, his advice for fellow entrepreneurs and to ask him if a guy who runs an office space company has any space in his life for something other than work.


Once you start to learn about Wasserstrum, it doesn’t come as a surprise that the idea for his company was an outgrowth of him trying to help someone out. He’s just that kind of guy. Nice. Helpful. The kind of dude who sits with his employees without making everyone—him or them—uncomfortable.

“A friend of mine reached out while he was struggling to find real estate for his company,” he remembers about starting SquareFoot with fellow founders Justin Lee and Aron Susman. “We saw that there was a big need in the market to help businesses find, transact and occupy real estate. We recognized a hole in the market, which led us to start our own business.”

Wasserstrum wasn’t coming at the problem from out of nowhere. He studied economics at Emory University and then went on to get his MBA from Columbia Business School where he studied entrepreneurship and real estate. He also had nearly three years experience as an analyst for Jones Lang LaSalle, a commercial real estate and property investment firm.

Though the company was entering the office space business, SquareFoot didn’t have their own home. In fact, Wasserstrum started the business in his parent’s attic, which had the bonus of him not having to look far for motivation since he considers his mom be his biggest inspiration.

“She grew up in a Lower East Side tenement and commuted both ways in the snow to school,” he says. “She became one of the first women at Harvard Business School and had a successful career. She was one of the few women in the executive room before it was cool.”

Following in the footstep of this trendsetter, Wasserstrum had no choice but to take big swings, including leaving home for the big city—New York. It helped that SquareFoot was chosen to be a part of the Entrepreneurs Roundtable Accelerator (ERA), an early stage fund and technology accelerator based in Manhattan.

“Houston is an entrepreneurial city, but at the time it did not have a very strong tech startup ecosystem. Real estate is done here in NYC, the capital of the world,” Wasserstrum recalls. “In 2013, we were accepted into the ERA accelerator and the stars just aligned.”

In some ways, the move speaks to everything the company is about. SquareFoot helps growing companies handle their on-going development by finding offices that fit their current needs without forsaking the future vision for organization. It all comes down to one thing Wasserstrum says: flexibility.

“Recognizing the right space for today may not necessarily be right in the long run. That’s only growing as a trend that business owners are grappling with and growing wise to,” he continues. “At SquareFoot, we have to offer the right solutions for growing companies at all stages and sizes.”

Because of this approach, it has been said that SquareFoot and Wasserstrum have broken the model of the traditional brokerage industry. Instead of working backward from an available space with the company, then having to figure out how to make it work, SquareFoot finds out what the company needs and then finds the best fit. This customer-focused approach is a game-changer.

“Your chosen office space should mirror what you want from your employees. I encourage our brokers to start with those conversations with clients: What do you hope staffers get out of working for you, and what does that look like?” Wasserstrum says. “We have to lead by example. That’s why it matters so much to me.”

It also matters to their customers who have turned the attic startup into a $5 million dollar industry player. Just read the customer reviews online and you’ll see people calling out by name—Chris, Brett, Kyle, David, and Elliot—the SquareFoot staffers who helped them find new office space.

“Our clients come to us because we offer things that nobody else does, including technology and transparency to make the process much better. When you have a differentiated market, it works,” he points out. “Remember, the typical SquareFoot client isn’t necessarily a real estate person, it’s a growing company just like us who are seeking answers.”


Wasserstrum doesn’t claim to have all the answers. Still, he has created a professional approach that’s not only successful but also defines him and his business. As we’ve mentioned, it’s hard to talk about Wasserstrum’s business style without coming back to him sitting in the middle of the office with all his employees. Part of it is Wasserstrum just being himself. As a leader, he tries to bring an element of authenticity to everything he does.

“People have an idea of what the CEO is, or should be, and I want my employees to see me as a problem solver just like them,” Wasserstrum says. “I rely on them to solve problems I can’t. We work best when we all work together.”

And Wasserstrum isn’t blowing smoke when he talks about getting along with employees and collaborating with his staff. Do a little digging on him and you’ll find that even his competitors say he’s as nice a guy as you’ll find in the business world.

Though he won’t take credit for his agreeable demeanor, giving his mom (“She worked hard and was nice to people the whole way.”) and his upbringing (“I act how I was told to act”), he does understand the value of treating people with kindness and respect.

“I’ve never found being a jerk helpful,” he says. “I know when I’m dealing with other people who are jerks, I lose interest in working with them or in helping them out. I sense that that’s a common feeling for many. There’s no reason to be mean when being nice is easier.”

Sadly, nice guys do finish last—at least some of the time, as Wasserstrum lists failed furniture salesman as one of his previous jobs. Most successful CEOs would probably have this type of information expunged from their record, but not Wasserstrum. Instead, he leans into this less than stellar performance in his background and recommends that others be comfortable with their failures too.

“I not only tolerate failure, I encourage it from my team,” he explains. “That’s how we make sure we’re pushing ourselves further than we did yesterday.” Wasserstrum adds that this idea of overcoming obstacles and persevering is key to becoming a successful entrepreneur.

“Don’t second-guess yourself when things go wrong. Some things are bound to go wrong,” he advises. “Hold onto your conviction even when others tell you it won’t work. It’s your vision for a better future and conviction that will get you through the tougher times.”


Luckily for Wasserstrum, the good times have exponentially outweighed the bad times. But with success comes other drawbacks, like constant pressure and high expectations.

Because of that, running a multi-million dollar company is more than a full-time job and, obviously, nobody knows more about putting time in at the office—even if it is a great space designed for productivity and comfort—than Wasserstrum. But even with all his professional obligations, drive to succeed and affinity for his desk, he still understands the importance of downtime.

“No matter how much is going on, I make sure at least one day on the weekend I’m not trying to think about work at all,” Wasserstrum says. “I frequently go to concerts, and try out restaurants to keep me sane.”

Another way he keeps from going crazy is by hitting the gym—and we mean that literally as boxing is one of his favorite workouts. He also has an affinity for being in the saddle, though not the way most of his fellow Texans would do it. “I bike up the West Side Highway into New Jersey when the weather is nice,” he explains.

He’s is also a big supporter of Covenant House, an organization that’s working to combat youth homelessness. The nonprofit conducts a fundraiser called Sleep Out, in which people, including Wasserstrum, sleep on the streets in place of homeless kids.

“A friend of mine, who also works in real estate, was organizing a Real Estate Sleep Out. When he reached out to me to join, it was a no-brainer to participate,” he explains. “I’ve always been passionate about advocacy for the homeless so this organization’s mission rang true for me.”

A CEO that finds homes for business helping out a charity that’s trying to find homes for kids—sounds almost too good to be true. But you can bet that doesn’t bother Wasserstrum. Like sitting with his staff, he’s just being true to himself, and as we’ve seen, that usually works out quite nicely for him so long as selling furniture isn’t involved.

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