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Jonathan Wasserstrum, SquareFoot : “Any CEO who puts on a smiling face and says that everything is going just fine is misleading you”

kokou adzo



jonathan wasserstrym squarefoot

First of all, how are you and your family doing in these COVID-19 times?

Jonathan Wasserstrum:  My wife and I, at the beginning of all of this, moved out of Manhattan and into her father’s home just north of the City in Westchester. We are thankful everyday that we, and our loved ones, have stayed healthy. She’s due to give birth to our first child this month, and while it’ll be a challenge to deal with under the circumstances at hand, we feel enormously blessed.

Tell us about you, your career, how you founded or joined this company

From an early age, I knew that I had the entrepreneurial bug. I’ve long itched to make existing projects better, and looked for one to start myself. I worked in real estate before going to business school, but on the finance side. I never dreamed that my first company would be a tech disrupter to the traditional commercial brokerage. But that’s what fell into place for me in  2011 when I founded SquareFoot. It’s been a thrilling nine years. Last November, we announced our Series B funding, and I’m excited to see what this next stage of growth will produce for us and our clients.

How does your company innovate?

We innovate in some way every day, multiple times a day. Every business is founded on the idea that there could be a better way of doing things. We take that responsibility seriously; it’s not just a mission or a part of messaging for us. Our tech team is building new tools to make office tours better for clients, our brokers think critically about how they can improve the process for today’s clients, and our operations team leads the way to ensure that our company culture is the best it can be. If our clients will turn to us for expertise, we must lead by example. Innovation is key to our success, and it starts with each and every one of us on the team. We make sure to hire problem solvers and self starters because we want innovation to be at the heart of everything we do and decide to build.

How the coronavirus pandemic affects your business and how are you coping?

At a time when we’re all working from home, it’s probably difficult to imagine being excited about office spaces. However, we’re delighted to hear from so many business owners who are telling us every day that they need to go back. Work from home is a decent idea, but it’s a challenge for many to actually make work effectively.

We’ve spent the past few months speaking as often as we can to both landlords and clients about the changing landscape and evolving needs of both sides to these negotiations. When we do start to see society reopen, we believe that SquareFoot is poised to lead the way in showing people how to reimagine the workplace to best appeal to the world we’ll be embarking on. We anticipate a real desire to get back to office spaces, but those offices will surely look and feel a bit different than people will remember. We will help keep people safe first. That’s our primary concern right now.

Did you have to make difficult choices and what are the lessons learned?

We were fortunate enough to have raised a round of funding just ahead of this global health scare. That has allowed us to get through this pandemic, and the accompanying economic downturn, without having to do job cuts. We believe that we have the right team in place to execute on our goals. It would be more expensive for us to reduce our workforce and then to look to rebuild later this year. We wanted to do right by our team.

At the same time, we have had to do pay cuts and marketing budget costs to get in line. The vision for the company has remained the same, just at a more compressed, consolidated level than we had anticipated when we sketched out what 2020 would be for us and for our clients. So I’d say the biggest lesson I’ve learned is how creative and proactive our team has been. None of us were prepared for a pandemic like this one, yet over the past 10 weeks, I have been impressed with how many of our team members have found additional ways to step up and to contribute.

How do you deal with stress and anxiety, how do you project yourself and your company in the future?

Personally, I go for long bike rides. I find it to be freeing. I saw in the first few weeks of the pandemic what the working from home situation was doing to some of our team members. I recognized that they, and I, needed a break. So we’ve been closing our business every other Friday to give people time off. We encourage them to get away from their computers and to focus on other aspects of their lives.

Longer-term, I don’t have any of the big answers to the tough questions. We protect one another by checking in on one another. I’ve been pinging different team members as much as I can, especially those I don’t interact with as much, to make sure that they know I’m thinking of them. At the office, I can do this in person. Removed from the office now, I’ve made these gestures digitally. It’s a small gesture, but I know it goes a long way.

Who are your competitors? And how do you plan to stay in the game?

We make our money the way traditional brokerages do. When a deal closes, we get a commission for our work done throughout the deal. We hustle to find people who are looking for new office space. Our brokers have to be empathetic, kind, creative, and helpful. Those may not be the characteristics you naturally associate with real estate brokers, however, I want my team to do things differently and to find better outcomes on the other side. I marvel at what past clients write so positively in online reviews about the experiences they’ve had. We hold each other accountable to carve out a better path forward.

Your final thoughts

These past few months have been more challenging than any other period of our company’s history. Any CEO who puts on a smiling face and says that everything is going just fine is misleading you. At the same time, I am optimistic that we have the right ideas, and the right staff in place, to go execute on our vision in the second half of this year and in the years that follow.

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Kokou Adzo is the editor and author of He is passionate about business and tech, and brings you the latest Startup news and information. He graduated from university of Siena (Italy) and Rennes (France) in Communications and Political Science with a Master's Degree. He manages the editorial operations at

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