Jonathan Wasserstrum of SquareFoot: “Whatever you’re building, you need to be passionate about”

First off, you need to be dedicated to the cause. Whatever you’re building, you need to be passionate about. There are so many highs and lows that if you’re not mission-driven by what you’re building, you’re in for an unpleasant journey. Rough seas are only worth traveling if you want to go to the destination. […]

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First off, you need to be dedicated to the cause. Whatever you’re building, you need to be passionate about. There are so many highs and lows that if you’re not mission-driven by what you’re building, you’re in for an unpleasant journey. Rough seas are only worth traveling if you want to go to the destination.


Being a founder, entrepreneur, or business owner can have many exciting and thrilling moments. But it is also punctuated with periods of doubt, slump, and anxiety. So how does one successfully and healthily ride the highs and lows of Entrepreneurship? In this series, called “How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur” we are talking to successful entrepreneurs who can share stories from their experience. I had the pleasure of interviewing Jonathan Wasserstrum.

SquareFoot Founder and CEO Jonathan Wasserstrum, who hails from Houston, has worked for over a decade in commercial real estate. He began his career at industry leader Jones Lang LaSalle (JLL) as part of the International Capital Group, where he advised foreign and domestic clients on more than $3B worth of transactions globally. Outside of work, Jonathan is interested in the three Bs — bourbon, buffalo wings, and brass bands.


Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

I studied economics at Emory University and then later pursued an MBA from Columbia Business School where I studied entrepreneurship and real estate. Before business school, I worked for several years as an analyst at JLL, one of the big players in the commercial real estate industry. The idea for SquareFoot was born when a friend of mine reached out to me and shared that he was struggling to find real estate for his company. This highlighted an immense need in the market to help businesses find, transact, and occupy real estate. Recognizing this hole in the market led us to start our own business.

What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?

While working for JLL, I learned a lot about how to serve clients, but I also noticed some gaps in the commercial real estate industry that I was able to turn into an opportunity. None of the big firms were thinking about how to best serve the growing or evolving companies that makeup 75 percent of the leases signed every year. I wanted to come up with a solution that would cater to them without compromising on the quality of the service being offered to them.

In your opinion, were you a natural born entrepreneur or did you develop that aptitude later on? Can you explain what you mean?

Both — I’m not one of those “OMG, I could never work for someone else” people. Nor do I have a list of 54 companies on a piece of paper on my nightstand that I can’t wait to start. I am, however, good at figuring out where there’s a hole and how to go plug that hole. And sometimes the fix for that hole is starting a company 🙂

Was there somebody in your life who inspired or helped you to start your journey with your business? Can you share a story with us?

I started running the business from the attic of my parent’s house. From an early age, my mom was my biggest inspiration. She spent her childhood growing up in a Lower East Side tenement, commuting through all weather conditions to get to school. Her determination led her to become one of the first women at Harvard Business School and to pursue a successful career, paving the way for women to take a seat at the executive table. It was her experiences that really motivated me to become an entrepreneur.

What do you think makes your company stand out? Can you share a story?

When it comes to technology, the commercial real estate industry is lacking. We at SquareFoot depend on technology to guide us. Finding office space can be daunting, and navigating the process can be murky at times. In today’s world, the majority of our clients turn to the internet to help find answers to their questions. That is where our clients find us — online, delivering the right, tailored answers to their questions. Additionally, we created an app to solve many of the inefficiencies that arise when a client is out touring office space. Our clients can use the app to take notes and photos of the space during the tour; it also allows them to share these notes with the rest of their team. We use technology to facilitate communication between the multiple stakeholders that are often involved in the search for an office space. Lastly, we have unique solutions that give our clients additional flexibility, such as PivotDesk, a shared space marketplace, and FLEX by SquareFoot, a service that offers clients move-in-ready, traditional office space with a flexible term.

Our clients come to us because we are able to offer real estate solutions that no one else does. We make the entire process transparent, which is important to our clients who aren’t necessarily knowledgeable in real estate, but rather are part of a growing company just like we are, seeking answers.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

Problem-solver: Being a problem-solver has driven me to hire employees with similar traits. I rely on my team to be able to solve problems I may not be able to; when we all work together, things come together seamlessly. This has never been more true than it was over the past year. As the world entered a period of uncertainty, being able to problem solve as a team was necessary to keep the company moving forward.

Perseverance: There will always be those people that tell you it won’t work. If it doesn’t work, that is okay. As CEO, I don’t just tolerate failure — I encourage it too. Embracing your failures ensures you are better positioned for the future. Perseverance and overcoming obstacles are key in the path to becoming a successful entrepreneur. Remembering that things can always go wrong and not second-guessing yourself will help you get through the tougher times.

Approachability: I pride myself on being approachable to my employees, so much so that my desk is situated in the middle of the office. This ensures that I am available to my team as much as possible, that I can more easily receive valuable business information, and that the team can be themselves around me. Employees will come to me with questions or in search of advice, and it’s important to me to provide mentorship and support to my team members.

Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?

There’s really no piece of advice that I wish I had never followed. I don’t second guess the decisions I make or the advice I act on. When I make a choice, it’s always based on the best available information I have at the time. If it works out, I’m happy; if not, that’s okay, too. As long as I know that I did the best I could with what I had, I sleep well (most of the time).

Which tips would you recommend to your colleagues in your industry to help them create a work culture in which employees thrive and do not “burn out” or get overwhelmed?

For my team members to be the best they can be at work, I recognize that giving them space to have downtime is crucial. This is something that I practice myself. No matter how busy I am, I try to ensure that at least one weekend day is spent doing things I enjoy and not thinking about work, and I encourage my colleagues to do the same. During the lockdown, we gave employees “rest and relaxation” days to help them recharge. In general, we have always encouraged the team to take vacation days. Productivity will be at its best if employees have a good work-life balance.

Just as I practice conviction and try not to second guess myself, my colleagues are expected to do the same. I believe that a culture of conviction helps employees to thrive and reduces the likelihood of stress. I trust the team I have around me, and I want them to be able to learn and grow from the work they do.

What would you advise other business leaders to do in order to build trust, credibility, and Authority in their industry?

In my experience, business leaders who are able to pivot seamlessly are able to run the most successful businesses. Changing up how things operate at a company at least once a year can go a long way. This may mean having to cast aside some of the old ways of doing things or reevaluating the company culture, but it is necessary for business growth. Making adjustments does not mean that something is wrong. It’s just the nature of an evolving business, and recognizing that is an important part of being a business leader.

Can you help articulate why doing that is essential today?

The businesses that we’re able to pivot during the pandemic are the ones that will be able to survive longer-term. In a rapidly evolving world, agility is crucial to being a successful business leader — now more than ever.

What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?

Scaling a business without processes in place is like building a plane mid-flight. It isn’t going to work. Having the right people working for the company can really help shape the business culture and environment. We saw this firsthand in a hiring misstep. During the first few years at SquareFoot, we didn’t do much hiring, so we really had no experience in the practices and norms of recruiting. Winging it through the interview process and asking candidates irrelevant questions didn’t provide accurate insight into whether they were capable of performing well in the job role. One candidate ticked all the boxes we had, but we were not screening for behavior. Not long after they started at the company, it was clear they were not going to work out. They were just not a fit with the rest of the team and with our company culture. From there, we realized that behavioral analysis was key to the recruitment process and to building the team with the right people.

Another common mistake I see is CEOs or founders being rigid in their ways. I learn from my team every day, and I try to surround myself with talented people that have different skillsets and perspectives than I do. Fresh ideas and innovation come from a varied workforce and the willingness of business leaders to be flexible and open to the views of others around them.

Ok fantastic. Thank you for those excellent insights, Let’s now shift to the main focus of our interview about How to Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur. The journey of an entrepreneur is never easy, and is filled with challenges, failures, setbacks, as well as joys, thrills and celebrations. This might be intuitive, but I think it will be very useful to specifically articulate it. Can you describe to our readers why no matter how successful you are as an entrepreneur, you will always have fairly dramatic highs and lows? Particularly, can you help explain why this is different from someone with a “regular job”?

Luckily for me, the highs have drastically outweighed the lows. But with success comes setbacks, even failures. As CEO, there are constant pressures and high expectations. Running a business is more than a full-time job.

Do you feel comfortable sharing a story from your own experience about how you felt unusually high and excited as a result of your business? We would love to hear it.

When we hired Michael Colacino as our President. He’s one of the best and brightest in the business, and the fact that he was signing up to join our team and sit next to me every day to help build the commercial real estate firm of the next generation was surreal. It was one of those moments when I had to pinch myself to make sure it wasn’t a dream.

Do you feel comfortable sharing a story from your own experience about how you felt unusually low, and vulnerable as a result of your business? We would love to hear it.

The first 6–7 months during COVID were really tough. Office space leasing was one of the hardest-hit parts of the economy, especially in NYC, which was our main market at the time. We knew there would be light at the end of the tunnel, but we had no idea where in the tunnel we were at the time.

Based on your experience can you tell us what you did to bounce back?

As Winston Churchill says, “when you’re going through hell, keep going.” We knew that we were in a tough time, but we also knew that the tough times weren’t going to last forever. So we kept our heads down and kept pushing forward, building the business that we wanted to have when the world started going back to normal.

Ok super. Here is the main question of our interview. What are your “Five Things You Need To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur”? Please share a story or an example for each.

  1. First off, you need to be dedicated to the cause. Whatever you’re building, you need to be passionate about. There are so many highs and lows that if you’re not mission-driven by what you’re building, you’re in for an unpleasant journey. Rough seas are only worth traveling if you want to go to the destination.
  2. Surround yourself with great people. I believe that if you work on great things with great people, the rest sorts itself out. Great people make the lows tolerable and the highs that much better.
  3. Take care of yourself. Get enough sleep, eat well, exercise, have hobbies.
  4. Hang out with other entrepreneurs. The highs and lows are normal. It’s helpful to hear firsthand from others experiencing the same.
  5. Pick the right partner in life. Someone who’s there for you in the highs and lows. In many ways, this is your most important teammate.

We are living during challenging times and resilience is critical during times like these. How would you define resilience? What do you believe are the characteristics or traits of resilient people?

I’ve said it before and I will say it again: Conviction will get you through the tough times.

Did you have any experiences growing up that have contributed to building your resiliency? Would you mind sharing a story?

I don’t think that resiliency necessarily needs to stem from one touchstone experience. Rather, it’s the culmination of hundreds of little setbacks that we all encounter on a regular basis going through life.

In your opinion, do you tend to keep a positive attitude during difficult situations? What helps you to do so?

It is important to remain positive but realistic. Throughout the pandemic, I have remained bullish on the future of the office market and have been transparent with my team on this. I stay positive during difficult situations by working hard and being nice to people. Treating people in the same way you would expect to be treated fosters a positive and respectful work environment even in the hardest of times.

Can you help articulate why a leader’s positive attitude can have a positive impact both on their clients and their team? Please share a story or example if you can.

I was told early in my career that leadership casts a big shadow. What you say, what you do, and how you act will be viewed and imitated up and down the organization.

Ok. Super. We are nearly done. What is your favorite inspirational quote that motivates you to pursue greatness? Can you share a story about how it was relevant to you in your own life?

“It’s a long way to the top if you want to rock and roll.” AC/DC

How can our readers further follow you online?

Twitter: @jmwass.

LinkedIn: Follow SquareFoot on LinkedIn for company updates

This was very inspiring. Thank you so much for the time you spent with this. We wish you continued success and good health!

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