Being a founder, entrepreneur, or a 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?
Jonathan Wasserstrum: 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?
Jonathan Wasserstrum: 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?
Jonathan Wasserstrum: 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?
Jonathan Wasserstrum: 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?
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?
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?
Jonathan Wasserstrum: 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?
What would you advise other business leaders to do in order to build trust, credibility, and Authority in their industry?
Jonathan Wasserstrum: 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?
Jonathan Wasserstrum: 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?
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”?
Jonathan Wasserstrum: 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.
Jonathan Wasserstrum: 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.
Jonathan Wasserstrum: 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?
Jonathan Wasserstrum: 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.
- 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.
- 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.
- Take care of yourself. Get enough sleep, eat well, exercise, have hobbies.
- Hang out with other entrepreneurs. The highs and lows are normal. It’s helpful to hear firsthand from others experiencing the same.
- 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?
Jonathan Wasserstrum: 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?
Jonathan Wasserstrum: 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?
Jonathan Wasserstrum: 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.
Jonathan Wasserstrum: 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?
Jonathan Wasserstrum: “It’s a long way to the top if you want to rock and roll.” AC/DC
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This was very inspiring. Thank you so much for the time you spent with
this. We wish you continued success and good health!