The FORT Podcast: Jonathan Wasserstrum

Jonathan Wasserstrum is CEO and Co-Founder of SquareFoot, a personal commercial real estate assistant. Prior to business school, Wasserstrum worked in the International Capital Group at Jones Lang LaSalle where he advised foreign and domestic clients on more than $3 billion worth of transactions globally.

On this episode, Chris and Jonathan discuss his experience starting his career in capital markets during the financial crash, starting SquareFoot in his parents’ attic and the New York office environment through the pandemic. They also discuss the process of raising capital, operating a rolling fund, and the world of Angel Investing.

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(02:30) – Jonathan’s Story

(03:39) – What did the ’07-’08 crisis look like for you as you started your career in real estate?

(04:31) – What was your specialty when you worked in capital markets?

(06:05) – Do you remember any moments during the crash where it hit you how bad it was going to be?

(07:14) – What’s the fulcrum piece of the capital stack?

(09:47) – What was the journey like from business school to launching SquareFoot?

(11:25) – Did you have a co-founder from the jump?

(12:31) – Was the domain name available when you started SquareFoot?

(13:08) – How did you go about purchasing the domain?

(13:43) – What is SquareFoot? How are you all doing things differently?

(16:12) – What’s a management agreement?

(20:04) – Do you have a target customer?

(21:00) – Is this target market trying to lease within a certain amount of time?

(21:56) – What markets are you located in?

(23:10) – What’s the office environment like in New York City right now?

(25:46) – Are you seeing data of new folks moving to New York or is it an internal movement?

(26:39) – What was it like raising capita? How was your experience working with VCs?

(30:46) – How many VCs are there in the country that would be interested in something like SquareFoot?

(31:28) – What are your thoughts on the office in the future? How will it be different and how will it be the same?

(33:36) – Is there a world for the Airbnb home-office?

(34:40) – The WFH vs. Office Debate

(36:18) – How do you find new customers?

(37:20) – What’s the ultimate goal for SquareFoot?

(37:49) – Where are the brokers that you hire coming from?

(39:55) – What technology do you provide your brokers with to give them a leg up?

(41:32) – What was your experience buying PivotDesk?

(43:14) – Jonathan’s Night Hobby as an Investor on AngelList

(43:45) – How does a rolling fund work?

(45:52) – Are you still doing syndicates?

(46:58) – How many investments have you made?

(47:45) – What’s considered a good performing fund?

(49:10) – Do you have a childhood experience that’s shaped who you are today?

(51:04) – What’s a book that’s had an impact on you?

Danny Meyer – Setting the Table

Meditations – Marcus Aurelius

(52:13) – If you had a billboard that you could put anything on, what would it say?

(52:35) – Contact Jonathan:

Jonathan on LinkedIn:

Jonathan on Twitter:

Link to Jonathan’s Rolling Fund:


Episode Summary

Jonathan Wasserstrum, the visionary co-founder and CEO of, graced Chris Powers’ podcast, providing listeners with an enlightening exploration of the real estate terrain, particularly in the realm of office space leasing. Distinguished for his seasoned experience, Wasserstrum’s journey in the real estate domain began with a notable tenure at JLL, where from 2007 to 2010, he played a pivotal role in capital markets work. This period, marked by the capital markets’ turbulence, forged his astute understanding of the industry’s intricate fabric.

A significant chunk of the discourse was devoted to unmasking the complexities inherent in the real estate market. Deliberations on the dynamics of property transactions, especially the buying and selling interplay across diverse markets, took center stage. Introducing listeners to the intricate concept of the “fulcrum piece,” Wasserstrum painted a vivid picture using an illustrative example of a building, shedding light on its valuation intricacies. As the narrative flowed, the birth and ethos of emerged prominently. Despite his profound real estate roots, Wasserstrum candidly acknowledged the hurdles he encountered while spearheading a technology-centric venture, especially navigating the initial technological facets of business evolution.

Further enriching the dialogue, Wasserstrum delved into the DNA of A mosaic of diverse backgrounds unified by a shared zeal for real estate, the team’s collective mission resonated clearly: infusing the traditionally murky waters of the real estate market with unparalleled transparency and cutting-edge technology. This ethos was exemplified by “Flex by Square Foot,” an innovative program tailored to address the burgeoning demand for adaptable spaces. Acting as a bridge between landlords and tenants, this initiative ensures bespoke lease negotiations, catering to the unique needs of both parties.

The global pandemic’s aftershocks on the real estate panorama were also dissected. Wasserstrum emphasized the prevailing market ambiguity, accentuating the hesitancy in lease commitments amidst this uncertainty. Elaborating on Squarefoot’s symbiotic ties with landlords, he outlined their evolved strategy, offering landlords enhanced flexibility compared to their initial lease-holding model. Highlighting the value proposition Squarefoot presents to landlords, the conversation touched upon the myriad benefits, ranging from ready-to-move-in spaces to seamlessly catering to tenants with short-term leasing appetites.

On the geographical front, Squarefoot’s footprint and expansion aspirations were spotlighted. Predominantly anchored in New York City, they are poised to plant their flag in multiple new markets soon. Despite the pandemic-induced expansion delay, the evolving landscape, especially noticeable shifts in Manhattan, were highlighted. Wasserstrum also illuminated the varying leasing needs of businesses, stemming from diverse triggers such as lease expiry, organizational growth, or spatial downsizing.

Pivoting to the burgeoning PropTech horizon, Wasserstrum reminisced about Squarefoot’s early days when PropTech was a nascent term. Navigating initial VC skepticism due to their unfamiliarity with the commercial real estate tapestry, Squarefoot carved a niche by successfully engaging real estate stalwarts during fundraising phases. The acquisition of PivotDesk, and the subsequent market feedback, also found mention, offering insights into Squarefoot’s growth trajectory.

In the realm of avant-garde leasing paradigms, Wasserstrum touched upon emerging models, such as home spaces doubling up as offices. Clarifying Squarefoot’s strategic focus on traditional office spaces, he emphasized their unwavering commitment to be the beacon for companies, especially those scouring for spaces up to 50,000 square feet.

The FORT with Chris Powers is produced by Straight Up Podcasts

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