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:

The FORT with Chris Powers is produced by Straight Up Podcasts

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