RE #102: Jonathan Wasserstrum - Co-Founder & CEO of SquareFoot

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. Enjoy!  Follow Chris on Twitter: www.Twitter.com/FortWorthChris Learn more about Chris Powers and Fort Capital: www.FortCapitalLP.com Follow Chris on LinkedIn: www.linkedin.com/in/chrispowersjr/ (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 capital? 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: SquareFoot.com PivotDesk.com Jonathan on LinkedIn: www.linkedin.com/in/jonathan-wasserstrum-8a77533/ Jonathan on Twitter: www.Twitter.com/JMwass Link to Jonathan's Rolling Fund: www.angel.co/v/back/jonathan-wasserstrum The FORT with Chris Powers is produced by Straight Up Podcasts

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Here, we uncover the proven strategies, insights, and inspiring stories of today’s greatest leaders in the worlds of business, real estate, entrepreneurship, and investing. Each episode’s mission is to help you to level up your entrepreneurial game by hearing directly from the men and women in the arena. Chris is able to uniquely uncover things not commonly discussed because he is an entrepreneur himself. We not only cover business, but we also cover the personal side of entrepreneurship. The Fort began in 2018 as a way for Chris to publicly explore the fascinating world of entrepreneurship. Since he was a child, he’s been characterized as obsessively curious about the world around him.  The Fort has now been downloaded over 2M times, across more than 50,000 unique listeners. Each week features conversations with entrepreneurs, Founders, CEOs, and Executives from some of the leading companies in America. Past guests have represented companies such as JLL, Hillwood, S2 Capital, Chick Fil A, Morning Brew, Founders Podcast, Tiny Capital, Permanent Equity, Fort Capital, Matthews REIS, Bonobos, and ConvertKit. 🐦 Follow Chris on Twitter: www.twitter.com/FortWorthChris 💡 Follow Chris on LinkedIn: www.linkedin.com/in/chrispowersjr/ 📹 Subscribe to The FORT on YouTube: https://www.youtube.com/@FORTpod