Jonathan Wasserstrum

I do about half PropTech, half other stuff where other stuff includes Healthcare, Marketplaces, and things tickle my fancy. I've been running SquareFoot for 8+ years now, we help companies of all shapes and sizes with their commercial real estate needs. In that process we get to know the leadership team and their businesses intimately and oftentimes they are about to raise their next round of funding. I am also active in the PropTech arena including being a mentor at MetaProp--the premier real estate tech accelerator and seed fund. I also remain actively involved in ERA, the accelerator that SquareFoot went through.
New York, NY
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Questions & Answers

Origin Story: In a couple sentences, how would you describe your path to becoming an investor?

Through building my own company over the last 9+ years, I've learned a ton.  We were doing "PropTech" before it was a word.  Over time I've been asked for help and then I started investing in those companies as well :)

Investment Approach: What are the key factors you consider when evaluating a founding team?

- Desire to go all of the way.  

- Are these people that I want to spend time with.

- Know their space inside and out.

What's your style and approach when it comes to working with founders post-investment? What are the characteristics of founders you've worked well with?

There when you need me and not when you don't.

If I'm coming to pitch to you or your firm, what's the one piece of advice you'd give me?

Be genuine.  I know first hand that nothing everything is perfect.  Let me know what you're struggling through...other than financing at the moment :)

As an angel investor, how many deals do you aim to do each year?


How would you describe your own personal mission and values, and how do they impact the way you invest?

- Do well by doing good

- Have fun

- Add value.

What do you like best about investing in NYC, and what’s your outlook on the future of NYC tech?

Collaborative.  People want to help others. Big and just getting started.

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