Trusting your instincts

I’m back in New York for the week before spending a week in Baltimore for Thanksgiving. Afterwards, I’ll be off to Europe for a week. Three weeks away from home is going to be tough. I’ve gone into this trip making sure I pace myself, rest and not overdo things.

New York is amazing as always. The energy is next level and I’m always happy to be here. We’re meeting with partners, recruiting and onboarding new hires this week. Our New York office is starting to take shape and I’m excited to spend more time out here.

This morning, I read that a company that I was targeting to do a personal deal in 2+ years ago is raising at a $10b+ valuation. I won’t divulge into details or mention the company name due to confidentiality but I love the space and the founders.

I wrote a two page memo in August of 2019 to share with some potential partners on this deal. Things were lined up and candidly we just got too busy to deal with getting the money together so I decided to pass on it. The valuation was under $500m at that time.

I knew back then I was onto something. In investing, you’re often wrong more than you’re right but this is one that I nailed. Unfortunately, timing and perhaps a bit of laziness prevented me from capitalizing on it. I should’ve trusted myself.

I’m kicking myself for this one, but it’s a good learning experience for next time.