Pinterest founder Belsky met through an intern in 2010
While still running Behance with no business angel investing, Belsky met Pinterest's Ben Silbermann in 2010 through his intern. Pinterest pins were driving growing traffic to Behance, which tipped him off to the opportunity.
“my first ever investment was Pinterest. So I met Ben Silverman back in 2010, and I had no business being an angel investor. I was just leading my own company.”
Belsky rationalized his first Pinterest investment, a good chunk of his salary, by reframing it as tuition: he'd learn from Ben's Google and West Coast network. Worst case, it was his education.
“Ben had worked at Google. He had a network on the West Coast. I was just like, you know, new entrepreneur in New York that didn't have any of that network. I actually felt like I would learn a lot from this. And so in some ways I was like, you know, I'm sort of paying for an education.”
Steal thisJustify a high-risk early investment as tuition; the relationship and learning are the floor on your return.
Belsky rationalized his first risky Pinterest check (a big chunk of his salary) as buying an education from Ben Silbermann, who had the West Coast network he lacked. His takeaway: when you deeply respect someone you can learn from, find a way to work with them.
“And, you know, the one or the other thing I did though to rationalize it for myself, I remember is Ben had worked at Google. He had a network on the West Coast. I was just like, you know, new entrepreneur in New York. Didn't have any of that network. I actually felt like I would learn a lot from this. And so in some ways I was like, you know, I'm sort of paying for an education.”
Steal thisJustify an early angel check by the education and relationship, not the return — then the worst case is you learned something.