Several years back, while raising money for one of my previous companies, we had a fair amount of inbound interest from investors.
It goes without saying, but I'll say it anyway: If you're going to raise money, having inbound interest is the way to go.
Aside from the intro requests we'd receive on AngelList, we'd also get random, unsolicited emails from angel investors. To be honest, we had enough tire kickers and faux investors reach out during our raise that we started to really discredit these inquiries.
On one of these occasions, we received an email from someone I'll call Anthony Green. He simply asked if we were raising--no sales pitch, just a simple question.
Suspicious that this was yet another tire kicker, I nearly didn't respond. On a whim, I decided to respond with, "Yes, why do you ask?"
Shortly thereafter, I received a response from Anthony stating that he and his father invested in companies together and they really liked what we were doing.
We set up a call.
As most founders do, we did a surface-level Google search to learn what we could about this potential investor in advance. Since the name was rather common, the best that we could conclude was that this was an accountant from Southern California. Probably a $5,000 to $15,000 investor at best.
It's worth noting that the search also turned up a result from the New York Post about a young kid, covering his extravagant bar mitzvah, but I didn't think it was relevant.
Research complete, but still skeptical, we scheduled a call for a Sunday afternoon.
At our scheduled time, I called the father-son team and Anthony answered. After exchanging a bit of small talk, it was clear that something was off. Unless my ears were deceiving me, it sounded like I was talking to either a grown man with a pinched scrotum or a 12-year-old kid. I was utterly confused.
After about 15 minutes of discussion, the father finally chimed in and said, "We're in."
At this point, I thought I was being punked.
First off, a decision normally doesn't come that quickly, especially with such little discussion. Pair that with the fact that I believe I'm talking to a 5th grader, and I was about to call bullshit.
Instead, I went with it and took it as an opportunity to learn a bit more. I asked if they could tell me more about themselves and their investment background. This is where Dad took over.
"As Anthony mentioned, we're a father-son team that has invested in a few companies over the past two years, most recently in [X] and [Y]. My son, Anthony, is 14 years old and has a knack for picking investments. My name is Josh Green [not actual name], and I'm the former president and CEO of [Huge Media Company]...."
I heard nothing past that. I was blown away.
Turns out that Anthony really was a kid. Just finishing up 7th grade. In his free time, rather than playing PlayStation, he was reading tech blogs and playing with new products. Instead of playing pick-up basketball after school, he was learning how to code. He aspired to be a venture capitalist someday, and was already well on his way.
As fate would have it, he turned out to be one of the most active and useful investors we had on our side.
This was an extremely important lesson for us: From that moment forward, I never discredited any inbound inquiry from anyone again.
Since that time, I've been through numerous fund raises, none of which have been easier than the first. I come back to this experience often to remind myself that opportunities occasionally crop up where you least expect them.
Startups can bring about really fascinating encounters sometimes, all you have to do is be open to accepting them.