Every week, my inbox fills up with the same email. Different logos, different founders, same fantasy: Dear Glen, given your background as an active angel investor, we’d love to share an opportunity…
Active angel investor. That’s adorable.
I haven’t written an angel check since 2010. So if you sent me that email, here’s my first piece of free advice—and it’s the most valuable thing you’ll get out of this whole exchange: go back to whoever sold you my name and demand a refund. You paid good money for a list that has me filed under “investor,” and that list is older than some of your interns. Whoever sold it to you took your cash and handed you a corpse. Get it back.
But let’s pretend, for a minute, that I were still in the game. I’m not—I no longer have the risk portfolio or the time window to throw money at illiquid bets that take a decade to maybe break even. But if I were, your email would still go straight in the trash. Here’s why, and pay attention, because this part is actually useful.
I Never Answered Cold Outreach. Ever.
If you couldn’t figure out how to get someone—anyone—to introduce you to me, that told me everything I needed to know about your ability to build a company. Startups are nothing but a long, brutal sequence of people you have to convince: customers, hires, partners, the next round of investors. If you couldn’t navigate your way to a single warm introduction to me, how exactly were you planning to do all of that?
A cold email isn’t hustle. It’s the opposite of hustle. It’s the lazy version—blast a thousand strangers and pray one of them is dumb enough to say yes. I was never going to be that one.
I Invested in My Backyard, On Purpose
I’m in Washington. I made my money in Washington. So when I invested, I invested in the DC region—companies I could drive to, founders I could look in the eye, management teams I could ask around about. I could watch. I could check. I could show up.
So if you’re emailing me from India about your Indian startup, understand the math from my side: I can’t watch you, I don’t know your team, I don’t know anybody who knows your team, and I have no way to check on a single thing you tell me. On top of that, I have exactly zero vested interest in a company outside my region succeeding. I made my success here. The way I pay that back is by investing here. That’s not provincialism. That’s knowing what I actually know.
Here’s the Part Nobody Says Out Loud: It Wasn’t Investing. It Was Philanthropy.
Let me tell you how my “successful” run as an angel actually went, because I think the numbers are clarifying.
Over the ten years I invested, I did fine. I made money. Call it a 30% return on what I put in over that decade.
Now run the comparison. Had I taken that exact same money and parked it in the S&P 500, I’d have tripled that return—at roughly one one-hundredth of the risk. No board meetings. No 2 a.m. “we need a bridge round” phone calls. No watching a founder I believed in run a great idea into a wall.
And it gets better. If I’d skipped the whole circus and just handed that money to the Red Cross, I could have written it off the day I wrote the check—instead of tying it up for ten years and waiting on a liquidity event to maybe, possibly, take the loss.
So let’s call angel investing what it was for me: angel philanthropy. I dressed up charity as finance and told myself a story about returns. The companies got my money. I got the warm feeling and a tax treatment worse than an actual donation. If you’re doing it for the love of the ecosystem, God bless you—that’s a fine reason. Just don’t kid yourself that you’re doing it for the money.
If You Genuinely Want to Reach an Investor—Any Investor
Since I’ve spent this whole post telling you what not to do, let me leave you with what works. This is the roadmap, and it’s the same for me as it is for anyone worth pitching:
Learn the thesis first. Every serious investor invests in a narrow lane—a sector, a region, a stage. I only put money into things I actually understood. Before you reach out to anyone, know what they invest in, where, and at what point in a company’s life. If you’re pitching a late-stage biotech to a guy who only does seed-stage regional software, you’ve already lost, and you’ve wasted both your time and the click it took me to delete you.
Then find the introduction. Figure out who you know who knows them. Work the network until someone who has credibility with your target is willing to vouch for you. That warm intro does two jobs at once: it gets your email opened, and it proves you can do the exact thing building a company requires.
Do those two things and you don’t need a purchased list. You never did.
And me? I’m out. Permanently. But now at least you’ll spend your next pitch on someone who might actually say yes.
