The Cold Email

One thing about this is you never can tell how one thing will lead to another, so even if you don’t get a good response to your cold email, if you do it well, it can still unlock doors later on that you never expected to.

To illustrate this I’m going to share a personal anecdote that actually isn’t a cold email, but it’s similar enough that hopefully it demonstrates the point. I made the crucial connection in a meeting, but it could just as well have happened from an email.

I was co-head of a startup that built enterprise saas risk software of a highly specialised type and one of our investors convinced me to take a meeting with a very successful and highly-regarded hedge fund. I was expecting a very initial call, but when I got on the phone it was just me, the COO, the chief investment officer, their head of trading and their CTO. So pretty much the top of the house.

Now, I could have just gone straight for the big pitch and tried to sell them on our solution but it was super obvious right at the beginning of the call that we were solving a problem they just didn’t have, and there was no pivot we could make that would make our software relevant for them. So I did the high-integrity thing (even though we were pretty desperate for clients) and said that to them, thanked them for their time and ended the call cordially, but early.

Years later I got a cold call from a recruiter working for two founders looking for a CTO for a fintech. Turns out she was the wife of one of the guys on the call that day and he had told her about it, said he had been impressed by how I handled the situation, so when the opportunity arose I ended up on the shortlist (and got the gig btw) for a job I would never even have known existed yet alone applied for.

The point is sometimes if you just do the thing it may not even work out in the immediate short term in an obvious way, but could have positive long term ramifications that you can’t necessarily know ahead of time, whereas if you do nothing, nothing will happen.

Yep they went from a rare to an almost daily occurrence for me this summer. It upsets me because I have met so many interesting people through my inbox.

Here's my cold email story.

In the Netflix series The Good Place, there is an AI character named Janet, who helps assist people who have gone to that place where you go after you die.

One quirk when you're in the Good Place: you can't use swear words. If you try to say "fuck" it comes out "fork".

Janet is portrayed brilliantly by D'Arcy Carden. Her dad is Dennis Erokan, who published MicroTimes and BAM (Bay Area Music) Magazine and produced the Bammies award festival. MicroTimes was one of those big thick magazines like Computer Shopper, full of interesting ads and a few articles.

After I discovered this, I found Dennis' email and wrote to him:

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Hi Dennis!

Yes, I know it's usually D'Arcy who gets the autograph requests.

My friend Ro and I recently finished watching The Good Place. What a wonderful series!

I always enjoy learning about the people who worked to create a great show like this.

After a bit of research I was like "What the fork? Janet's real life dad is the MicroTimes guy!"

So I checked my archival drawer and found one of my old MicroTimes from 1996.

Ro lived in New York in the late 1980s, and she flew to SF a few of those years just to go to the Bammies.

Her secret hope was to somehow get acquainted with Steve Perry. But she did see Ted Nugent staring at her in a bookstore. So that was at least a consolation prize.

Ro's birthday is coming up later this month. I stealthily searched eBay and got the 1986 and 1988 BAM Magazines with the Bammies Scrapbooks.

I wonder if you could autograph these? I would be more than happy to take you out for lunch or dinner at any of your favorite places up in your neck of the woods. Or I could just bring them to your office or any location you want if that's more convenient for you.

And if we can work out a time when Ro could join us (probably easier on a weekend), she would be delighted to meet you!

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Dennis was quite tickled by this. We took him to lunch at his favorite restaurant, he signed our MicroTimes and BAM magazines, and we all had a great time sharing stories about some of the people we knew.

Also, lots of them seemingly read emails themselves, or at least have their secretaries forward emails written by passionate people to them, as I've also gotten replies to a bunch of emails from people I didn't expect such involved reply to, even when they're "celebrities".

"It never hurt to ask."

Rejection can hurt if you are fragile, but one can learn to handle and accept it.