The Cold Email

Something I learned awhile ago is that most people that I consider "celebrities" really aren't that famous, and as such are generally pretty happy to respond to emails.

In ~2014 I sent an email to Joe Armstrong (one of the creators of Erlang) asking some questions about concurrency because I still didn't fully understand why Erlang was supposed to be better for it. I expected him to just point me to an FAQ or simply not respond [1], but instead he wrote a very long, detailed explanation about the rationale of Erlang's design. It was well-written and it made a lot of things "click" in my brain.

That simple act by Joe was extremely instrumental in my career, I think for the better. I became very interested in Erlang, but also just concurrency theory and distributed systems, and I would like to think I almost understand it now :)

He and I would exchange emails occasionally over the next few years and he seemed genuinely enthusiastic about programming, Erlang, and people using it, and despite me barely knowing the guy, I was genuinely pretty sad when he passed away in 2019.

I think about that a lot; if I hadn't sent a dumb cold email my entire life would likely be very different.

[1] Which, to be clear, would have been perfectly fine!

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.

I'm probably somewhat older than most here. What OP is describing is what used to be normal and should still be!

In the past it was normal to write a CV (resume) and a covering letter that was mildly tailored to each target firm, either in response to a job advert or on spec. I'm not talking quill pens here - you'd do a mail merge and buy a really large book of stamps.

Linked In is possibly the worst thing that ever happened to HR but it was inevitable and someone else would do it instead if they did not.

The whole point is ... show interest, actual interest in an employer you are interested in and whatever they are doing. Find a way in. If they only use LLM based 'bots and can't be arsed with a 'phone call then fuck 'em!

I started to write my story here along the same lines. Perhaps more along the lines of don't be afraid to ask. Almost every job I got, and they've mostly been pretty fantastic, I got cause I called and ask for it. I was told some of those jobs just weren't available or impossible to get but I called and got them. One job the manager wasn't even thinking about it till I called but I got him thinking about it and he hired me. Two impossible to get jobs I got cause the secretary left her desk for a moment and the manager answered the phone instead. I got two half hour interviews in prime time for someone and his business cause I called someone and asked for it.

It never hurt to ask.

This is a great read, but I wonder how effective cold messages are in the AI era. I now receive customized cold emails and LinkedIn messages. There are several tools like Clay that make AI messaging effortless. It is becoming increasingly difficult to determine if message are AI-generated or if a human actually took the time to write them and care.

I see in-person networking becoming increasingly valuable. Unfortunately, for me, I live in the Detroit Metro area. We just don’t have the tech community that other areas like the Bay do, and despite several people‘s best efforts. We don’t have the best networking opportunities and I don’t see that changing anytime soon.

  > but my dad kept saying it wouldn’t hurt to really make it clear I wanted to get into the school.

My mother convinced me to do the same after I was also wait-listed at my top choice university. I sent them an email updating them on things I had done since applying (in May, two weeks before graduating), and two days later, I got my acceptance letter.

I got my first job (an IT traineeship) because after my interview, I rang them every few days to ask how I did and if they were keen to progress further. In the end they said they gave it to me because I was obviously SO keen, what withi the ringing every other day, and I had interviewed well.

Anyway my point is, as the author implies, showing interest is key. I genuinely wanted that job and I showed them that.

Sadly these days (that happened to me in ~1998) it's so, so much harder to stand out. There's a wall of bits and "employment services" between you and the person who'd hire you, and I don't know how the younger generation is going to be able to navigate that easily.

In the late 90s I was a huge Michael Schumacher and Ferrari fan. I found Jean Todt’s (the Ferrari F1 team principal at the time) email address and wrote a passionate email asking if there was any way I could join their team - even if it was sweeping the floor. Never got a reply :(

Previously I worked at Auth0. I joined fairly early, just a couple of years after their founding so the company was still small. I remember one of my collegues who joined around the same time got his job by sending (multiple) cold emails to my manager at the time telling how much he admired the company and wanted to join. Eventually he gave in and gave him the job. The guys stayed on long after I left so it obviously work out well for both parties.

As to what to write as a "starting point" in a cold email:

It's nice to write nice things about the things that person has done. nice tweet, nice post etc.

But it's nicer to write about things they've created and you paid money for. a book, a course, a software etc.

('nice' in this context means the chance of getting a reply.)

My own cold email story:

I was in a paid telegram group of a fitness guru I followed on Twitter. He once complained about how he's having a hard time managing his many info products, emails, having to write promotional content etc.

I then spent the night collecting all the things he's could do better: dusting off his unused wordpress site to keep as source of content rather than just tweeting bangers and let them be forgotten due to the algorthm after some time, writing better sales copy for his copy instead of just trying to list its merits in every tweet and email, new ebook ideas based on stuff that people in his telegram group are already complaining about (how do I recover better?!) etc.

I didn't expect much out of this. It just felt nice to come up with ideas honestly. but he replied with with 2 sentences: "How can I pay you" and "When can you start?".

That started a 2 year sidegig as a copywriter, a profession I didn't know I was interested in at all before this, lol.

Hmm.. thinking back.. have I learned this lesson myself? I can't think of any other instances where I replied to people's stuff that I purchased. But maybe I forgot. I'm going to think about it though, and write hot cold emails!

And thanks Zach for this. The one thing I remember about you from your early blogging days. That "glue technologies" blog post - where you said about how things like bash, sql, server management etc.. are all not main character skills, but are glue skills that are still important. That term stuck with me, and I do see their importance.

This is why I tend to write real letters using my IBM Selectric III and send them via physical mail. I enjoy writing. Writing with purpose is time well spent. 90% of the time I get no response. I’m not actively trying to find the next recipient, it just comes naturally, so I see no reason to stop.

When is the last time you got an actual typed or hand written letter? That’s my advantage.

Hold up.... you created good-tutorials in high school? I credit that site with launching one of my first 'hobbies' back in middle school and teaching me a new skill I was able to use to help friends/family for years to come. Thank you!

One key turning point in my life was approaching Red Whittaker, the head of the Field Robotics Center at Carnegie Mellon. I knew who he was and had met him briefly before, but this was pretty much a “cold call” even if happened to be in person. I was finishing up my degree at CMU and felt like if was going to stay in Pittsburgh, I wanted to work somewhere that was working on really cool projects. My degree was a BFA in sculpture, but I guess my enthusiasm and interest in novel mechanisms was enough for him to take a chance and make a position for me. I learned a lot from (and with) the team of PhD students and staff. The job had me starting to use parametric CAD at very early point (Pro/E 6.0). After a few years I moved on and eventually left Pittsburgh for SF, but without taking that chance, I really don’t know what path my life would have taken.

I was rejected from a job interview a few years ago - wow 13 years ago now - and was honestly shocked after how well the interview went.

I decided to write a letter (email) to the HR department implying they'd made a huge mistake (the head of HR was in the interview too). She (as much as I knew at the time) overruled my would-be boss and the rest is history.

Best email I ever sent.

Yeah people replied to cold emails back when they received one once every 3 months. Now we get dozens a day. Straight into the garbage.

I got my first job in the U.S by emailing the local PHP user group introducing myself. The CEO of a dev agency was on the list, and 2 weeks later I had a job offer.

Moving to a new country not knowing anyone and with barely any money, fair to say that one email changed my life.

I got a cold email recently and was happy to engage, but I warned them upfront that LLMs change the game, and asked for more info about their background (to authenticate them as a human). They replied with another unnecessarily long email that was light on details and reeked of AI Voice, so I ghosted at that point, unconvinced they were acting in good faith.

Demonstrating authenticity and effort are super important in this space.

I once called the phone number on a website for an obscure local event, and it happened to be a local business magnate's personal cell phone number, and he helped me out with my request, so that was awesome.

I cold emailed a researcher in Japan about gut bacteria e. Americana for cancer treatment and registering my dad for clinical trials as and when they happen. And hell yea - professor replied :)

So yes — just do it!

Things evolve though. Early 2000, I received a lot of reactions to cold emails (eg when organising events), but these days, it's rather rare. Even people I know might ignore my mails! One explanation I got is that there are a lot more phishing mails these days, and people have learnt to be suspicious.

Is human-like cold emails (with stuff like :D) better or worse than professionally written formal emails? Im a student and would like some tips. I know it depends on the situation but what would you rather see? And based on your experience, what would you respond to more?

Fuck it, I feel the hype. Time to cold email some people a couple of tokens of appreciation. I don't expect anything, but they need to know the positive impact they've had.

Thanks once again HN, this is gonna be fun.

Also, feel free to reach out to me ;-)

On average it currently happens once per month (or every 2 months?) so I have the bandwidth atm, haha.

The most fun conversation was when I met a fairly good Haskell or Erlang programmer (I forgot) and we were talking about dating and I think, I made it click for him a bit. It probably only helped slightly but it helped and that felt good.

For people with dating problems, I've had them too. If I can help engineers to find their dream partners, even if it's just a little bit, that'll probably the most productive thing I'd do in my life anyway.

I've been out of the game for the past 4 years already, happily married nowadays, kinda made a mini science out of it, haha.

Also open to other topics, I love to learn about everything.

Now, I'm going to cold email a couple of people!

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Edit: damn this is getting me emotional. It really presses the question who has had such a positive impact on my life that I feel the need for them to know that.

I'm literally writing mails now with stuff like "in 2006 you had a talk and it really helped me build the foundation of my current life. Thank you."

Epic.

My closest friendships and two relationships started with a cold email. I love when strangers write to me and I give them my full attention. I also write words of praise to bloggers. A simple heartfelt email goes a long way. An LLM-authored email goes right to spam.

I struggle to apply this openness to real life, where the rejection is a lot more instantaneous and awkward. All the data shows that it works and that failure won’t kill me, but my whole being is trying to stop me.

Any advice?

I met Zach wayyy back in 2016 via a code email to him! (hey Zach!)

When something like this was happening to me, I heard people were saying "Oh, he is just lucky". It kinda made me a bit mad because of how much work I've put in a particular thing behind the scenes and in general how unlucky I was with many other things.

Then I stumbled upon the concept of "luck surface area" [1] and it's kinda clicked with me. Yes, luck is a factor, but you definitely can increase your chances. Cold emails from the post is one of such instruments.

[1] https://umbrex.com/resources/tools-for-thinking/what-is-luck...

Nice to see Zach still posting.

I have had reasonable success with cold emails. My favorite genre is every so often I email a musician or author whose works I tremendously enjoyed asking for a signed copy, an opinion, or simply to say thank you for having a profound influence on me. Some are very well known. But almost all reply with enthusiasm.

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:

---

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!

---

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.

It's the lottery, you can only win if you play

Cold outreach is great when it's personal.

SPAM isn't: I don't want automated cold outreach. I don't want something trying to fake making it look personal.

I wish that we could turn off email / phone where anyone can reach out to anyone, and instead make it so that you have to work through your network; and your network acts as the first filter. (And if some bozo in your network passes too much SPAM to you, you can block them.)

I read a dozen inbound cold emails every day. I used to love it. I don't anymore, because every other single email uses The Sentence. Or, The Paragraph.

Whatever model these people use, it always always puts in The Sentence (I don't want to disclose it publicly! I'm running an experiment. I'll write it up when it concludes. :) ). Or, worse, The Paragraph.

Please use models to research people and learn about them. But please write the email yourself.

It's instantly obvious. And even though I do my best not to hold it against someone, I would be lying if I didn't say that it isn't a bit annoying.

Imagine reading endless variations of The Sentence 3,240 to 4,000 times a year. It feels straight out of the Twilight Zone.

I once got a job by sending a cold email. I was overqualified and took a pay cut of more than 50%.

It was a stepping stone. I would rather have done it in my 20s than in my 50s, but I had been unemployed for a year.

When I had an academic job I used to receive cold emails from students in Asian countries. They uniformly came across as desperate.

No other way to initiate a conversation has a higher chance of being completely ignored.

My biggest mistake in life was thinking too big and aiming too high. Now I absolutely hate the saying "If you want to reach the moon, aim for the stars." This belief ruined me.

The people who were writing desperate emails and bending over to get a wage-slave job are much better off now.

Meanwhile I was trying to raise funding for big ideas from big investors; it was a complete waste of time.

Reality is "If you want to reach the moon, aim for the clouds." Then you have a better chance of actually achieving something, even if it's not your first preference.

I hired someone when we were contemplating a Linux version of our product. The unsolicited email I received just radiated passion and interest. Easiest decision ever.

when I started my vidalia onion project, I cold called the vidalia onion committee, explained my domain purchase and rough plan, and asked if I could stop by their office to say hello & see if there were ways i could serve that industry. They said 'sure', so I did, and then I began selling onions on the internet.

I agree wholeheartedly with this article and this is something I'm struggling with my daughter about: the worst thing anybody can say is no and in some cases, they already said no. If you ask (or ask again), you might get a really good answer or more.

Zach is good people. I still can’t believe I met him at a random meetup in SF once and he walked up to me to say hi and I didn’t connect the dots until many hours later that he’s the Zach whose blog I’ve been reading on and off my whole career and is one of the inspirations that got me to Silicon Valley.

Zach if you’re reading this, thanks

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I thought the post will be about writing cold emails :)

> You can’t win unless you skate to where the puck is going to be buying a lotto ticket.

though - I'm not as successful as Zach, but damn cold emails & cold phone calls have helped me a ton.

Thanks to the strangers that helped me out while not owing me anything.

it's the same reason - I try respond to every cold email.

As a teen and in my early 20s I was a pretty skeptical / negative dude. I probably would be on team "not worth it, don't bother" when it comes to cold email.

I was also kinda bad in school (not really trying and not doing well) and so on.

Buddy who worked outsourced tech support with me while he took school seriously and I did not graduated (while I did not) and got a job. They had a referral bonus at his company and he convinced to "just apply". I hadn't graduated and really wasn't making much progress or very impressive, but I did it just for the interview experience.

I got the job, the guy who hired me later said "you seemed honest". My whole tech career took off from there, good money, I got lucky and worked with good people. Later after age 40 after a layoff I decided to try a coding bootcamp when folks were downplaying those programs. Some rando small company took a chance on me and didn't pay much but it was a job and I took a chance on them.

Nearly 10 years later I'm happy with my work, doing good financially, all because I took a couple shots.

The local university has a coach who is big on "failure is progress" and other cute slogans, and in my collage years I would have been cynical brushed it off as "just words". But it was also just words when the guy told "just apply".

I watch that coach's team and there are kids out there failing, I think they're some of the bravest guys. They daring to bust their ass year round and maybe just fail in front of tens of thousands people. I wouldn't have done it at their age, but they're taking their shot.

It took me a long time to understand the value (and low cost) of taking a shot, and what "just words" really represents.

Also known as spam.

If you don’t run for the bus, you won’t catch it!

First email, then phone. Always works for me.

I think another aspect of this is that the author experienced positive feedback from this approach early on. Rejection is tough to deal with, but having an instance that turned out well in mind is a huge benefit.

The author is doing his article a disservice by calling this cold email. He just sent a few one-off emails to strangers. That's quite different than the BDR team at Startup Du Jour scraping LinkedIn and blasting out an enless stream of "hope this message finds you well" slop.

I'd wager that the majority of us do not differentiate between cold email and spam, especially in the AI era.

"Cold email" - I hate this term. Call it what it is. Spam.

And no, personalizing your spam doesn't make it any less spam, especially with AI these days, but this is a hot take for a VC forum whose companies survive on spam.

Shame to send cold emails to strangers.

Send me a "cold email" or any other sort of spam, and I will never see anything more from you, as your address will be blocked. Spamming is against the law here in EU, and for a good reason.