The Cold Email
Zach Holman
Currently /<br>Founder of Signed and<br>Calendearing. Invested in hundreds<br>of startups via Tifo.
Previously /<br>Second engineer hired at GitHub, and advised GitLab ahead of their IPO.
Football /<br>Minority owner of<br>Oakland Roots (USL-C) and<br>Cagliari (Serie A).
More about Zach →
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The Cold Email
July 29, 2026
Three of the biggest changes in my life all stemmed, in part, from cold<br>outreach.
Originally I was waitlisted at Carnegie Mellon. Getting waitlisted is like,<br>being the first loser: you’re good enough to be in the topic of conversation,<br>but they make it clear that you’re not good enough to actually get accepted.<br>My dad had me next day air an additional essay about what I was working on at<br>the time (I had built Good-Tutorials, which was the largest tutorial website on<br>the planet, so that was something different). I also included a bunch of other<br>material and things about me and my senior year.
I thought doing all of this was pretty silly and a waste of time — didn’t I<br>mention this all before? — but my dad kept saying it wouldn’t hurt to really<br>make it clear I wanted to get into the school. I got in shortly thereafter.<br>Didn’t realize it at the time, but CMU clears something like 1%-10% off the<br>waitlist, so it was indeed more rare than I had realized. Guess it did make<br>sense to reach out about it after all.
In 2010, Chris Wanstrath tweeted about looking for junior developers who knew<br>Ruby (I did) and Java (uh, sure, I could maybe fake it). GitHub at the time was<br>kind of the most clique-y of startups; they had made it clear that practically<br>all hires at that point they had worked with previously or interacted through<br>open source. No one knew who I was, and it was frankly pretty intimidating to<br>fire off this email:
Couple weeks later we met at Hotel Utah and they hired me on the spot. Still<br>don’t know why they did; there were plenty of better programmers of both<br>languages out there to choose from (this is back when you had to type code with<br>your fingers). In hindsight, the company was fairly broke — or at least revenue<br>neutral each month — and a $60k junior developer salary was probably low-risk<br>enough to try. Still, I had reached out and lucked out.
Six years ago I sent a cold DM through Twitter and ended up owning part of a<br>soccer club, which<br>I’ve written about to an excessive degree.<br>That one DM led me on an eventual path to ownership in another soccer club, this<br>time in Serie A, and led to a ton of investments I’ve made<br>in sports/tech and the professional and volunteer work I’ve done across the<br>sport. It has very much become my life’s focus, and it’s not something I would<br>have at all believed you had you told me about it a decade ago. It’s never too<br>late to switch gears.
When cold emails didn’t work for me
This is when the Hacker News commenter or Twitter complainer or whoever will say<br>“well who gives a fuck, it’s just survivor bias”. It’s true; I’ve had a stupid<br>run of great luck in my career, and cherry-picking past results don’t inform<br>future performance. But the difference is I’m also going to tell you all of the<br>cold emails I’ve written that when nowhere and didn’t end up changing my<br>life.
…yeah no; no fucking idea.
I’ve done tons of cold outreach to people I admired, half-contacts I had met<br>once, people who might share interests with me, I’m sure of it. I actually just<br>sent a cold DM this afternoon to someone on Instagram who has a super<br>interesting overlap with me, thought we could have a chat sometime.
But I don’t remember those, not really. It’s kind of the opposite of gambling,<br>where the gambler won’t remember the huge pots won, but they can tell you every<br>second of the bad beat they had in their careers. In this case, you tend not to<br>remember the awkward chat you had with the famous CEO at the meetup, or that one<br>email you fired off three years ago, but you remember the outcome of the things<br>that did go well.
Just do the thing
You can’t win unless you skate to where the puck is going to be buying a lotto<br>ticket.
That is to say: you gotta actually do the thing and reach out and say hi<br>sometimes. It’s occasionally awkward and weird and strange, but it’s usually<br>worth a shot. Standard disclaimer applies, as it does to everything in life,<br>though: actually give a fuck, be interested in the other person, and be genuine.<br>Trust me, I get a ton of cold outreach and virtually all of it I can see through<br>as to whether or not someone’s trying to play me, or is honestly trying to make<br>a real connection.
And the most important part to keep in mind: if you’re reading this and<br>thinking, wow, this is awesome, he’s totally right, I should send that email to<br>Zach right now! That’s definitely not what I’m saying here- leave me alone and<br>go bother someone else.
All jokes aside, the other part of this equation is the recipient. Even though<br>warm job referrals are a fantastic way to hire, I’ve long since decided that no<br>matter what the circumstances were...