I remember one time I had this guy call me up, wanted to pitch me, right? Wanted to sell me stock. So I let him. I got every fuckin’ rebuttal outta this guy, kept him on the phone for an hour and a half. Towards the end I started askin’ him buying questions, like what’s the firm minimum? That’s a…
Zach Holman
https://zachholman.com/ · 10 posts · history since 2024 · active
1 May
24 Mar
Awhile back I asked my friend Leah Culver about how she tracks angel investments, because I was just getting into angel investing and it seemed weird that everyone just had some shitty spreadsheet setup to keep track of all this stuff: Anyway, her answer was “a spreadsheet”. And that was the same for all the others I asked then, too.…
27 Feb
Part of the annoying thing about angel investing is that you’re ostensibly investing in CUTTING EDGE FUTURE STARTUPS who are about to BRING THE FUTURE TO YOUR FACE and in order to do this you have to go through some of the worst software and processes on the goddamn planet: banks, and laws. Some cool stuff remains, though. Money EUROPEANS…
30 Oct 2025
Recently I had a long call with an old friend who was facing an age-old predicament that I’ve been seeing more and more these days: Lucked out, worked hard, employer is crushing it, and now she’s sitting on a large amount of paper money gains at her startup Company does a tender offer, either buying their stock back or allowing…
29 Sept 2025
For when you have too many calendars Once upon a time I built a calendar and then wrote an exhaustively long talk about working with time, timezones, calendars, and everything in between. For a few unrelated reasons we ended up not shipping the calendar, but in general, as I mentioned in the post: Zach, whatever you do: just don’t ever…
21 Jul 2025
It’s mind-boggling how many in the general public don’t understand this, so let me rant about it for a bit: many companies are designed to lose money this year. That’s the fucking point. Today’s main character energy is the news of WNBA players wearing Pay Us What You Owe Us shirts during the All-Star game. The knuckle-draggers on social media…
3 Feb 2025
Most developers know about red teams: a specific group of people chosen to be the antagonist to your system, trying to sniff out vulnerabilities in your code or organization. Basically, like Sneakers, or the annoying plotline in The Newsroom season two. (Someone should have really red team’d Sorkin himself on that one.) There’s a few other concepts of a red…
30 Jan 2025
<!doctype html> From Cold DM to Owning a Soccer Club Oakland Roots, a club in the USL Championship, the second tier of soccer in the US. So: what is sports ownership like, anyway? How similar is it to my startup experiences? Can I write a way-too-long of a post about it all? Yes. Yes I can. January 30, 2025 Look:…
28 Aug 2024
I’ve made like a hundred angel investments over the years, and I get the sneaking suspicion that the most successful startups in my portfolios are the ones that talk to their investors. Like, that’s it. That’s the nugget for this post. Holy shit no one can help you if they don’t know you need help Like most good advice, this…
11 Apr 2024
Quick little announcement: I’m launching my own kind-of-weird-venture-fund today: Tifo. Over the last five years I’ve been doing a lot of angel investing- I’ve made close to a hundred direct angel investments, and then have made dozens of others through syndicates (which again, I highly recommend as a way to start out with angel investing). I really enjoy doing it-…