the most stressful question while living in san francisco is do you pay 6x the price for a waymo or do you instead suffer a human driver
Zach Holman
@holman.bsky.social
building signed.com and calendearing.com. investing: tifo.com. formerly: @github, @gitlab.
Quick new post: no, I probably won't pass you on to another investor. (I wish founders would stop asking me, too, for their sake.) zachholman.com/posts/invest...
Probably Won’t Pass You on to Another Investor
Written pieces, talks, and other bits by Zach Holman.
zachholman.com
GitHub, university, and football. I owe a lot of the good things in my life to reaching out to people I didn't know: zachholman.com/posts/cold-e...
The Cold Email
Written pieces, talks, and other bits by Zach Holman.
zachholman.com
"Make the strongest possible case that my worst investment was actually my best one, and that I'm the only person who can see it." Been having a lot of fun with our new MCP server in Signed: signed.com/blog/mcp-ser...
Signed’s MCP Server for AI assistants – Signed
Today we’re launching an MCP Server for your investment portfolio. [mcp.png] MCPAt its core, MCP just enables your AI assistant — Claude, ChatGPT, Gemini,…
signed.com
walking directly behind a woman on the street and i was horrified to cat call her. by that i mean i have my cat in a backpack and he’s absolutely whining about having to go to the vet, but i still feel awkward about it
Every developer should volunteer for a non-profit on the side these days. There’s unlimited things to do, a magic tool for your knowledge that accomplishes things in minutes, and you learn a *ton* about a huge undervalued chunk of the world.
Open sourced a repo for angel investors and VCs and others called `deckk` that will extract a PDF out of a docsend link (and eventually others). PDFs rock. github.com/holman/deckk
GitHub - holman/deckk: Point it at a URL, get a PDF.
Point it at a URL, get a PDF. Contribute to holman/deckk development by creating an account on GitHub.
github.com
Founders need to stop worrying about the check size when they raise from angel investors: zachholman.com/posts/minimu...
There’s No Minimum Angel Check Size
Written pieces, talks, and other bits by Zach Holman.
zachholman.com
Signed is live for everyone! VCs and investors keep saying they know technology so well and they're living in the future and yet... they use trash tools for themselves. Almost makes you think that tech investors who go on podcasts aren't as smart as they say they are. 🤔
all my friends are just building shit again, it’s an incredible time to want to do things
it's very fun to work on a financial product so I can add real quick wins like this; i wish more apps had flexible behavior like this
The IRS made a typo on my company name and incorporated it with the typo, lol. Off to a great start here.
One of the annoying things about startup investing is how weirdly anti-social it is. There isn't really even some kind of "list" of "angels" out there (I have no idea what you'd call it, though). Anyway, added some social aspects to Signed today: signed.com/blog/social-...
Social investing – Signed
Investing is inherently a social activity: founders meet investors, investors recruit other investors to put a check in, then everyone recruits employees to help work on the company. Strangely, ...
signed.com
i'm pretty sure Messages has been indexing since the first Obama administration and this message has never changed. apple still hasn't figured out how to use the `LIKE` keyword in sqlite, stg
Did a post on the actual mechanics of angel investing: from banks to legalese to mostly complaining a lot more about banks: zachholman.com/posts/the-to...
The Tools of Angel Investing
Written pieces, talks, and other bits by Zach Holman.
zachholman.com
When I started investing in startups 7 years ago, I asked other angels how they track their portfolio and I got a lot of "uh… spreadsheet, it's a mess". It's 2026 and everyone still says "uh… spreadsheet, it's a mess". So I started building Signed last year because wtf.
LLMs: Over the last three minutes I've written 67,283 lines of code to build a sophisticated system to manage failover infrastructure in high-throughput environments, with zero bugs. Also LLMs: I've spent the last 13 minutes designing a bold new brand identity for your startup.
Prevailing sentiment is to treat agents like a "very smart intern", but I feel like that's exactly wrong. I treat it like "the dweeb who only has read a specific RFC for the last 30 years". I no longer get stuck for days on some dumb technicality that's blocking me.
writing a new talk for the first time in nearly a decade and i'm really off to a great start imo
I think Republicans are overestimating liberals' emotional attachment to Bill Clinton.
can't believe nas just dropped a track named "git ready" when he could have used "git init" instead
It’s amusing seeing all the “[project] is moving off of GitHub” posts on Hacker News lately. When I first started there, HN had near-constant “[project] is moving to GitHub!” posts. It’s the life of software. Improve or die.
Hella excited to be joining the ownership of Serie A’s Cagliari. Some real over-the-moon excitement for the club and for The Island. LFG!
zachholman.com decided to redo the blog for maybe the tenth time. turns out if you write every now and then and do it for over fifteen years that leads to a shit ton of posts, wowza. how did you all listen to me for so long?
Zach Holman
Written pieces, talks, and other bits by Zach Holman.
zachholman.com
Just finished up a two-month jury duty stint and I’m really realizing how much solo projects depend on inertia and motivation. You take a break and it takes ages to get back in the swing of things.
Added a free/busy calendar to Calendearing this morning: calendearing.com — so now you can have a more public calendar without any of your personal data visible.
calendearing.com
The year is 2013: - password managers worked - you could get most TV content from one or two streaming services - you could paste links into chats and previews would actually unfurl correctly - google results contained actual search results