iiinova — where your digital self keeps evolving

Zach Holman @hol.mn · 27/09/2026

If you like this AI stuff and think it's pretty cool and you want to just *build* these days... you should just go get an LLC: zachholman.com/posts/you-sh...

zachholman.com

You Should Have an LLC

Written pieces, talks, and other bits by Zach Holman.

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Zach Holman @hol.mn · 16/09/2026

don’t talk to me unless you have sound effects enabled on linkedin i only talk to winners

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Zach Holman @hol.mn · 16/09/2026

if you're telling someone about their own job from 15 years ago, TURING TEST DENIED zachholman.com/posts/llm-wr...

zachholman.com

As Someone Who Has Written This Blog Post,

Written pieces, talks, and other bits by Zach Holman.

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Zach Holman @hol.mn · 15/09/2026

Added a new runway feature to signed.com to sort which of my portfolio companies are facing cash crunches. (As a side note, always fascinated by startups who run out of cash and haven't talked to their investors about it. That's what they're there for, to help!)

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Zach Holman @hol.mn · 14/09/2026

Still really enjoying Muse. I use Things.app for all of my todos, and though it has cloud sync they (still) haven’t added an official API. I told muse to build it and a minute or two later I have ongoing todo sync from my LLM across all my Apple devices. Wild.

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Zach Holman @hol.mn · 12/09/2026

as you get older you realize that the hardest problem we all face in life is what to eat for dinner this time. like we just had dinner last night why do we have to make this decision again

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Zach Holman @hol.mn · 10/09/2026

i just had muse set up my vestaboard to display messages in my zoom background about whichever meeting i'm in next. worked great. then i told it to do a fun one for me in the meantime. this is the message it chose and then this is what it told me in chat after lol send help

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Zach Holman @hol.mn · 10/09/2026

friends, i’m sadly here to say that meta has cooked with muse and it’s everything every personal ai assistant has tried to be. it just like… works. i remain skeptical and continue to be really impressed

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Zach Holman @hol.mn · 24/08/2026

best we can tell, an onlyfans or similar model has been using our address for her simps and we keep getting bouquets of flowers this week for her apparent birthday (or for one guy, their two week anniversary together). the house is now mostly flowers.

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Zach Holman @hol.mn · 22/08/2026

Opening day is incredible. It’s basically like back-to-school days, where you get to see all the familiar faces and see what everyone was up to over the summer. Granted, we’re doing it at 9:30am at the pub, but it’s basically the same thing. ⚽️

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Zach Holman @hol.mn · 21/08/2026

Had a lovely time talking with Marcia Dawood about angel investing, building Signed, investing in sports, and how AI can help unlock all three of those. Yes, I used `unlock`. That's how you know it's business-oriented™. Full episode is on YouTube: www.youtube.com/watch?v=Dtca...

youtube.com

Tracking Angel Investments w/o Spreadsheets: Manage your Portfolio with Effortless Tax & Exit Org

YouTube video by The Angel Next Door

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Zach Holman @hol.mn · 19/08/2026

imagine: running an agent which was solely trained on the hardest problem remaining in computer science: staying signed in to any anthropic service for longer than a few days

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Zach Holman @hol.mn · 18/08/2026

finally succumbed to the bluesky custom domain vanity url

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Zach Holman @hol.mn · 11/08/2026

MRI results came back today from a human doc: a herniated disc. Obviously I had tossed the raw scans in to LLMs last week; Opus and Fable missed it, Sol caught it. This is now the gold standard in analyzing performance of frontier models. First step: herniate your back.

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Zach Holman @hol.mn · 07/08/2026

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

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Zach Holman @hol.mn · 05/08/2026

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...

zachholman.com

Probably Won’t Pass You on to Another Investor

Written pieces, talks, and other bits by Zach Holman.

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Zach Holman @hol.mn · 29/07/2026

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...

zachholman.com

The Cold Email

Written pieces, talks, and other bits by Zach Holman.

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Zach Holman @hol.mn · 29/07/2026

i can't believe we used to type code with our fingers

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Zach Holman @hol.mn · 28/07/2026

"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.com

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,…

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Zach Holman @hol.mn · 27/07/2026

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

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Zach Holman @hol.mn · 05/06/2026

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.

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Zach Holman @hol.mn · 25/05/2026

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.com

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.

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Zach Holman @hol.mn · 01/05/2026

Founders need to stop worrying about the check size when they raise from angel investors: zachholman.com/posts/minimu...

zachholman.com

There’s No Minimum Angel Check Size

Written pieces, talks, and other bits by Zach Holman.

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Zach Holman @hol.mn · 24/03/2026

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. 🤔

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Zach Holman @hol.mn · 20/03/2026

all my friends are just building shit again, it’s an incredible time to want to do things

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Zach Holman @hol.mn · 13/03/2026

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

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Zach Holman @hol.mn · 12/03/2026

The IRS made a typo on my company name and incorporated it with the typo, lol. Off to a great start here.

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Zach Holman @hol.mn · 06/03/2026

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-...

signed.com

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, ...

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Zach Holman @hol.mn · 02/03/2026

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

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Zach Holman @hol.mn · 27/02/2026

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...

zachholman.com

The Tools of Angel Investing

Written pieces, talks, and other bits by Zach Holman.

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Zach Holman @hol.mn · 20/02/2026

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.

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Zach Holman @hol.mn · 16/02/2026

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.

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Zach Holman @hol.mn · 04/02/2026

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.

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Zach Holman @hol.mn · 09/01/2026

back doing my first talk in eight years 🤘

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Zach Holman @hol.mn · 05/01/2026

writing a new talk for the first time in nearly a decade and i'm really off to a great start imo

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Reposted by Zach Holman

Elon Green @elongreen.bsky.social · 20/12/2025

I think Republicans are overestimating liberals' emotional attachment to Bill Clinton.

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Zach Holman @hol.mn · 12/12/2025

can't believe nas just dropped a track named "git ready" when he could have used "git init" instead

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Zach Holman @hol.mn · 30/11/2025

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.

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Zach Holman @hol.mn · 24/11/2025

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!

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Zach Holman @hol.mn · 21/11/2025

i mean that’s not how this works but okay

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Zach Holman @hol.mn · 18/11/2025

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?

zachholman.com

Zach Holman

Written pieces, talks, and other bits by Zach Holman.

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Zach Holman @hol.mn · 13/11/2025

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.

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Zach Holman @hol.mn · 10/11/2025

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

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Zach Holman @hol.mn · 31/10/2025

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

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Zach Holman @hol.mn · 30/10/2025

Taking money off the table: zachholman.com/posts/money-... Wrote a bit this morning about tender offers and that "oh god do I sell my stock?" decision startup employees face.

zachholman.com

Taking Money off the Table

Written pieces, talks, and other bits by Zach Holman.

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Zach Holman @hol.mn · 12/10/2025

Single hardest thing in computer science: getting the people who wanted to beta test your software to actually beta test your software.

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Zach Holman @hol.mn · 08/10/2025

I see endless people dragging WNBA & NWSL teams for “losing money” (“the NBA is subsidizing the WNBA”, etc)… but the Yankees, Clippers, Mets, Everton, Barcelona, etc aren’t losing money… they’re “investing in the club”. Just can’t *quite* put my finger on the difference here.

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Zach Holman @hol.mn · 30/09/2025

fox, always with their one-track mind

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Zach Holman @hol.mn · 29/09/2025

I built a calendar again! Sort of. This one is super tiny: take all the bunch of calendars you might have, and then spit out a single URL that you can share with others. Here's a post: zachholman.com/posts/calend... And here's Calendearing, the product: calendearing.com

zachholman.com

Shipping Calendearing

Written pieces, talks, and other bits by Zach Holman.

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Zach Holman @hol.mn · 23/09/2025

It's going to end up taking 1x-2x longer to get my new LLC registration and EIN than it was to create the actual code and product for a new company. Wild.

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