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

literally was thinking that while typing it. it’s very compelling to not have to worry about food again. con: regular shitting of yourself

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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

much more than the small startups out there offering similar approaches. will have to see how their encrypted VMs work, too

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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

same. i wouldn't have thought meta would be good at this stuff either, but here we are. (you can see the whole filesystem and then dump everything out as an export, too, etc) apple would be ideal, but their software side would be lacking. no web view, etc. it's an interesting spot.

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Zach Holman @hol.mn · 10/09/2026

yeah, that might be a good approach. basically all the AI stuff nowadays is "how do i limit the blast radius", hah

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Zach Holman @hol.mn · 10/09/2026

that'sssss the one where i'm super skeptical of, lol. i guess if they gate it to explicit access to one specific password i might be interested, but it's pretty wild in general

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Zach Holman @hol.mn · 10/09/2026

I was somewhat helped by looking at other assistants like Instinct, which people are raving about. Like... I'd — shockingly — trust Meta more than a 10 person company or whatever. that said, they're promising a fully encrypted version by EOY? no idea how that'll work but we'll see

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Zach Holman @hol.mn · 10/09/2026

i am deeply skeptical of my own reaction, too. i must run a self diagnostic on my brain tbh

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Zach Holman @hol.mn · 10/09/2026

haha i do not, but that’s a banger name for them

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Zach Holman @hol.mn · 10/09/2026

i thought it’d be pretty corny but the more i use it the more i like it. the headline is “it just works”. i’ve tried hermes and zeroclaw and they’ve both been a nightmare of actually getting things to run long-term. kept breaking in weird ways. but muse is pretty fleshed out, and very open (!)

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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

maybe it’s a metaphor for the plot of the movie tho? is it possible this is the deepest, most intelligent movie we’ve ever filmed?

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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 · 25/03/2026

First of all, yikes on that conversion, hah. But yes, absolutely- it's high on the list. (Yay, currency fun!)

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Zach Holman @hol.mn · 24/03/2026

Anyway, I've been working on Signed for months now and it's been a joy to see my investments and employee stock in a new light. Give it a looksee: signed.com

signed.com

Portfolio tracking for angel investors – Signed

Automate your job before your portfolio company does. Performance tracking, AI diligence, investor updates, pitch triage, and tax reporting.

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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

100%. early rails and llm-cocaine have a lot in common. (also why rails and llms work so well together, too)

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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 · 17/03/2026

definitely an interesting take. so much has changed from those days.

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Zach Holman @hol.mn · 17/03/2026

hm. Bound to be somewhere, but I’m not sure! I should have stored all those separately haha

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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 · 11/03/2026

I mean, what they mentioned seems quite plausible- toss 'em on a ship and launch them.

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Zach Holman @hol.mn · 11/03/2026

I mean... seems very doable? Not sure why you're so confused about this one.

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Zach Holman @hol.mn · 06/03/2026

Here's my investor profile, for example: signed.com/@holman

signed.com

Zach Holman – Signed

Founder, signed.com.

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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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