signed.com: because angel investors apparently can't keep track of their investments

So I recently built Signed, after years of investing in startups as an angel and honestly being a bit flabbergasted at how bad investors are at... doing their job?

Signed handles all the document upload, reporting, tax packages, and financial projections that seemingly no one tends to do on their own.

Launched it publicly about a month ago, and it's been a ton of fun. You know that bit where you've been using your product for awhile, and it's been really great for your own use cases, and then... other people use it and they love it too? Wild. It's like an adrenaline chase that still hasn't gotten old, decades later.

My background is developer tools — early at GitHub, then advised GitLab — and have been investing in the area as well as other oddball areas (ask me about getting deep into soccer/football sometime!)

Anyway: it's been fun to build. After spending a bunch of years meandering around some other software markets, having something that's insanely dogfood-able has been a breath of fresh air. Early GitHub we could just... get irritated by something on our open source project, and then just go into work the next day and build something out to fix it. Now with all my angel investments I can just directly build things for me again. Not all products can be dogfooded... but man, I really love the ones that are.

Signed combines my classic Rails stack with a lot of newer and interesting LLM approaches. The act of investing in a startup usually involves a ton of red tape and legal documents: parsing them via LLMs, fine-tuning performant search over all your documents without making for a miserable experience (or costly experience) has been fun, as much as that kind of fine-tuning can go. But other than that it's been a really perfect example of "this would have sucked to build even a couple years ago": the amount of information you can glean from cap tables and dozens or hundreds of pages of legalese is actually pretty amazing. Who would have thought they actually put REAL important things in all those words? Sheesh.

Anyway, just wanted to pop in here and mention it, because though not everyone is an angel investor, you can also track your employee equity on Signed, and I'm really trying to make the scary concept of equity and cap tables in general a lot less scary. Happy to chat about it if you have any thoughts or questions!