sbraford

Hi,

tldr; got in early at a startup. exercised stock for ~$6k. got valued at ~$90k+, received a 1099 for that. company subsequently declined in value, now the stock might never be worth anything, but I owe $30k in taxes.

I was a very early contract hire at a startup right around pre-covid. Rode the unicorn wave to a $1b+ valuation. Good ARR. Everything going well. I exercised some stock options after they vested for around $6k. I did not pay any taxes at the time. It was through Carta. It never asked me to pay taxes on it or anything. At the end of the year, I get a surprise 1099 from the startup stating I made ~$90k+. Of course it was just paper stock gains (of private shares).

There was no way to sell the privately-held shares. I tried sites like Forge Global but there was zero market for these.

Subsequently, some things happened that I won't get into, but the company declined in value. I have no idea what it's worth today, but it's highly unlikely that it is worth anywhere near $1b anymore.

I am finally trying to figure out a better solution to the whole situation. I've contacted tax attorneys and CPAs. One guy said there _might_ be something I could do if I could show the current valuation of the company had declined starkly in value, compared to the value I was assessed the gains at.

Anyone in a similar boat?

I feel like this is an un-talked about thing in the startup world. It really sucks tbh.

Also note: I am not some big FAANG guy with $300k+ in TC that I pay taxes on each year. I won't say how much I make but it is a small fraction of that, so simply "depreciating" (?) or whatever the shares would not help me very much in this situation. That is--I hardly make enough in income each year to "save" in unpaid taxes if I take a giant loss from the shares, and hence just pay less in taxes going forward. I'm trying to figure out a way to reduce the $30k overall burden that I'm paying, not just reduce my future tax obligations. But maybe I'm missing something.

I've been looking for a new contract/client for the past three months, to no avail. The market seems to have really dried up compared to the last several years.

I'd love to co-found a startup, but have had trouble in the past finding a co-founder. I don't have any previous co-workers who want to start one right now, so I'm looking for other options (i.e. a website / etc).

I'm also open to offering my services (backend mostly, Ruby on Rails) to a startup for mostly stock + a small stipend of $1,000 a month until further rounds of funding have been raised. Not sure if that's a viable idea or not.

Hello,

I'm looking for a web designer or two who isn't afraid to get their hands dirty in rails-land. Familiarity with git is also a plus.

Does anyone know the best place to find someone like this?

Upwork? If you have any suggestions, please leave a comment. Thanks!

ps. not looking for an agency and US-based is a plus due to time zone reasons.

Coming back to ruby development after several years off. I'd be open to other frameworks, but don't feel like learning a new language at the moment.

It would be a Firefox/Chrome/etc plugin. On any webpage on the internet, it would allow you to click a button in the browser and "mark up" the page a la "Skitch."

e.g. recently I was on a page with un-hotlinked images and I just wanted to yell at the designers "WHY U NO hot-link images???"

I know this is not the typical direction for YC startups. You'd normally want to build an app or service that could eventually generate tens of millions of dollars. But what if you could be satisfied with just one million?

i.e. would it be a new SaaS website, an iPhone app, an Android app, a multiplayer game, or what.

The more details the better, but if you have an idea that you'd like to keep on the downlow, maybe just mention the app/service type. Thanks!