| Hey - founder of http://offerletter.io here - some thoughts, in no particular order. My first thought is, get a lawyer and accountant, immediately. My second thought is, yes, you kind of screwed up. Generally if you have the opportunity to early-exercise + 83(b), you should take it if you can afford it - it's far, far cheaper in virtually every case, especially for the really early stage. In terms of forward action, you have a few options: 1) Do a full (or partial) exercise with your own money, pay AMT on the spread 2) Take a loan from someone to help finance the full or partial exercise, let them offset your risk in the short term. 3) See if someone (probably an investor, or your former co-founder) is willing to buy your stock back (probably at a discount) 4) Do nothing and see what happens over the next few months/years, and only take (a potentially much more expensive, but also much more certain) once the company is reaching some liquidity event (or lack thereof). Here's a more comprehensive blog post on startup equity: http://www.offerletter.io/blog/201412-understanding-and-nego... Also, even though they're not "your" lawyers, per se (they are the company's) you should still reach out to the company's legal team to understand your options. And if you have a good, open relationship with the cofounder and/or board, then you have a lot more latitude in terms of next-steps as well - if they're doing well they can nicely ask an investor in a subsequent round to give you some liquidity should you desire it. If you really believe in the company, it may make sense to exercise now and pay the taxes, but if doing so requires a meaningful portion of your net worth, you'll have to make sure you understand you're putting a lot of eggs in one basket. You would basically be going in on an asset that is opaque, and statistically failure-prone. But if you believe in it, it may be worth it. Maybe. Drop me a line [ mallyvai at offerletter dot io ] if I can be helpful here more specifically too. No easy solutions - all have tradeoffs - but it's definitely a manageable situation. Disclaimer: I am not a lawyer or accountant, this is not intended to be formal legal or tax advice, etc etc. |
I'll reach out to my former partner and legal team. We're all on good terms and I still give advice, direction to the engineering team when they need it.
Thanks for the input and offer to follow up. This is why I keep coming back to HN :)