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I was in a similar situation two years ago. I'd advise having both a plan and a backup plan before you pull the trigger on leaving.

This is generally pretty good, if verbose:


Talk to esofund and friends ahead of time, and see what their offers for your company's stock are, and make sure they're acceptable to you if you think you'll have to go that route.

Don't count on definitely being able to sell the stock to finance the taxes. I left after seven years in very good standing (I believed) but when I went to sell the deal was shut down [1]. Luckily I had a backup plan and I was ok [2].

[1] Had a handshake deal with an investor in the company, then the investor went silent on me. When I followed up he said the deal was "just much too small." I reached out to the company for help, and they said they'd actually told him not to buy from me. I never would have known if they hadn't decided to tell me for some reason. The takeaway is that the markets for private company stock tend to be small, and the buyers care more about their relationships with the company than they do about having your shares. Even if the stock terms allow them to buy, and they might not.

[2] However I was trying to sell for roughly double the current (public market) price. The private/public valuation gap is real! Don't put too much stock (haha) in the value at the last tender offer. If you can sell privately at close to that price it's possibly smart.

With regards to [2], are you saying the private price at the last tender offer was much higher than the current public price?

Both the price of the final pre-IPO tender and the sale price I privately arranged were higher than the current public market price.

I reached out to the company for help, and they said they'd actually told him not to buy from me.

See, it's shit like this that further erodes any faith I have in the ponziconomy of startupcanistan.

Based on what? A conversation between two people you've never met, as relayed to you online by someone you've never met?

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