11–20 of 172 posts
Sell at the valuation, e.g. 5% of $XX,000,000. Maybe offer them a 20% discount on the shares if you really want to sell. Otherwise don't sell. Not selling is your leverage, as they clearly want you to sell.
People that know better than me: How nuclear an option would it be to ask the investors directly?
Aside: If the co-founder is an HN reader, then they probably know the throwaway account is you. That is going to skew this negotiation.
Sell at the valuation, e.g. 5% of $XX,000,000. Maybe offer them a 20% discount on the shares if you really want to sell. Otherwise don't sell. Not selling is your leverage, as they clearly want you to sell.
Ask for more.
CEO refuses. How do I apply leverage?
I'm not saying you should do this. Nor am I suggesting it's a good tactic. But it may provide leverage if you need some.
Investors in the round would probably buy your shares for 1/3rd - 2/3rds of their value and you should consider asking if that's an option and then negotiate from there. The only reason to let the company buyout your shares for a lowball offer is if you left the company after a short period of time without proper vesting and you want to do the right thing for the company's sake. Doesn't sound like that's the case.
Earlier quoted context omitted.
CEO refuses. How do I apply leverage?
You could say that if the CEO doesn't improve the offer, you're going to write directly to the board / new investors. I'm not saying you should do this. Nor am I suggesting it's a good tactic. But it may provide leverage if you need some.
Sell at the valuation, e.g. 5% of $XX,000,000. Maybe offer them a 20% discount on the shares if you really want to sell. Otherwise don't sell. Not selling is your leverage, as they clearly want you to sell.
Note that he probably owns common shares, and the investors are buying preferred shares. Also, he's going to be diluted below 5% in the post-money era.