Did you consider using something like ESO Fund to finance the exercise of your options? If so, why did you decide not to use them?
Assuming they're willing to do the deal, if your alternative is letting the options expire worthless, it seems like a no-brainer to take a loan with no recourse unless there's a liquidity event. You wouldn't have made the full $300k, but at least a solid portion of it.
The story I related was at my previous company from about 4 years ago. I had never heard of ESO Fund until this moment. Thanks for the info, I will definitely look into that (I currently have a lot of options at my current startup).
You are correct! Our pricing depends on a bunch of factors including how much money it takes to exercise the shares and what we think the company can exit at. We aim to take less than half the proceeds. Sometimes if the exercise cost is higher and the exit isn't as high as we anticipate, we may end up taking more than half. For the most part, our business is a referral business and happy clients means they will refer their friends/co-workers.
Assuming they're willing to do the deal, if your alternative is letting the options expire worthless, it seems like a no-brainer to take a loan with no recourse unless there's a liquidity event. You wouldn't have made the full $300k, but at least a solid portion of it.