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I was thinking about the exact same model the other day (even to the point of paying new hires a signing bonus to cover the stock purchase + tax liability). The wall I ran into was how long I would be able to continue such a model -- how big of a bonus would I be willing to dole out? 20k? 50k? 100k?

If switching to a stock options at some point, what is the proper time? Post-A/B round? (obviously a nice problem to have if you have to worry about such things)

Would be keen on discussing it further sometime, since we seem to have arrived at the same conclusion independently.




Like you, I don't have a good answer yet.

I think as long as we have the goal of equity = ownership instead of options to own we will figure out how to structure it. Sounds silly but it is fairly innovative/progressive stuff we are trying to do - which is our whole goal anyway to innovate and progress.


Remember, the part of the bonus used to buy the stock comes right back to the company, it's just one pocket to the other.

The tax piece is out the door (and is mostly a dead-weight loss if the company doesn't make it, one of the rationales behind options.)


Wow I completely overlooked this fact. Thanks!




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