Recapitalization like this would generally not happen before an acquisition-- because it would likely be a breach of fiduciary duty.

There are other things, though, like carve-outs.

If company A is being acquired by company B, and company B needs key people from company A to stay, and the employees do not have enough upside for company B to be assured they'd stay... you might set aside some acquisition proceeds for those people. This tends to hurt both investors and past employees.

To dumb it down, what you’re describing is when a press release says a $1B acquisition price, but officially it’s technically a $500M acquisition, and a coincidental $500M bonus/incentive pool that the acquirer is choosing to award to whoever they want, under whatever terms they want? That’s called a carve-out?

It would be nice if someone maintained a list of all of these “tricks” and what to watch out for in your options agreements. I try to pay attention to this as a layperson, yet I am frequently learning of more lingo and new deal structures that introduce a lot more risk to both founders and employees.

Yes, but that's pretty rare, because it doesn't make much sense.

A much more common carveout would be something like this:

- A $15M acquisition of a distressed company that may very well be insolvent if the deal is not completed

- $10M is owed to investors to repay liquidity preferences

- A founder is gone who would get $1.5M of the remaining

- Any reasonable escrow fund, etc, on the $3.5M that would go to the remaining shareholders is not enough for the acquirer to be sure they retain key talent.

This deal can't be reasonably done with $15M split according to the capitalization table.

So instead, the investors take $9M (10% haircut, since they're first in line for any fall-back plan); $4M goes to existing shareholders (20% haircut)-- including that missing founder who now gets $1.2M; $2M is held in an escrow for people that the acquirer needs to keep.

This isn't a breach of fiduciary duty, because it's mostly being dictated by the acquirer and because no shareholder class ends up worse off than they'd be in any likely alternative.

Thanks for this. What you described is another practice that was described to me by a few execs who I happen to know quite well: they explicitly said it's a way to not only screw employees (especially the ex), but also investors, and basically redistribute the wealth just to a very small subset of very very key employees.

It isn't, though. Any deal has to make sense for everyone who has to agree to it.

E.g. my last time around-- there was a deal that would have paid back investors and even paid a little to employees... but the acquirer would have required key technical staff to stick around.

The only way that deal would have gotten done would be if it was possible to carve out enough funds for those key technical staff. (It wasn't, so instead it was an asset sale that did not pay back investors).

Just to be explicit:

- I have never been part of a recapitalization or carveout (though I did do diligence on a couple of companies that would have recapitalized as part of a fundraise if funded)-- other than the normal term of stepping up the incentive option pool as part of a capital raise.

- Even so I pretty strongly feel there are times they are necessary tools, and are mostly used in this way.

- Of course, anything can be abused by people with poor ethics.