It doesn't matter if you have a 'great lawyer' - because any 'fine print' in other investors deals can very easily fundamentally change the value of the offer.

It doesn't matter if you have a 'great lawyer' - because any 'fine print' in other investors deals can very easily fundamentally change the value of the offer. Major investors could have 3x 'participating' in which case they get 3x their investment back before anyone else gets anything. There are debtors: if the company has big debt - money goes to them first. Sometimes the debt is convertible - which could mean major dilution. The number of outstanding options, not actually stocks, obviously makes a big difference. Major cash bonuses to execs, IP holders etc. upon sale. And that's the 'relatively normal stuff'. The contracts can literally say anything. Like 'Investor ABC who put in $1 gets first rights to the first $100M in valuation' or something insane like that. Now - that would be very bad actually for the company obviously, so it's not likely to happen ... but it could theoretically be there. So there's an immense amount of trust that has to be in place, which is why you need a very 'clean' situation, a credible team - and then of course a 'hot enough' company for it to even make sense. Equity is a legit form of comp. but everything just has to be 'just right' and often it's not. If there is any 'odour' at all in the situation, I would assume shenanigans, in which case, any form of equity is considerably more risky, and then probably not worth it.