It's purely observational on my part, but a founder who is sitting comfortably vs. a founder who is not -- I've seen the difference, and it very often comes down to motivation, drive and determination.
Each situation is different, but given the hungry founder (like, actually hungry) vs. the comfortable founder -- I'll take the hungry founder almost every time.
There's clearly a level of financial uncertainty where a founder is LESS productive. But, there are ways (which don't necessarily overlap) a founder could spend "excess" money which don't inhibit drive at all.
Probably the lowest hanging fruit would be to eliminate actual debt (founders may have student debt, credit card debt from earlier in the company, etc.); getting rid of debt probably won't change behavior. Maybe other health-related things. Actually, a lot of this could just be handled as "generous startup perks" vs. payouts; if I knew I could always fly in domestic E+ or upgrade-to-F on my preferred airline, and stay in a decent hotel, I'd be a lot more into taking back to back business trips all the time.
Taking care of someone else's expenses (e.g. kids, parents, or other dependents) probably won't reduce motivation, either. Fixing things which inhibit a founder's productivity (paying for a housekeeper, driver in some cases, closer apartment to the office, ...) seems like a good idea.
It's probably a bad idea to pay someone enough to become an investor, or to buy/build a house (oh god no for BUILDING), indulge in expensive AND time-consuming hobbies, etc.
The gray area is when founders would actually take an outright sale, but are given a choice of $5-10mm now and continue instead; that's enough to possibly reduce drive, but not as much as selling out.
One option might be to put some of the payout into a "lockbox", where it's safe for reasons of diversification, but not accessible. e.g. you sell, get $1-2mm into your 401k, or into an account which is inaccessible (but safely invested) for 5 years. That way, your downside risk is covered if the company tanks, but your lifestyle doesn't change.
Although, anything like this will make Bay Area luxury car dealers very sad. :(
If I cashed out a few million, what would I do with it? I'd pay my debts, buy a respectable place to live, eat healthy meals, buy a car, and buy generous gifts for all the people who've helped me along the way. Maybe most important, I'd show my friends and family I made the right decision.
But a few million is not nearly enough to buy everything I want, and there's no way I'm going to ditch such a high-potential project just for a quick payout. In fact, now that I've tasted wealth, it's more likely that I'll make sure I keep it.
The hungry founder fears staying hungry. The comfortable founder fears becoming a hungry founder and staying hungry - and I think the latter is a much more prominent fear.
Do you have a list?
Also, if living comfortably was a founders goal, why would they start a company instead of getting a steady job working for a comfortable 6 figures at an established company?
This worldview seems completely cynical and utterly immoral, and reality runs roughshod over it in any case. Two words: Steve Jobs.
A) That phrase is a classic copout to try and draw attention from the fact that you're generalizing based on your own biased opinions with no evidence.
and
B) It was immediately followed by further reinforcement that you believe your opinion holds in "almost all" situations.
You didn't actually admit that every situation is different, you used oratorical sleight of hand to try and make people agree with your sweeping and unsupported statements favoring the greedy, self-serving worldview of VCs.
If you can reach that logical summary based on my comment that I trust a hungry founder over a sitting-comfortably founder, then we don't have much to talk about.
BTW, I'm not a fan of the VC crowd -- I'm a fan of the early-stage employee crowd. The one who loses out in this conversation about 99% of the time.
Conversation over.