Thread by @patio11

If you have the preference, real or stated due to peer pressure, "I am relatively indifferent to money", people will tend to give you proposals which cut a value cake such that all the money frosting it ends up on their side.

There are many things you can put on a value cake. Creative fulfillment. Social impact. The ability to work in a bathrobe. etc, etc

Money is one of the relatively few which you can bank for later in life when your needs or preferences change, and it tends to compound.

I broadly try to avoid telling people "Your preferences are not the right preferences" but I sometimes struggle with needing to say "Your preferences lead fairly directly to your outcomes."

n.b. If you're cutting a value cake with someone and the money question comes up and you're worried about being seen as greedy, messaging along the lines of "Oh, you know, the money is only as important to me as it is to you" might help you.

"Valuation? Oh I'd never prioritize my selection of investors based on valuation. Pish posh. I want the best possible fit for a 10 year working relationship. Now granted I have a fiduciary duty to get the best possible valuation from the best fit, but we're all capitalists."

"Salary expectations? Oh I'd never take a job just because it offered the highest possible compensation package. I want to to the best work of my career to date. Contingent on this being a great fit, if we arrive at a number which is mutually satisfactory, great, let's do it."

"Won't they know I'm lying?"

They, and it is very possible that the "they" you really are modeling is not the actual flesh-and-blood human you are speaking to but rather the emergent behavior of a system, are socialized to treat negotiation as more of a dance than as testimony.