Earlier quoted context omitted.
Suppose your present hope of future utility from your startup varies linearly with the number of shares. (This is not a radical assumption; essentially all startup shareholders feel this, at least for numbers near that of shares they own.) Suppose you trade 6% of your stock in a deal that will increase your average future utility by 6.4%. You've made a straight trade of hope of future utility for future utility. We d…
Not to split hairs, but at different points you said - that for essentially all startup shareholders, the present hope of future utility varies linearly with the number of shares, and - that the utility function for most founders is a step function. Both sound right to me separately, but don't they contradict each other? Maybe most founders just live with this paradox without realising?
Most startup founders (initially at least) hope to get a few million, and wouldn't risk that to get a few billion. That's the step. And the most common form of liquidity event is a small-scale acquisition that gives the founders just that level of wealth, since otherwise they won't sell. So in the most common (and most commonly hoped for) good outcome, happiness varies linearly with the number of shares.