An important detail here is that the raise was a whole year ago, back when Block's market cap was far higher: I don't have their issuing/buyback data on hand, b

An important detail here is that the raise was a whole year ago, back when Block's market cap was far higher: I don't have their issuing/buyback data on hand, but their shares were flying as high as $270 per share, when today they are at $123. So the 95B is probably more than Stripe would be worth today if they raised. Compared to the old Block share price, Stripe's valuation back then was good, but not crazy.