Like how it happened for Bartender, another macOS app which required a lot of permissions. It was sold to a company and they told no one, until a user noticed via the now defunct MacUpdater that the app signature changed.

Ben Surtees (Bartender’s original developer) burned all the good will accumulated over years in one moment. Never again can anyone trust software under that name.

> I think the type of users it attracts (techies, crypto ppl, etc) makes it worth more too.

No, this by itself doesn't make Little Snitch or any business worth $50M. You're dreaming. That's a crazy valuation.