> 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.

Various intelligence agencies are willing to pay 2-3M for a working exploit for iphone or android. I think that they would be fine with paying 50M for a userbase that has a high population of devs, admins, etc. Being able to backdoor someone like this in the right organization down the line is probably worth 50M.