Jan Koum Is entertaining. He was a frequent flyer and wanted to build an app that could tell people what time zone the person they are talking to was in, that they were on a flight, etc He posted on flyertalk about it and got a "meh, you have to install something? Why bother?" response 5 years later, as a frequent flyer he was into collecting miles and using them on tickets, and he had managed to get business class f…
I overheard a billionaire say he got worried when the market for his primary stockholding dipped by 20%. “I lost $200M. I actually started worrying I might go broke. Then I realized I still had $1.2B...”
Likewise a lot of the wealthy people have no real concept of the fact if you don't work, you don't eat. Maybe you've got savings that tide you over for a year or two, or even a 401k that keeps you going for the rest of your life, but that's not really the same thing.