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Sounds fun. Normally I would say that sounds expensive, but he can afford it and like he said it is certainly a way to experience quality control.

I do have some questions about what his experience will be like. I have lived out of a suitcase before (duffle bag) while traveling from place to place constantly, but I as in Afghanistan with almost no physical assets to manage. Considering his wealth I suspect there would be some real life things to manage that would make this variable temporality more complicated.

I don't believe he mentioned selling any properties he owns. I'm sure his things are safe in high end residences.

I appreciate you sharing your story, but I can't imagine Brian Chesky's experience is at all relatable.

I did this for almost six years, traveling in the US, Asia, and Europe. I also stayed at hotels sometimes and rented apartments/condos for short terms. With some effort (and compromise) living like this can turn out cheaper than renting an apartment or house in the US (depending on where you live in the US). You have to travel light and stay flexible. With more countries offering long-stay visas to people with income from somewhere else (not competing with the locals) this digital nomad lifestyle is getting easier.