I knew a guy who sold ~3-4 startups after every exit, he was spending all the money to 0, just enjoying life for a while Then he repeated the whole cycle over and over again He said to me once: "If you can dream serious in life, 1-2 months in poverty is your max. Then you'll figure out how to 'make it' again" Not a fan of all of his actions, but 100% agree with his last sentence