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I'm guessing the cycle is; work at an insurance company, figure out a solution to their problem, ask your boss if you can work on that solution, be told no, quit and start a startup to do it, sell it to that company, get bought by that company.

This sounds complicated but remember that there is little downside risk for the insurance company that buys you. If you don't make a good product, then you or your investors are out the cash, and they are out $0. This is probably 99% of cases. If you do make a good product, then they can just buy it later when the $ is worth less! (There is also a risk that a competitor buys you, I guess.)




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