Financially, yeah, you can cash out and get similar liquidity to what you'd get from an exit while keeping plenty of upside. But investors are only going to provide that option in the situation where they like you as a CXO and think you're the right person to continue growing the company to a $1B+ valuation, which is just a nice way of saying that they'll expect you to continue to pour your heart and soul into the business, work long hours and think about the business 24/7. If you sell your $100M startup to a strategic acquirer, generally you won't still be CXO. You'll get a comparatively chill director-level job, or you can quit relatively quickly and just find a beach somewhere.