If you look at the distribution of exists/mergers/sales, it is infinitely easier to grow and sell a company for $20-$50m than it is for $100m+. The number of potential buyers rapidly diminishes, once you get into 9 figures, deals get more complex, take longer to execute, and have a higher chance of failing.<p>Over the past 18 months, I've seen four of my friends "cash in". Most of these guys were at it for 7-10 years before the exit, and all but one of these was a sub-$30m deal.<p>In order to justify these "NEW" valuations, entrepreneurs & investors have to hold out for VERY high value exits, which will dramatically reduce the chances of success and statistically extend the exit time for the angels and entrepreneurs by over a decade.<p>For most entrepreneurs who are on their first business, $5m or $10m is a life changing amount of money - by declining exits at prices that could achieve that outcome, they are forced to keep rolling the dice, over and over again, hoping that growth continues, a new competitor doesn't emerge, someone doesn't undercut their pricing, and everything is going at 110%.<p>It doesn't seem to make sense on the surface of it.