My point isn't that it is moonshot or bust - but that you may (like a friend of mine) find yourself having raised $5m to create a business that is very nice, bu

My point isn't that it is moonshot or bust - but that you may (like a friend of mine) find yourself having raised $5m to create a business that is very nice, but won't scale to the level the VCs expect or want. And the exit might be good or might be bad depending on market timing. But the contrast here is that he'll often talk about how much happier he'd be if he'd just bootstrapped the company. Now you can make the argument that he may not have been able to - but the point remains - he's got a good, non-scalable business where his investors are expecting him to magically solve for scalability. Not a great place to be. Your numbers are a bit off compared with what I'm thinking as well - "say you have a $10m business" - that misses the point - he starts the business and there is little to no revenue. He raises a bunch of money but doesn't know if he can create a business that can get bought for $20m. He takes the money and then discovers he has a nice $2m business - but he can't scale it anymore. Because he doesn't have a great growth plan, no one is buying him out for 10x revenue. Thus he's a bit stuck.