I think the first 10k a month app will inevitably be the hardest, but like Justin says it'll be a lot easier than becoming the next Facebook or Google. Most people chase/fantasize about being the next Google because they think it will buy them freedom. If you are lucky enough to get close, depending on how you play it, it might do exactly that for you. But I agree with Justin the odds are just so small it's difficult to justify spending your life in eternal lustful pursuit of such dreams.

I'm sorry to roll out the cliché, but gaining time is more likely to make you happy and free. And a few slow grown bootstrapped 'dipshit companies' are much more realistic and likely to provide you with that time along with a boatload more autonomy. Instead it seems everyone is aiming to be the head of the next big thing and indebted to VC's in to the bargain. What do I know though, perhaps it's not all that bad...?

I do think that with a couple of $10,000 a month semi-automated apps in your pocket you've got a lot of choices. Especially if you are young. It can give you the free time to really work out what you want to get out of your life. With time to think you might find it's not what your doing and/or aspiring to right now.

For me if my startup ever starts to make 10K+ a month it'll simply mean trying to spend a little less time sat behind my keyboard. Spending more time outdoors travelling and experiencing the world instead of too much time indoors reading about it sounds like a good plan to me.