The bigger question is "how to not be useless?" Useful people will do well in the market whether they're an employee or an entrepreneur. Useless people, by definition, fail whether they're an employee or an entrepreneur. If you can figure out how to build skills & assets that other people want - which is much harder than simply starting a business - then you'll always be in demand.
If you make society about being useful to the top 5% of the population, then the rest of the population is always going to be left in the dust unless you turn to geneticaly modified workers ala Gattaca.
The question is, how do you create a society where everyone can make a living?
It is ingrained into modern society thinking that in order to make a living, you need to be useful to someone else that has the money, power, and natural resources that you don't have simply because of age, luck, or someone being naturally smarter.
But what if everyone was guaranteed land to live in and produce their own sustenance? In a different type of society, or perhaps far into the future, this may be a possibility given population control.
In this manner, people are guaranteed to at least make a living. The tendency for riots will be greatly diminished when basic needs are met. Everyone else who wants to create more wealth and enter the monetary exchange will be free to do so.
Q: What do you trade? A: Things that others find useful.
Even if you give people land they will need tools, supplies, medicine, housing, plumbing, fuel, electricity, roads, computers, phone/internet, etc. They will need to trade, they will need to be useful.
One can easily move to the middle of nowhere montana/north dakota/alaska and live off the land with a little bit of planning. Most don't want to.
There have been studies documenting this. Here is a short story from Tim Ferriss which sums this up where he realizes that a Mexican fisherman really has a very high quality of life.
http://www.peterbe.com/plog/the-4-hour-work-week-by-timothy-...
Most of the arable land has been concentrated in the hands of a few, and the technology needed to generate sufficient harvest to weather downturns such as drought or flooding are out of reach for everyone in 3rd world countries.
That's why you can't look at 3rd world country farmers and just say that no one would be able to live "off the grid" comfortably.
In the 20th century an American of average ability could sustain themselves doing office work or industrial labor.
Beginning sometime in the late 20th century, the average American seems (to me at least) to be less and less needed in the modern American economy. Jobs are automated or off-shored.
What do we as a society do about/with those "useless" people? It's a lot of people.
Or am I too pessimistic?
That's the subject of the whole novel, and it's a really great one.
Of course, if the products are also exported, eventually the exploited people will figure out that they can cut out the "useful" middleman. Then we useful and useless Americans are all in the same boat.