They are more akin to projects than businesses. The majority of the businesses could be categorized as small web apps and Amazon affiliates. Most appear like he didn't find a problem to solve, but tried to create a solution. There also doesn't appear to be much thought given to market size for each product.
The title of the spreadsheet is “Josh Pigford's Absurd List of Products, Apps, Websites & Businesses”...they definitely weren’t all full on “businesses” and the large majority of them were terrible ideas. I definitely don’t recommend most people go the route I did. :)
No clue. Everybody's route is different. This is just how I've figured things out (and I'd still say there are many things I definitely have not figured out).