I worked with a guy who freelanced for a while, and he had an interesting observation.

When the economy is shit, most large companies outsource a lot of work because they can't afford or don't have the workers for the amount of work they have. So if your a freelancer, business can be pretty good.

When the economy is great, those same businesses try to bring all those efforts in-house, so all those contracts dry up.

Not sure how it relates with entrepreneurship, but this guy had to quit freelancing and get a full-time gig (which is how I met him) because no one was handing out the contracts he wanted anymore.