If you read all my ramblings, you'll notice that I emphasise that any enterprise needs to be grown quickly to the point where it becomes valuable so that it can be sold.
All the businesses that I started are now obsolete. One of the earliest attempts at making money was in printing instant name cards. I could charge 100 bucks for 20 in 1989. You can now order 500 high quality instant name cards on the net for USD29.95 and have them delivered within 24 hours. It cost me $5000 to start that business and I sold it for about $30,000 18 months later.
When I started doing web design, all I knew was html and photoshop. It was sufficient to earn good money as the web was in its infancy. Had I not cashed up, I'd be bankrupt now. I can no longer keep up with the ever increasing technology requirements.
Once you have banked your money, it doesn't matter what happens anymore. Not so with employment. Your ability to pay a 20 year mortgage is determined by how long the business you work for can keep going and whether or not you can find another job if it can't. If you haven't kept pace with the changes, you become unemployable with very little money in the bank.