I’ve never owned a business, but I’ll tell you about two good friends who have.

Xboxboy’s advice all seems very solid, and the part about “sexy” applies to the first example. A friend bought a business that bought waste grease from restaurants and sold some of it to…I don’t know, whoever uses used grease. Very unsexy. Disclaimer, he was doing ok before this, and he might’ve paid a lot for the business, but a couple years after he bought it, he moved from Carmel Valley to Rancho Santa Fe, so it was working out for him.

Another friend started a restaurant. We’ve all read that most restaurants fail within X amount of time. I’ve read that that’s usually because the owner gets tired of working hard 100 hours a week. My friend worked those 100-hour weeks for about 5 years. He had previously managed a successful restaurant for years, and he had also owned several pizza joints, so he had lots of knowledge. He started his own restaurant, and he worked, and worked hard, all day every day for about 5 years. He wasn’t making any money at all. He had to borrow money from his brother (a partner in the restaurant) just to pay his bills. Finally, he gave up. This guy was an extremely hard worker, and he had lots of knowledge. But he couldn’t make it work. He wasted 5 years of his life and a significant chunk of his life savings on that restaurant and got nothing out of it.