I've given tons of great advice on /r/business but now I find myself in an area that I know nothing about – selling my business. I was contacted a week ago by a firm that represents a competitor. The competitor, turns out, was bought by some company that buys up companies for portfolio. Now they are interested in mine. I always thought that companies only by small businesses when they are doing bad. My business is very successful. The only thing I am not happy about is the amount of time it still eats up and all the things that go wrong out of my control. That is with any business, but the thought of selling and not having to worry about employees screwing up, quitting, wanting raises when they have preformed poorly, and the asinine drama, it is really appealing. However, I don't want to sell and then several years down the line realize I made a mistake. Right now, I am king of my market. I do close to 3 million a year, and take home about 400k before tax. I figured I would sell it for less than 9 million, which after tax should give me enough to pay off both houses and cars, and put enough in the bank to generate interest that should pay for our bills and lifestyle for life. But what if there is a market crash? What is there is a massive inflation? I figured with no debt, I would need to make 20,000 for interest, but I don't know anything really about depositing large savings and living off interests. I can keep the business and never have to worry about money again BUT I still spend 8-10 hours a day answering emails and dealing with stuff I shouldn't have to at this stage in the game. I worked so hard at the beginning that I sacrificed my health. I was always overweight, but the sedentary life of working on a computer has now made me fat. I wan't to be able to have time to loose weight so I can be there for my son when he's older. At the same time, I don't want to throw away a successful business for a future that won't last. Any Advice? Any Suggestions? Anyone done this themselves? Is there anything I should look out for?