Comment Hope for the best, prepare for the worst (Score 1) 412
Weigh the positives and negatives. List all the positive aspects of your current situation, and give each a percentage totalling 100% (i.e. "working with friends: 10%, creative control: 50%, looking forward to work every day: 40%"). Divide the buy-out money into those percentages ("working with friends: $100K..."). See if you're getting a fair prices for selling those assets. It's important to know yourself. If the joy you feel working every day is derived from your executive and creative control over your own work, you will likely be less happy when someone else is calling the shots. Cashing out is great if it gets you what you want, but what will you do then? If you are already making enough money to support yourself and you enjoy your work everyday then you may not want to cash out. Only you can decide.
If you do decide to sell, assume your buy-out goes as poorly as it possibly could. Your new bosses change everything, use fine-print clauses in your contract to screw you over, etc. What will you do? Things change when money comes into play. People change. Do not naively assume that the buyer cares for you in any way personally; this is business. Consult a lawyer and ensure that the buyout contract allows you an unobstructed and agreeable way out should things take a turn for the worse. Many buy-outs lead to the ousting of the leadership of the absorbed company at some point, and there's a reason. Make sure you have a backup plan (i.e. money, resources, contractual guarentees) if things go badly. "An ounce of prevention..."