Guys, I'm not looking to piss him off.
I'm looking just to mess with him. He can take it. We all mess around. I'm not looking to harm or hurt anyone. Just a good classic prank to mess with him..
Are you the only one that has an issue? If so it something you are or are not doing. If everyone has an issue, it might be time for a conversation and let him know how people feel.
I'm not defending him, there are plenty of a-hole bosses. But consider that he put everything on the line for this. He runs the business, he has put his money, his time into this and sacrificed a lot to make it work. So no matter whatever you do for him, you are still not cleaning out your bank account and mortgaging your house to make a business that may fail.
The cold hard truth is, he will not change because you pulled a prank. That is a passive aggressive route and nothing good will come from it. No boss ever wants to be embarrassed. If I screw something up, the first person I tell is my boss. Explain what happened and have a plan to correct it. Stuff happens but no surprises. If he's a good boss he's got my back and we figure out how to not let that happen again. Good employees are worth gold, bad employees are a liability.
If it's that bad there are a few options.
1. Talk to him straight up and figure out how to improve the relationship.
2. Shut up and take it.
3. Find a new job
4. File a law suit.
I would consider
#4 your last resort. There is no law that says he can't micromanage your work, or have the personality of a potato. Consider this off the table unless, he egregiously shorts your pay, breaks a labor law or, chases you around the desk. Even then it's not likely you will win unless it's documented and/or there are others. If you do file a complaint of any kind, everyone in town, in the business will know and
you may become the pariah and limit other job opportunities. Think long and carefully before you go this route
#1 You own 50% of this relationship. If he is F-ing around and you do it too, that's a problem you encouraged. You'll need to be the adult here. Having a straight conversation about performance and expectations, on both sides, is a very hard conversation to have but it can clear the air and get things in order.
I have exceptions from my boss. Be a BS filter and let me focus on what I need to do. Be as transparent and honest as they can with my performance. If I didn't do it and it needs to get done - Tell me. Be a mentor - They don't need to be an expert for everything I do, but if I run into a wall and I go to them, help me figure it out. Maybe there is someone else that has done that.
From that conversation you may decide that what he expects isn't something that you can or are willing to do. It's better to part on good terms know it wasn't the right job. Or he may tell you I really need you to work late on Tuesdays cause my kid has ball game. Do that and he appreciate that.
#2 & #3 are sort of the same - deflection, which is fine. Either way the issue is resolved and you will have a job. You may like it or you many not? You could jump ship and find the new boss is even worse.
Do your homework and good luck!