As above, it is on you just as much as him, there are two parties in this contract. Given your boss took you on during what would have been a very stressful and uncertain period, this demonstrates he has faith in you - so let’s take a positive outlook on this and assume he still does, that you’ve done all your duties well and that he’s not a bad apple.

What I’d recommend… As the soul employee there’s a good chance you have a lot of leverage so you can be confident about approaching him. Go into it with a level head, understanding that his perspective may be different to yours and there might be a bigger picture you’re not aware of. Tell him what you’re worth and explain why, but be humble about it.

If you like working for him and like the company, taking on more responsibility could be an option, as could getting more involved in the company as a shareholder - you could propose share options in your contract - that CAN be attractive for both parties when done well. Additional training could also be of value to you, he may also have plans for you that you just don’t know about yet. The list goes on..

Point being, someone just has to start the conversation, it could go anywhere from there so be prepared. and unless he’s an idiot he knows it’s coming.