If he wants upside, consider paying him commissions for growing the business. This way he can make more money and you can benefit from the growth. He should be

If he wants upside, consider paying him commissions for growing the business. This way he can make more money and you can benefit from the growth. He should be happier with this than holding illiquid stock. Sometimes people just want to be able to tell their family that they are owners of the business. It seems like he already has an inflated title so he doesn’t have much else to ask for to show or feel progression in his career. It sounds like a role that would be attractive to many people.