Lease to someone else that already has a business or is experienced in starting a certain type of business. Don’t risk your profit starting a business you have no passion for or experience with.

Try to avoid the anchoring bias of his current pay rate. If you had to replace him and wanted someone of similar skill, how much would have to pay? Offer him that with an explanation, he’s right, wages have gone up lately and the current market rate for his role/skills is $X. You could always back it up with something from Glassdoor on average salaries for job title. Also, don’t forget to tell him you really appreciate the work he’s doing and keep up the good work (with a smile) :)

1. Turn it into passive income - Hire people to take over any tasks possible in the business. Maybe you get a few part time dog walkers to start and if any of them show the competence and work ethic, teach them to manage more of the business. Be the owners of that business, not an employee.

2. Discuss selling the business if no one wants to do the work. I don’t know enough about the dog walking business to know if you could sell the business? (try googling on this topic if interested). Ex. bookkeeping businesses can sell at around 1x annual revenue. Its good to show as much profit and growth as possible for 1-2 years before trying to sell as this greatly increases the value.

3. Get away from the business, devices as much as possible, etc, for a few days and just think about what brings you joy and explore ways to do more of those things. (within some context of earning money lol)

I don’t think there is anything that would make you avoid the deal entirely but you might want to be even more thorough with due dilligence.

It sounds like there are probably some very key dependencies. Him being fully remote + his paranoia + age of employees tells us this. I’d try to get him to tell you who those people are (after deal closes) and also get on site and try to make your own evaluation of who those people are asap after close. Then bribe them with a retention bonus or some reason to stay (Ex. if you are still here in a year i’ll give a $5000 bonus). Assure them you value them and sell them on a vision of the future.

Definitely try to define your goals and align with your other stakeholders as much as possible.

Are you trying to grow as much as possible?

Are you shifting out of growth mode and trying to maximize profitability?

Are you maximizing profitability maybe to sell the business for one big payday in the next few years.

Are you trying to reduce your time required in the business to focus on other ventures by making key hires, getting good standardized processes, etc?

What do you want out of life personally?

Tough questions I know. Start journaling and make notes of things that make you happy or get you excited about the future. Likewise, make notes of things that make you miserable or indifferent today or in the future.

Good luck!