in lieu of another job that pays $1 more and buys lunch. This makes me feel like ****. I think his decision also had to do with me not keeping him busy everyday the last couple of months. He likes fast paced work and everyday work. Last year was our best year, due in large part to him, but I quickly realized that I would need to re-organize some things in order to not repeat some the same issues we had last year. 1. Need scheduling & billing software 2. Need a dedicated office & shop - CHECK 3. Need to hire somebody with driver's license to drive (he doesn't have DL) - IN THE WORKS 4. Need to focus more on commercial rather than residential. 5. Start Payroll He's been with me almost a year and I've never had a helper with his level of experience, work ethic, etc. I just don't like the ultimatum part about it because I really hate manipulative moves; "You pay me more or no mas". We've been really slow the last few months, and in the process of doing all the things above, I couldn't be driving around to every yard. I explained this to him, or at least attempted to. I've already decided that I'm gonna pay him in order to keep him, but I'm looking for suggestions on how to go about it. Should I make his raise contingent upon a few conditions that "I'll need him to become" in the future? Also, I've been paying him cash... I told him last summer that eventually I'd need to pay him a check, but with it being our best year I was stretched thin and didn't get around to payroll. Finally, how do I go about hiring a second guy to drive and still wanting my main guy to be crew lead, even though he doesn't have a license? Is it plausible to require a new guy to have something that his crew leader ?doesn't have?