After a lot of thinking about this, I made a second offer to buy Jack's LLC shares back from him again today. I won't say that Jack has "checked out" of the company, but my opinion is that his work is more suited for someone at a much larger company than ours, and I don't think that's a good attitude for a major shareholder to have.
I didn't put anything in writing, but I told him that since we weren't able to sell the company for anywhere near $2M, the company was clearly not worth that. I told him that I'd be glad to buy his shares back on the assumption the company was worth $1.4M, or $14,000 per share (where again, I use the term "share" to mean 1% of the LLC).
I told him that I wanted him to remain at the company, and told him I'd be glad if he kept 5% Class A ownership in the company. I didn't focus on the negatives I felt, but instead tried to frame everything in a positive manner, saying I wanted to offer the other partners more ownership in the company, that he seemed a little down from time to time, and maybe this would take some of the weight of his shoulders.
I haven't written about his "feeling down", but in my opinion, he is clearly not the same person I started working with all those years ago. The best way to say it is to say the he seems pessimistic to me, and I don't think that's a healthy trait in a partner. We all get down from time to time, but this seems to be an ongoing thing, and David and George have both asked me what's wrong with Jack. I've thought about talking to Jack's wife about this, and have tried to leave the door open in some conversations with her, but she hasn't volunteered anything, and I don't feel comfortable pressing her.
If Jack didn't think I was serious last time, he just plain didn't take this well this time. He didn't offer anything to me, didn't try to explain his behavior, and generally didn't want to discuss this at all, and just said he wasn't interested. He appeared pretty upset, and abruptly ended the meeting, saying he had another meeting coming up he needed to prepare for.
I have to say, I long for the days of our old relationship. I miss the Jack that brought positive energy to the table, that just assumed we were going to work late to get things done, and was all-around a great partner.