He is very smart but had a difficult upbringing. I don't want to play armchair psychologist, but maybe this will help to understand it, or help in case others here find themselves in a similar situation and may want to consider treatment.
https://www.promisesbehavioralhealth.com/addiction-recovery-blog/stages-of-compulsive-gambling/
Here are some excerpts:
Action Compulsive Gambler Profile:
Generally male, the action compulsive gambler possesses an I.Q. over 120, is controlling, manipulative and domineering and has a big ego. He is also confident, assertive, energetic and very persuasive, yet with a low self-esteem.
... Games of choice are typically those of skill
...The numbing or narcotic-like effect ... acts as a kind of medication to the action compulsive gambler. But it doesn’t stop the progression of compulsive gambling.
... Gambling to cover pain – Since gambling is the only activity that makes the action compulsive gambler feel better – he thinks – he continues gambling in order to cover up the increasing pain that he feels.
Like I said before, I personally don't think John is a compulsive gambler, but he is complicated and shares many of the traits they describe. I think his best solution would be to never bet a single penny again. Ever. If somebody goads him into betting, he needs to say "I can't do that. It's hurt me and my life. I don't want to be ruined."
If that means quitting pool, so be it.
Yes, I've known many of these types in the pool room. Too many. It's unfortunate when someone can't play pool because they love the game.
First, let me say - John is a great casemaker...but I'm not sure about his "business" skills. And he has no business trying to play pool for money. At all.
He and Karen came through Richmond, VA in April of 2014. I ordered an Air Force themed custom case from him in person, gave him a 50% deposit, talked my friend who owned the pool room (Diamond Billiards in Midlothian) into buying some cases John was selling from his vehicle (because they ARE great cases), which he did, and John told me my case would be made in 8 weeks.
BTW - I have ALL of the FB messages saved, which I'm reviewing.
Fast forward to Jan 2016. It never happened. I was really disappointed. I told him, dude, I just want to pay you whatever you ask to make this case and I just get ignored. Super disappointing. So I unfriended him on FB and wrote it off.
If John put all of his tremendous FOCUS and ENERGY into strictly his business and customers he could be a millionaire. Quit the bs and trying to be Mr. Gambling Big Shot and start trying to be the best business man you can be and the sky is the limit. And I'LL STILL take that case and pay you the remainder for it if you ever want to complete it (6 years later). I still think your cases are the best.