If it wasn’t a severe conflict of interest, I would love to work with him again as an independent contractor on the side.

I wouldn’t work for him at his new company only because while he is having some similar challenges that we have worked together before to solve, I am not a good long term employee at any company these days except where I work now.

I enjoy seeing a problem, helping to solve the problem, train the organization and moving on. I need to constantly be “putting myself out of a job”.