[brk]

The two entities are completely unrelated, except for having him as an employee of both.

If the first venture was truly a company, as in a corporation, then frankly any vendors/bills related to that can be left hanging without making him personally responsible. I know this isn't the "ideal" thing, but it happens frequently.

If he personally guaranteed any debt for that company, then that is is personal problem and has no bearing on your new company (which I hope for multiple reasons is being properly incorporated).

I don't see where it makes much sense to handicap the new venture to cover his personal issues, that is what is usually chalked up to "learning experience" and is, if anything, part of the value he brings to this new venture vs. a person with no experience. Or, to put it another way, if it were not for that experience he might have zero value in the current case, in which he would have the same debt obligations, but no potential income to cover them...