It's not clear to me why "closing of my conference and publishing businesses" results in medical expenses.

I'm not questioning it! I just don't understand the mechanics.

I think people are misreading the statement. The full statement is:

> Listen, I’m struggling with medical debts and financial obligations incurred by the closing of my conference and publishing businesses

People are reading it as

> Listen, I’m struggling with (medical debts and financial obligations) (incurred by the closing of my conference and publishing businesses)

but I suspect it was meant to be read as

> Listen, I’m struggling with (medical debts) and (financial obligations incurred by the closing of my conference and publishing businesses)

> Listen, I’m struggling with (medical debts) and (financial obligations incurred by the closing of my conference and publishing businesses)

If I were Automattic I would be deeply embarrassed if any of my employees were struggling with medical debts. That just shouldn't be a thing.

I thought it would be rude to speculate on details since it's speculating on a person's life and decisions. But when times are tight, independent contractors and sole proprietors might make the decision to temporarily cancel their own health insurance to save money, since premiums are considerably more expensive than the income tax penalty. This works for saving month-to-month income, at the cost of potentially enormous medical debt if you get sick or injured during this period.

I assumed the situation was something like that.

I think those are two separate issues. He's had medical issues and he needs to deal with the closing of his business.