There were at least a handful of storefronts he was running or involved with at the time, including a furniture/carpet company which had taken in a lot of investment money last summer. Tax records were public for all of these, and all but that new one were basically tanked with regard to solvency.
Just conjecture ... did you notice a pattern of creating artificial losses for accounting purposes for any of his father's clients, with the purpose of (for example only) reducing tax liabilities ?