I usually give them a snide remark or two. Some get it, a few don't. Once an old guy was belittling me about using a colored ball after the round. A total stranger and a poor golfer - worse than my bogey golf. The guy was so out of touch that I didn't think he'd get my hint.
I understand the concept of Goodwill. My question is how did the intangible get generated
In your example, the Habs have been sold to various owners, most recently to back to Molson. Molson's purchase price probably was for more than could be allocated to specific assets (like cash accounts, receivables, fixed assets). The excess is booked to Goodwill. See, it was the sale's proceeds that gave rise to the asset.
In Rory's case, how did the intangible actually arise? This, apparently, was a corporation he set up himself to handle his various business activities. If this number is supposed to represent revenue to be generated in the future (supposing all goes well), it seems like improper revenue recognition.