This story is a sequel to Somepony Tries to Sell Twilight Insurance
Ponies were very surprised when Jackpot Enterprises' managing director, Crystal Jackpot himself, started allowing Ponyville's richest residents to insure their properties with his company - not least because the last thing anypony ever expected was that Jackpot Enterprises would do something enterprising. However, they were even more surprised when a crippling blow was dealt the idea by none other than Princess Twilight Sparkle.
Not only did she not have her castle insured: she also urged every single one of her friends - her rich, powerful friends - not to take insurance out either. Nopony would suggest that Jackpot was a resentful stallion - nopony who didn't want to find himself homeless within the week, anyway - but it was, all the same, surprising for Twilight when just about everypony she knew took out insurance against, er, her.