Big things are happening on TV Tropes! New admins, new designs, fewer ads, mobile versions, beta testing opportunities, thematic discovery engine, fun trope tools and toys, and much more - Learn how to help here and discuss here.
Subverted: Bob loses some money in the stock market, but then earns some money on another investment.
Double Subverted: This is insufficient to break even, though.
As soon as Bob cashes the check, the stock market crashes, society and civilization collapse, and anarchy ensues, rendering paper money and liquid assets useless. Then he gets mugged.
Bob wins $5000 from a one-dollar lottery ticket. As soon as he gets his winnings, he buys 5000 more lottery tickets which proceed to win ... nothing.
Bob wins $50 on a lotto ticket, then starts strutting around wearing a monocle and top hat and attempts to buy a boat.
Zig Zagged: Bob wins the lottery, but loses money in the stock market because the company in which he invested the lion's share of the money has just gone down. Then his stocks recover, and he's rich again. This happens repeatedly.