"Buy High, Sell Low" is an expression which usually signals massive losses. It can mostly be found in Reddit's well-known /r/wallstreetbets and other like-minded online forums.
Despite being commonly posted as such by users there, the complete saying is actually "Buy High, Sell Low, Repeat until Broke".
The sentence serves as one of the forum's mottos precisely because it is right in tune with /r/wallstreetbets self-deprecating running jokes about their users being poorly-educated investors and, of course, because it is the exact opposite of the well-known saying "buy low, sell high".
Its use has now been widespread as there are countless posts and threads entitled "Buy high, sell low" spanning across many different stocks and crypto related subreddits.
These posts are almost guaranteed to be accompanied by a screenshot of the user's massive losses. When investors lose large amounts of money on a trade and - as if to brag about it - post it, they are met with joy by other users, as they often reply with the encouraging expression: "This is the way".
Sometimes they even welcome the original poster into the community. Users cheer these investors on by saying "One of us! One of us!" and other expressions which serve as positive reinforcement. These losses are seen as first-hand experience of the forum's humor and make investors earn the right to become part of the subreddit.
A variation of the original saying has surfaced as Gamestop (GME) investors have continued their efforts to buy and hold the company stock. Reddit users have even created what they call an "infinity pool", meaning GME shares that they will never sell any under circumstance.
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