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Shorting bubbles often fails due to timing issues, even when the underlying thesis is correct, as shown by Overstock.com's 2017 blockchain pivot.
- Famous short sellers like Robert Wilson and Jim Chanos have admitted to barely breaking even on their short positions over their careers.
- During Overstock's 2017 blockchain pivot, shorting at $20 would have required covering a $78 margin call when the stock hit $60, potentially wiping out investors.
- An alternative to shorting bubbles is the mercenary approach: riding multiple liquid bubble positions while diversifying to avoid simultaneous collapses.
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