Based on Daniel Kahneman's Prospect Theory, once investors feel they are losing money, their behavior inverts. Instead of cutting losses, they adopt a "double or nothing" mentality, chasing high-risk gambles to escape the psychological pain of loss.
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In a rising market, the investors taking the most risk generate the highest returns, making them appear brilliant. However, this same aggression ensures they will be hurt the most when the market turns. This dynamic creates a powerful incentive to increase risk-taking, often just before a downturn.
Top investors experience an "asymmetry of emotion." The pleasure of significant gains is muted—a feeling of satisfaction rather than euphoria. However, the pain of losing capital, particularly during irrational market events, is disproportionately intense, driven by the responsibility of managing other people's money.
Post-mortems of bad investments reveal the cause is never a calculation error but always a psychological bias or emotional trap. Sequoia catalogs ~40 of these, including failing to separate the emotional 'thrill of the chase' from the clinical, objective assessment required for sound decision-making.
Molly observed that extremely wealthy players reacted to losses with disproportionate fear and anger, despite the amounts being trivial to their net worth. This reveals that for high-achievers, losing triggers a deep-seated fear of losing control, making it a powerful psychological threat, not just a financial one.
The primary driver of market fluctuations is the dramatic shift in attitudes toward risk. In good times, investors become risk-tolerant and chase gains ('Risk is my friend'). In bad times, risk aversion dominates ('Get me out at any price'). This emotional pendulum causes security prices to fluctuate far more than their underlying intrinsic values.
When facing economic ruin, humans don't become conservative. They enter a psychological 'lost domain' where they become risk-seeking, making high-stakes gambles like meme stocks or crypto in a desperate attempt to recover their losses in one move.
The common bias of loss aversion doesn't affect investors who have done exhaustive upfront work. Their conviction is based on a clear understanding of an asset's intrinsic value, allowing them to view price drops as opportunities rather than signals of a flawed decision.
Emotion drives poor financial decisions. Negreanu notes the biggest leak for most players is their session length. They'll play for hours trying to "get even" on a bad day (when they're likely tilted and playing poorly), but cash out after a small win on a good day (when conditions are favorable).
We focus on how to win, but failure is inevitable. How you react to loss determines long-term success. Losing money triggers irrational behavior—chasing losses or getting emotional—that derails any sound strategy. Mastering the emotional response to downswings is the real key.
People feeling financially trapped don't become more responsible. Instead, they enter a psychological "lost domain" where they re-evaluate risk and seek a single, high-stakes move to recover everything at once, often leading to a downward spiral.
