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Science

The Frequent Winner Effect: Why Your Investment Choices Are Backwards

Edmund Ayitey
Last updated: September 21, 2025 2:54 am
Edmund Ayitey
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Investors systematically choose stocks that win more often, even when those frequent victories lead to lower overall returns.

New research from the University of Basel reveals that people prefer investments generating daily modest gains over those offering occasional massive payouts, fundamentally contradicting traditional financial wisdom about risk and reward.

The study tracked participants as they selected between different stock profiles, discovering what researchers call the “frequent winner effect.”

Test subjects consistently favored securities that produced positive returns on the greatest number of days, regardless of whether the cumulative gains were actually smaller than alternative investments.

This behavioral pattern explains a puzzling market phenomenon: why catastrophe bonds—which pay small, regular dividends until a natural disaster wipes out the entire investment—often attract more capital than IPO shares that occasionally skyrocket.

The frequency of winning matters more to human psychology than the magnitude of those wins.

The implications extend far beyond individual portfolios.

Government pension systems, institutional investors, and financial advisors who understand this psychological bias can better predict market movements and structure investment products that align with how people actually make decisions.

The IPO Paradox That Stumped Economists

Initial public offerings present a classic investment puzzle that has confused financial experts for decades. IPO shares typically underperform the market for years after going public, yet retail investors continue flocking to these high-risk securities.

Statistical analysis shows that most newly public companies deliver below-average returns during their first several years of trading.

Only a handful of exceptional performers—think Facebook, Google, or Tesla—generate the massive gains that capture headlines and investor imagination.

Why do rational people keep buying these statistically poor investments? The answer lies in prospect theory, which explains how humans consistently overestimate the probability of rare, high-impact events while underestimating more likely but mundane outcomes.

This same psychological quirk drives lottery ticket sales. Players understand the astronomical odds against winning yet purchase tickets because they inflate their chances of hitting the jackpot.

The possibility of life-changing wealth overwhelms mathematical probability in human decision-making.

Traditional financial models assume investors evaluate expected returns rationally. But real-world behavior suggests something entirely different drives investment choices—something the Basel research finally identified and quantified.

The Cat Bond Alternative Nobody Talks About

While investors chase IPO moonshots, a completely different investment category offers steady returns with an unusual risk profile. Catastrophe bonds, or “cat bonds,” flip the traditional risk-reward equation entirely.

Insurance companies issue these securities to create financial buffers for natural disasters. Investors receive regular, predictable payments as long as no major catastrophe strikes the insured region.

If an earthquake, hurricane, or wildfire meets predetermined severity thresholds, investors lose their entire principal.

Cat bonds represent the polar opposite of IPO investing: high probability of small gains with rare but total losses. Yet many institutional investors prefer this predictable income stream over the volatile uncertainty of newly public companies.

The psychology behind cat bond preferences reveals something profound about human risk tolerance. People feel more comfortable with known, quantifiable dangers than unpredictable opportunities for extraordinary success.

This preference structure challenges fundamental assumptions in finance textbooks. If investors truly sought maximum returns, cat bonds would remain a niche product while IPO fever would dominate every portfolio.

But Here’s What Traditional Finance Gets Wrong

Most investment advice assumes people evaluate options in isolation, comparing each stock’s risk-return profile independently. This assumption fails spectacularly when investors can directly compare multiple alternatives side by side.

The Basel experiment demonstrated this by presenting participants with detailed day-by-day performance data for different investment types.

Instead of calculating expected returns or analyzing risk metrics, test subjects simply counted which stocks produced positive results most frequently.

This pattern interrupt reveals a crucial flaw in classical financial theory. Academic models predict that rational investors should prefer higher expected returns despite greater volatility. Real human behavior shows the opposite: consistency trumps profitability in actual decision-making.

When participants could examine daily performance records, they overwhelmingly selected investments that won more often, even when those frequent victories generated smaller total returns.

The psychological satisfaction of regular success outweighed the mathematical advantage of larger but less frequent gains.

This finding challenges decades of financial planning advice that emphasizes long-term thinking and patience with volatile high-growth investments.

If people inherently prefer frequent winners, investment strategies must account for this bias rather than fight against it.

The Laboratory That Changed Investment Psychology

Dr. Sebastian Olschewski’s experimental design revealed the mechanics behind investor decision-making with unprecedented clarity.

Participants faced choices between stocks offering “low probability of high returns” versus “high probability of modest returns with rare but potentially high losses.”

The key innovation involved providing complete historical performance data. Test subjects could examine exactly when each investment generated returns—day 1, day 2, day 3, and so forth.

This transparency eliminated guesswork and forced participants to confront the actual frequency of winning versus losing.

Results demolished conventional wisdom about investor behavior. Participants selected stocks that generated the highest returns on the greatest number of days, with overall return totals having minimal influence on their choices.

To confirm this frequent winner effect, researchers manipulated the data in a second experimental phase. They modified performance histories so that previously unattractive “lottery-like” investments appeared to win more frequently.

Participants immediately shifted their preferences toward these same investments they had previously rejected.

This manipulation proved that winning frequency, not winning magnitude, drives investment psychology. The same securities became desirable or undesirable based solely on how often they produced positive results.

Why Your Brain Sabotages Long-Term Wealth

Human cognitive architecture evolved for immediate survival, not long-term financial optimization. The frequent winner effect represents an ancient psychological mechanism that served our ancestors well but undermines modern investment success.

Early humans who consistently found small amounts of food survived better than those who occasionally discovered massive but unpredictable windfalls. This evolutionary bias toward frequent small rewards persists in contemporary financial decision-making.

Modern markets reward patience and tolerance for volatility. The greatest wealth accumulation typically comes from holding growth investments through multiple boom-bust cycles. Yet our brains remain wired to prefer the psychological comfort of regular positive feedback.

This creates a fundamental mismatch between optimal investment strategy and intuitive human preferences. Investors who follow their instincts end up with portfolios that feel satisfying day-to-day but underperform over decades.

Understanding this bias doesn’t eliminate it, but awareness creates opportunities for better decision-making.

Successful long-term investors either structure their portfolios to provide frequent small wins or develop mental frameworks that override their psychological preferences.

The Pension Crisis Nobody Saw Coming

The frequent winner effect has massive implications for retirement security across developed nations.

Government pension systems and individual 401(k) plans consistently underperform because they cater to human preferences rather than mathematical optimization.

Swiss pension investments, like many national systems, allocate significant capital to low-volatility bonds and conservative equity funds.

These investments provide steady income streams that satisfy political and psychological demands for predictable returns. But this preference for frequent winners may be sabotaging long-term retirement security.

Target-date funds and balanced portfolios designed to minimize day-to-day volatility often sacrifice decades of compound growth. The psychological comfort of avoiding negative months comes at the expense of adequate retirement savings.

Financial advisors face an impossible dilemma. They can recommend mathematically optimal high-growth strategies that clients will abandon during inevitable downturns, or suggest psychologically comfortable conservative approaches that likely won’t fund decent retirements.

The frequent winner effect explains why so many Americans are unprepared for retirement despite decades of systematic saving.

Market Predictions Just Got More Accurate

Professional investors and economists can now incorporate the frequent winner effect into their market forecasting models.

Traditional analysis focused on fundamental valuations, technical indicators, and macroeconomic trends while ignoring the psychological factors driving actual investment flows.

Understanding how retail investors seek and interpret information enables better predictions of stock price movements. Securities that provide frequent positive feedback will attract disproportionate capital regardless of their fundamental merit.

This insight explains several market anomalies that have puzzled financial economists. High-dividend stocks often trade at premiums despite offering lower total returns than growth alternatives. The monthly dividend payments provide psychological satisfaction that justifies paying higher prices.

Similarly, bonds with regular coupon payments attract more investor interest than zero-coupon bonds offering identical yields through capital appreciation. The frequency of positive cash flows matters more than the mathematical equivalence of returns.

Gaming Your Own Psychology for Better Returns

Individual investors can exploit their own psychological biases to improve long-term outcomes. The key involves creating artificial frequent winners within portfolios optimized for maximum growth.

One strategy involves dividend-focused investments that provide monthly or quarterly income streams. These regular payments satisfy the psychological need for frequent wins while still participating in long-term market appreciation.

Dollar-cost averaging serves a similar psychological function by creating regular “wins” through systematic purchasing. Even during market downturns, investors can celebrate acquiring more shares for the same dollar amount.

Rebalancing portfolios quarterly provides another source of frequent psychological victories. The process of selling high-performing assets and buying undervalued alternatives creates a sense of active success even when overall returns may be temporarily negative.

These strategies acknowledge that optimal investment behavior requires working with human psychology rather than against it. Pure mathematical optimization fails because most people can’t maintain discipline through inevitable periods of poor performance.

The Future of Investment Design

Financial product development will increasingly incorporate psychological insights about investor behavior.

Investment platforms and advisors who understand the frequent winner effect can design products that align mathematical optimization with human preferences.

Structured products that provide regular small payouts while maintaining long-term growth exposure will likely gain popularity. These hybrid investments satisfy the psychological need for frequent wins without sacrificing return potential.

Gamification elements in investment apps already exploit similar psychological principles. Features like daily portfolio updates, achievement badges, and progress tracking provide the frequent positive feedback that keeps investors engaged with long-term strategies.

The research suggests that successful investment management requires as much understanding of human psychology as financial mathematics.

Products and strategies that ignore how people actually make decisions will continue underperforming regardless of their theoretical merit.

The frequent winner effect represents just one piece of a larger puzzle about human decision-making under uncertainty.

As behavioral finance continues evolving, expect investment approaches that work with human nature rather than against it to dominate the industry.


References:

  • University of Basel Psychology Research
  • PNAS Journal Publication
  • Neuroscience News Coverage
  • Behavioral Finance Studies
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