Pilecki argues that classic value investing fails by ignoring momentum. He waits for a stock's chart to form a base before buying and lets winners run past initial price targets if momentum is strong. This avoids buying "falling knives" and cutting winners short.

Marks frames contrarian investing not as simple opposition, but as using the market's excessive force (optimism or pessimism) against itself. This mental model involves letting the market's momentum create opportunities, like selling into euphoric buying, rather than just betting against the crowd.

Market-cap-weighted indexes create a perverse momentum loop. As a stock's price rises, its weight in the index increases, forcing new passive capital to buy more of it at inflated prices. This mechanism is the structural opposite of a value-oriented 'buy low, sell high' discipline.

The sign of a working diversification strategy is having something in your portfolio that you're unhappy with. Chasing winners by selling the laggard is a common mistake that leads to buying high and selling low. The discomfort of holding an underperformer is proof the strategy is functioning as intended, not that it's failing.

Wilson advised against trying to perfectly time the peak of a successful company's dominance. Competition will eventually emerge, but anticipating its impact is futile and often leads to premature selling. He believed you can make a fortune by riding a winner for years before the problems become acute.

To combat endowment effect and status quo bias, legendary trader Paul Tudor Jones advises viewing every position as if you were deciding to put it on today. This creates a zero-based mindset, forcing you to justify each holding's continued place in your portfolio.

Rather than passively holding a stock, the "buy and optimize" strategy involves actively managing its weighting in a portfolio. As a stock becomes more expensive relative to its intrinsic value, the position is trimmed, and when it gets cheaper, it is increased, creating an additional layer of return.

The effort to consistently make small, correct short-term trades is immense and error-prone. A better strategy is focusing on finding a few exceptional businesses that compound value at high rates for years, effectively doing the hard work on your behalf.

McCullough advocates for a "promiscuous" investment strategy, quickly moving capital to where signals are strongest. He argues that emotional attachment to winning positions, or "bag holding," is the primary way investors lose ground. The goal is to compound returns by avoiding drawdowns, not by marrying a single investment thesis.