Gaonkar identifies her biggest error with NVIDIA wasn't selling too early, but failing to re-evaluate and buy back in later. The psychological pain of "sunk cost bias" makes it incredibly difficult to re-enter a position at a higher price, even when the fundamental thesis has improved.

Contrary to the instinct to sell a big winner, top fund managers often hold onto their best-performing companies. The initial 10x return is a strong signal of a best-in-class product, team, and market, indicating potential for continued exponential growth rather than a peak.

Unlike most AI opportunities locked in private markets, NVIDIA was a liquid, $420B public company when ChatGPT launched. This allowed retail investors to easily invest significant capital and realize a 10x return, a scale of accessible growth typically reserved for venture capitalists.

Since it's impossible to know upfront which investments will generate outlier returns, the key isn't picking them but holding them. The biggest mistake is 'cutting your flowers to water your weeds'—selling winners to invest in underperformers. You must 'circle the wagons' around your core assets.

Big Tech's sustained outperformance presents a portfolio anomaly. These companies are simultaneously the largest market components and among the fastest-growing, a rare combination that breaks historical patterns where size implies maturity and slower growth, forcing managers to adapt.

The asymmetrical nature of stock returns, driven by power laws, means a handful of massive winners can more than compensate for numerous losers, even if half your investments fail. This is due to convex compounding, where upside is unlimited but downside is capped at 100%.

The S&P 500's high concentration in 10 stocks is historically rare, seen only during the 'Nifty Fifty' and dot-com bubbles. In both prior cases, investors who bought at the peak waited 15 years to break even, highlighting the significant 'dead capital' risk in today's market.

Holding a winning stock is psychologically brutal. NVIDIA, one of the best performers ever, lost over 80% of its value in 2008 and 60% in 2022. Enduring these gut-wrenching drops, which are a normal part of the journey, is the price of admission for capturing life-changing gains.

The dot-com bubble didn't create wealth in 1999; it destroyed it. Generational wealth came from buying and holding survivors like Amazon *after* its stock had fallen 95%. The winning strategy isn't timing the crash, but surviving it and holding quality assets through the long recovery.