Warren Buffett Reflects on His Biggest Investing Mistake

Warren Buffett has publicly acknowledged his biggest investment regrets were not buying Amazon and Google early — admitting at Berkshire’s 2018 meeting “I blew it” on Amazon and echoing Charlie Munger’s remorse over Google — decisions he attributes to a conscious avoidance of technology stocks outside his “circle of competence.” The missed opportunities are large in dollar terms (Amazon has rallied over 1,000% since 2008 and both names would have turned hypothetical $1 billion stakes into tens of billions), and they prompted Buffett to adjust his approach by backing Apple in 2016 and buying Amazon belatedly in 2019. For institutional investors the takeaway is pragmatic: a disciplined, value-oriented process can avoid losses but may forgo outsized gains in structural-growth winners, so governance should allow for principled flexibility when business models exhibit durable competitive advantages.

Analysis

At Berkshire Hathaway’s 2018 annual meeting Warren Buffett acknowledged that his biggest investing regrets were not buying Amazon during its rapid expansion (“I blew it”) and missing Google earlier, a sentiment echoed by Charlie Munger who said he felt like “a horse’s ass” for not identifying Google sooner. The article notes Amazon has rallied more than 1,000% since 2008 and that Google went public at $85 in 2004 (with subsequent splits), illustrating the scale of foregone gains and the hypothetical outcome that $1 billion stakes in each could have grown into tens of billions.

Buffett attributes these misses to a disciplined value approach confined to his “circle of competence,” which historically favored banks, insurers and consumer franchises over technology because of rapidly changing industry dynamics. That discipline avoided major losses but also caused Berkshire to forgo structural-growth winners; the piece highlights Buffett’s partial evolution through a large Apple position established in 2016 and a belated Amazon purchase in 2019.

The practical takeaway is that a strict value process can be materially costly in opportunity terms when enduring tech franchises emerge; the article recommends maintaining investment discipline while creating principled, criteria-based flexibility for companies that demonstrate durable competitive advantages, predictable economics and recurring revenue characteristics.

Key Decisions for Investors

• Reevaluate the firm’s circle-of-competence rules and create a limited, governed sleeve for high-quality technology franchises that demonstrate durable competitive advantages and recurring revenues, similar to Berkshire’s eventual Apple allocation
• Apply strict selection criteria—predictable economics, strong brand loyalty and long-term vision rather than chasing short-term hype—and size positions conservatively to capture upside without abandoning value discipline
• Implement formal review triggers and governance to permit principled exceptions to core strategy when a company evidences persistent scale and competitive moats, while documenting missed opportunities to refine process
• Resist reflexively chasing late-stage momentum; preserve the aspects of the value approach that avoided busts, but balance that preservation with measured exposure to structural-growth winners