The Tech Investments That Got Away: Buffett's Most Candid Confessions About Amazon and Google

When it comes to picking winners in the stock market, few names carry as much weight as Warren Buffett. Yet even the legendary investor from Omaha has been remarkably open about his greatest portfolio oversights. What makes these confessions particularly striking is that they don’t involve losses or failed bets—instead, they represent the phenomenal successes he watched from the sidelines without participating.

The Amazon Story: “I Blew It”

During Berkshire Hathaway’s 2018 shareholders meeting, Buffett delivered a particularly memorable admission about the e-commerce colossus. “I blew it,” he said flatly when the conversation turned to Amazon. For years, he had observed Jeff Bezos building his empire, watching the company’s explosive trajectory unfold, yet never pulled the trigger on an investment when prices remained accessible.

Buffett’s self-assessment was brutally honest: “Obviously, I should have bought it long ago. I admired it long ago, but I didn’t understand the power of the model. It’s one I missed big time.” The regret extended beyond simple profit-taking calculations. He recognized early that something transformative was happening, but psychological barriers held him back. “The problem is when I think something will be a miracle, I tend not to bet on it,” he explained, offering insight into his decision-making framework.

In perhaps his most candid moment, Buffett conceded, “I did not think Jeff Bezos could succeed on the scale he has” and “I was too dumb to realize” what Amazon would eventually become. This admission revealed a fundamental limitation in his analytical toolkit when confronting paradigm-shifting business models.

Google: Charlie Munger’s Shared Frustration

Amazon wasn’t alone in Buffett’s technology graveyard. His late business partner Charlie Munger felt equally stung about Google. “I feel like a horse’s ass for not identifying Google earlier,” Munger said with characteristic bluntness. “We screwed up.” Neither man could claim ignorance about the search engine’s potential. Both acknowledged making the wrong calculation by not acquiring shares when Google went public in 2004 at $85 per share.

The subsequent stock splits and market performance created generational wealth for those with the foresight to invest early. For Buffett and Munger, it remained the one that got away.

The Circle of Competence: Strategic Conservatism That Cost Billions

Understanding why these omissions occurred requires examining Buffett’s foundational investment philosophy. For decades, he maintained strict adherence to companies within his defined “circle of competence”—enterprises he could thoroughly understand and evaluate with confidence. Technology simply fell outside this boundary.

His preference ran toward tangible, predictable businesses: insurers, financial institutions, manufacturers of consumer staples, and utility providers. These generated steady earnings, possessed durable competitive advantages, and behaved according to understandable economic principles. Tech companies violated this framework. Their valuations seemed detached from immediate profitability, their competitive landscapes shifted rapidly, and predicting winners felt more like speculation than analysis.

This conservative philosophy proved remarkably effective for wealth accumulation. Berkshire avoided numerous technology sector disasters and maintained consistent returns through disciplined selectivity. Yet the strategy carried a significant cost: exclusion from the era’s most transformative wealth creation vehicles.

The companies Buffett pursued typically traded at reasonable valuations with predictable cash flows. Amazon and Google represented entirely different animal—high-growth enterprises trading at premiums justified by long-term potential rather than current earnings. Investing in them required faith in visionary business models, something that conflicted with Buffett’s preference for mathematical certainty.

Quantifying the Opportunity Cost

The financial magnitude of these decisions reaches almost incomprehensible levels. Amazon’s equity appreciated over 1,000% from 2008 onwards—a period when Berkshire maintained sufficient capital to participate meaningfully. Alphabet’s parent company delivered comparable returns to patient shareholders. A hypothetical $1 billion allocation to each company during their growth trajectories would have swollen to tens of billions in subsequent years.

These represent among the largest unrealized gains in investment history, numbers that dwarf many of Berkshire’s actual investment victories.

The Eventual Pivot Toward Technology

The sting of these regrets eventually catalyzed adaptation. In 2016, Berkshire initiated substantial purchases of Apple shares—a pivotal shift in positioning. Initially, Buffett delegated the decision to his investment managers, but he eventually embraced the thesis personally. Apple satisfied his classical criteria: dominant brand loyalty, recurring revenue mechanics, and fortress-like market position.

The Apple allocation became spectacularly successful, validating that Buffett retained capacity for strategic evolution when suitable opportunities aligned with his core investment principles. By 2019, Berkshire finally accumulated Amazon shares, though Buffett candidly acknowledged the purchase arrived far too late to capture the lion’s share of the company’s growth narrative.

The Underlying Lesson for Individual Investors

Buffett’s transparency about these misses carries profound implications beyond investment community gossip. The central insight isn’t that disciplined approaches deserve abandonment or that chasing momentum stocks produces superior returns. Rather, his experience illustrates how even exceptional investors encounter blind spots, make judgment errors, and occasionally misread their own frameworks’ applicability boundaries.

The circle of competence strategy generated extraordinary wealth across multiple decades and market cycles. The Amazon and Google oversights sting precisely because they were such outlier performers—yet they don’t invalidate the overall methodology that created Berkshire’s value. The real takeaway involves maintaining sufficient intellectual flexibility to reconsider assumptions while preserving investment discipline. Buffett ultimately proved capable of this calibration, first through his Apple pivot and later through his Amazon acquisition.

Where does Warren Buffett live remains perhaps less important than understanding how even titans of investing confront humbling reminders about market complexity, personal bias, and the perils of excessive rigidity in applying proven frameworks to fundamentally novel circumstances.