The modern M&A and advisory business exploded in the 1980s due to a confluence of factors, critically including a rule change that legalized stock buybacks. This, along with deregulation and a new focus on shareholder value, created immense demand for transaction-focused bankers to help companies manage their balance sheets.

Once a clear buy signal for investors, large-scale share repurchases now often indicate that a company with a legacy moat has no better use for its cash. This can be a red flag that its core business is being disrupted by new technology, as seen with cable networks and department stores.

Since the 1990s, U.S. companies have returned more capital through stock buybacks than dividends. An investor focused solely on dividend yield is missing the larger part of the shareholder return story and cannot accurately assess a company's total capital allocation strategy.

Most buybacks fail, but Applovin's was a huge success. Instead of buying shares on the open market, they identified large, known sellers on their private cap table who needed liquidity. They used their capital to directly absorb this selling pressure, stabilizing the stock for new, long-term investors.

During a market crash, Henry Singleton stopped acquiring companies and did the opposite: he used cash to buy back 90% of Teledyne's stock. While Wall Street saw this as failure, it was a rational trade—repurchasing his own company's earnings at a low multiple—which caused earnings per share to explode.

Despite S&P 500 companies spending over a trillion dollars on share repurchases, the aggregate share count has not meaningfully decreased in 25 years. These buybacks primarily serve to counteract the massive stock dilution from executive compensation, creating an illusion of shareholder return while enriching insiders and levitating stock prices.

Companies termed "share cannibals" aggressively repurchase their own shares, especially when undervalued. This capital allocation strategy is often superior to dividends because it transfers value from sellers to long-term shareholders and acts as a high-return, low-risk investment in the company's own business.

Profitable, self-funded public companies that consistently use surplus cash for share repurchases are effectively executing a slow-motion management buyout. This process systematically increases the ownership percentage for the remaining long-term shareholders who, alongside management, will eventually "own the whole company."

Fairfax executed a brilliant capital allocation move by selling a 10% stake in its subsidiary, Odyssey, to pension funds for 1.7 times its book value. They then used the billion-dollar proceeds to buy back their own undervalued parent company stock, which was trading at a discount of 0.9x book value.