Contradicting the youth-obsessed narrative of entrepreneurship, Henry Singleton founded his wildly successful conglomerate Teledyne at 43 years old, after a career in engineering and management. He had never founded a company before.

Henry Singleton viewed aggressive share repurchases as a superior investment to acquisitions or internal projects when Teledyne's stock was cheap. He controversially bought back 90% of the company's shares, generating a 42% compound annual return on the tenders.

Unlike most CEOs who focus on day-to-day operations, Singleton delegated operational control to focus almost exclusively on deploying the company's cash. Warren Buffett noted this skill is rare but critical for long-term success, as most executives rise through operational roles.

Henry Singleton avoided detailed strategic plans, believing the future is unpredictable. He preferred to "steer the boat each day," retaining maximum flexibility to react to market conditions, such as his abrupt halt to acquisitions when prices rose.

Conglomerates like Litton Industries relied on their high stock price as currency for acquisitions. When the market turned and their stock fell, they could no longer afford to buy growth. This revealed a lack of true operational excellence, causing a vicious cycle of stock price collapse and multiple compression.

To prioritize cash generation over reported earnings, Henry Singleton created the "Teledyne Return" (cash flow + net income / 2). This metric formed the basis for manager bonuses, preventing them from boosting paper profits at the expense of actual cash.

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.

Henry Singleton's core belief was that a CEO's job is to increase per-share value, not just grow revenue or headcount. This principle guided all his major capital allocation decisions, from acquisitions to aggressive share buybacks and avoiding dividends.

Corporate leaders are incentivized and wired to pursue growth through acquisition, constantly getting bigger. However, they consistently fail at the strategically crucial, but less glamorous, task of divesting assets at the right time, often holding on until value has significantly eroded.