Tim Cook’s departure as Apple CEO allows us to revisit an old question concerning the greatest investor of all time—Warren Buffett—and investment timing. Even the greats make mistakes; even the greats, if they could go back in time, would make different choices. The greats, however, unlike us small investors who close profitable investments too early, never regret them.

Warren Buffett earned more than $100 billion—subject to tax—from his position in Apple, yet in an interview a few months ago, he confirmed what we all suspected: he sold too early. Although… he does not regret it.

Warren Buffett, Tim Cook, Apple and timing

It sounds like the beginning of a joke, but it is not. On the contrary: hundreds of billions are at stake, along with perhaps the most profitable investment ever made by the greatest investor… ever.

Warren Buffett is a long-standing investor in Apple. He held enormous positions for almost the entire period when Tim Cook was at the company’s helm and earned more than $100 billion from the transaction, by his own admission.

So what is wrong? We can see it, if we wish, from this chart. Warren Buffett sold more than 65% of his entire Apple position over the course of one year. It was 2024; the stock fluctuated between $185 and $255 around Christmas, while today it is worth $325, with the company having repeatedly topped the ranking of the world’s most highly capitalized companies.

I got out too early.

I got out too early.

This admission by Warren Buffett went around the world last March, when the Oracle of Omaha revealed this feeling during an interview with CNBC.

Do you regret it? No

Everyone focuses on the first part of the exchange between Warren Buffett and Becky Quick. When asked whether he regretted it, WB replied:

No, no.

No, no.

He then explained that the investment had nevertheless earned him more than $100 billion, subject to tax. This is an attitude that perhaps we, as retail investors who want too much and hold on to nothing, should try to adopt. We may feel slightly annoyed about exiting a market too early or entering at a less-than-optimal time, but at the end of the day, the numbers always matter.

And—to put it much more crudely than Warren Buffett did—no one has ever gone broke taking profits.

Apple is still Berkshire Hathaway’s largest holding

It is worth remembering that Apple, despite the sell-off, is still the company with the greatest investment value in Berkshire Hathaway’s portfolio. As of the latest 13F filing, dated June 30, 2026, the investment was worth approximately $228 million, with the number of shares unchanged from the beginning of the year. After the 2024 sell-off, Buffett stayed put.

The reason? He explained it in the same interview:

I don’t have the power to predict what stocks will do next week or next month, and I will buy them again [Apple shares, editor’s note] if the price is low. I’ll buy a lot of them if they’re cheap and I believe I understand their business. Apple is still our largest investment.

I don’t have the power to predict what stocks will do next week or next month, and I will buy them again [Apple shares, editor’s note] if the price is low. I’ll buy a lot of them if they’re cheap and I believe I understand their business. Apple is still our largest investment.