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Personal Finance

Bill Gates reveals his greatest mistake — and says it cost him billions of dollars

Bill Gates has a multi-billion dollar regret that still haunts him.

“The greatest mistake ever is whatever mismanagement I engaged in that caused Microsoft not to be what Android is,” he told a conference over the weekend. Gates was speaking with Eventbrite co-founder and CEO Julia Hartz at an event hosted for founders by venture firm Village Global. “That was a natural thing for Microsoft to win,” Gates said.

Microsoft MSFT, -0.14% tried to create a mobile phone operating system to compete with Apple’s AAPL, -0.91% but by the time Windows Mobile launched with a touch-screen feature in 2010 it was no match for Android, the Google-owned GOOG, +0.46% GOOGL, +0.57% OS that runs on non-Apple phones. Microsoft ultimately ended its mobile OS. Gates said that market is worth $400 billion.

“It really is winner take all. If you’re there with half as many apps or 90% as many apps, you’re on your way to complete doom. There’s room for exactly one non-Apple operating system and what’s that worth?” he added. “If we had gotten that one right, we would be the leading company, but oh well.” Android has 75% of the mobile OS market; Apple’s iOS is at 22.7%; Windows has 0.24%.

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Gates isn’t alone in acknowledging his biggest mistakes. On Sunday, President Donald Trump said his biggest mistake as president was appointing Jeff Sessions as his first attorney general. “If you would have one do-over as president, what would it be?” NBC’s CMCSA, +0.67% Chuck Todd asked the president on “Meet the Press.” Sessions was replaced by Attorney General William Barr.

“I would say if I had one do-over, it would be, I would not have appointed Jeff Sessions to be attorney general. That would be my one,” Trump replied. Sessions recused himself from working on the investigation on Russia’s interference in the 2016 U.S. Presidential election. “That was the biggest mistake,” Trump said of his appointing Sessions.

Former Apple CEO Steve Jobs, who died of pancreatic cancer at age 56 in 2011, revealed to his biographer Walter Isaacson that his biggest regret was personal. Jobs said his biggest mistake was delaying chemotherapy and surgery for nine months after his diagnosis in favor of alternative medicine. Isaacson said Jobs had “magical thinking. It had worked for him in the past.”

Share of Microsoft are up 32% so far this year, compared to a 14% gain for the Dow Jones Industrial Average DJIA, +0.28% and a 17% increase for the S&P 500 Index SPX, +0.58% .

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