Steve Ballmer's Missed Call: $1000 Investment Then Worth $289,000 To Apple Investors Today — Why Ex-Microsoft CEO Once Admitted 'Religious Transformation' Came Too Late

Former Microsoft Corporation MSFT CEO Steve Ballmer once admitted that his biggest regret as chief executive was not jumping into smartphones early—an oversight that allowed Apple Inc. AAPL and Samsung Electronics Co. SSNLF to dominate a market Microsoft was late to enter.

What Happened: In a 2014 interview with Charlie Rose, Ballmer acknowledged that Microsoft should have pivoted to hardware.

"I probably would have started doing hardware earlier so that we could have been more effective in the phone business," he said, adding, "We were the number one most profitable company in our business for a long time. Two guys have passed us and they both did it by making phones: Apple and Samsung."

Despite Microsoft's long-standing software-first approach, Ballmer admitted the shift to mobile should have been a "religious transformation" for the company.

"Bill Gates told Paul Allen when Paul first wanted to do hardware back in the 70s ‘we are software guys, ' so for us it was kind of a religious transformation," Ballmer stated.

Microsoft did eventually enter the hardware game with the Surface tablet and the acquisition of Nokia's phone business, but by then, Apple and Samsung had already built commanding leads.

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Why It's Important: In 2012, Forbes named Ballmer one of the “Five CEOs Who Should Have Already Been Fired,” reflecting growing criticism of his leadership during a transformative era for the tech industry.

Ballmer had taken the reins from Bill Gates in 2000, stepping into the role as Microsoft grappled with the challenges of a rapidly evolving digital landscape.

During Ballmer's tenure, Microsoft lagged behind emerging rivals like Google and Apple, both of which capitalized on major technological shifts in the 2000s.

One of the most consequential missed opportunities came in 2007, when Apple unveiled its first iPhone. Ballmer famously mocked the device, saying, "$500? Fully subsidized? With a plan? I said that is the most expensive phone in the world."

He also dismissed its lack of a physical keyboard, calling it "not a very good email machine."

That skepticism proved costly. The iPhone went on to define the modern smartphone era, while Microsoft's mobile strategy faltered.

For investors, the contrast is stark. A $1,000 investment in Microsoft stock on Jan. 13, 2000—the day Ballmer became CEO—would have been worth only about $915 by the time he stepped down. Today, however, that same investment would be valued at approximately $13,685.

Meanwhile, had an investor chosen Apple stock on the same day, their $1,000 would now be worth over $289,000, underscoring just how much Ballmer's misstep in mobile ultimately benefited Microsoft's fiercest competitor.

Microsoft currently holds the title of the world’s most valuable company with a market capitalization of $3.36 trillion, while Apple ranks third at $3.17 trillion.

Benzinga Edge Stock Rankings assigns Microsoft a robust growth score of 65.56%. Click here to see how it stacks up against other top companies like Apple, Samsung and Google.

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