Sometimes the doors that close turn out to be the lucky ones. Microsoft Corp. (MSFT) CEO Satya Nadella once had his sights set on cricket fields and banking offices in India, not corner offices in Redmond. But a few early rejections pushed him down a path that would eventually make him one of tech's most transformative leaders.

Middle-Class Roots and Intellectual Foundations

Nadella's story starts in a middle-class Indian household that valued education and intellectual curiosity. His father, Bukkapuram Nadella Yugandhar, worked for the Indian government, while his mother, Prabhavati, was a Sanskrit scholar. Not exactly the typical tech executive origin story.

During a 2023 conversation with LinkedIn CEO Ryan Roslansky, Nadella reflected on how his parents gave him space to explore his interests, even when they didn't see eye to eye on everything. His father's government job meant frequent moves, so Nadella bounced between schools across India before eventually settling at Hyderabad Public School. The constant relocation taught him early on how to adapt to new environments, a skill that would prove useful later.

Cricket Ambitions and the IIT Dream That Wasn't

As a teenager, Nadella's ambitions had nothing to do with software engineering. He wanted to play cricket for Hyderabad and imagined a career in banking. "I was mostly focused on playing cricket. I was not great academically, growing up middle class in India, that sort of sometimes is challenging," he told Roslansky.

His introduction to personal computers began shifting his thinking, but when it came time for college, he didn't secure admission to the Indian Institute of Technology. That mattered because IIT is basically the holy grail of engineering education in India. In a 2020 Reader's Digest interview, Nadella called it exactly that: "the holy grail" for middle-class students trying to climb the ladder.

Not getting into IIT isn't just about missing a good school. In India's competitive academic system, it can define your trajectory. But for Nadella, it opened a different door entirely.

From Manipal to Milwaukee and Beyond

Instead of IIT, Nadella studied electrical engineering at Manipal Institute of Technology. Then he made a leap that would change everything: he came to America for graduate school, landing at the University of Wisconsin–Milwaukee. He's joked that before arriving in the U.S. on his 21st birthday, he couldn't have found Milwaukee on a map.

The transition wasn't easy. New country, brutal weather, homesickness. But Nadella pushed through, starting his career at Sun Microsystems before joining Microsoft in 1992. He even squeezed in a part-time MBA at the University of Chicago while working full-time.

"But it wasn't that simple … Only in America would someone like me get the chance to prove himself rather than be typecast based on the school I attended," he told Reader's Digest. That quote gets at something important: in the U.S. tech industry, at least back then, what you could do mattered more than where your degree came from.

Turning Microsoft Around

Nadella became Microsoft's third CEO on February 4, 2014, replacing Steve Ballmer at a moment when the company was struggling. Apple Inc. (AAPL), Alphabet Inc. (GOOG) (GOOGL), and Amazon.com, Inc. (AMZN) were eating Microsoft's lunch in mobile, cloud, and consumer tech.

When Nadella took over, Microsoft shares were trading at an adjusted close of $30.16. Let's do some fun math: if you'd invested $1,000 at that day's high, you would have bought 33.1564 shares. Today, with Microsoft trading at $476.12, those shares would be worth $15,786.43. Not a bad return over a decade.

Microsoft now sits at a market cap of $3.54 trillion. That's trillion with a T. Under Nadella's leadership, the company shifted its focus to cloud computing with Azure, embraced open-source software after years of hostility, and positioned itself as a major player in artificial intelligence. The culture changed too. Out went the combative, competitive internal atmosphere of the Ballmer years. In came empathy, collaboration, and what Nadella calls a "growth mindset."

The Unlikely Path to the Top

Here's the thing about Nadella's story: it's not a tale of straight-line success. He didn't get into the best school. He didn't have connections in Silicon Valley. He showed up in Milwaukee in the dead of winter without even knowing where it was. But he kept moving forward, adapting, learning.

The cricket dreams faded. The banking plans never materialized. But the kid who couldn't crack IIT ended up running one of the world's most valuable companies. And he did it by landing somewhere that gave him room to prove what he could do, regardless of where he started.

That's the part of the story that matters most. Not every setback is actually a setback. Sometimes it's just a different route to somewhere better.