As Redfin CEO Glenn Kelman found, this can be a thorny question— especially when you end up in an unexpected industry.
Glenn Kelman thought of himself as a software guy. He loves software. He cofounded a company called Plumtree Software. “When I applied for a passport or had to fill out my tax forms, I wrote down that I was a software entrepreneur,” he says.
So when he became CEO of a real estate startup called Redfin, he had a natural direction: “I wanted to solve every real estate problem with software.”
This would create a years-long crisis for the company. And for Kelman, it would come to highlight an often-unspoken business challenge: Entrepreneurship means exploring unknown paths, and sometimes that leads an entrepreneur somewhere different from where they started. The result can challenge not just their business philosophies but also their very sense of identity. A company’s future may end up riding on what happens next.
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