Glenn Kelman thought of himself as a software guy. Then he became CEO of a real estate company called Redfin, but insisted on seeing it as a software company. Confusion reigned. Cultures clashed. For Glenn, it would come to highlight an often-unspoken business challenge: Entrepreneurship means exploring unknown paths, sometimes leading entrepreneurs to a very different place from where they started. The result can challenge not just their business philosophies but their very sense of identity.
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