The second week of October in 2008 was one of the most painful and emotional times of my career. We ushered 50 Zillow employees into an off-site conference room. I was COO then, and we were about to lay them off -- one-quarter of our staff. The Great Recession had hit, and the management team was following our gut and also the advice of our investors at Benchmark Capital and TCV: cut early and cut deep. Extend the runway. Conserve cash. Survive. I knew we had to make a hard decision to ensure Zillow would continue to thrive.

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