How Nextdoor Became a Missed Opportunity for Benchmark’s Gurley

Nextdoor once looked like the next great bet for Bill Gurley, the prominent Benchmark venture capitalist known for early investments in Uber, Zillow and Stitch Fix. Now the neighborhood social network is looking like a missed opportunity for him.

Gurley urged Nextdoor co-founder Nirav Tolia not to sell the startup in 2018, when it was valued at $1.5 billion, according to people close to Tolia and Nextdoor. Google was among the potential companies with whom Nextdoor had discussed a sale, the people said, though it’s unclear whether an offer was made. The M&A debate played a role in Gurley spearheading Tolia’s ouster as chief executive that year, Tolia told people at the time.