[7] At Benchmark, Gurley has led investments in and holds board seats on Brighter, DogVacay,[8] Good Eggs,[9] GrubHub, HackerOne,[10] Linden Lab, LiveOps, Nextdoor, OpenTable, Sailthru,[11] Scale Computing,[12] Stitch Fix,[13] Vessel,[14] and Zillow.

In a 2015 interview Gurley said of private tech investing, "It’s my belief that Silicon Valley and the venture-backed businesses have moved into a world that is both speculative and unsustainable.

[26][27][28] An advisor for Uber during allegations of misconduct and sexual harassment, Gurley was reportedly instrumental in the resignation of CEO Travis Kalanick.

[29] Gurley shared his support for Kalanick on Twitter, stating "There will be many pages in the history books devoted to @travisk - very few entrepreneurs have had such a lasting impact on the world.

"[30] In April 2020, The Wall Street Journal reported that Gurley would be stepping back from Benchmark as he was not investing in a new fund that his venture capital firm was raising.

[31][32] A fictionalized version of Gurley portrayed by actor Kyle Chandler appeared in the Showtime drama series Super Pumped.