Yet in many ways, Uber now epitomizes many of the excesses Mr. Gurley has publicly condemned,
and Mr. Kalanick has said he is in no hurry to take Uber public.
In one post in 2015, as investors were pouring money into what became known as “unicorn” companies — venture-backed companies valued at more
than $1 billion — Mr. Gurley wrote, “We are in a risk bubble.” Last year, he wrote that there would be “inevitable failed unicorns.”
Among Mr. Gurley’s main concerns are Silicon Valley’s growing self-importance, which he has said is expertly captured in “Silicon Valley,” the HBO show
that lampoons the misadventures of several entrepreneurs who hope to strike it rich.
Mr. Gurley is “calling B. S.
on the relentless, blind confidence,” said Roger McNamee, a Silicon Valley investor, adding that it was “brave.”
That outspokenness has not meant Mr. Gurley is always right.
In one of three interviews last year, he said of his warnings for start-ups
that “I say these things because the longer bad behavior goes on, the worse things end up.”
Uber declined to comment on Mr. Kalanick’s relationship with Mr. Gurley.
