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