The day after Barack Obama won his second presidential term, @FakeDorsey, a satirical Twitter account mocking serial entrepreneur Jack Dorsey’s precious worldview, tweeted, “Pretty incredible to think we made any progress at all in this world before we had twitter, and @anildash telling us all what we should do.”
As the adage goes, it’s funny because it’s (partly!) true.
While Karl Rove demanded a recount on cable news, Twitter offered up real-time polling data. And Mr. Dash—the first employee of proto-blogging company Six Apart, who has been writing about how technology shapes culture since 1999—has also swayed public opinion on a number of knotty issues recently, from whether hosting a marathon after Hurricane Sandy was the best use of the New York City’s resources (nope), to how to close the gap in tech talent (train “blue collar coders” rather than just a “priesthood of highly-skilled experts”), to how startup investor Ashton Kutcher could avoid caking on brownface to sell potato chips (“Make some different decisions”).
His disarming combination of radical empathy and prescriptive real talk tends to humanize discussions about technology that are otherwise siloed in the startup world’s upbeat echo chamber. A sense of humor helps. “I’m sort of like Gandhi in that way,” Mr. Dash tweeted back, gently ribbing the real Mr. Dorsey’s celebrity crush.
But in a Quora question about his influence in Silicon Valley, Slacktory editor Nick Douglas compared Mr. Dash (once tapped by the White House to help federal agencies innovate) to a more contemporary leader, calling him “the Obama of tech”: “Someone trustworthy with important matters, who also has good shit on his iPhone. He can banter with curmudgeons without becoming one, and he can work with snobs without becoming one.”
Many of his blog posts on Dashes.com and his tweets to his 430,000 Twitter followers are about trying to “make sure that technology does the right thing,” Mr. Dash told Betabeat. “The tech world doesn’t acknowledge that there are values built into your apps and into software and its features.”
Mr. Dash takes the same tack at Activate, his strategy consulting firm, to help big media and tech companies to get with the digital program, urging them towards building app-like streams instead of antiquated web pages, for example. Although Mr. Dash and his co-founder Michael Wolf keep mum about clients they advise, Daniel Loeb—another insurgent on our list—named Mr. Wolf to Yahoo’s board not long before the company installed Marissa Mayer. Sources have also mentioned Activate’s work with Reuters.
“The people that are in these positions of power understand that my value is in telling them the truth. Right? That’s the trick to play, to tell people the truth and have them thank you for it instead of getting mad about it,” he said.