In early October Andrew Rasiej, chairman of the New York Tech Meetup, and Kevin Ryan, chairman of Gilt Groupe, organized an off-the-record meet-and-greet for Democratic mayoral candidate Bill De Blasio and 70 to 80 members of New York City’s tech community. By a couple of accounts, it wasn’t the most successful speed date. De Blasio, the Democratic front-runner, came off like an out-of-touch, old-school lefty; for example, he referenced the City University of New York as a cutting-edge educational resource (not, say, General Assembly, Hacker School, or Codecademy).

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Whatever happens, the relationship between one of the city’s economic powerhouses and the City of New York is about to get a lot more complicated “It’s really hard for a lot of people in technology to understand whether Bill might be a good mayor,” says Rasiej. Interviews with several members of the tech community suggest that whatever happens, the relationship between one of the city’s economic powerhouses and the City of New York is about to get a lot more complicated. The twelve-year reign of Michael Bloomberg coincided with the explosion of the New York City technology industry, which now boasts 262,000 workers contributing $30 billion in wages to the local economy. According to a Bloomberg report released in September, the tech and information sector is credited with New York reaching its highest share of the nation’s private employment in 20 years. Temperamentally, too, it was a match made in heaven between a billionaire tech and finance CEO-in-chief and the “Silicon Alley” investors and entrepreneurs who, during his reign, launched household-name companies like Etsy, Foursquare, Kickstarter, and more. “The community for the first time found their mayor in Bloomberg,” says Kane Sarhan, who as the founder of Enstitute works to place its apprentices with startups all over the city–from Warby Parker to Bit.ly. “[Bloomberg] launched all these great initiatives and made it a priority for the city to support this booming tech sector. The concern is that that could all go away. As a politician, you don’t hear Bill talking about our needs, our industry. He doesn’t have that track record or history of entrepreneurship.” The Fate Of Tech-Centric Programs Part of what the tech industry wants is programs and offices tailored to its needs and interests. “I think in general, we’re worried a little bit,” says Jon Oringer, founder and CEO of Shutterstock, a publicly traded company and one of New York City’s biggest technology outfits. “Tech should definitely be one of the main pillars of the campaign of whoever is planning on running the city, and we haven’t heard too much detail.”

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The list of tech industry initiatives pioneered by Mayor Bloomberg is long, from creating the position of Chief Digital Officer, to the Take the H.E.L.M. Grant and a series of open data hackathons across areas like education and sustainability. All of these initiatives have helped build relationships with the tech community. Christina Wallace, director of Startup Institute New York, asked DeBlasio at the New York Tech Meetup whether these programs would be continuing. “He wouldn’t give a solid answer,” she told me. “He admitted tech is an important part of the New York City economy (and indeed we are second only to finance at this point, and for every tech job created four non-tech ones follow as a result), yet he wants to roll responsibility for our sector into the portfolio of one of the deputy mayors. To me, this sounds like the end of the Chief Digital Officer role. As for whether Take the H.E.L.M. will see a third class of grantees, it’s anyone’s guess (I’m glad we applied this year).” A Tale of Two Issues: Airbnb vs Verizon Infrastructure, education, and the general business climate in New York City are top issues for Big Apple tech these days. Rasiej says that broadband provisioning in the city may be De Blasio’s best chance to prove himself to the tech community. Under its contract with the city, Verizon is supposed to provide New Yorkers with universal fiber optic Internet access by next summer, but De Blasio’s public advocate office released a report in April that shows less than half of the city currently has the hookup. “Broadband, I think, may become sort of the lightning rod issue to galvanize the tech community to understand why [De Blasio] deserves its support,” says Rasiej. On the other hand, DeBlasio has sided with the hotel unions against Airbnb, the “sharing economy” platform for short-term rentals, which is currently the target of a subpoena from the New York Attorney General, which is investigating violations of the city’s hotel and short-term rental laws. “That’s a turnoff when the local government is going after a company that my friends and I love,” says Sarhan. “That leaves a bad taste in your mouth.” Time to Give Back? Regardless of their business interests, most every New York techie I spoke with admitted they’d be voting Democratic when the time came–and that they support DeBlasio’s advocacy for public education and economic rights. In the end, the relationship between the new mayor and the technology industry may be exemplified by partnerships like P-TECH, the Pathways to Technology Early College High School. This is the public school in Crown Heights, Brooklyn that President Obama recently visited to highlight its six-year program that offers every student the chance to earn a technical associate’s degree for free. IBM provided the academic blueprint and mentors for the school, a format that is spreading across the city and state with other corporate partners including SAP. Stan Litow, President of the IBM Foundation, says P-TECH is connected vitally to IBM’s business interests.

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“No company is going to prosper unless it’s connected to what cities need,” he says. “If we can turn cities around and graduate a significantly larger number of students with marketable skills, that will benefit every company.” So far the tech industry has been looking at this issue from the perspective of, what can you do for us? So maybe New York City’s technology industry will come to meet De Blasio halfway if he’s elected. Rasiej highlights education as a major issue where entrepreneurs need to roll up their sleeves and get involved. “So far the tech industry has been looking at this issue from the perspective of, what can you do for us? If the NYC tech community wants to make New York the #1 place in the world for tech and entrepreneurship to thrive, what they should really be saying is: what can we do to help you?” Note: As of publication time, the DeBlasio office did not return calls for comment.