Most of his colleagues at Boston City Hall have probably packed up and gone home by the time Rory Cuddyer strolls in front of two dozen techies munching pizza and swigging free happy-hour beers at a Back Bay co-working office.
As the city’s new “startup czar,” Cuddyer has a job title that sounds a little grandiose. But it frequently means he is doing something pretty humble: taking his spiel to new audiences and asking for their help. It’s the sort of hat-in-hand marketing a lot of entrepreneurs would recognize.
“Right now, I’m a one-man band with no funding within City Hall,” Cuddyer says to knowing chuckles from the crowd. “I’m kind of like a startup.”
Cuddyer’s job is part of a broader effort by Mayor Martin J. Walsh, the city’s first new leader in a generation, to establish his administration’s high-tech bona fides. Walsh’s chief information officer, for example, once built key fund-raising software for President Obama’s campaigns. City Hall also has partnered with the fast-growing transportation tech services Uber and Waze to gather traffic data, and Walsh has taken a noticeably active role on social media.
The technology sector has been a key part of the region’s economy for decades, but in recent years, tech startups have also begun flexing their political muscle more directly. In 2012, a vigorous digital lobbying campaign from the startup sector stopped Uber from being shut down by state regulators. The following year, tech startups forced state lawmakers and the governor, Deval Patrick, to undo a multimillion-dollar tax on software services.
Some in the region’s startup scene, however, have been vocally disappointed in the “startup czar” program, pointing out that the 25-year-old Cuddyer, a former assistant to Walsh’s chief of staff, has no real experience working in the entrepreneurship world. That, critics say, forces Cuddyer to spend time finding out what startups need from City Hall rather than taking built-in knowledge to the mayor’s office for quick action.
“Rory needs to get some serious mentorship and a very intense crash course in the startup world,” said Apollo Sinkevicius, chief operating officer at the Boston office-technology startup Robin. “The mayor deserves to get advice from someone who truly gets what the startup world is all about: guts and glory, pain and joy, the ups and the downs.”
“To plop this person in and have them be the main liaison between the City of Boston and the startup community, and have that person have no experience or little experience in running companies or being a founder — or even in a tertiary way be connected to the startup scene beforehand — yeah, I am quite skeptical of that,” he said. “Does that mean I think he won’t be able to learn on the job? Absolutely not.”
Leaders in the startup sector also cite the need for Boston to market itself nationally as a top center of innovation. But hitting the road to raise the city’s profile with tech-industry leaders is not among the czar’s duties.
“My day-to-day is pretty Boston-based,” Cuddyer said. Broader travel, he added, is more the job of the city’s economic development chief, John Barros.
Cuddyer points out that his connections in City Hall should be a boon to startups that need help in navigating the arcane pathways of local government. For example, he recently helped a tech-industry charity group, TUGG, secure the permits it needed for its annual benefit. It may not sound sexy, but “that’s really the nittiest, grittiest thing you can do in City Hall,” Cuddyer said.
“Prior to this position, questions that people had were just going all over the place” in City Hall, he said.
Cuddyer is also quick to mention some broader issues the city is paying attention to, especially the affordable, short-term office space that fast-growing startups need.
But he acknowledges that getting to know the startup scene — and making sure startups know how to get a hold of him — is perhaps the biggest hurdle to overcome right now.
“The first challenge is making sure people understand this resource exists,” he said. “If people don’t understand that I’m here, the position itself is useless.”
Some of the complaints about appointing a junior staffer to this new job are probably tied to the fact that it’s called a “czar,” one of those lofty-sounding titles that don’t mean much in a practical sense.
There is also the question of how much city government actually can do to affect the trajectory of fast-moving young companies with ambitions that stretch far beyond city limits. A lot of the most significant policy issues — taxes, immigration, increasing tech-focused education — are mostly handled at the state and federal levels.
During Cuddyer’s Q&A session at the Oficio co-working space, one attendee grabbed his coat and walked out in a huff after grousing that he was already sick of hearing about small-bore issues like helping startups get permits.
Others at the meet-and-greet felt there was a reason to be optimistic. Michael Kelley, the founder of HireMeLocal, is building an online search service that lists local service providers like movers, handymen, and housecleaners.
Getting those small, old-school businesses online is often a hand-to-hand affair, Kelley said. If the mayor’s office could organize meetings with large groups of Boston-based small businesses, startups like his would be knocking down the door to attend.
“An introduction is a game-changer,” Kelley said. “And they can provide introductions on a mass scale.”