Metro, Business, Featured Story

How ‘Startup Czar’ Rory Cuddyer Plans To Shape The Future Of Boston Business

Ask Rory Cuddyer, BC ’11, what businesses he remembers from growing up in South Boston, and he’ll tell you about family trips to Filene’s Basement in Downtown Crossing. He now works in City Hall, a short walk from the Boston department store’s former home. Visit its Washington Street site, and you’ll see a neighborhood very much changed from the one Cuddyer first came to know a little over a decade ago on shopping trips with his mother and grandmother.

On the blocks surrounding the historic Filene’s property, you can see sure signs of the city’s changing economy. The eight-story building that once housed the Mass.-based retail giant is soon to be eclipsed by several high-rise luxury condos, and this September, the flagship store for Irish fashion brand Primark will be moving into Filene’s old storefront. These days, Downtown Crossing is referred to by many area realtors as “Midtown,” and the neighborhood is quickly populating with young professionals, with the old-fashion charm of its facades attracting several small tech firms.

For Cuddyer, the City of Boston’s recently named “Startup Czar,” the past decade has been a time of renewal for the city, characterized by the arrival of businesses like HubSpot and RunKeeper, as well as the loss of several others. The rebranded Boston Seaport, now referred to as the city’s Innovation District, is a 10-minute drive from his childhood home on Telegraph St. And an eight-minute drive from his secondary school, Boston College High, is the soon-to-be-opened Roxbury Innovation Center startup incubator in Dudley Square.

Fewer than four years out of college, Cuddyer is the prime point of contact for city startups working in these sites.

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“Over the past 10 years or so, Boston has changed dramatically,” Cuddyer said. “It’s now becoming a tech hub essentially. I think rightfully so, because of the talent we have for it and the infrastructure.”

In early March, Mayor Martin J. Walsh, WCAS ’09, named Cuddyer the leader of StartHub, a regional program geared toward attracting new businesses to Boston. He describes his as heavily involving conversations with small business owners and young professionals considering Boston as the city for their careers. Cuddyer’s work in City Hall is part of a broader Boston initiative to make City Hall friendlier to potential entrepreneurs, with points of contact created in Government Center to help them navigate the stream of paperwork required of founders.

The StartHub concept is also geared toward creating partnerships between the city government and the startup community to work on larger infrastructure projects.

Cuddyer graduated Boston College in 2011 with a degree in English and philosophy, and from there, worked for a little over a year as a paralegal. After discovering law was not the career he expected it to be, he entered into politics, serving as an organizer for the campaign of U.S. Senator Ed Markey, and later, Mayor Walsh.

It is his experience as an organizer that Cuddyer plans to draw back to in his new role as the city’s startup manager. At the end of his work day—which is spent meeting with business owners, city officials, and professors—Cuddyer considers his role that of a community builder. Instead of selling a candidate, he’s selling the city, and it’s his responsibility to make sure the city delivers on the ecosystem it’s promised to young companies.


A cloud of dust is kicked up as a small convoy of construction vehicles passes over the Evelyn Moakley Bridge. On one side of the Boston Harbor is a busy horizon full of cranes and glass facade buildings. And on the other side of the water, at the Boston Tea Party Museum, is a Revolutionary War reenactor, tossing fake bales of tea to the harbor.

It is Friday afternoon, and a few blocks down the street, a line of young people, dressed in business to casual attire, has formed outside of Trillium Brewery, a Boston company which celebrated its second birthday on March 10.

Meanwhile on Seaport Boulevard, a street cleaning vehicle lays into a pile of construction dust, with visible rubble left behind in the city’s still-melting snowbanks. As a mud-covered flatbed drives by, hauling off worksite debris, a fresh layer of dirt is caked onto the road, creating a job for the street cleaner the next day.

This is the Innovation District, and before former Boston Mayor Thomas M. Menino christened it as such, the area was little more than a collection of parking lots and old brownstones. Today, you’d be hard pressed to find a block without a major construction project in the works or scaffold hanging over the sidewalk. In the center of the war zone is District Hall, a space opened in the fall of 2013 as a meeting place for young workers. As Startup Czar, Cuddyer will help bridge the gap between the city and the young companies working in this space.

On the other side of the road is the Institute of Contemporary Art Boston, making the Seaport its new home in 2006 (then situated in a sea of pavement). The ICA has plenty of neighbors these days, and next to a glossy, soon-to-open condo building, the silver, glass-faced building already looks slightly browned with age.

The sidewalk is bustling with the briefcase crowd—they make their way home from nearby offices.


Cuddyer notes that his title as “Startup Czar” is a somewhat loose description, and that many of the businesses he works with are not startups, but several years old. A big part of the StartHub program is to grow local entrepreneurship. It’s his responsibility to work toward keeping the approximately 50,000 thousand college students that graduate from the Greater Boston area each year in the city, but StartHub is also about supporting small businesses already in Boston. In Cuddyer’s vision of the city, places like the Innovation District serve as models for other neighborhoods and are not the end-all when it comes to Boston’s status as a tech hub.

After the Great Recession of 2008, a Vornado real estate site, located on the Filene’s property, was left inactive for several years. Next to the then-closed retail mecca was a two-story hole in the city, construction held still as financial headwinds kept the economy at bay. Over the past few years, many local writers have appropriated the imagery of the stalled condo as metaphor, a symbol of a grand vision for city that ofttimes can’t deliver on its promises.

That hole next to Filene’s has since been filled.

Cuddyer’s isn’t in the business of digging holes (or filling them for that matter). The new face of Boston’s startup scene is that of a young graduate, one who’s spent his life in the city, and one with no significant background to this point in construction or entrepreneurship. He’s fresh off the job as an organizer in Jamaica Plain and Roslindale. And as he starts his new job, he’s eager to get back into Boston’s neighborhoods.

Featured Images by John Wiley / Heights Editor

March 26, 2015