May 28, 2012
Rage Against The Machine - Boston's War on Mobile Retail and the Renegades Who are Fighting Back

I remember the first time I heard about the Green Street
. I was hanging out with my buddy Chris Yim and I asked him what all of
the noise was. Chris is a venture capitalist who lives on Newbury Street and we
were walking towards the Common for some afternoon Frisbee.

"That's Green Street.", he says. "These
guys play rap music and sell shirts out of this converted U-Haul truck. They use
Twitter and Facebook to tell their fans and friends where they'll be and people
show up. It's in-person flash sales through social media, basically."

We walked past the mysterious truck playing Jay-Z and
went on our way.

Meanwhile, I was actually impressed with this for
multiple reasons and couldn't get it out of my mind. First of all, I had never
heard of such a thing. I've grown an appreciation for what modular technology and
businesses have become in what seems like months, and this was a perfect
example. These guys didn't invent Twitter and they didn't invent Square, a
device that plugs into a smartphone and allows you to run credit cards on the
go, but they were the first people that I noticed, to hook these previously unconnected
services together to create something new. It's a
simultaneously simple, elegant, cool, and yet obvious business model that
hadn't been done before. Second of all, I really like Jay-Z. I had to meet
these guys.

Following the local news over the next few weeks, I heard that
brick-and-mortar businesses had begun calling the police whenever they spot the
big green truck. Green Street held a "Hawkers and Peddlers"
license, but have been told that this form of license is not appropriate for their operation.
The permit they need doesn't actually exist yet.

The only permits that currently exist are for vendors
selling roasted nuts and sunglasses.  Some brick-and-mortar businesses are
afraid that mobile retailers like the Fashion Truck and Green Street could be
stealing their customers.

I reached out to Green Street through Twitter and connected with Derrick Cheung, one of the co-founders. He invited me to attend a
meeting with the handful of other mobile retailers to discuss the problems
they've been having with the city.  I met Derrick at
their temporary popup shop on Newbury St.  After grabbing tea at Wired Puppy, we walked down Dartmouth Street towards SOWA for the meeting. Derrick is a young guy with cool
hair, tattoos, and a confident walking style that belies his young age.
Swagger. And when he talks, it takes you only a moment to realize he completely
understands business, his goals, and the future of commerce. He knows what he
is talking about and can be articulate about it when he waxes poetic about

"I was educated in this city", the Emerson
graduate says. "Everybody keeps talking about this "Brain Drain"
going on around here, with people getting their education in Boston and heading
elsewhere. I'm trying to show love to this city. I'm trying to employ people in
this city. I'm trying to pay taxes in this city." Derrick is referring to
the depressing fact that in 2008 the Federal Reserve Bank of Boston
reported that half of college students leave the Boston area after graduation,
and that New England had the greatest rate of outflow of recent college
graduates of any US region. Things haven't gotten any better either. Wasn't a
little startup called TheFacebook started here and is now located in California?

Derrick and I hit the SOWA where I met a few other mobile
retailers, including Emily Benson. Emily started the Fashion Truck in 2008
after being inspired by the mobile food truck revolution in New York City, she
brought her mobile boutique to Boston. "Some of these retailers love
me," she says. "I get emails from brick-and-mortar businesses all of
the time asking me to park on their property. I can go to the right building,
send a few emails, post to twitter and have 30 girls come out to buy stuff,"
she tells me.

Fighting Back

Emily, Derrick, and a few other mobile retailers get
right to business and discuss their strategy. "Intellectually, I understand
the city's position," Derrick says. "Mobile retail was basically
invented here and there is a lot of pressure on the city to get it right.
People all over the country will start doing this and people will look to
Boston to see how they regulate it. However, they need to move faster or it will
kill our businesses." Emily goes over a list of potential parking spaces
to present to the city in an effort to show that they are interested in being
partners with them in creating a solution.  Mahlon Williams of Boston
Sports Apparel Company, a truck that sells sports related shirts at ballgames,
says "Don't sleep on Dorchester, now.  Dorchester has money." I made a mental note to adopt
that rather inventive turn of phrase and the other mobile retailers confirm his
statement. "I've made a bit of money in Dorchester myself," someone
says. They complete their list and divide up tasks amongst themselves and end
the meeting. Mahlon says to Derrick, "I was so happy when you guys
appeared on the scene. I've been fighting the city about this for years and now
I've finally got others shaking the same tree."

Derrick and I walk back through the South End and head
through the Back Bay.  I couldn't help but notice a few boarded up stores
that we passed along the way, and I felt hopeful that Green Street and the
others won't meet the same fate. These guys were ambitious and creative enough
to invent a new retail model and I certainly think that working with this group
of smart young men and women would be a great way for Boston and Mayor Menino to
show him commitment to Boston innovation. After all, he just broke ground on
the Boston Innovation Center. The center supposedly will be "a hub for
entrepreneurs to meet and exchange ideas, to convene programs and events, and
to build the City’s innovation economy." I imagine there were no problems
getting the proper permits.


Jesse Waites is an animal lover, writer, technology
activist, Founder and CEO of, and is on the MIT Enterprise Forum
Innovation Series Planning Committee.  You can usually find him walking
his dog Finn in and around Boston or reading physical novels made out of actual
paper in locally owned coffeeshops.  He can be reached @JesseWaites on Twitter.