Dart Boston: The Hub’s New Hub for Twenty-Something Entrepreneurs

Apparently, social media services like Facebook and Twitter aren’t everything they’re cracked up to be, even for the twenty-somethings who are supposedly their most devoted users. Here in Boston, there’s a new group for young startup types who prefer to talk about their entrepreneurial ambitions in person at actual bars, of all places. It’s called Dart Boston, and it’s now going into its sixth month, with its 22nd meeting planned for this Thursday night.

You don’t have to be under 30 to attend a Dart Boston event—in fact, co-founder Cort Johnson says “people of all ages and backgrounds” are welcome at the weekly meetings, which take place at a different bar or restaurant each Thursday. But you do have to be in your twenties to be a presenter or panelist on “Pokin’ Holes,” the podcast/video/live-streaming show that is the centerpiece of each gathering.

With Johnson as moderator, the show gives one guest entrepreneur each week the opportunity to describe his or her startup and collect feedback from the panelists and the audience. Last week, for example, guest Fan Bi described Blank Label, an online “mass customization” service for men’s dress shirts that will launch at the end of this month. (Bi, 21, is Blank Label’s chief evangelist.)

The show is “really an opportunity to give kids who wouldn’t otherwise be asked to speak their minds a voice, and to give these entrepreneurs who wouldn’t have an opportunity to promote their company the opportunity to share with our community what they’re working on,” says Johnson, who is 24.

Still from Pokin' Holes Episode 21, Blank LabelJohnson and two fellow twenty-somethings, Jake Cacciapaglia and Alexa Scordato, told me they dreamed up Dart Boston over dinner one night last spring. “Jake and I had been working on a company before this, living out in Foxborough, and we would be driving into the city all the time and meeting all these cool young people,” says Johnson. “We finally decided to get an apartment on Dartmouth Street, and we started inviting all these people over to chat about what was going on. Jake had met Alexa, and we had dinner one night and we thought, ‘Why not turn these conversations we were having about the business ideas that kids were executing upon into a more formal atmosphere?'”

The club was originally called Dart 102, after the address of Johnson and Cacciapaglia’s Dartmouth Street digs, but the gatherings quickly grew too large for the apartment, which sent the group barhopping and led to the name change. A typical Dart Boston evening starts with “Pokin’ Holes” at 6:45 p.m. and includes a couple of hours of cocktails and networking after the show. (You can watch or listen to the recorded shows here.)

Scordato, a former employee at Burlington, MA-based social software startup Mzinga who recently took a job in New York with public relations giant Porter Novelli, says she thinks Dart Boston fills a troubling vacuum in the Boston area. She notes that there’s a ton of young talent coming out of the regions’ universities—she calls Boston an “academic Acropolis”—but she says that once these young people have left school, they’re basically cut loose by their former home institutions and social groups, and they often feel they need to leave for places like New York or California to find a new community.

“If you’re twenty-something and you’re an entrepreneur, it’s really daunting and intimidating to find resources to help you once you graduate,” says Scordato, a 23-year-old Barnard College graduate. “Unless you’re tapped into MIT or Harvard, the barriers to entry can be very high for someone thinking about starting a business. In connecting with Cort and Jake, I wanted to help build out an organization that specifically tackled that issue.”

Cort Johnson
Jake Cacciapaglia
Alexa Scordato

Dart Boston meetings typically attract a crowd of 25 to 30 participants. The events give young entrepreneurs a chance to critique one another’s strategies—hence the name “Pokin’ Holes”—but they’re also a place to recruit other kinds of help, such as the software engineering talent a young CEO might need to build her new Web service. “The typical scenario for the people I talk to is they’re just graduating from an undergraduate business program and they need to connect with a technical person to execute some sort of backend system to support their idea,” says Cacciapaglia, who is 25 and, like Johnson, graduated from Bentley College with a degree in economics and finance.

Entrepreneurs who have presented at Dart Boston meetings walk away not only with fatter contact lists but with ideas that can guide them through the next few months of their companies’ growth. As an example, Cacciapaglia points to Sian-Pierre Regis, the editor-in-chief of Swagger, an online style magazine based in Paris. “I had a conversation with Sian-Pierre over the weekend and he said he has kept in mind all of the action items that he was left with when he asked how he could increase the number of hits on his site,” syas Cacciapaglia. “He definitely uses those notes as a sort of guideline.”

Cacciapaglia, Johnson, and Scordato want to make sure that Dart Boston meetings keep growing, but they’re already talking about ways to branch out too. Scordato is working with peers in New York to launch a Manhattan version of the group, and she’s collaborating with Alan Webber, the co-founder of Fast Company magazine, to launch Dart’s second regular show, a podcast that will be called “Rule 53.” The name is a reference to Webber’s book Rules of Thumb: 52 Truths for Winning at Business Without Losing Yourself. Rule 52, Scordato says, is that “teachers are everywhere,” so the podcast will feature weekly advice sessions that bring together young entrepreneurs and experienced professionals.

The trio are also discussing launching “Dart Boston Pro,” a version of the Dart meetings where marketing firms or major brands could present new products or campaigns and invite criticism. “Marketing to ‘millennials’ is a huge business,” Scordato observes. “Instead of a focus group, we’d be a hyper-aware, very articulate group that you could speak to and get detailed feedback.”

Johnson and Cacciapaglia are in the process of incorporating Dart Boston. But not to be outdone by their hyperkinetic peers, they’re also brewing up a separate company, to be called Pique. It’s an online service designed to help college students sublet their apartments faster than they could on Craigslist.

“It’s currently under development, and hopefully we’ll have a beta up in the next month or so,” says Johnson. “You’ll definitely see it soon on ‘Pokin’ Holes.'”

Cacciapaglia says the group is always seeking companies to sponsor its evening events; if you’re interested, you can contact him at [email protected] Or if you’re under 30 and you’d like to talk about your startup on “Pokin’ Holes,” you can contact Johnson at [email protected]

Wade Roush is a freelance science and technology journalist and the producer and host of the podcast Soonish. Follow @soonishpodcast

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5 responses to “Dart Boston: The Hub’s New Hub for Twenty-Something Entrepreneurs”

  1. Wade,

    I really appreciate you taking the time to highlight our organization. It’s a lot of fun getting all of these passionate young people in Boston under one roof to talk start-ups. We would always love to have you out to an event on a Thursday night when you have some free time.


  2. Fan Bi says:

    Kudos to Cort for being so passionate about getting young Boston entrepreneurs exposure, there’s such a need for it. It’s great for startups like ours, we get the publicity, interesting feedback from an audience we care about, and we get a really useful backlink from Xconomy!

  3. Aaron Gerry says:

    Dart Boston has been a true joy to be a part of and is a great way to meet young entrepreneurs in the city. Though there is a prominent student-entrepreneur community in Boston, inter-school collaboration is something to be desired. Dart Boston has no boundaries and is helping to foster the interconnectivity that Boston needs. Keep up the great work!

  4. It’s hard to quantify how valuable DartBoston is to the young entrepreneur community. Simply having a place where we can get together with shared interests and support one another in our entrepreneurial goals is so vital; this support keeps us all focused and motivated in ways that other events in the city can’t.

  5. Maria Ivanovna says:

    It’s nice something like Dart Boston features young entrepreneurs like Blank Label to have their ideas shared. That will inspire the many people to get into business. Keep up the good work.