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

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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]

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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.