Why Boston Fails Young Entrepreneurs

In: Boston|Start-Up

27 Sep 2010

If I hear one more person ask me ‘How do we keep young entrepreneurs here in Boston?’ I will run headfirst into a wall. Not because it’s a bad question but because in my experience the people asking the question are blowing so much hot air that I can’t take them seriously anymore. My head might actually feel better after plowing through a sheet of drywall.

Now let’s deconstruct why I believe Boston fails the young entrepreneur and how you can help.

1. How to build a business

In Boston, we spend way too much time focusing on how to raise capital and nearly zero time on how to build a business. Ask yourself the last time you saw an event on how to sell a product or how to acquire users. The lean startup events have been a great start, but there is a serious need for more.

Boston startup culture focuses on sucking up to the capital/angel community. The investor ends up telling the entrepreneur all the things that they don’t like about their business and why they won’t invest.

Great, you’re not going to invest but after you say no, why not mentor these entrepreneurs and help them achieve those milestones you want to see? I know a lot of you guys in the capital community have a ton of experience building businesses, so let’s get our hands dirty, get back in the trenches and share some of that incredible insight with the young entrepreneurs in Boston.

Forget money being the rocket fuel for propelling a startup. If you’re not going to invest you can still provide rocket fuel in the form of helping the company sell it’s product or acquire users. Who knows, with your help the startup might actually generate revenue and maybe even achieve positive cash flow.

2. Building a network in Boston

Boston startup events feel more formal than a White House black tie dinner. Over the past 18 months I’ve gone to a lot of events. . . a lot. There are two things in common between 90% of them: suits and Sam Adams. Imagine how difficult it is for a young guy to approach a group of ‘buddies’ at one of these events as they sip on their Sam Adams, and chat about their golf game.

In order for this kid to have an effective conversation, he has to have the insane confidence to breach the group, command everyone’s attention, and sell himself within 10 seconds before the suits’ eyes glaze over and they tell the kid anything they want to hear in order to get them to go away. I’ve seen this happen a million times.

What’s the solution? I wrote an article in MHT a year ago on how to help the twenty-somethings in Boston build their network and I still think it rings true today. If the experienced entrepreneur/capital crowd stepped up and was more proactive in introducing themselves and their colleagues to the young guys, we would drastically change the feel of Boston for the young entrepreneur. I might even venture to say that by giving the community a more inviting feel, we might actually see more brilliant students coming out to let the investment community in on their new venture.

So the next time you’re at WebInno and you’re nursing your Sam Adams, look for a young guy you haven’t met before and ask them what they’re working on. I promise the young entrepreneur won’t bite and you might actually be doing a little bit to put a suture on the mass exodus of young brilliant minds to the West Coast.

3. “Please promote our event.”

Jake and I get about 20 requests a month to promote some event or program around town. Now don’t get me wrong, I would love to promote everyone’s event and we try to do as much as we can. But let me tell you what makes me want to take a baseball bat to my computer:

If you ask us to promote your event, it better not cost money for the young entrepreneur. Most young entrepreneurs are at the same financial level as starving artists. In plain English, they are poor. The reason you aren’t getting many young people out to your event is because they can’t afford it.

If you don’t know what your event’s value proposition is for the young entrepreneur, do not ask us to promote it.. If you tell us your value proposition is relationship building, how will you run the event to make sure these young guys will leave with one more great relationship than when they arrived? If the topic is on helping entrepreneurs learn how to raise capital, I won’t be able to respond to you because a baseball bat has destroyed my laptop. If you have a compelling topic of conversation, great, let us know what it is.

Alright, you have a compelling topic— you’re going to be a serious connector and make sure people who don’t know one another are introduced, but your event is during the day on a weekday. Ask yourself how you expect twenty-somethings who are moonlighting or treading water with part time work are going to be able to show up to your event?

Finally ask yourself what you’ve done to reach out to young entrepreneurs personally. Have you come out to a Dart event to introduce yourself to the 100+ twenty-somethings and college students we have at our startup parties each month? Have you gone to a startup event at a university (not just at MIT mind you)? Have you gone to a One in Three event? If you really want to kickstart college and twenty-something involvement in the broader community you need to reach out to them on a grass roots level. In fact if you come out to a Dart event I’ll introduce you to everyone there personally and, better yet, you don’t even have to pay for a beer because they’re already on us (Gansetts, not Sam Adams).

So if you want us to promote your event to our 1,000+, twenty-something, entrepreneurial focused DartBoston list:

a. Provide us with free tickets to give away
b. Help us to understand why your event is valuable for the young entrepreneurial community
c. Tell us which Dart event or any other Boston young entrepreneur event you’ve recently gone to and how you’ve introduced yourself to young entrepreneurs.

4. Why smart young people who have created a business leave for the West Coast

I’ve had conversations about this topic with several successful entrepreneurs, angels and VC’s over the past couple months as I’ve watched my friends take off for the West Coast. While it’s awesome that I have plenty of couches to crash on when I go to the Valley, it’s a real bummer that we’re losing these highly motivated kids who are willing to take risks and create startups.

It’s understood that many first time young entrepreneurs won’t have huge exits from their first venture. However the ones who succeed do so because they work with other young experienced entrepreneurs, have solid networks, learned how to build a business, raised seed rounds and were mentored. But unfortunately that’s only happening out West and not in Boston.

If we want to keep young, smart, motivated entrepreneurs in Boston, who are willing to risk everything on building a company, it is going to take action on everyone’s part and not idle chatter at the Unconference, Future Forward or Nantucket Conference.

37 Responses to Why Boston Fails Young Entrepreneurs



September 27th, 2010 at 4:25 am

looking fwd to coming back to boston and busting some caps


Jason Evanish

September 27th, 2010 at 4:44 am


Thank you for writing this. I 100% Agree on All Counts.

After about a year in this ecoystem, I’ve seen a lot of change, but it’s almost all from the bottom up: Dart, Greenhorn, Bostinnovation, NU’s IDEA and Husky Innovation Challenge…but I haven’t seen a lot of change through the rest of the ecosystem (we all remember the Nantucket Conference story of 1 person under 30 being there).

Sadly, much of this is not new…many of us have been saying these things for months, but hopefully people will hear this loud and clear.

With the unConference coming up, hopefully that can be an opportunity to make waves and move the needle, but then again, they’re having some of us act as intermediaries so that young people can break through and reach the folks with the Sam Adams.



Kevin Bedell

September 27th, 2010 at 10:33 am


Thanks for adding your voice to the mix. It’s important that everyone hear this and do what they can to help out — for all our sakes.


Galen Moore

September 27th, 2010 at 10:52 am

This is great, Cort. Any VCs out there need to shed suits from your wardrobe? I wear a 40 long…



September 27th, 2010 at 12:37 pm

Well said Cort!


Josh Bob

September 27th, 2010 at 1:11 pm

Harsh truths, Cort – but well-said. Few things are as disappointing as looking at the page for an event that sounds great and seeing that it costs “$45 for members, $60 for non-members,” or feeling like an event is “see and be seen” rather than providing value.

Jason’s point about the unConference – which, yes, costs money – is a great one. That was my first Boston entrepreneurship event, and was worth every penny ten times over. Highly recommended (http://masstlc.org).


Scott Kirsner

September 27th, 2010 at 1:37 pm

First, my bias: I’m involved in some way with all of the events you mention at the end of your post.

I agree with a lot of what you say – our competitive advantage as a city rests on how open and supportive we are of students and fresh-out-of-college entrepreneurs.

However, I actually believe that what serves our ecosystem best is a mix of free and paid events (and I am involved with both kinds) … since they end up attracting different crowds. The problem with free events *can* be that they don’t attract more senior people … and the problem with paid events *ususally* is that they don’t attract enough younger people. And those are problems that event organizers of both kinds of events need to grapple with. I know with the UnConference, Future Forward, and Nantucket, there are various kinds of free or sponsored tix available to young entrepreneurs and students.

I’d also note that in San Francisco today, TechCrunch’s Disrupt conference is starting. Despite having sponsors like Google & Sequoia, it costs $3000 to attend. Even student passes are $200. But I don’t think that means that the Bay Area is a bad place for young entrepreneurs…


Ash Martin

September 27th, 2010 at 1:39 pm

Couldn’t agree more Cort. As a young entrepreneur trying to make a go of it in Boston, I feel the key difference in WC vs. EC is the “establishment’s” lack of support, especially when they aren’t writing checks. This community needs to support each other and I think you’re seeing a lot more of that at the grassroots level then you are at the establishment level. The QUEST was a prime example, every entrepreneur in town (young and old) should have been there supporting one of Boston’s fastest growing startups right now (SCVNGR), so where were they all??? The talent is here, the ideas are flowing, and Jason is right, change is coming. I for one am excited to be a part of this community right now, but we’ve got to do a better job connecting the experience with with the drive or we’ll never get out this slump.


Tom Pincince

September 27th, 2010 at 2:32 pm

Agree with you now, and agreed with you when we spoke about it on Friday.

A couple pointers:

+ We are holding a Cleantech mixer at Tommy Doyles tomorrow night. Scott will be speaking, the event is free, and the bar is open — see http://www.eventbrite.com/event/845078653

+ Flybridge Capital Partners has a scholarship program to pay event registrations (for students and up to $100) — see http://www.stayinma.com/about



September 27th, 2010 at 3:09 pm

Found this in my Hacker News feed this morning. Well done Cort – hopefully you’ll get a bunch of suits to put down their Sam Adams and say hello instead of simply handing over a check.


Michael Kuznetsov

September 27th, 2010 at 5:11 pm

Nice, Cort. Good to see you hitting hackernews.


Simeon Simeonov

September 28th, 2010 at 12:27 am

Cort, you are right–many events are not practical-enough. A few people in the community have been working to change that.

Given the timing of your post, I have to plug FutureM. Next week Boston will be home of 40+ separate events focused on what’s next in marketing. Many of them are free and are about acquiring customers, doing PR on the cheap, etc.

While I’m at it, I might as well also plug the customer development event I’m doing with General Catalyst Partners. Free, top-notch content (Steve Blank’s co-author Bob Dorf) and all about product/market fit and acquiring new customers. There will be Sam Adams. As for the suits–we can laugh at them.

You are coming, right?


Dan Croak

September 28th, 2010 at 12:37 am

Paul Graham has an interesting quote in an article published today:

“When we started [Y Combinator], in Boston, our goal was to help founders, not to help Boston.”


Seems like an important distinction to me. There’s a lot of “build the ecosystem in our area” talk, events, and organizations out there. Maybe the best efforts are those that target helping specific people (entrepreneurs, developers, designers, investors, whoever), not city pride.


Punit Shah

September 28th, 2010 at 2:12 am

As a young entrepreneur learning about how to build a company, I agree with you on many points you bring out – specifically of suited individuals hiding behind their sam adams. The mix of free/paid events in my view are ok, paid events are worth it if they provide value and often times, I meet more serious individuals at these events. The question is which events succeed in this? Marc recently went to a paid event where a panelist fell asleep! One thing I am proud of is all the different ventures still working here. I rely on them quite a bit and am thankful for the feedback I’ve gotten. Taking Josh’s feedback about the MassTLC unConference is validation that some events may be worth the money and with that I’m looking to give it a shot!

This is a good point to write that Dart Boston _really_ got me introduced to the start up scene when I began to venture out in the Boston Entrepreneurship scene. I wouldn’t have gotten this far without their support when starting out and point anyone starting out to their events!


Bill Warner

September 28th, 2010 at 1:13 pm

These are real issues….but Boston is changing…maybe not as fast as we need to.

Here’s my detailed response: http://billwarner.posterous.com/a-response-from-bill-warner-boston-is-changin




September 28th, 2010 at 3:23 pm

Many excellent points, and I hope those potential investors put down their Sam Adams and take notice. One quibble: referring to entrepreneurs as “young guys” no less than four times, and in other places as “he”. Young women are every bit as likely to be entrepreneurs these days, and we are even more likely to be overlooked by the old boys network.


Timothy Yandel

September 28th, 2010 at 4:13 pm

Cort – having worked in technology recruiting in both San Francisco and Boston has given me first hand experience between the two ecosystems and how they approach networking in general. I think both geographies are actually more similar than you think when it comes to networking and getting help and advice. The only differences I see stem from the amount of coverage and press San Francisco gets – it’s just more established. I see Boston developing a larger presence with the emergence of BostInnovation (our Techcrunch), your own DART Boston (seems very similar to SFNewTech) and then MassHighTech (similar to silicontap.com).

There are two distinct differences I can see between the two. One major difference I see is swagger. San Francisco has a swagger about itself and while it sometimes comes off as elitist, you really see a community of people that have “made it” in the Valley. It’s similar to why young people move to New York for fashion or LA for acting – it’s the idea that if you’ve made it there you can make it anywhere. Boston always acts like the ugly sister, when in fact, it’s set up even better with the infrastructure that’s around here than the Valley itself!

The other difference I see is from more Senior entrepreneurs that support new ideas from a younger crowd. The “Silicon Valley Veteran” that goes out to events in San Francisco to help out the younger generation to succeed is something I don’t see much of here. I don’t know why that is, but I feel once a company “makes it” here they end up forgetting about helping the rest of the community to get to where they are. I hear a lot about small startups that get funding suddenly “big time” the people that were giving them exposure before they were anything.

So the only solution I can see is to keep developing this great infrastructure that’s in its infant stages, encourage established companies/entrepreneurs to help the younger generation, and to stop complaining about how Silicon Valley is better. Who wants to stay on in a company when their employees always complain about the competition being better than them? Get a swagger Boston, because from where I stand, they’ve got nothing that you don’t.


Lora Kratchounova

September 29th, 2010 at 12:39 am

Hey Cort,
insightful post – glad I came across it. I do think that there are resources for young entrepreneurs to learn how to get a business but they don’t know about most. I am part of the MIT Forum and help with the marketing of the events – I got passionate about and decided to get involved with the Forum when I attended a concept clinic and then a start-up clinic (yes, Bob, the events are paid but they are worth it – try one and you will speak with the same conviction as you do for the unConference:). You do get to meet other entrepreneurs – but if you don’t get a chance to speak to all of them, you get their contact info as a handout. You not only meet other start-ups but you meet experts in our field who have already made it and can be great connections for you. Check out the types of events we do – you will see that most offer hands-on training beyond getting funded – http://www.mitforumcambridge.org/programs/programs-2/
And if you seriously don’t have the money for a membership, you can apply for a grant (although I am the first to admit that info is missing on the site so I will get on this right away)
PS. I do try to attend Dart, Webinno, etc, and do my best to talk to as many young folks as I can


Samuel Johns

September 29th, 2010 at 2:19 am


Well said!

Arriving in the ecosystem just on a year ago now, where the first event I went to was actually the Unconference due to Fan Bi telling me it will be the best event of the year and that if I don’t skip class I will regret it. It was the best $90 I have spent in the US to date. The reason being, it set my whole year up with a vision of what the Boston community had to offer and set in my mind that this was a community wanted to be a part of. 2 weeks after the Unconference I secured a 6 month extension of my visa to stay the full year at Babson. Who knows, if it wasn’t for listening to Bill Warner talk passionately about the “Entrepreneurs Intent,” or Brad Feld talk about “what it really means to be an angel investor,” or even just watching Fan hustle the room to get critical feedback and build connections to help spawn Blank Label into what it is today, I’m not sure if I would still be here. Certainly an event to get the blood flowing.

Beyond the Unconference, I was fortunate enough to attend many great free (Innovation Open House, DartBoston) where I have made some great friendships with other moonlighters, young entrepreneurs. However that being said I agree wholeheartedly that mentorship and quality support at the grass roots is something that is lacking.

My question: Is it a numbers game?

With the highest density of college students in the world in relation to the population. Is there a disconnect between the number of young people who want help and the number of people who are willing to give it?

Compared to San Fran with a larger population and one would think a more dense population of entrepreneurs and less students (i.e Young people) in the area.

Thanks for sharing your passion for the Boston start up community and it truly shows with the effort Jake and yourself have put in with the founding of Dart.

Some articles found whilst reading this:

Top US City for Young entrepreneurs: Boston #4

2003 data: 374,000 college students in Boston and some insight into the cities effectiveness to keep students in a city once they graduate



Jeff Bussgang

September 29th, 2010 at 11:36 am

Great post, Cort. That’s why I never wear suits! :-)


Vinay Singh

September 29th, 2010 at 2:44 pm

Cort, very true about building a business. It is not that you need funding to start a business. You have talked about you young entrepreneurs but what about working professionals who are building a business and trying to network with like minded professionals. I have been going out but not met much people except in Venture Cafe.


Jason Evanish

September 29th, 2010 at 6:24 pm

Sorry, Lora, but you’re missing the point. Young entrepreneurs have no money and often less than that (hooray student loans!).

Before I made the choice to start working at oneforty, I was living on a weekly budget that was less than the price of your concept clinics. There is no way on a weekly basis I would ever consider spending that kind of money ($30-$50). No young entrepreneur is going to dip into his savings that might otherwise cover cloud server costs or rent to pay for a networking event.

One of the things I do have to commend the MIT Enterprise forum on is giving away a few tickets to their big events like Jeff Pulver’s panel and the event Sim organized last year with Dave McClure, David Cohen and others. These have been great events and the added exposure to young people has certainly benefitted them while not affecting the revenue stream significantly.

I’m really looking forward to the unConference; I’m hopeful the community can candidly discuss these issues and talk about how we can resolve them.



Kevin Vogelsang

September 29th, 2010 at 7:39 pm

To Boston’s young entrepreneurs,

Have that insane confidence you need to go approach the guys in the suits with the Sam Adams. You’ll need that insane confidence later anyway, might as well start practicing.

More than that, if you’re a capable person, they’ll want to meet you. If they don’t, they’re the wrong people.

Build something. Quit paying attention to TechCrunch and who is getting funded. And quit worrying about raising money. Just keep building your business.

Tear down the doors. It’s the only way.


Andy Cook

September 29th, 2010 at 8:11 pm

Right on Cort! Some strides seem to have been made though in the last year or so, and I hear a lot more people talking about opening up entrepreneurship in Boston…So at least that’s good? You’re right though…It could be so much better


David Hauser

September 29th, 2010 at 8:17 pm


While I agree on some of these points, the Boston community for young entrepreneurs has grown 10x in the past years and maybe we should look at some of the things that are working well compared with caring about if events are free or paid. As Scott said there are valid reasons events should have a cost and even the Lean Startup conference (in SF of course) had a cost and people even paid to travel to it.

What the Boston community needs now is more public recognition of young entrepreneurs and interesting bootstrapped startups as this is what will be the catalyst to take Boston to the next level. Look at the communities that people talk about all the time, SF, New York, Austin, even Boulder and what you find is a system of public recognition and even celebrity status of those that are doing well.


Christopher Mirabile

September 30th, 2010 at 8:26 am

Cort: You raise some great points. There’s more we need to do. Point taken. -Christopher


Andre Porter

September 30th, 2010 at 1:11 pm


I think you have raised some important issues confronting young entrepreneurs. As you know we here at the Office of Small Business and Entrepreneurship (OSBE) have a particular interest in supporting young entrepreneurs in every region of Massachusetts. OSBE would love to collaborate with you and any other stakeholder on events, programs or activities that would enhance our outreach efforts. As you know we have an event next week on the 5th with Inc. Magazine that celebrates three Massachusetts companies run by entrepreneurs under the age of 30. These three companies are featured in Inc. Magazine’s 2010 “ 30 Under 30: America’s Coolest Young Entrepreneurs.” This free event will also provide an opportunity for young entrepreneurs to network and learn about various resources and programs throughout the state that can help them start and grow a business. Please share this invitation with your network: http://inc30under30boston.eventbrite.com/ .

I hope you are able to attend our event and I look forward to speaking to you about ways to address the issues you have raised.

Andre M. Porter, Executive Director


Dan Weddle

October 1st, 2010 at 8:19 am

Greetings Cort and others! Thanks for your thoughts. While I may be a bit out of the targeted age group here – I’m 45 – I think there are similarities in how entrepreneurs starting out approach building a business regardless of age. I work in a VERY conservative industry = clinical trials for biopharma + device companies, on the SERVICE side. Started in 2003, my company has focused on cost-effective process improvements leveraging technology, not inventing and selling technology. Having said that, and having gone through the rounds of conferences to approach suits (which actually doesn’t bother me), my gripe is GREED. Look, if I can give a reasonable return over a longer period in an ultra-conservative market using a service model, it seems someone might want to invest, but alas, everyone who already has money needs to reach short-term high exits. This mentality has killed the killer app investment opportunity. I’ve kept my equity in response, which is a good thing, yet still wonder if you’ve found circuits at your age that follow someone looking to really scale a service model globally …


Roger Wilson

October 4th, 2010 at 10:24 am

I had a Narragansett at the best event I went to last month and there was nary a suit in sight. I made some good contacts and ended up cutting a little deal as a result. To anyone who has a beef about Boston, I say simply “make it better by helping somebody.” Boston can and should be the best place on the planet to live, work, build a business, raise a family, and enjoy life. Commitment, not complaints, will carry us forward.


Jonathan Kay

October 4th, 2010 at 10:59 am

Wow – Quite a post Court…and i think this reaction speaks volumes (30 comment replies!)

People here CARE a lot, there certainly isnt a lack of passion. And i think the problem you touch on with the VC’s and “Suit/Sam Adams” events are because those are the events put on by VCs and big law firms.

Look at some of the events we have put on as well as anything WorkBar has done…does not get more casual, inviting, and educational than that.

Having said that…i would be happy to talk with some other young entrepreneurs who are also “doing it right” and put on a larger scale free event. We are certainly willing to support (both with time, effort, and money).

Jonathan (@grasshopperbuzz)


Thierry Hubert

October 4th, 2010 at 2:58 pm


I agree with you. As a matter of fact we gave up on investors and bootstrapped to focus on customers and getting industry traction. Now we have a nice problem; we are stuck with limited resources to capitalize on the momentum, prospects and managing the few customers that we have. The dilemma has now become a balancing act between managing the business and spending the time we don’t have to seek investors.


Laura Hales

October 4th, 2010 at 9:24 pm

All entrepreneurs should enter the MassChallenge competition when it opens again next spring (www.masschallenge.org). You will find all that is listed here (as lacking) and more… as a finalist company in the competition, we have gained by leaps and bounds.


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October 11th, 2010 at 10:40 am

I just saw a Tweet about MassTLC, and now I find it ironic that this article talks about events are too expensive around here, and yet I see a bunch of you are going to an event that is $200-400, and a “steal” at $95 for early stage entrepreneurs. Are we that desperate for help that we’re willing to fork over money even when we feel it’s the wrong thing to do?


Chris Myles

October 11th, 2010 at 11:03 am

It was a little frustrating to see 50% no show rates at some of the FREE #FutureM events even with wait lists and reminders.

What message are we sending to supporters who are trying to help Boston? Some flew in from out of state only to find 1/2 or 1/4 filled rooms with left over pizza and food (at THEIR expense).

Adam I agree about the $95 “steal” for the unconference.


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Adrian Wong

April 15th, 2011 at 2:48 pm


Thanks for the truthful painful rant. I feel see the frustration and us service providers need to understand we can’t be the stuck up pricks who think the young entrepreneurs need to kiss you know what to get something out of us. I will say being in the other side of the wall, I do try to take the tie off to look approachable but let’s make sure our young guys know it’s ok to cut into a conversation and if the group snubs you, forget them.

I agree we need more events on how to make the business works and not stuck on the fundraising side (still working on the sales series! need help). But I do see some points on the paid side too, brings in a different crowd of entrepreneurs and sometimes the content is better than a free event (I did say sometimes).

And to be blunt, only way you can keep young motivated talent here is when you have the young guy sell their business for big dough and comes back to use that dough to spread it around. You will NEVER get it from the older treps. It’s going to be a painstaking journey but until we can lead the next generation of wealth into Boston, not happening.

I’ll keep my rant short because I want to help and I don’t want the service provider side look like vultures preying on young treps. Ride and die with you guys!

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About this blog

Hi, my name is Cort. I'm a venture partner at Accomplice, an early stage venture firm and run hack/securehack/secure, a community of cybersecurity thinkers and doers.

Prior to Accomplice, I co-founded Terrible Labs, Boston’s premiere web and mobile development company which was acquired by Autodesk. While at Terrible Labs, I also co-founded TicketZen, a mobile, parking ticket payment provider.

I am all about getting out into the community to meet other passionate entrepreneurs so get in touch if I can be of any help.


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