A frank discussion on the best place to build your startup as a young entrepreneur…

We all have goals in life. Those of us in the startup community are particularly aspirational. We dream of building great products with millions of users. We dream of leading great companies filled with awesome people.  We dream of TechCrunch articles, keynote speeches, magazine covers, and the opportunity to create great wealth. We dream of beating the ridiculous odds that say we’re idiots for even trying, especially those of us still so young.

On Friday evening at #WhiskeyFriday, which was sadly under-represented this week (really? Boston can only find 5-10 people to grab drinks after work in Central Square?), I was involved in a discussion about whether, as a young entrepreneur, it made more sense to move to the Valley or try to build a company in Boston.

This wasn’t another b*tch session; this was two friends honestly and frankly talking about the facts at hand. We’ve both been around the block here, had our own and seen our friends’ experiences in this community and so we’re well aware of the situation here and we also have enough contact with the Valley to feel qualified to understand what’s there as well.

I’m not here to make this some magnificent, articulate post, so here’s just in simple bullet form, the Pros & Cons of our two ecosystems and how two young entrepreneurs think about it as we sit in the midst of a new tech bubble (which is what sparked this discussion in the first place):

{Disclaimer: If you’re “tired” of the Boston vs. SV discussion, this post is not for you. Please close your browser window and go back to putting your head in the sand. Don’t worry,the bubble will be over in a few years and you’ll barely have noticed…}

The Valley:


  • Massive access to money
  • Stronger culture of helping each other
  • Companies that can acquire you
  • More industry experienced people around
  • Early adopter culture
  • Great tech press


  • Finding & keeping engineering talent is VERY hard
    • Try competing with Godfather offers from Facebook, Zynga, Google, etc
  • Very small fish in a HUGE pond
  • If you move there, you’re basically starting over



  • HUGE talent pool to recruit from
    • Universities and less competitive environment overall
  • Established network here


  • Underdeveloped mentoring
  • Very Weak acquisition market
    • How do Boston co’s exit? Seems “rarely” is the right term…
  • Weak funding climate
  • No press that gets users or national attention


So with all of that…the question basically boiled down to:

Is it better to build a company in the Valley and try to return to Boston to recruit


Build a company in Boston and travel a ton (literally and virtually) to NYC and the Valley to try to leverage the advantages there.

I don’t have the answer to that, but I think you can guess what side I’m betting on for now…


Got comments? Let’s keep this discussion productive and please review the disclaimer at the top in case you missed it and are irritated by the comparison.

This is two individuals talking about what’s best for their careers not an ecosystem taken at a macro level…although in many ways it’s one in the same.


Interested in more like this? You can follow me on Twitter by clicking here or find more of my blog posts at my site GreenhornConnect.com

4 thoughts on “A frank discussion on the best place to build your startup as a young entrepreneur…

  1. jason, this a really great, to-the-point, summary of how i think many of the pre-business school category sees the situation in boston. i’m not sure if the above negatives on boston are as true if you’ve graduated from HBS (or Sloan).

    the disparity between east vs west is most clear in the pre-business school “young entrepreneurs” as you’ve categorized here. if you’ve got the money, you can pay for the signaling to access a new network and have better access to capital.

    i agree with your conclusion from which i deduced things for young entrepreneurs isn’t likely to change. from the handful of mentors and couple of investors i really trust, they’ve all suggested going out to the valley is the best thing. stay for personal reasons, not if you want to optimize for success.

    • Fan,

      I’m actually surprised they encourage you, specifically, to go given the clothing startups actually around here (not to mention other mass customization), but it would put you closer to your manufacturers.

      I like to think things are going to change here, but unfortunately the old saying “if you want something done right, you’ve got to do it yourself” applies. With that in mind I’m working as hard as I can to build infrastructure I know we need, which is what inspired this post and actually got some great responses: http://greenhornconnect.com/blog/3-thoughts-boston-startup-community Watch in coming weeks for some new stuff to get off the ground.

      You know I’m here to help, so let me know how I can.


  2. I appreciate the namedrop for Founder Mentors, but there’s some subtlety to your comment and I want to make sure our mission is clear.

    I didn’t organize Founder Mentors because there was a lack of mentorship in Boston, I just wanted to provide some organization to close the inefficiencies of the supply/demand gap that I saw, in the same way that Angel List didn’t seek to address a lack of angel funding so much as to streamline and organize the communication process.

    I haven’t done a full inventory but I’ll go out on a limb and assert that every single mentor in our program was a mentor before it existed and would continue to be if we never did. But, there does remain a community awareness challenge that we’re hoping to help rectify.

    It’s also worth noting that we’ve been contacted by entrepreneurs in San Francisco, as well as Seattle, Toronto and London, about whether our program is available for them locally.

    All the same, some thought provoking stuff (a broader topic on which you know I have deep and strong opinions, especially given my experiences with Viximo and StarStreet). I hope talented young people like yourself can withstand the siren song of the grass-is-greener set.

    • Sean,

      Thanks for sharing the thoughts. Maybe mentorship always was there, but it certainly seems like you’ve relieved a major barrier, so thank you.

      The siren song is certainly strong and I think we’re in for a major battle to keep talent here. The fact is most students still have no idea about our local startup ecosystem and so we’re not utilizing our greatest strength.

      I’ve watched a number of friends leave here and on one level it definitely hurts and saddens me, but on the other, it excites me because now I have a close friend with a network in another city. I think any startup has to think about having a presence in all 3 major cities to succeed.


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