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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

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