My Love Hate Relationship with Boston

I spent 12.1 years of my life living in Boston (and Cambridge) – from age 17.7 to 29.8.  This morning I spent an hour having a picture perfect run around the Charles River, listening to the Red Hot Chili Peppers on my iTurd (my podcasts are still not syncing correctly, but whatever), and reminiscing on my time here.

I’ll always be defined by the seven years I spent at MIT (two degrees, one ABD ejection.)  I lived in Cambridge for four of them and Boston for the other eight (Devonshire Place, Fort Point Channel, and Bay State Road.)  I got married, got divorced, and met my soulmate

I started my first company (Feld Technologies), sold my first company, did my first angel investments (successful: NetGenesis, Thinkfish, Harmonix, Abuzz; unsuccessful: Virtuflex, Trellix, NetCentric), and learned an enormous amount about starting and running entrepreneurial businesses.

I met three of my best friends (Warren, Dave, Raj) who I think of as step-brothers.  I met two father figures (Eric, Len) who have had almost as much influence on me as my dad and my uncle Charlie.  I had some amazing highs, a very deep two year depression, and eventually realized that I only got one shot at this life thing.

I often say that I spent 11 years and 364 days too many in Boston.  But – that’s not really true.  On a morning like this, as the sun shines down up me and I put one foot in front of the other, Boston feels like a special place.

  • Dave

    Ha. I knew there was some love in there somewhere for Boston 😉

  • Bruce

    It was the view from the middle of the Harvard Bridge that originally inspired me to move to Boston. I loved the scale of the surrounds, I loved the scale of the potential.

  • Yeah but as soon as you get in a car to drive anywhere in Boston, the hate part of the love-hate relationship comes back to bite you in the ass!

  • Bob

    Hey Brad, thanks for that, I feel the same way!

    I spent closer to 20 years in the Boston area; 10 before college and 10 after. I loved Cambridge, the ocean, the intense green in the spring and even the occasional blizzard in the winter.

    Most of my family is still there so I go back often, but it was a bittersweet departure 10 years ago.

    Lots of reasons to get out and start over someplace new.

    I’ve been in Boulder now for 10 years and can’t imagine living anywhere else! Boston is a distant, but still mostly pleasant memory, and a wonderful place to visit.

    Bob Rose

  • What a great post.

    I think of Atlanta as the same for me. Maybe I should head down south for a nostalgic run through Piedmont Park and downtown ATL…

  • “… one ABD ejection …”

    Since you opened the door, Brad, did you mean they tossed you out, or that you pulled the face curtain?

  • i, too, have a love-hate thing with boston. my parents emigrated from hong kong and settled in south boston in the 60’s (ghetto). then we moved to malden (boring). then it was newton (too tony). then two decades later i lived in cambridge (no complaints, except that parking is a bear). it is a cool city both old(founded in 1630) and new(the tech corridor) vs. silicon valley and sand hill road, which is just new and new. i think you might be a different kind of VC being from boston. how? i am not sure, but there is most certainly a difference in style and manner that i have observed from west coast VC’s and east coast VC’s (and i will throw in third coast too as in austin). but the MIT people i’ve met are in a class (or ether) all by themselves.

  • @D.C. – while it depends on who is writing the history, it’s probably some of both.

  • AM

    Great post. I have been living in Boston for the past 7 years but will move to NYC in a few days. Boston can be irritating sometimes, but I really enjoyed this city. Pride, brains, risk taking… are some of the words that come to my mind when I think of Boston. Education is Boston’s main driver, both for quantity and quality. Universtities are everywhere. No better guarantee for the future. I also love the contrast between tradition and modernism: architecture, politics, sports, values, neighborhoods… I will definitely miss Boston.

  • Boston says, “Thanks for the visit.”

  • J.G.E.

    I am from Boston but grew up part in the Carribean and part in the northshore of boston. I lived way too long in the northshore and now live in
    Brookline but always worked or went to school in Boston. I realized at 16, while working in fanuiel hall that Boston was boring and the people were rude. Has that been true for you? Over the past 20 years I have spoken to many people about this and they all say that bostonians are not friendly people. As a matter of fact, you can tell right away that someone is "not from around here" because they are friendly. Don't get me wrong, I made some good friends here and made the best of it, but I always think about what my life may have been like if I had grown up in the midwest – I have family in Missouri. Anyway, I gues I'm stuck here for now, but someday want to live in Cali, Arizona or back in the Carribean.

  • Boston has always had the “locals aren’t friendly” rap – even when I lived there 25 years ago.  My experience was that there was a particular style – which wasn’t unfriendly – that was pervasive.  I eventually learned to interpret it as “neutral” – and as a result discovered loads of friendly people everywhere.

  • I'll never been to boston but i have a lot of expirience about love-hate relationship. it (sometimes called a Frenemy) which is a personal relationship involving simultaneous or alternating emotions of love and hate. This relationship does not have to be of a romantic nature, and may be instead of a sibling one. It may occur when people have completely lost the intimacy within a loving relationship, yet still retain some passion for, or perhaps some commitment to, each other. so for me having a love hate relationship is not good.