First month as a start-up founder in Portland, OR

For those of you who don’t normally read this blog, about a month ago I moved from Lexington, MA (Yes, the famous shot heard around the world Lexington) to Portland, OR. I moved to Portland for a few reasons. My girlfriend lives here, my (now former) co-founder lives near Portland, I like the city, it has a small but growing tech scene, etc.This blog post is about my first month as start-up founder in Portland.

Getting plugged into the Portland Tech Scene
I knew coming from Boston that Portland’s start-up / tech scene would be significantly smaller. That is exactly why I wanted to come here. When I was in Boston, I went to a few networking events and met some awesome people, however, I was definitely a small fish in a big pond. Part of the appeal of Portland was that the pond in question is significantly smaller. Though I’m still a small fish, it has been significantly easier and more rewarding  to work with a smaller group of tech and start-up people. I’ll give you some examples:

a) I got to meet Rick Turoczy of the Silicon Florist and am currently helping him out with a few guest posts for the blog

b) Interviewed Darius Monsef IV, the founder of ColourLovers and YC Alum, for a Silicon Florist blog post. Also got to discuss TrekDek with him and received some great feedback (Thanks for backing my Kickstarter by the way).

c) Attended the launch event for the Portland Seed Fund and got to talk with one of the fund managers, Angela Jackson, for a bit. Oh yea, apply by May 31 if you want to be considered for the summer class.

d) Met some fantastic entrepreneurs and start-up founders, including Jason Glaspey, the current Product Manager at Urban Airship, PeeKay Chan from the soon to be launched HubGenie, and Sean Keener and Riel Manriquez from BootsnAll.

When I arrived in Portland I deliberately sought out people heavily involved in the Portland start-up scene. What I didn’t expect was how friendly and welcoming they all were. I pretty much cold-emailed everyone and they were all happy (I think) to meetup for coffee and chat for a bit. I am extremely appreciative of all the people that I’ve met here. Though its possible that tech peeps are just a friendly bunch no matter where they are, I really believe the laid back Portland vibe has something to do with it. In Boston, most of the entrepreneurs and investor types I met were very friendly, but it was a different mind-set all together. It might just be a function of the size of the tech crowd, but I think its also a city culture thing. I would love to read a blog post comparing Portland to Silicon Valley.

Finding a co-founder in Portland

When I arrived in Portland, I had a co-founder. Unfortunately for me, it turned out that he was too busy to take on that co-founder role. He was busy managing his own software that he licenses out as well as several rental properties that he owns. C’est la vie. No hurt feelings or anything but that put me in the position of having to find another tech co-founder.

Progress to date? Several leads but haven’t found one yet. The most promising leads have actually resulted from non-tech related activities. I went to a few Meetups. One was a travel group and the other was a Portland New In Town book club meetup. It just happened that there were a few coders in both groups that liked the concept and seemed fairly interested, but those conversations are stills taking place.

Most of the coders that I’ve met through tech related activities have also been interested in the concept, but it seems as if they are all happy doing consulting work and working on some side projects. I don’t know how this compares to the valley, but that seems kind of Portland like as well. There is definitely an emphasis on “just enough success” and working to live. Though frustrating for someone looking for a co-founder, its great from a lifestyle perspective.

I think I may have to change my approach quite a bit. Suggestions?
The roller-coaster emotions of being an entrepeneur

My personal experience in this area seems to be fairly typical. Most of the time I’m fairly optimistic. My happiness is highly correlated with discover different possibilities for the project, meeting other entrepreneurs, and making incremental progress on the project. The severe semi-frequent depression is highly correlated with mean hacker news comments (amazing how affected I am by anonymous feedback), perception that the project is not progressing and you can’t do anything about it, and the occasional glance at my dwindling bank account. Overall though I think it helps to be in Portland in both cases. When you’re happy, you feel so lucky that you’re in a great city with lots of natural beauty around it. When you’re bummed, well, you’re still bummed but at least you’re still in a great city with lots of natural beauty around it. Boston is a little too much city and not enough nature for the emotional ups and downs of a start-up founder.

Job Search

There’s a certain piece of advice that Portlanders give people thinking about moving to Portland. It is BYOJ, or Bring Your Own Job. Indeed that seems to be the case here. Granted, I haven’t been trying very hard to get a job, but I’m also trying not to end up in a job where I will want to throw myself off the Burnside bridge. I even wrote a blog post about one of my job interviews at a law firm. This may not be a realistic attitude, as I either have to start generating revenue or be homeless. Lame. If anyone reading this post knows about any start-up jobs for non coder positions let me know.

Concluding thoughts

If you want to start a start-up in Portland, I think its a great place to do it. If you want to raise some serious funding, you’ll probably have to leave. But, in the early pre-launch stages, I don’t think you can beat the lifestyle or the culture of Portland. I imagine that the most ideal scenario (other than having funding) is having a part-time job that pays the bills while you work on your start-up. Working part time here is something that is celebrated so no worries about being shunned.




13 responses to this post.

  1. Portland has been a great place to start our business. Lots of talent, creative, low cost of living and great food. Best of luck with your venture here!


    • Hi Nick!

      Thanks for the kind words, and I’ve now solved the mystery of who made the Powell’s bookstore app!




  2. Posted by RM on May 8, 2011 at 11:04 pm

    I have lived in a few cities with not much luck. Its simple – if you wanna be an actor you go to Hollywood. You wanna find founders and funding you go to Silicon Valley. Why go anywhere else and you may not decrease your chances of success, but your not increasing your chances.



  3. Posted by tip on May 9, 2011 at 12:20 am

    Most of your links to external sites are broken. Add http:// before the www. Good luck.


  4. Portland’s a small pond, but larger ponds are in driving distance to the north. Could you try to find a partner in Seattle, or even Vancouver, and meet up often enough? Surely, it’d be much easier to find talent. And if you do a little traveling further west, you find the world is full of ponds bigger than Portland…


    • What you say is true. However, I’m not in much of a position to be doing much traveling back and forth. But who knows, maybe there will be a Seattle developers meetup here in Portland.

      Thanks for the feedback.




  5. I’m in the early stages of a startup in Pittsburgh and feel the same way! It’s great being able to connect with other tech people without feeling out of my league and like I’m just another business card. Good luck!


    • Hi Janelle!

      Thanks for the kind words. I took a look at your blog. Good luck with your recovery process! I’m a runner myself and I’m just starting to get back into it after a 6 month hiatus in Egypt.

      Just out of curiosity, what’s your start-up? My e-mail is if you ever want to chat.




  6. Dale:

    Please contact me and I shall try to help any way I can. Was organizer last two Startup Weekend Portlands, co-own a blog Check it out.



  7. […] First month as a start-up founder in Portland, OR For those of you who don’t normally read this blog, about a month ago I moved from Lexington, MA (Yes, the famous shot […] […]


  8. Posted by kommunication on May 17, 2011 at 3:26 pm


    As a fellow startup founder, welcome to Portland. I could also lend you a hand. Just drop me a line anytime.

    I moved from the Midwest 9 years ago and don’t regret my decision at all. I love Portland.


  9. Hey Dale,

    I am also moving from Boston (worked in CIC – Kendal Sq /MIT Area) to Portland in Sept. I am moving my startup there and would certainly like to chat. Shoot me an email –


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