Portland, Oregon – The City of Entrepreneurs & Weirdness

What more can I say about Portland, Oregon? One of my favorite cities in the U.S. (alongside San Diego).

Needing an escape from the East Coast (still love you New York), I ventured off to The City of Roses during the last week of June. I was excited to meet cool entrepreneurs, to wander around NE & SE Portland neighborhoods, to stay with more Couchsurfers, and to network with sportswear industry folks … quite the busy fun-filled one week.

The weather forecast called for rain on first night. But the beautiful sunset I was greeted to instead. (Gateway Transit Center – Portland, OR)

During the descent into Portland, my gut started getting the “tingly” feeling. Not the bad tingly feeling, but an over-excitement emotion. I was coming back to the city that I previously once felt like I could call home.

I had first visited Oregon 2 years ago, on the All You Can Jet pass with JetBlue. At that time, I fell in love with the natural beauty and eccentric personality of the city and people. I loved Portland for its extreme concentration of sportswear organizations and outdoor recreation.

But this second time around, I also love the city for its high concentration of  all types of entrepreneurs and “weirdos“ (like someone riding a unicycle to work, or you may run into some random person naked in town … don’t ask me why).

Obviously entrepreneurs live anywhere around the world. However, I noticed that so many of them I connect with on communities, blogs, or Twitter … list Portland, Oregon as their home. Not surprisingly, this city embraces all the eclectic types, and if you’re looking to “be normal“, then Portland is definitely not for you.

One of the entrepreneurs I was glad to meet up with is Emilie Wapnick of Puttylike. Her strong community of Puttypeeps and resources revolving around combining multiple interests into a sound business has definitely influenced me in embracing all of my passions, instead of choosing one and specializing on it forever (how boring would that be?). I explored a little bit of NE Portland as we both ventured up to a Sunday Farmer’s Market with her adorable puppy, Grendel.

With founder of Puttylike, Emilie Wapnick and her puppy Grendel. (NE Portland, OR)

Later in the week, I would reconnect with a Portland artist that I first met up in the Dominican Republic one year ago. Amy Louise of She Likes to Draw,  took her fine arts background and created a successful animal and people portrait business, that continues to grow (if you are looking for quality portraits, I definitely recommend her!).

She would also become my first client on my SEO service start-up. That is the power of reconnecting, and I encourage you to stay in touch with some of the people you meet “on-the-go” as you may never know how your interests and skills can really help each other.

Me looking super happy with Amy Louise in her art studio. (NE Portland, OR)

Did the meetups stop there? Nope!

Like the first two entrepreneurs I met, I was excited to connect with Sean Ogle, the founder of Location180 and Location Rebel, at a coffee shop in the Pearl District. He is a Portland native that first got his life changing experience when he set up his first coffee meetup with the infamous Chris Guillebeau several years back.

Fast forward to the present, he’s inspired many people to “take action” and make sustainable money off online businesses to become location independent. I’ve learned so much from Sean in such a short time that I’m excited to see where it’ll take me in the near future.

While no longer an “entrepreneur-sized” organization, Nike had its roots in entrepreneurship, back when it was first founded in 1964 under Blue Ribbon Sports. Besides the awesome footwear and branding that goes behind Nike, I enjoyed reading up on the history and growth of the organization … where founders Bill Bowerman and Phil Knight hustled to get the fledgling business to its current day success.

And not surprisingly, this “hustle” still resonates with many of the company employees I got to meet during my visit at Nike HQ (and if you are a Nike fan, the Employee Store is simply heaven!).

Where all the amazing innovation is made. Nike HQ in Beaverton, OR just outside of Portland.

So what’s the takeaway from all the meetings and meetups? I learned that I connect well with the Portland, Oregon community on personal and career scale. That the clean, chill environment, sportswear industry, and concentration of entrepreneurs is close to what I’d be looking for if I decided to live somewhere in the long-term. My previous experience living in Minneapolis, Minnesota and how I felt disconnected from that community gave me further perspective on how important it is to consider “location” as a huge factor in happiness of overall lifestyle.

Which city do you feel most connected too?

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