Gone West

San Francisco from Potrero Hill after a rain

Around this time a year ago, I found myself at a crossroads. My freelancing gig was coming to an end, and I was interested in going back to product development. Out of no where, I got an offer from one of the few real technology product companies in the Twin Cities. It was attractive and I liked what the company built, but my heart wasn’t in it. I tore myself up over how to respond instead of spending time with family.

In the end, it didn’t work out. I was ready to move on from freelancing, there were now even fewer technology companies I considered worth working for, and I didn’t want to slog through building a consulting shop or startup. I resolved to look for a job at a startup in Silicon Valley.

I think most software developers wonder, at one time or another, if they should move to Silicon Valley. My own relationship with the capital of tech has been complicated. After graduating in the midst of the dot-com bust, I sent resumes to every big-name tech company I could think of and got no replies.

After nearly six months of looking, my friend Ry4an got me an interview at a small local software company, and so I stayed in Minnesota. I was able to learn a lot and advance my skills. I was fortunate to get a job at a software company instead of the IT department of some corporation. From the beginning of my career, I have worked in the revenue side of the company instead of the cost side.

In 2006, I attended the first MinneBar and got involved in the Minnesota developer community. Inevitably, tech communities that aren’t in Silicon Valley define themselves in terms of it. I have immense pride in the Minnesota community, because I know there are lots of smart and friendly people in it. But the fact is that investment is hard to get in Minnesota, and exits are rare, so there has not been a virtuous cycle of angel investment. For better or worse, the kinds of tech companies that thrive in Minnesota aren’t the same as those in Silicon Valley.

I saw this first-hand when I participated in Y Combinator in 2009 in Silicon Valley. I used to tell a story to illustrate the sheer density of the technology ecosystem in Silicon Valley: there was an office building near our apartment in Mountain View with four companies in it that had raised more money than every startup in Minnesota for the past several years.

Typical Silicon Valley office park (circa 2009)

After YC, we came back to Minnesota. The company didn’t work out for me, but the pull of the Valley was still there.

Not sure what to do, I started freelancing. I loved solving problems to help businesses, and I loved the freedom freelancing gave me (like spending a month in Paris). However, I could never commit to turning freelancing into a real business by landing my own projects and hiring my own developers. I wasn’t sure that was what I wanted. The project-based work I was doing was very short-term and I found myself wanting to build a product again.

After failing to seal the offer last December, I started preparing to interview in San Francisco. I was tired of wondering what it would be like to be a part of a “real” startup. Y Combinator’s birthday party in May provided an excellent chance to network. Through a chance meeting, I connected with a former co-worker of the Swiftype co-founders and he introduced us. I was impressed with their product (I implemented the full-text search for the digital asset management system at my first job) and we hit it off. I agreed to come in for an interview the next month and they gave me an offer.

Even though I wanted to try working in Silicon Valley and I liked the company, it was still a hard decision. I felt like I needed to give myself permission to leave. After much reflection, I said yes and became Swiftype’s first non-founder employee in August.

The last few months have been a whirlwind. Moving and navigating a new city has been stressful, but working on a product that is much-needed and personally exciting has been great.

Minneapolis Skyline in Winter from Lake Calhoun

I miss my friends and the tech community in Minnesota. I love Minneapolis – the best small city in America – so don’t be surprised if I return. But for now, I’ve gone West.