Three Years in Chile

Three years ago last week, I was in New York getting the last few things together before my trip to Chile. I’d never been to South America, barely spoke Spanish and really had no idea what to expect when I got off the plane. As I waited in the airport lounge at JFK, it still didn’t feel real. It was just like any other of the numerous flights that Jesse and I had taken during our year and a half running Entrustet.

It didn’t feel like we were going to a foreign country that had promised us $40,000 (that we couldn’t verify we’d actually receive), to a place where we didn’t speak the language, 16 hours from home.

Three years later, I’m still here. I’ve spent 27 of the past 36 months in Chile, learned Spanish, immersed myself into another culture, pushed myself out of my comfort zone, made incredible friends, started multiple businesses, taught at three universities, wrote two books and received my permanent residence. It’s been a long road, but after three years, I think I finally pretty much get Chile.

What have I learned over the past thee years? What’s changed in my life and in Chile? And why am I still here? Why did I stay? And what’s next?

It was a big change coming from the US and resettling in Chile. I’m very privileged in that in the US things usually came easily for me. I almost always knew what to say, how to talk my way into and out of situations, all the cool local tricks, the best places to eat, the best parks, the hidden treasures. I knew what body language meant and what each local reference or slang word really and truly meant. It wasn’t very difficult to be successful.

When I first got to Chile, I was completely lost. I could get around the city, order food, get a drink at a bar, but could barely keep a real conversation. I had to concentrate all the time. I wasn’t myself: I couldn’t be the leader that I was used to.

I didn’t know the culture, I didn’t know what slang meant. Even though most people were very friendly, I really learned what it is like to be an outsider. I wasn’t in on the inside jokes, the turns of phrase, longstanding friendships and so much more. It really made me appreciate how hard it must be to be an immigrant in the US. When people say “immigrants should just learn English” I used to think, yea, they should. But it takes a big effort and it’s not as easy I used to think.

Even after three years, I’m still not truly able to express myself perfectly in Spanish. I’m still not fast enough to make the same jokes I do in English. I probably tell half the stories that I would in English. And the ones that I do tell are half as good as the ones I tell in English! It’s really made me realize what it’s like to be an outsider, or at least someone without all of the built in advantages that I’ve been lucky enough to have.

I certainly miss things. First, my family and friends. In the US I lived my entire life in Milwaukee and Madison and was always within 90 minutes of my family and friends. I miss good customer service. I miss good cheese. I miss being able to listen to every conversation that’s going on around me without actually trying. I miss 250 different beer choices. I miss having a yard. I miss telling an awesome joke with perfect timing. I miss top quality, spicy and flavorful food that doesn’t cost an arm and a leg. I miss my bike. I miss going to northern Wisconsin. Kopps ice cream. Watching all of my favorite sports on a big HDTV instead of illegally streamed on my little computer.

chilean beach

But I can get used to many of the small things because Chile really is an amazing country. I love being close to the pacific and the beach. Amazing seafood. Some great new friends. Playing more soccer. Sun 80% of the year. Being close to Argentina for long weekends. Traveling and exploring in South America. Peruvian food. Pisco sours. Going out dancing. Friends that have taken me into their homes, their families. Asados. The metro. Incredible business opportunities. An amazing $7 bottle of wine. Hearing the entire country scream goaaaaaal, when Chile scores. I certainly miss these things when I go back to the US.

As with all things, there are things that I’ll never get used to. Santiago’s pollution, especially in winter, makes the city just a few notches above unlivable. I’ll never get used to the massive amounts of dust. The classism. The Chilean “two dogs meeting” interview ritual. The rigid conservatism and class structure. Price fixing in big businesses. Going to three separate cash registers to buy an empanada. Waiting in long lines. Customer service reps who flat out lie to you. Living in small apartments. My new expat friends leaving every 6-12 months. So many smokers! Massive inequality and the inability for many people to see outside their own bubble of their own experience.

santiago smog


Chile’s changed, mostly for the better, since I arrived in 2010. My two favorite changes are the smoking ban in public places, plus the crackdown on drunk driving. Both of these laws have made Chile much more livable. I might not even still be in Chile if they hadn’t passed the smoking ban. It used to be terrible!

There are way more foreigners in Chile now compared to 2010. When I first got to Chile people asked us incredulously “why are you here???” Now it’s fairly typical to see foreigners in parts of the city. Rents have gone up 30-100%, depending on neighborhoods. I wouldn’t be here if it weren’t for the ban. There’s been a micro brewery renaissance, with a huge increase in of good beer. People seem to be more accepting of foreigners. Chile has become much more livable over the past three years.

Business-wise, from 2010-2013, the startup scene is completely different. While there were a few successful Chilean startups and entrepreneurs prior to Startup Chile, the program really has changed the mentality in the country. In 2010, people would ask me what I did and when I answered that I had my own business, they’d ask “where do you work” again, then look at me as if I were homeless. Now its cool. Probably too cool. I worry that the country has been sold a narrative of startup rockstars, heroes, gurus and celebrities that when the first round fails might ruin entrepreneurship in the country.

Asech, the Chilean entrepreneurs association, should be the model for the rest of the world. They are a lobby group that pushed through a law that allowed companies to register online in one day, for free. Before it cost $2000+ and took 2-3 months. They’ve convinced banks to let entrepreneurs open bank accounts, which was nearly impossible before. There are way more coworking spaces. More chilean startups and some incredible opportunities.

But there’s still not much funding. Not many Chilean success stories. Big companies and established players still crowd out entrepreneurs. The people with money still generally have an aristocratic yet provincial, anticompetitive attitude that seeks to divide up the riches and keep their place in the economy, not create new innovation and grow the economy. And the new rich still isn’t thinking bigger. The government isn’t helping much by allowing anticompetitive banks and large companies to gouge consumers and price fix.

I used to socially liberal and be very free market: I believed that if you just got government out of the way, economies will work. After being in Chile for three years, I’m even more socially liberal and still generally believe in getting the government out of the way, but my zeal has been tempered.

In Chile, I’ve seen what happens when there’s little to no competition and the government doesn’t really enforce price fixing or monopoly laws or just doesn’t have big enough penalties to stop basically institutionalized price fixing and corruption by large companies. Along with tax structures that benefit those in power to keep their wealth, and be extractors, sucking out wealth from society, rather than creating new, innovation and expanding the economy for everyone.

I have a better realization of what its like to try to move up in the world and how hard many people work for little money. I see what a problem inequality is and can be. People are physically, mentally, emotionally divided. The rich live physically separated from the rest, consuming different entertainment, different food, different clothes, everything. They never meet and talk, which causes misunderstanding, jealousy and a lack of empathy. This phenomenon is happening more and more in the US and I don’t want it to happen after I’ve seen what its like in Chile.

Overall, coming to Chile has been an incredible experience. I’ve learned so much about myself and about the world, made great friends, learned spanish and gotten to explore an incredible country and part of the world. I’m currently teaching entrepreneurship at three universities and working on a two projects that I think have the potentially to be very interesting over the next few months. I don’t know what my future really holds, but I’ll always be thankful that Jesse and I took the risk to come to Chile back in 2010.

Thanks to everyone who’s helped me in Chile, helped me learn about myself and this great country. I couldn’t have done it without you all. A final thanks to my parents, who haven’t demanded that I come back yet.