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.


  • Nate, it’s a great round up on things in Chile! Although I am yet to discover many things you faced in the last three years you hit the nail right on the head. As an immigrant to the states I do appreciate your comment about making things happen in a foreign country. It doesn’t come all the way sudden and one needs to learn the local culture and eliminate the language barrier. Funny thing, for the last few days I was thinking about writing up some of my experience in Chile. Your article just came on time giving me some brain food:)

    • Thanks for commenting, send me the link when you write you post! I had really under estimated what it’s like to be an outsider before I came to Chile. It’s made me much more empathetic toward people.

  • Great read, I miss Santiago a lot, always love to hear what you’ve been up-to there.

  • You nailed it with the description of our economy and social structure.

    Thanks for the perpective

  • From MK on Facebook: thats a nice read . Though, a serious question, how did you not see real inequality growing up in the US? I find it worse there than anywhere else I’ve been to (not because the gaps are neccesarily the largest – but because I can never wrap my head around how such gaps even manage to exist in the US.)

    • MK, there’s absolutely inequality in the US and its getting worse. everyday the US looks more and more like Chile and other extremely unequal countries. its the biggest problem we’re currently facing. the US economic distribution was historically shaped more like a bell curve, with a significant middle class and fairly smooth differences as you moved up and down the spectrum. the rich and the poor had shared heritage, lived in the same neighborhoods, ate the same foods, consumed the same pop culture. in chile, there’s physical, economic and cultural separations. it’s getting worse in the US everyday.

      Another big difference in the US is that if you do manage to make something of yourself, you can move up BOTH economically and socially. In chile, you have potential to move up economically, but you hit a very low glass ceiling if you’re not from the right starting point, so to speak.

  • You just made a better analysis of Chile than most of chileans will ever make.

    Thanks for everything you’ve shared with us this year in HTBAS!

  • Compadre, la economía de este país fue impuesta por el suyo por una dictadura que no se quiso, la diferencia entre la salud también, cuanta gente que ha tenido cáncer en EEUU conoces? Se queda sin plata, al igual que acá. Quizás sea bueno empezar a aprender a ser inmigrante y ya no del primer mundo como solía ser EEUU. Hoy eres otro más, nadie te va a abrir las puertas como pensaste, lo mismo que allá en el norte, en tu país. Hoy tienes que aprender idiomas, no es malo, sino de lo contrario nadie te va a valorar, amigo, las cosas cambian, tus abuelos nunca pensaron en inmigrar, hoy tu claramente si, eso te hace grande a ti y a tu país, quizás sean más generosos de verdad y dejen de vender castillos en el aire como un disneylandia gigante, eso ya hasta lo más incrédulos no lo creen, si te molesta algo de acá vuelve y compáralo en tu idioma, lo más probable es que te acomode más, a nosotros no.
    Esto es América, lo que viv

    • Nicolas, tu comentario no tiene mucho sentido y dudo que leíste mi artículo. Sería bueno que lo leyeras antes de comentar.

      Compadre, la economía de este país fue impuesta por el suyo a través de una dictadura que no se quiso, la diferencia entre la salud también, cuanta gente que ha tenido cáncer en EEUU que conoces? Se queda sin plata, al igual que acá.

      Sí, estados unidos apoyaba el golpe de estado y a la dictadura, pero no tiene sentido echarme la culpa, nací 12 años después. El sistema de salud en estados unidos es una verguenza (y nunca dije nada sobre el salud en este articulo…)

      Quizás sea bueno empezar a aprender a ser inmigrante, ya no del primer mundo como solía ser EEUU.

      Ya he aprendido. Eso era el proposito de escribir el post.

      Hoy eres otro más, nadie te va a abrir las puertas como pensaste en algún minuto porque “salvaste el mundo”, hoy lo mismo que allá en el norte, en tu país, sin embargo te tratan mejor.

      Nunca pensaba ni quería esto. Comentario muy idiota.

      Hoy tienes que aprender idiomas, no es malo!, de lo contrario lo tienes que valorar, sino nunca lo hubieras hecho (como tanto gringo que lleva años y sin embargo balbucea el idioma nuestro)

      Ya he aprendido. Espero que hables un idioma extranjero perfecto también.

      amigo, las cosas cambian, tus abuelos nunca pensaron en inmigrar, hoy tu claramente si, eso te hace grande a ti y a tu país, quizás sean más generosos ahora de verdad y dejen de vender castillos en el aire como un disneylandia gigante que fue, eso ya hasta el más incrédulos no lo creen

      Mis abuelos inmigraron a estados unidos desde europa. Otro comentario muy idiota, pero lo voy a pelear. Porque es culpa de los que venden? No los que compran un “castillo en el aire”? Yo nunca viviría en un McMansion, pero tu comentario no tiene sentido.

      si te molesta algo de acá vuelve y compáralo en tu idioma, lo más probable es que te acomode más, a nosotros no.

      nunca dije que estados unidos es mejor que chile. hay algunas cosas mejores en los dos. No entiendo porque estás tan defensivo…

      Esto es América, lo que vives acá es lo que se vive en el 90% de los países ql lo más probable. Ven un ratito y se testigo de eso, de como la gente se endeuda se rompe el lomo y paga altas sumas por salud y/o educación, es un sistema impuesto por Uds. Insisto …Gracias!!! Lo queríamos, no para nada, a cambio que…tarjetas de crédito, endeudamiento más autos e imbecilidad…tan lejos de dios y tan cerca de EEUU, como se dice en México 😉

      Ahora es claro que no leíste nada del articulo. Es claro que eres de la izquierda, soy del centro. Es interesante que echas toda la culpa de la situación de hoy a estados unidos y no a tus políticos de la izquierda y derecha que han tenido muchos años de empezar a cambiar cosas que no les gustaban.

  • We just arrived in the latest generation 8 of StartupChile, and this post was excellent reading. In our very limited experience here (we are living within an apartment which is within the compound of a family in Providencia) – much of this echoes the observations and chats we’ve been having. I do hope there isn’t a feeling of exuberance around StartupChile in the way that you describe it. I guess it’s the inevitable path of something pioneering.

    • Welcome. I hope you enjoy your time in Chile!

      I disagree that it’s inevitable in something pioneering. They made a conscious choice.

        • Sorry for the slow comment, I just saw this now. They made a choice to go for numbers over quality and to promote startups as rockstars, superheroes etc rather than tell people the truth about what it means to be an entrepreneur.

  • I can absolutely and completely related to you! I was literally laughing out loud when you said that the salespeople flat out lie to you! SOOO TRUE! haha Or when you ask for directions from someone on the street..they will say oh ya it is this way. And actually they had no idea!

Comments are closed.