How Building a “Business” in a Foreign Country Changed my Life

I found out pretty quickly after college that the 9 to 5 was not for me. I also discovered that wearing dress slacks and collared shirts made me feel claustrophobic and phony. It wasn’t me, and it didn’t feel good to have to wear something I felt terrible wearing.

So when a relationship ended at 24, I quit everything and ran off to Europe with my best friend. The next year marked a monumental point in my life that changed the course of everything.


This friend was Jess Giffin, and the year was 2008.


Together, we had no money. We lived off of Spanish red wine, bread, olive oil and free tapas. The only jobs we could find were in a shady Irish bar run by Russians in the center of Madrid making 3 Euros an hour and working 10 hour shifts (no joke). We said no way, but no one else would hire us without working visas.

So we traveled to Cadiz hoping we could find jobs near the coast. Once we arrived, we found out Cadiz had one of the highest unemployment rates in Spain. No bueno. Our couchsurfing host Nacho, who became one of our good friends, was so kind to let us stay with him while we put together a plan of action.

We recognized a need for Spanish people to practice English in a conversational setting, and since we loved conversing, we decided to promote conversational English practice with two American university graduates.

Nacho let us use his computer while he was at work during the day, and in a week, I had built us a free website (check out this old 2008 design), designed flyers and started an email account. We then bussed it to the capital city of Madrid, where we stayed with other couch surfers until we finally negotiated the price down for one bed in a small room for two months of rent with a guy named Pablo.

One of our kind couch surfing buddies would print our flyers at his work. We would pick them up and start posting them around the city on every light pole and bus stop we came across. Here’s a look at the very first version of our advertisement:

Before long, we had our first student. And then another. And another. Eventually we had a full time job. All the while, we had only 30 minutes of internet time each on the public library computer. The Spanish libraries around Madrid became our offices where we would answer emails from prospective students who had come across our flyer, schedule meetings, research lesson plans, update our website and answer emails from everyone back home in the States.

When we finally started making enough money to invest back into our business in the form of flyers, we became regulars in a small print shop. The owners were three generations of men who chain smoked and stared at us in a funny way when we tried to tell them what we needed in sign language and broken Spanish. We loved those guys.

The Limpieza, or the street cleaners, became a threat to our marketing endeavors because they tore down our flyers on the poles. So we devised a way to follow them down the street as they worked, buying our advertisements more time around the city.

We worked with many amazing people who needed help with their English. A doctor who was giving an important speech at an international convention wanted to make sure he didn’t say something awkward during the cocktail and dinner hour. We worked with many children, who were the best at our language. A girl our age wanted to live in New York, so we would meet her for cidre and answer all her questions about social customs and slang terms in total girl talk. One of my favorite and funniest students was a government official who we would meet in his office. We met many students at their offices, and also in their homes and at bars or restaurants. We were offered a very unique look into the warm hospitality of the Spanish culture.

Jess and I had bought our return tickets before we had even left for Spain, so after three months we went home for the Christmas holiday. However, our little underground operation was so successful that we decided to return to Madrid right after New Year’s. It was December 2008 and it didn’t seem the best time to go home and look for jobs. We also could not imagine going back to the jobs we had before, especially after working for ourselves in a foreign country, traveling and getting to know the inside lives of Spanish students.

It was a highlight of my life, for sure. Jess and I were building something. We had no experience, no credentials, no visas and started it all with no money. We were self sufficient. Sustainable. Proud, fulfilled and super happy.


We met a lot of other native English speakers who were also teachers, but they all worked in language schools. We knew that language schools charged students quite a bit of money, but paid teachers very little. We heard many complaints from these teachers. Jess and I were making good money and the students were paying fair rates. We wanted to share with others how they, too, could build their own book of business.

So we designed a seminar for our fellow native English speakers, put up an ad to invite them to our event in our flat and suggested a fee they would only pay if they felt the seminar was valuable.

We got lots of wine and tapas and busted out the power point to a circle of people. I think one was Irish, another two American and probably an Australian. I can’t quite remember. But I do remember that Jess got drunk because she was so excited and couldn’t stop drinking the wine. I also remember that every person paid the full amount.

And then one day we were walking down the street and we saw our flyer but something was different about this flier. The photo of us was replaced with another girl’s photo. The website listed was almost exactly the same as ours. As soon as we got to a computer we found the website was an exact replica of our website, only it was all replaced with someone else’s information. We recognized the girl as one of the people at our seminar. She sure had followed all of our steps! I would have thought she might customize things a bit, but we didn’t care at that point, because we were already making plans to sell the business and head home.


Despite our success, we wanted to go home. We were ready. We missed our families. Jess had a boyfriend back home (who is now her husband). We were building an amazing life in Madrid, and it would have been easy to continue going down that path, but I think we both knew we didn’t want to stay in Madrid forever, and at some point we had to go home.

So we found an American girl that wanted to take over all of our students, and we created an entire takeover plan on how to roll it all out. On a sunny day in May, we met this New Yorker at a cafe in Sol and over sangria we handed her our baby in the form of student informational sheets detailing every student, their schedules, their levels, etc. In exchange, she handed us money that we put inside the brand new rolling suitcase I had just bought for the return trip home. We walked away from that cafe with giant smiles on our faces and laughed about the cash in our “brief case.” And I think we went and bought nasty cigarettes to celebrate.

We continued to receive installments by check even after we had returned to the states.


Since Jess and I had no jobs lined up for when we got back, and were actually busy planning another business idea to do in San Diego (which never came to fruition), we marketed a Skype class campaign that we could continue back home. We spent that next summer speaking to one of our favorite students, Fidel, from our computer in California. Jess and I would fight over who had to talk to Fidel at 10:30PM each night, and eventually the time difference proved to be too much.

We continued to pursue conversational English practice as a form of income for quite a few months. We held an online class for people around the world in our living room, but I don’t think they thought it was cool when our mail man came to the door and Herbie the dog went ape shit right in the middle of our live class.

Over time, the English thing fizzled out and faded. We went on to other things, and I entered the brokest period of my life. But the lessons I learned from that time in Spain will stay with me forever.

I realized what I am capable of. That I don’t necessarily need fancy credentials or a ton of experience to do something amazing. That I’m happiest when I am creating and building. That the nine to five office life is not for me, nor are dress clothes. And that if there is an idea and a will and some creativity, anything can happy.


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