My story starts like many others, and could have easily ended the same way. Like many people, one day I realized that I was living a life I didn’t enjoy.

While in college, I joined a few classmates who had started an online textbook marketplace to compete with the high prices of college bookstores. After graduation I became the Director of Marketing and we spent the next six years turning that dorm room start-up into a multi-million dollar business.

The problem, however, was that I was working long, tiresome hours for a paycheck and someone else’s dream. I was pouring my heart and soul into something I didn’t love.

Before I knew it, the company reached its selling point and I had a big decision to make…

Get another job, and continue on the path to a safe and successful business career, or, drop everything in search of a dream.

I had always wanted to travel the world, dance with exotic women, eat foreign foods, and lose myself in wild adventures.

I had gotten a small taste of that while studying abroad in London, but this time I wanted to do it differently. I wanted to travel deeper, outside the structure of a program or tour group, and really get to know foreign communities on a more authentic and intimate level.

So, In October of 2009, I dropped everything, left my comfortable life behind and took off on a one-way ticket to Buenos Aires, Argentina.

With zero knowledge of the language, a minimal budget and no contacts, I was on a quest to immerse myself in a foreign culture and push my personal limits. It was time to start writing my own story.

I had no idea what I was doing, but my passion for travel and search for substance guided me.

I spent a year in Argentina learning Spanish, bartending at a local brewery, and developing a great community around me. I got hooked on life in Latin America and developed the site monetarily to keep the dream alive.

From Argentina, I mapped out a five-year plan with a mission for each country I wanted to visit…

1. Argentina: Learn Spanish and Find a Local Job in Buenos Aires.
2. Colombia: Learn to dance Colombian Salsa in Medellin.
3. Peru: Learn to cook like a Peruvian in Lima.
4. Bolivia: Help build libraries in Sucre.
5. Guatemala: Work with developing small businesses around the Lake Atitlan region.
6. Brazil: Learn Portuguese and work at the World Cup.

With the help from so many incredible individuals along the way, I was able to turn fantasies into reality and accomplish each goal on my list.

Over the past five years, there have been moments of incredible loneliness, doubt, setbacks and frustration, but I wouldn’t have changed it for anything.

My life is now based on passion instead of a paycheck.

Now it’s time to write the next five-year plan…


With my plan to transform from tourist to townie I should probably share my definitions of the two:

The Tourist – Someone who sees the sites, eats the food and gains a broad understanding of the layout of a particular place. I have been a tourist before and its nowhere near as much fun as being a local. Tourists tell you all about their trip while they rarely step off the tour bus or outside their hostel crew. Tourists you can spot coming from a mile away. A tourist is loud, annoying and lost.

The Townie – A local. A regular. Someone who has been around since everybody else can remember. They have their own seat at the bar and the waitress always asks them if he’ll have “the usual”. He’s the guy who can tell you stories about “the good ‘ol days” and will never let you forget where he came from. I townie is knowledgeable, connected and smooth.

 Frequently Asked Questions 

What are your major life dreams/aspirations?

Besides love, knowledge and financial freedom, I have 14 major, tangible aspirations. T2T will focus on the first 8 (to begin with). check out the list for more details.

    1. Live in a foreign country for at least 1 year.
    2. Learn to speak (fluently) in a second language.
    3. Learn to salsa dance like a latin heartthrob.
    4. Complete a “Great American Road Trip”.
    5. Learn to cook like a chef.
    6. Help a specific cause.
    7. Become versed in a martial art.
    8. Work at the World Cup.
    9. Learn to play an instrument (guitar and/or piano).
    10. Sail the Mediterranean.
    11. Heliskiing in British Columbia or Swiss Alps
    12. Motorcycle across a country.
    13. Run a successful business (that doesn’t run my life).
    14. Be applauded by more than 1,000 people.

How do you finance your travel?

Right now marketing consulting is my main source of income. I’ve worked with Spanish learning programs, medical tourism sites and other textbook companies. I also offer advertising and sponsorship opportunities on the site to help support my travel vices. My slow, long-term travel strategy also helps me keep costs down by staying in apartments instead of hotels/hostels and grocery shopping instead of eating out on the regular.

What’s your dream job?

If a travel show or “Hawaiian Tropics lotion boy” isn’t in the cards, I would love to start something like Room to Read or Toms. My dream would be to to create an organization that is both highly profitable and socially relevant.

What’s your biggest fear?

Being average.




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