I first met David in Medellin a little over a year ago. He wasn’t yet in the country much longer than I was, but seemed to know the entire expat scene (in the couple times we hung out he was constantly running into groups of gringos that he knew).

His love for Medellin helped make him the go-to guy for advice on the city, which he shares on his popular Medellin blog. I used him a couple times when I needed fresh ideas for where to take girls on dates.

Right now he’s back in Medellin, subsisting on income from his internet properties. He took the time to answer some questions…

1. Can you give us a little background on your age and the type of environment you grew up in? What are some things that influenced you earlier in life that put you into the position you are in now?

I recently turned 34, and by all accounts, grew up in a stable, upper middle class American family. My parents have been married over 35 years. My mom stayed at home with me and my younger brother, while my dad, a businessman, worked hard to provide a comfortable standard of living for us all.

I began listening to punk music very early. By age 10, I can remember owning a Sex Pistols tape. In my early teens, I was listening to bands like The Dead Kennedys and Suicidal Tendencies. By my late teens, I was getting into the California bands like Pennywise and NOFX. Even though I was very introverted and reserved growing up, the lyrics by these bands and others affected my developing attitudes toward how a guy should live his life.

After college graduation, three of my best friends were planning to travel around Europe for the Summer. It seemed like a great opportunity, so despite my parent’s protests, I joined them. It was my first time traveling abroad without my parents, and I quickly learned how easy it was to find a place to stay, meet other travelers, and get around. After about 10 days, my friends all wanted to go home due to lack of funds, or girlfriend withdrawal. I thought they were crazy, and since neither problem was an issue for me, I spent the next 6 weeks traveling on my own. Despite some loneliness, I had an amazing time, and was officially hooked on the freedom that backpacking and solo travel afforded.

2. Talk about your ideal girl. What does she look like? Where is she from? What’s her personality like?

img-1785088729-6a664ad99f5ad0.53435975.jpgThe more time I spend outside the United States, the more I realize my ideal girl is from a European or Latin American country. I love to travel, and discovering new cultures through relations with women is a lot more exciting than talking to taxi drivers and walking around a city with other backpackers.

Right now, it’s safe to say I’m smitten with the women of Colombia, where I’m currently living. Here, my type is the norm: a few inches shorter than me (I’m 5’8″) or equal in heels, with tan skin, long black hair, and a petite body. She doesn’t speak English, which forces me to improve my Spanish. That provides a fun, sometimes frustrating dynamic to the dating experience. She’s dependable and punctual, which seems to be a rarity in Colombian women, and is pursuing her own passions in life. We absolutely must connect on the dance floor, as it’s a big part of the nightlife here, and an activity I can’t get enough of after being a wallflower all my life.

One of the downsides to Colombian women (who don’t have dual citizenship, in say, the USA), is that travel is very difficult and expensive for them. Since traveling and living abroad is extremely important to me and my work, I don’t know if I could ever be in a long term relationship with a Colombian girl. In that respect, Western European women (French, Italian, Spanish) become a more attractive option.

3. What type of game do you run? How does your typical bang go down? How do you change your game when you’re abroad versus in your home country?

I began reading and practicing game in early 2009. I was a member of the Stylelife Academy for about a year, and was able to connect with other guys in the Washington, DC area to go out with. My game is the antithesis of cocky/funny. If there’s such a thing as “sincere” game, that would sum up my approach. Early in conversation, I focus on highlighting my travel experiences and independent lifestyle. Ideally, a first date will be at a salsa club where I can DHV, gauge her attraction via body language, and be in an easy position to go for the first kiss.

In the USA, I find Internet dating to be a waste of time. It requires far too much effort, and offers too little in return. By comparison, in Colombia, I can copy/paste the same message to a hundred attractive women, and get enough results to keep me occupied for months. The interested ones respond back with their phone number or e-mail address, as if to say “let’s cut to the chase.”

As other interviewees have already mentioned, I’ve discovered in Colombia that it pays to line up dates via the Internet before you visit a new city. I think this strategy will change how I travel going forward.

4. Describe your travel experiences and strategy. What kind of lodgings do you stay in? How do you approach integrating yourself into a new culture with regard to food, language, local customs, etc.? What do you fill your days with? Do you have a basic strategy for meeting women while you travel?

In November 2007, I resigned from my management job at an insurance company to take a 15-month trip around the world. I visited over 20 countries on 5 continents, staying in a mix of hostel dorms, beach bungalows, cheap hotels, and private homes via Couchsurfing.

When I got to Medellin in early 2009, and decided to stay for 6 months, I spent the first month living in a party hostel which was terrible from a logistical standpoint. Even with a private room for part of the time, I wasn’t allowed to have overnight guests. Once I made the switch to renting rooms in apartments, I didn’t have to worry about such rules. If I’m traveling to other parts of Colombia, I pay more for private, budget hotel rooms. I do this not only because it makes it easier to bring a girl back if the opportunity arises, but because I’m getting tired of the hostel scene and like to have a quiet, comfortable place to work.

Until I got to Colombia, I put little to no effort into learning other languages because I was always just passing through, and it’s easy to rely on English, or simple body language to communicate. In Colombia, I began to learn Spanish, and am being rewarded with more dates as a result. Couchsurfing has been a great way to see cities and cultures from a local’s perspective. Trying new foods has become an increasingly important part of my experiences, and I’ve been greatly influenced by Anthony Bourdain.

While traveling, my days are filled with typical sightseeing activities. During my RTW trip, I spent more time than I expected updating my blog at Go Backpacking. I was earning a few hundred bucks a month from advertising, but that kept me motivated to publish content 6-7 days a week. While living in Medellin, I spend a lot more time blogging/working in my apartment, and fill my free time with the gym, salsa lessons and dancing, movies, and hanging out with friends. In the countries I visited before Colombia, I was always trying to hook up with other travelers, but that changed when I got to Colombia and my attention was focused squarely on the beautiful locals.

5. How do you make a living? How did you get into it? What are some skills you had to learn?

I currently make a living through travel blogging. My primary blog is Go Backpacking, while I began Medellin Living last year to document the expat lifestyle in Colombia. I also launched a membership website, Travel Blog Success, earlier this year to help other people build high quality travel blogs. Most of my income is from selling advertising on the two blogs, though I am beginning to offer private consulting services as well.

After my first trip to Europe in 1998, I returned home and taught myself basic HTML so I could publish my handwritten journal on the Internet. After people actually started reading the thing, and emailing me for advice, I bought the GoBackpacking.com domain and added more content. I even made a few hundred bucks from a Eurorail affiliation at the time. But creating an HTML site wasn’t fun or easy, so I went on a 5-year hiatus, before getting into blogging in 2007, ahead of my RTW trip. My friend had convinced me there was money to be made, and he was right. In addition to knowing some HTML, learning how to build websites using WordPress, write effectively for an online audience, and optimize content for the search engines has been important. I’ve also learned a lot about negotiating with advertisers, leveraging social media to build a brand, and Internet marketing.

6. What are your future goals? How do you see your life playing out in the next 10-20 years?

I’m currently planning to spend New Year’s in Tokyo, Japan, and then see a little of the country in early January 2011. Afterward, I’d like to address some business-related needs back in the US, and then return to Medellin for another 6 months. Starting in July 2011, I’d like to see the rest of South America. In terms of my online income, my goal for 2011 is to average $5,000 per month which means I’ll need to do more work, and less partying.

In the next 10 years, I’d like to continue splitting my time between traveling and living abroad in a variety of countries, such as Brazil, Italy, and France. I’d also like to be earning six figures from my web business. Along the way, I’d get married, and maybe have a kid or two.

7. Tell us more about Colombia. Why are you drawn to the country? How are the women like? How is it like to live there? Has the country changed your opinion of America, either the culture or the women?

Colombia as a travel destination first entered my mind in May 2005 when I met a Swiss backpacker in Costa Rica who had been there. He said it was safe, and the women were beautiful (specifically, they had big tits). From that point forward, I was determined to get there to see the women for myself, and also to go somewhere everyone else in the world deemed too dangerous.

In January 2009, I couchsurfed with a cute university student my first week in Bogota, and as she took me around the city, I began to realize most Colombians were normal, well-intentioned people. It helped that I wasn’t being shot at or kidnapped either. When I flew the 25 minutes to Medellin, I immediately knew I was in a city I didn’t want to leave. Medellin sits in a valley 1,500 meters above sea level, surrounded by big green mountains. A metro system and cheap taxis make getting around the city easy, and the temperatures are Spring-like year round. For a city of 2-million, it has a small village feel to it.

In the 30+ countries I’ve seen so far, there have always been beautiful women, though some have far more than others (sorry Rwanda and Nepal). For me, the typical Colombian girl is the sexiest. She’s very image conscious and thus takes care in her appearance, whether at the gym or a nightclub. She displays a sense of femininity that seems lost in American women. Chances are she has a good sense of rhythm, and can dance well. Unfortunately, they have strong jealous streaks, and are also very flaky, and far less punctual than American women. And while I’ve come to expect it, I still get annoyed.

8. What’s the most important thing you’ve learned so far in life?

Have the courage to pursue the kind of life you want to live—follow your passions, regardless of what others say, and don’t give up. Chances are it will take a lot of hard work, patience, and persistence, but it’ll be worth it.

David maintains two travel blogs: Go Backpacking and Medellin Living. Read other lifestyle interviews here.