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Gareth Leonard

‘‘ I had no intentions of turning this into a career… and on the first night, I almost canceled everything. ’’

By Gareth LeonardNovember 8, 2017

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Hi Gareth, can you briefly describe your YouTube channel to new viewers?

Hello! My YouTube Channel is about “Traveling Deeper.” My goal is to showcase a different side to “travel vlogging” than you normally see these days… I strive to highlight foreign cultures in a meaningful and authentic way. By traveling slower (usually three months to one year in one place), I am able to connect with local communities and experiences to show a different side to most travel videos.

You were part of a fast-growing startup called ValoreBooks. Can you tell us more about this experience and how it impacted your definition of “success”.

Along with a small group a friends, we managed to turn a dorm-room business into a multimillion dollar enterprise with stores in New York, Utah and California. We worked nonstop and my life was dedicated to a payday… the only problem was, it was a business that I wasn’t passionate about.

My life lacked substance.

I learned a million things from my role as Marketing Director, but perhaps the most impactful was what it taught me about myself and what I wanted out of life.

You ended up booking a one-way trip to Buenos Aires. Did you go with the idea to build a travel brand? What was the first night like?

I arrived in Buenos Aires on October 1st, 2009. My plan was to try and live abroad for one-year, learn some Spanish, figure out the next business, and then come home. I had no intentions of turning this into a career… and on the first night, I almost canceled everything.

I sat back, completely alone on my hostel bed, and thought to myself… what the f*$# did you just do? I didn’t understand Spanish, I didn’t have any friends or contacts there. I was completely lost.

Later, I got an apartment (below). Here is one of my videos from nearly 8 years ago!

How many months (or years) of blogging did it take before you developed enough traffic to earn income from the site? How did you support yourself in the meanwhile?

It took me one year to start earning money from my blog. The first way I did was by partnering with local businesses in Argentina on an affiliate basis (i.e. commission for recommending a tour).

Before this became enough to live off, I was a terrible bartender at a small micro brewery in the Buenos Aires neighborhood of Recoleta – which I kept to help me with my Spanish learning.

After your first year in Buenos Aires, you made a five-year plan. Can you tell us more about that?

After Argentina, I was completely hooked on this lifestyle and I wasn’t ready to go back to the “real world.”

I created the 5-year plan to push me further away from my comfort zone and hold myself accountable for accomplishing things I only dreamed of.

The 5-year plan was quite simple. Every year – one new country and learn one new life skill.

  • ARGENTINA – Learn Spanish & Find a Job in Buenos Aires
  • COLOMBIA – Learn Salsa dancing in Medellin
  • PERU – Learn to cook like a Peruvian chef
  • BOLIVIA – Help build libraries with Biblioworks.org
  • GUATEMALA – Small business development with KIVA.ORG

Then I broke down even more specific goals once I got into the country. For example, here were the specific goals for traveling and learning Salsa in Colombia:

It’s crazy to think, but almost all of my 5-year plan goals came true! I guess the one I wish I could do over again is “learn dance Salsa in Colombia” – because I tore my ankle playing basketball in Medellin and couldn’t dance for a month while living there.

I also listed out the goals for each of the other 4 countries here.

How was the experience working with Kiva? What were the biggest pros and cons of working for a non-profit organization.

I had an amazing experience working for Kiva because it gave me an excuse to work with a local organization in Guatemala, and meet people I would have never had the opportunity to cross paths with otherwise.


The biggest pro and con are actually the same in Kiva’s case… and that is, they were very organized, and had many checks and balances in place. This is great for those who needed the guidance, but it also limited freedom sometimes.

From all of the countries you visited, what are the Top-3 most memorable experiences?

1. Working at the World Cup in Brazil

2. Helping out in a village after the Nepal Earthquake

3. Diving with thousands of seals off the coast of Tasmania (alone)

When you travel for a living, do you get numb to the “next” new experience/destination? How do you keep travel exciting for yourself?

I have definitely caught myself on a few occasions not appreciating the moment I am in. The best solution to this issue for me is by surrounding myself with people who are new to the experience as well or who provide a unique local perspective to add a deeper meaning.

Also, reading and writing has helped me be more aware and present.

What is the last book, podcast and YouTube channel you have forwarded to someone?

Celestine Prophecy

What’s the worst advice you hear being shared often?

You can’t live your dreams.

What’s next for you (and your channel)?


Trying to go deeper – my goal is to tell more authentic travel stories and push the originality and creativity in my content. Travelwise, it’s off to the Philippines in January!

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  • Ansel John

    I am gonna say that find this great one article useful when was busy in https://www.topbustours.com/day-trips-local-tours-from-washington-dc/. I like this great sharing and love to say all keep sharing like this more.

  • Risto Raisanen72

    Good write up gareth. Also think the reverse is true too. Learn skills at home, so that you can do it another country as well. Scuba has taken me to many parts in SE asia.