Expat Interviews: The Happiest Place on the Planet

Today we meet Casey Halloran, a U.S. expat who, after moving to Costa Rica, didn’t guess for one minute the cascading effect that an advertisement in the local paper for “gringo roommate wanted” would have. Ten years later his entrepreneurial instinct, hard work and access to large quantities of ramen noodles have helped him to develop the Number One travel website in Costa Rica. Here Casey tells us what it is really like to live in Costa Rica and describes the three things that you need to live happily in Costa Rica: money, great friends and lots of patience.

Can you please tell us a little about your background and what initially made you move to Costa Rica?

I grew up in rural Pennsylvania and went to university in Virginia. While attending college, I studied abroad a semester in Spain. That’s when I caught the travel bug and love for Spanish speaking culture. Somewhere around my senior year I made up my mind that I wanted to start a business abroad. I graduated and worked one year for a dot-com company (just missing the boom & bust). As soon as I had saved enough money, I made the move to Costa Rica. I expected to work and travel my way around the company doing Internet marketing consulting. I never imagined that 14 years later, I’d still be here.

What were your first impressions of Costa Rica? Did you suffer from culture shock? How did you deal with your initial emotions?

I definitely suffered from initial culture shock. I moved to San Jose, the country’s capital, as that was the only area with somewhat reliable dial-up Internet. San Jose was going through a very awkward phase in the late 90s where there was a pretty brutal combination of construction, congestion and totally outdated systems. It was like living in a busy city, but without any of the perks, like services and transportation. The government has a monopoly on most of the services, so the service was (and still is) abysmal. The whole “mañana syndrome” they teach you about in 9th grade Spanish class is absolutely true. As a type-A person without a whole lot of patience, the different viewpoint that Costa Rican culture has regarding time was probably the biggest shocker for me. It’s also probably what has saved me from having several heart attacks, as I tend to put a lot of pressure on myself. Slowing down is really the only option here. As they say, “when in Rome”!

What are your favorite things about living in Costa Rica?
The weather is absolutely fantastic. As cliche as it sounds, so are the people. Costa Ricans or “ticos” are some of the nicest, most accommodating people you will ever meet. The country is regularly rated among the happiest on the planet and it’s really true. Being surrounded by kind people helps me keep perspective about what it really takes to be happy in life.

What things do you least enjoy?
I think that laid back attitude of the populace can sometimes lead to low expectations from their civil servants. I’m amazed with how patient taxpayers here are with inept government. I realize this isn’t a uniquely Costa Rican problem, but I sometimes think that the government could do just about anything before the locals would really get upset. The crime has risen in recent years and it’s not clear whether the government has a real solution to a problem that is still small, but could get out of hand if not addressed.

What advice would you give to someone who was relocating to Costa Rica for the first time?

Get ready to spend more than you thought. Costa Rica is no longer a cheap retirement spot, nor a tax haven. For some reason, we expats still love it here. Along with more money than you probably thought you’d need, you’ll also need three times as much patience.

While living in Costa Rica you set up your own business. Please tell us what you do and describe how that came about?

That was always my plan, I just never thought it would go so well. I was consulting to various hotels and real estate companies providing web marketing services, when my roommate (a fellow expat) and I had a brainstorming session (most likely over a few cervezas). He was teaching English classes during the day and helping me with some book keeping for my budding consulting gig at night when it hit us: we should start an online travel agency. We did, and Costa Rica Vacations was born. That was 11 years ago. We ran it out of our apartment and worked 12 hour days for around 3 years. With a lot of luck, good timing and a hefty supply of Ramen Noodles we’re the largest in Costa Rica today.

What key challenges did you face when trying to establish your business?
Whew, far too many to list here…but the major ones would be almost zero start up capital, staffing mistakes, ever-changing tax rules and very pro-worker employment laws.

What three top tips can you offer to expatriates who are considering starting out for the first time?
I’d say don’t listen to naysayers. I’d also say get your expenses to the most bare essentials and do nearly every job yourself that you can until you absolutely must hire. As a startup, you have to look at your time as the most accessible resource. Fancy offices and high paid managers can come later. Focus on profits first. From a cultural perspective, I think it helps to be really smart about your first hire, as they will be your guide in the jungle.

What experiences from your time as an expatriate have been most helpful in assisting you with your venture?
Stumbling into other expat mentors was crucial for me. I’ve been luck to have some great ones who were very generous with their time and tutoring. I’ve tried to do the same for others to pay back the good karma. Finding my roommate and future business partner was a lucky break, but through consulting I met a lot of great contacts, many of whom I’m still close with today.

What advice would you give to expatriates about setting up a business?
Utilize your unique perspective as a foreigner as an asset. Don’t be afraid to fail.

What’s next for your business?
We’ve expanded to Nicaragua and Panama in recent years, but I’d like to offer trips to Belize and Guatemala soon. Personally, I’d like to do something totally different in the near future. I’m not quite sure what that is yet, but I am passionate about wellness, tourism and the Internet, so I’m looking for something that might combine the three.

Author: ExpatInfoDesk