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“The biggest things we did right were a total focus on web marketing, hiring slowly and finding really good quality human beings to work with us, listening to our early customer to craft a service that met their needs.”

Founded in 1999, Vacationscostarica.com has grown from a 2 person startup to becoming Central America’s largest online travel agency. They offer unique, customized vacations to Costa Rica, Panama and Nicaragua. Their clients choose them for their superior in-country knowledge and outstanding service before, during and after their stay. From the moment they meet their customers at the airport until they leave, their team is on-call 24/7.

MO: Can you talk a bit about the journey from growing from a 2 person startup to a multi-million dollar organization with minimal startup capital or outside investment?

Casey: It was definitely an uphill battle but my partner Tony Silva and I look back upon the journey fondly. We were very fortunate in our timing; Internet marketing was still a fairly novel concept in Costa Rica back in the late 90s and since that was the only thing I really knew how to do, we decided to pull all of our advertising eggs in one basket. That meant a total focus on search engine optimization and a really cutting edge technique (at the time), cost per click ads. We were lucky to ride the wave of three very big trends:

1. The growth of the Internet as a marketing platform

2. Increasing interest in Costa Rica as a tourism destination

3. A monster bull market in the U.S. (2002-2007)

While we did a lot of little things right, I think we’d be remiss in not mentioning the fact that we were in the right place at the right time. Of the factors within our control, I’d say the biggest things we did right were a total focus on web marketing, hiring slowly and finding really good quality human beings to work with us, listening to our early customer to craft a service that met their needs and investing every dollar, minute and spare thought into building a great little business.

MO: When did you know the business was going to be a success?

Casey: I am still waiting to know! In all seriousness, I’m not sure I ever feel like we’re 100% “out of the woods” so to speak, but if there was a moment that I thought we’d moved on from being a hobby business to a viable concern it would be when we invested in some serious technology to run our operations. Once we had a high-tech, web based CRM software in place, the wheels were greased for0 growth. We posted some explosive growth years in 2004 and 2005. After that, providers and competitors took notice and some new doors opened for us.

MO: Startups typically need to pivot and evolve their business model over time, especially as customers start to use the product or service. Can you provide some advice or lessons learned to entrepreneurs on pivoting while keeping your business moving forward at the same time?

Casey: There have definitely been several key moments in our business when we needed to make pivots, large and small, in order to stay alive. It unfortunately becomes more difficult as a business gets larger, older and more stuck in its ways. The risk to change becomes greater and greater when there is more to lose, but we’ve done our best to retain some elements of a startup in our culture with the hope of not becoming so inflexible that we go the way of the dodo. My biggest advice to any entrepreneur would be to always retain some of the “nothing to lose” attitude you had when you started your business so that you’re open to change when necessary and also so that you still have fun in your own workplace. If it all becomes about dollars and cents, and year over year growth, you probably won’t stay motivated. Change is terrifying but also very exciting and gratifying.

MO: What advice would you give to a family considering a vacation in Central or South America?

Casey: I think it’s a wonderful place to visit as a tourist. Some destinations are definitely more family-friendly than others and each of the many countries in Latin America have something unique and wonderful to offer. As far as living abroad here, I would definitely recommend visiting several times on extended stays before even considering permanent relocation. Life in Latin America is very different and it’s not for everybody.

MO: Can you elaborate on the importance of constantly improving your technology to stay ahead of the competition?

CaseyI think that there are only a few things that allow businesses to remain relevant for long periods of time: serving customers, investing in people and technology. Investing in technology is crucial for creating operational efficiency, which results in margins. Margins permit a business to hire great people and deliver exceptional service to clients. I think all of those things are vital, but tough to achieve if you haven’t invested in technology.

MO: How do you plan on keeping the momentum going?

CaseyThe start of our second decade in business has presented very different challenges than the first. Keeping the momentum going at this point I think depends very heavily upon keeping our key players motivated and stoking the passion that our executive team has for the business. At our size, poor decisions and mistakes have a far more significant impact, so the tendency is to be much more cautious and move more slowly. We are working to balance the need for caution and profits with the need to take risks and innovate. It’s a challenge that every mid-size business faces, but I believe we’re on the right track to endure another decade in a very competitive environment.


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