We earn commissions if you shop through the links below. Read more

The Journey of Building a Premier Travel Agency with Casey Halloran

Written by:

Carolyn Young is a business writer who focuses on entrepreneurial concepts and the business formation. She has over 25 years of experience in business roles, and has authored several entrepreneurship textbooks.

The Journey of Building a Premier Travel Agency with Casey Halloran

Welcome, wanderlust warriors and entrepreneurial spirits, to a journey behind the scenes of travel magic and business grit! Today, we have the incredible opportunity to unravel the adventures of Casey Halloran, the mastermind behind Costa Rican Vacations.

Casey didn’t just create a travel agency; he crafted a gateway to paradise, stitching together breathtaking experiences, luxurious stays, and tours that make every traveler’s heart skip a beat.

Casey Halloran headshot

But how does one turn a passion for exploration into a flourishing business? What are the highs, the lows, and the wild rides in between? Buckle up as we dive deep into the world of travel, entrepreneurship, and all the bits of stardust that make Casey’s agency a treasure trove for adventure seekers.

Get ready to be inspired and enlightened, and maybe, just maybe, find the spark to start your own entrepreneurial adventure!

Embarking on the Journey

SBS – Can you share the story of how your business journey began? What inspired you to start it?

Casey – I moved to Costa Rica from the United States just after graduation from university. I had only a few skills and even less money. But I was (and am still) passionate about two things: internet marketing and travel. After helping many friends and family plan trips to visit me in Costa Rica, I was inspired to merge my passions and start an online travel agency — way back in 1999, on unreliable dial-up internet, that was a novel idea.

Crafting the Brand

SBS – Choosing the right name for a business is crucial. How did you come up with the name for your brand, and what significance does it hold?

Casey – I am a big believer in utilitarian names. Also, back then, having your target keyword in the company URL was a major factor. So I just picked my main keyphrase for the company name: Costa Rican Vacations.

Funding the Business

SBS – Starting a business often requires capital. How did you fund your business initially, and did you explore any unique financing options?

Casey – I bootstrapped — HARD. I leveraged personal credit cards, worked multiple side jobs, and lived very, very affordably for five years to allow the business to bloom. It required a lot of sacrifice and ramen noodles, but it worked.

Standing Out in the Crowd

SBS – How do you differentiate your products/services in your market?

Casey – Exceptional service, an exceptional, service-minded sales team, and an analytics-led approach to sales & marketing.

A Day in the Life

SBS – As an entrepreneur, what does a typical day look like for you?

Casey – Lots of virtual meetings, 1:1s with my reports, and, if I’m lucky…a few hours for actual work. I live inside my Google calendar, and as I’ve gotten older/wiser, I spend more time deciding what to work on and when. With a wife and two young kids, I put everything on my calendar, including personal life and downtime. If it’s not on my calendar, it’s unlikely to get done.

Overcoming Early Obstacles

SBS – What were the biggest challenges you faced in the initial stages of starting your travel agency, and how did you overcome them?

Casey – The biggest challenge was zero capital. We overcame that by being incredibly frugal, working long hours (mostly unpaid), and keeping the fragile business laser-focused on a very specific, narrow activity for the first few years until it took hold. The bootstrapping phase took about two years and was really hard, but those were some of the most fun and memorable times for the business.

Staying Current and Competitive

SBS – In a rapidly evolving industry like travel, how do you stay updated with the latest trends and ensure your travel packages remain competitive?

Casey – We monitor the landscape frequently, between industry events and regular scanning of keywords via SEO tools. We also read industry reports and subscribe to a few paid newsletters.

Costa Rican Vacations management team

Building Strong Partnerships

SBS – Can you discuss any partnerships or collaborations you’ve established to enhance your travel packages and customer experience?

Casey – Our strongest partnerships are with our suppliers: the hoteliers, tour operators, and transportation folks. These strong relationships, many of which are two and a half decades old, are a big part of our strategic advantage. Those relationships are also some of the most fun and rewarding aspects of the travel business.

Leveraging Customer Insights

SBS – What role does customer feedback play in the development and adjustment of your travel packages, and how do you collect and utilize this feedback?

Casey – Absolutely vital. We have accumulated more than 5,000 customer reviews online. We read these carefully, especially the negative reviews, and adjust accordingly. Because we are a middleman in the service industry, our reputation might be our most valuable asset. So we take reputation management seriously for marketing purposes, but also for intelligence gathering on how we can improve and adapt to add value to our customers.

Understanding the Audience

SBS – Many businesses have a target audience. Who is your primary target market, and how do you tailor your services to meet their specific needs?

Casey – Our target audience is upper-middle-class couples and families in the United States. We design everything with their needs in mind. And a BIG need is to make things as convenient, easy, and stress-free as possible. We emphasize speed, service, and ease of interaction long over debates about pricing and discounts.

Effective Marketing Strategies

SBS – In terms of marketing and promotion, what strategies have been most effective for your travel agency, and how have they evolved over time?

Casey – We lean heavily on SEO and PPC, which has been consistent since our start. The biggest change over time has been a greater emphasis on referral & repeat clientele as ad costs have increased. Fortunately, we’ve built a reputation and a book of business that we can leverage.

Resilience Through the Pandemic

SBS – The COVID-19 pandemic had a significant impact on the travel industry. How did your agency adapt to these challenges, and what lessons have you learned from this experience?

Casey – It was absolutely terrible for almost a year. We had to take drastic measures, and that included downsizing from 100 to 25 teammates. It was an awful yet exhilarating experience in that our team banded together, our suppliers worked along with us, and our customers continued to support us. A few big takeaways are:

  1. Do the right thing — If you did the right things prior to a crisis, your reputation will sustain you through a crisis. That momentum also makes it easier to take the high road in low times.
  2. Ask for help — It’s amazing who’ll show up for you when you need it most. But it helps to ask.
  3. Save for a rainy day — Boy, did this ever help us during Covid. It pays to be thrifty.
  4. Never give up — Probably #1 and seems obvious, but many of our competitors and decades-old businesses folded because their owners got tired of the fight.

I could write a book on this experience, but honestly, I don’t like to think about it too much because it was so stressful.

Advice for Aspiring Entrepreneurs

SBS – For someone looking to start their own travel agency, what advice would you give them regarding building a reliable and trustworthy network of hotels and tour operators?

Casey – It’s quite possibly the #1 most important thing. Your relationships are everything in this game. You need providers who understand it’s a symbiotic relationship that works best if you also share the long view and similar business and personal values.


Leave a Reply

Your email address will not be published. Required fields are marked *

The Journey of Building a Premier Travel Agency with Casey Halloran