From Corporate Life to Travel Entrepreneur: Joe Leo on Grit, Customer Service, and Going to Bat for Clients
Success rarely happens overnight. For Joe Leo of JBL Travel Group, it took years of corporate experience, a destination wedding, a side business, a leap of faith, and even a global pandemic to build the travel business he runs today.
On this episode of Grit Won’t Quit, Tom sits down with Joe to talk about his journey from corporate marketing and branding to entrepreneurship, the lessons COVID taught him about serving customers, and why personalized service still matters in an increasingly automated world.
A Destination Wedding Sparked the Idea
Before entering the travel industry, Joe spent more than 20 years working in the corporate world, primarily in marketing and branding. He also traveled extensively, but it was his own wedding that unexpectedly opened the door to a new career.
Joe and his wife wanted a destination wedding in Myrtle Beach. When they couldn’t find anyone who could coordinate everything they envisioned, they decided to do it themselves.
They arranged the hotel, wedding planner, photographer, videographer, transportation, and everything else needed to bring more than 50 people together for the celebration.
The experience went so well that someone at the wedding suggested they should become travel agents.
That suggestion stuck.
When Joe returned home, he and his wife started their travel agency. At first, Joe continued working in the corporate world while building the business on nights and weekends. He gave himself a clear goal: once the travel business could match or exceed his corporate income, he would leave his job.
It took less than two years.
Then COVID hit.
Building a Business, Then Facing a Global Shutdown
Just as Joe had successfully made the transition from corporate employee to full-time entrepreneur, the travel industry came to a near standstill.
Nobody was traveling. Flights were canceled. Hotels closed or changed their policies. Cruises were suspended. Travel businesses across the industry were suddenly dealing with unprecedented uncertainty.
For Joe, the focus shifted from booking vacations to helping existing clients recover their money and navigate cancellations.
But he also made a decision that would pay off later: he kept marketing.
Even though there was little immediate business, Joe wanted his clients and potential customers to know that JBL Travel Group was still there.
He also took a proactive approach before the full shutdown. When it became clear that travel restrictions were coming, Joe advised many clients to cancel their trips early rather than wait until the entire industry was overwhelmed.
For clients who listened, that meant getting their money back before the massive wave of cancellations hit.
It was a difficult period, but it reinforced something Joe believes strongly today: when customers have a problem, they need someone in their corner.
The Value of Having a Travel Advisor When Things Go Wrong
Booking a vacation online can be easy when everything goes according to plan.
The real test comes when it doesn’t.
During COVID, Joe spent countless hours working with airlines, hotels, cruise lines, and other travel providers to help his clients recover refunds and resolve problems.
That experience highlighted one of the biggest advantages of working with a travel advisor: having an actual person to call when something goes wrong.
Joe shared a more recent example involving two clients who became stranded in Cancun after their flight was canceled during a major snowstorm.
Instead of leaving them to figure everything out themselves, Joe contacted the hotel, arranged for them to stay for two additional nights, and worked with the airline to eventually get them home.
Because they had purchased travel insurance, Joe was also able to explain how their trip interruption coverage could help them recover the money they spent on those extra hotel nights.
That’s the difference between simply purchasing a trip and having someone help manage the trip.
Relationships and Referrals Drive the Business
After COVID, travel demand came roaring back. Today, much of JBL Travel Group’s business comes through a combination of social media, its website, and, most importantly, referrals.
Past clients recommend Joe to their friends, family members, neighbors, and organizations.
A successful trip doesn’t just create one customer. It can create an entire network of new customers.
Joe also has a strong follow-up process after clients return home. Automated emails check in with travelers, ask about their experience, and encourage them to leave reviews.
That focus on the entire customer experience has helped JBL Travel Group build a strong reputation and a steady stream of repeat and referral business.
Not All Resorts Are Created Equal
One of the biggest misconceptions about travel is that comparing vacations is simply a matter of comparing prices.
Joe sees it differently.
When someone is looking at hotels or resorts, there are countless variables that may not be obvious from an online price comparison. Room location, service, amenities, dining options, activities, policies, and the overall quality of the property can make a major difference.
The same is true with cruises.
A cheaper “guaranteed cabin,” for example, may mean the cruise line chooses the location of your room. For a family traveling with multiple rooms, that could mean being scattered throughout the ship instead of staying near one another.
As Joe put it, travelers need to compare apples to apples.
A travel advisor brings experience and context to those decisions. Joe has spent 14 years learning about resorts, hotels, cruise lines, and destinations. He also belongs to a large network of travel professionals who regularly share their experiences.
If an advisor hears that a particular resort delivered an exceptional experience, that information becomes part of the knowledge they can draw on when helping future clients.
The Right Vacation Starts With Knowing the Client
Perhaps the most important part of Joe’s job isn’t knowing every destination. It’s knowing the person sitting across from him.
Before recommending a trip, Joe asks a lot of questions.
How old are the kids? What does the family enjoy doing? Is it a honeymoon? A romantic getaway? A family vacation? A group trip? Do they want excursions? Do they want to relax on the beach? Do they care about being near the pool?
Those details help him narrow down the possibilities.
Rather than throwing dozens of options at a customer, Joe typically presents two or three destinations or properties that he believes fit what the client is actually looking for.
That personalized approach helps travelers make a better-informed decision and gives Joe a much better chance of delivering an experience they’ll enjoy.
Travel Trends Are Changing
According to Joe, cruising has seen enormous growth since COVID, with demand nearly tripling compared with the period before the pandemic.
All-inclusive resorts are also a major part of today’s travel market, particularly destinations such as Punta Cana, Mexico, Aruba, and Jamaica.
Joe points out that all-inclusive resorts can provide significant value because travelers aren’t just paying for a room. Meals, drinks, entertainment, and other amenities can all be included.
And today’s cruise ships are becoming destinations in themselves.
Modern ships can include restaurants, bakeries, bars, water parks, sports courts, entertainment, and countless other activities. Joe recently experienced a new ship featuring a pickleball court, illustrating just how much the cruise experience has evolved.
Whether someone wants nonstop activities or simply prefers sitting on a balcony with a cocktail, there’s a cruise experience designed around different types of travelers.
Entrepreneurship Requires More Than a Good Idea
Joe’s journey also offers a lesson that extends well beyond the travel industry.
Starting a business isn’t just about having a good idea. It’s about being willing to do the work that nobody sees.
Joe talks about long days, late nights, social media, bookkeeping, marketing, customer service, and all the other responsibilities that come with running a business.
There’s no boss telling you what to do. There’s no guaranteed paycheck waiting at the end of the week.
That’s why Joe believes anyone considering leaving the corporate world needs to take an honest look at themselves first.
Are you disciplined?
Are you willing to create your own schedule and hold yourself accountable?
Are you prepared to hustle when nobody is watching?
Joe didn’t quit his corporate job on a whim. He built the travel business alongside his career and gave himself a specific timeline to reach his goal.
That approach allowed him to prove the business could support him before making the leap.
Adaptability Can Make or Break a Business
One of the biggest lessons from Joe’s story is that entrepreneurship doesn’t come with a guaranteed formula.
You can do everything right and still face circumstances completely outside your control.
COVID was the ultimate example.
The businesses that survived had to adapt. Joe shifted his focus toward helping existing customers, communicating proactively, continuing to market, and preparing for the eventual return of travel.
He also later adapted his business model by joining the Cruise Planners franchise system.
The additional support helped take some administrative responsibilities off his plate, including website support, social media tools, automated communications, and other back-end functions.
That gave Joe more time to focus on what he considers the most important part of the business: taking care of his clients.
Customer Service Is Still the Competitive Advantage
After 14 years in business, Joe points to one thing above everything else when explaining his success: customer service.
His clients consistently mention the same thing in their reviews.
When they call, Joe answers.
When they have a problem, they can reach him.
They’re talking to a person—not a chatbot.
That’s especially important in travel, where problems don’t always happen during business hours or in convenient locations. A canceled flight in Cancun is a very different experience when you have someone back home helping you navigate the situation.
Joe isn’t against technology. In fact, he uses AI and even has a chatbot on his website. But when someone starts interacting with the chatbot, he wants to know about it so he can step in and help.
For Joe, technology should support customer service, not eliminate the human relationship that makes the service valuable.
AI Is a Tool, Not a Replacement for Experience
The conversation also touches on the growing role of AI in business.
Both Tom and Joe see AI as a powerful tool, but they also recognize its limitations.
Information generated by AI isn’t automatically correct. Travelers can find an answer online or ask an AI system a question, but that doesn’t necessarily mean they’ve found the right answer for their specific situation.
That’s where experience matters.
A travel advisor isn’t simply providing information. They’re applying knowledge, asking questions, understanding the client, and helping navigate situations that don’t fit neatly into a search result.
In an industry where something can go wrong thousands of miles from home, that distinction can be significant.
The Grit Behind 14 Years in Business
Joe’s story is ultimately about much more than travel.
It’s about taking an unexpected opportunity and turning it into a business.
It’s about building that business while still working a corporate job.
It’s about setting a goal, reaching it, and having the courage to walk away from a stable career.
It’s about surviving a global crisis that temporarily devastated the industry.
And it’s about understanding that success is built through the small things customers remember: answering the phone, solving problems, communicating clearly, and going to bat for people when they need help.
Fourteen years in, Joe is still doing exactly that.
His journey is a reminder that entrepreneurship isn’t a straight line. There are setbacks, long nights, unexpected challenges, and moments when the path forward isn’t obvious.
But if you’re willing to learn, adapt, take care of people, and keep showing up, there’s a good chance you can build something that lasts.
Connect With JBL Travel Group
Joe Leo and JBL Travel Group help clients plan cruises, destination weddings, all-inclusive vacations, family trips, honeymoons, and more.
You can connect with JBL Travel Group through its website and social media channels or reach Joe directly at 732-831-5200.
To hear the full conversation, tune in to this episode of Grit Won’t Quit and hear Joe share more about his entrepreneurial journey, the travel industry, and why having someone in your corner can make all the difference.
This podcast episode was filmed at Wingman Planning in Belmar.
