Josh Alexander: From Lawyer to Advisor

By Matt Turner Apr 5, 2018 9:54am

After using a Virtuoso advisor to plan his honeymoon to Africa, Josh Alexander, now of Protravel International, realized the value that a luxury travel advisor provided. At the time, he was practicing law in New York and New Jersey, but he was unhappy and seeking more from life. Things changed when a friend gave him a list of five travel agencies and people to speak with who could teach him more about the industry.

Alexander got in touch with Jonathan Epstein, who is president of Celebrated Experiences and very familiar with the world of luxury travel and travel advisors, and the two brainstormed for a bit. It was Epstein who gave Alexander the final push to speak with Priscilla Alexander, the founder of Protravel International. His pitch to this luxury travel icon? That travel needed to get younger.

“I had noticed that the travel industry had an identity crisis and was trying to get younger, and I knew that it had a wave of younger consumers that was about to hit, but it didn’t really know how to address those types of clients,” Alexander says.

He says that Priscilla Alexander (the two are not related), at first, didn’t understand why a lawyer would want to drop everything and start a new career. However, she clearly understood the need at the time for the industry to welcome younger people and to embrace those with professional background from other industries.

She also identified with his approach to running a successful business.

“She recognized that there were two basic principles: If you have a network and you have a great work ethic — you’re decent in business, you have the drive and you want to put in the time to learn the business — you can go far,” he recalls. “I knew that with a lot of hard work and hustle I could tap into my Rolodex of clients, build up a client base and open a business.”

In 2010, Alexander joined Protravel as an independent contractor. In the eight years since, he has added three employees to his management team and is on pace to pull in more than $10 million in sales this year. He was just asked to be a member of Aman Hotels and Resort’s newly created advisory board, and is part of Marriott International Luxury Brands’ Celestial Club, which he’s been a member of for the past two years. Alexander was also recognized by Four Seasons as one of their top 10 producers globally for 2017.

Gail Grimmett, the current president of Protravel International, says that Alexander’s passion for travel shines through in all that he does and that makes him an exceptional travel professional.

“Josh has built his business through extensive product and destination knowledge and superior service,” says Grimmett, who heads up Travel Leaders’ Luxury Brands. Travel Leaders now owns Protravel, and includes the agency, along with Tzell Travel Group, Andrew Harper Travel and Colletts Travel under its Luxury Brands umbrella.

“He takes the time to know each of his clients’ preferences in depth to ensure he creates trips that are aligned and tailored on an individual level. Most importantly, Josh devotes hours of time, educating himself on destinations, properties and activities within each region of the world,” she says, adding that Alexander has built significant relationships with hotel GMs, supplier representatives, ground operators and restaurateurs to ensure his clients get great advice and VIP treatment.

Priscilla Alexander took a shot on Josh Alexander when he first entered the business.

Keeping Busy

Alexander’s business is off to a hot start in 2018, with January being his busiest to date “by far.” January is typically strong for bookings because it’s a great opportunity to capture the people who just returned from their holiday trip. If they enjoyed the trip, they’re almost always very eager to start planning again. It works the other way, too. If the vacation wasn’t stellar (usually because the clients booked too late, Alexander says), it’s a great opportunity to pitch them on their next holiday vacation in advance so they have more selection.

Alexander tells us he doesn’t have a specific niche other than “luxury,” when it comes to selling travel. “I’m always hesitant to answer that because clients might be making a psychological judgment,” regarding whether they feel he is the right fit for them.

He reveals that he does know Africa, Europe and the Caribbean very well, and that if he did have a “specialty,” it could be honeymoons. That’s because his personal circle: His brother- and sister-in-law, and many of his colleagues and close friends were getting married when he first became an advisor. That gave him direct access to a network of potential clients who just happened to be booking honeymoons. In fact, within the first two month of opening shop, Alexander was able to book several $20,000 honeymoons to Asia, which helped him get his footing — in addition to some notice from Priscilla Alexander. “Once I did a successful job, those people then referred me to their friends and family, and it sort of took off,” he adds.

According to Alexander, honeymoons are a great specialty for a luxury leisure travel advisor since clients are more likely to splurge on that trip more than they would on any other. “They want to stay in the nicest places, and unlike some trips where people might want to cut corners or be more budget-sensitive, it’s a great way to potentially upsell,” he says.

Along with honeymoons, come destination weddings, and Alexander at press time had clients tying the knot in a castle in Northampton, England, creating large opportunities for expanded itineraries. Since the majority of the guest list was from California, they used the trip opportunity to explore more of Europe.

With a large number of honeymooners, the Zika virus over the past year did pose a small threat, according to Alexander; however, the result was more often rerouting than cancellations. “People felt that they could control the threat of Zika,” he says. If it was a matter of clients who were or planning on being pregnant, they would simply avoid the impacted destinations.

As for other potential threats, such as terrorism and natural disasters, Alexander says travelers are more resilient than they used to be, and that these haven’t stopped his clients from booking trips.

Another recent travel concern is the water crisis in Cape Town, South Africa. Alexander has nine bookings for the destination but isn’t deterring anyone from visiting. He has informed his clients about what’s happening in the area, what the hotels are doing to help and anything else they might ask about, but he also reminds them that tourism is one of Cape Town’s largest sources of income. So far, no clients have cancelled or altered their trip, but Alexander has precautionary solutions in place; the wine region operates on a separate water system, for instance.

Planning for challenging issues is one thing, and then there are unforeseen circumstances that force itinerary changes on the fly. For example, at the time of this writing, Alexander had happy clients enjoying a villa in St. Barth’s and were looking forward to rebooking the space for a few weeks during the holidays.

But the trip wasn’t always all smooth sailing.

The client — a hedge fund manager — and his family of two young kids, two adult children, a personal assistant, a nanny and an IT employee, had plans of visiting St. Barth’s for five weeks between Thanksgiving and Christmas but because of Hurricane Irma, the vacation had to be scrapped. The client put the trip off and decided to tack it into the end of a weeklong trip to Uruguay, where he and his family stayed at Bahia Vik Jose Ignacio.

One challenge arose when the client’s IT equipment (he has an employee who always arrives at each destination in advance to set up his work space) exceeded weight restrictions on the flight, so Alexander instead had it sent via courier from Buenos Aires to Punta del Este.

Exploring the world: Jack Ezon of Ovation Vacations; Sally Strange of NoteWorthy; Josh Alexander of Protravel and Michael Holtz of SmartFlyer outside St. Paul’s Cathedral in London.

At the end of the week, the client and his family were supposed to fly from Uruguay to Miami to St. Martin to St. Barth’s. At the final destination, they were to be met by a new IT employee, as the first had to return home to his family. Two days before the second IT employee was set to arrive, his hotel caught fire. Alexander had to scramble to find him new accommodations before the client arrived. And then a family emergency called this IT employee home. Alexander had to find plane tickets to St. Barth’s for a third IT employee, who would be traveling with entirely new computer equipment (Alexander tells us he had to book him extra seats on the plane to fit the equipment).

To boot, the day before the client left Uruguay, construction on St. Barth’s knocked out the island’s Internet forcing Alexander to call villas in Anguilla and St. Martin, looking for a short-term solution. The managing director of Eden Roc St. Barth assured Alexander that the Internet on property would be up and running by the time everyone arrived, and that his client could set up shop in the hotel’s conference room.

“It wasn’t just one e-mail, as you can image,” Alexander says. “That’s why a great team behind me is so important — so when I’m dealing with these major issues, which the client wants me to deal with, I have my team working on other projects.”

Ultimately, in the end, his client was happy, and that’s all that matters. “All the hard work pays off,” he says.

When bringing on new customers, Alexander now vets them — something he didn’t do when he first became a travel advisor. “My mindset was just wanting to hustle, and never say, ‘No,’” he says. But he’s now realized how valuable his time is and is now selecting his clients more carefully. He tells us he doesn’t have a set minimum budget across the board required for a booking, but that he does have a minimum budget depending on the trip — for instance, $1,000 for a weekend in Miami would make sense but a safari to Africa for the same price isn’t as plausible.

“I want to be sure they have realistic expectations and that they’re not going to waste my time,” Alexander notes.

While most of his clients are located where Alexander is based, he does have clients across the country. He tells us he’ll use e-mail only for quick correspondence with clients, but never for the details.

“I believe that travel is about details, passion and excitement. I’m always amazed when people are willing to spend $20,000, $30,000 or $40,000 on a trip but they can’t find time to speak to me on the phone,” Alexander says. “I’m happy to supplement that phone conversation with an e-mail, but there’s no better way than a phone call to convey not just important details and logistics, but also excitement and passion about a destination or a hotel. Some people would say that’s old-fashioned.”

As for his relationship with suppliers, Alexander says he prefers to work with one for each destination; that’s narrowed down from two to three for each, just a few years ago. It’s all about “relationships, relationships, relationships,” he says. On the occasion that a client is torn between two hotels, they will ask him which he has a better contact at. “It shows the power of real, genuine connections,” he says.

The Power of Mentoring

When Alexander first came into the industry, Priscilla Alexander matched him with Joshua Greenberg, who has been selling travel since 1996. “With no stake in it for him, he agreed to mentor me, and I learned a lot of the basic skills that have helped me grow my business,” he says.

For that reason, Alexander has been a big advocate of a mentoring program since becoming an advisor. One of his goals is to help bring younger people into the industry. Some of the bigger issues he sees? “There needs to be more support from the agency side on education, and from a personnel and financial level,” he says.

“I really want to be part of a mentor program — because people took a chance on me and invested in me. And if they didn’t, I can’t say I’d be here talking to you today,” Alexander tells Luxury Travel Advisor. He says such a program is coming in to fruition at Protravel.

“I want to pay it forward and be able to teach younger people the business,” he says. “And not only do I want to teach them the business, but I also want to show them how you can really make a career out of this. I’ve also tried to encourage other established colleagues of mine to take on the role of becoming mentors.”

While incoming advisors are being trained, Alexander believes they need to be given a salary and a smaller commission until they learn enough to become independent. His reasoning is that you may sell a big trip to a client but if it’s one year in advance, you might not receive the payment for that trip until 12-plus months down the line. “People need to have a roof over their heads and they need to pay their bills,” he points out.

Alexander’s advice for new advisors? “Hustle.”

Josh Alexander, with his wife, Nicole, two daughters (Hazel and Harper) and Duarte Bon de Sousa, GM of Chateau Saint-Martin & Spa in Vence, France

He did just that to garner new clients. With the help of Protravel’s marketing department, Alexander created a one-sheet explaining the benefits of a travel advisor. “I sent that out to every single person that I had an e-mail address for,” he says. His mindset was that it was a numbers game — if 10 percent opened it, and 3 percent replied, and even if only a few of those actually resulted in bookings, that it would be a start.

He says that Protravel has afforded him much more than the one-sheet that helped him get started. “There’s an incredible management team to help assist the ICs grow their business,” he says. Falling under the umbrellas of both the Virtuoso and Travel Leaders networks, Protravel has a very wide range of amenities and benefits that Alexander can offer his clients. Alexander tells us he has considered the possibility of opening his own agency (“One day that might be a goal,” he says) but right now, Protravel offers so much that he’s more than content staying put.

Either way, it’s night and day compared to his past life in law, Alexander says.

“Law was never a passion,” he tells us. “I was good at it, but it was so monotonous, not fulfilling…I was very unhappy, and I wanted to make a bold career change.” While he wasn’t exactly risking everything by leaving law, as he could always fall back on law, it was something he never wanted to revisit, which is why Alexander tells us “failure wasn’t an option” when transitioning to travel.

He does admit, however, that there are some positives from his time spent as an attorney: Being client-based, detail-oriented, having thick skin, and being able to solve problems are all skills that were transferrable to his travel advisor business. “While I wasn’t happy as a lawyer, now that I look back at how my life and career have played out, I don’t regret it because I think that the hardships that I encountered and the skill set that I developed helped me transfer into how I now approach travel,” he says.

Having a career that he truly now cares about has made all the difference in his life, he says.

“I wake up and I learn something new every day,” says Alexander. “I’m passionate about what I do, and that’s carried into my personal life and my relationship with my wife and my children. The happiness, the pleasure and the satisfaction that I get out of this job beats the hell out of being a lawyer any day.”