Pleasant Holidays has announced that its president and CEO, Jack Richards, will retire at the end of January next year, with longtime travel industry executive David Hu taking over as the tour operator’s president and CEO on Jan. 1, 2025. Richards will stay on as an advisor for a month, before his official retirement on Jan. 31.
Richards has worked for 46 years in the tourism business and spent 17 of those at the helm of Pleasant Holidays, during which time he helped transition the company from a largely Hawaii-dependent organization to a global tour operator that now sells products in more than 80 countries.
Prior to joining Pleasant, Richards was senior vice president of marketing and strategy for Hotels.com and Expedia, and earlier in his career, he held C-suite positions at America West Airlines in Phoenix and Adventure Tours USA in Dallas.
TravelAge West caught up with Richards to look back at his more than four decades in travel, discuss why he felt the timing was right to retire and ask what he sees ahead for travel advisors.
How did you get started in tourism?
My very first job out of college was in the travel business. … I found this classified ad that read, “Would you like to travel the world? Call us.” And I did. … It was [at] an airline that also had a luxury division that took groups all over the place, and my job was to plan and execute the trips for these groups and then go with them to make sure everything went well. So, I would take groups all over the world. I would spend two weeks in Hawaii. I would spend the winter in the Caribbean. I would go to Mexico. I would go all over the place, and that was great.
Was working in travel an early goal for you?
I got my advanced degree in international relations and foreign policy. I wanted to be a diplomat, and I figured the best way to do that is to start traveling the world. But I did not know that I would get the travel bug and the wanderlust, and it would last a lifetime. I mean, it lasts even until today. The wanderlust to explore the world is still with me 46 years later.
The wanderlust to explore the world is still with me 46 years later.
You’ve seen a lot in the tourism business since you started. Are there some events that stand out?
Do you know what day I was promoted to president and CEO of the airline vacation division [at American West Airlines]? Sept. 10, 2001. … I remember waking up and getting ready to go to work, and on my very first day as president and CEO of the vacation division of the airline, I said to my wife — as I watched an airplane going into the World Trade Center — “My career will be brief.” Then, of course, everything shut down, and [it] almost put the airline in bankruptcy, and it was just absolutely horrible. And then, not all that long after they recruited me to come work here at Pleasant Holidays in 2007, we immediately went into the 2008 financial crisis.
I have weathered three major crises in the travel industry during my career, and I will tell you that there will be another one. There always is. And it's how you deal with it that really defines you. But the pandemic, by far for me, was the single most challenging time I've ever had in the travel industry, because there was no ending date to that. I think we knew that the financial crisis would pass. I think we all knew that 9/11, after the dust settled, the airports would reopen and [travel would resume] in a certain period of time. But with COVID-19, you just had no idea when it was ever going to get better. And it dragged on for an inordinate amount of time.
Are there some Pleasant Holidays accomplishments you’re particularly proud of?
I was on the job about 90 days, and the CEO of the parent company said, “You need to put together a five-year strategy plan for Pleasant Holidays and send it down to us to look at.” Hawaii, at the time, represented 80% of the total revenue for the company. So, I identified that as a red flag, telling the owners, “Look, although Hawaii's been very good to the company over the years, if Hawaii catches the flu, we get sick and die.”
I don't ever see a day where we don't have travel advisors.
So, we needed to develop a plan to expand this company globally … to diversify revenue and reduce the risk of [relying on] a single destination. We needed to broaden out. And I listed all the destinations I wanted — Costa Rica, Las Vegas, the Caribbean, all of the destinations in Mexico, all the destinations in Asia, all the destinations in Europe, all the destinations across the U.S. and in Canada. And I just went on and on and on. And today, we have added every single one of those destinations that I outlined in 2007. We're now in 84 different countries worldwide. In fact, we just launched Roatan, Honduras, and in the first quarter, we'll launch the Philippines. So, we're going to continue to expand.
Why do you feel like the end of January is the right time to retire?
I contemplated this in January of 2020, and I was in conversations with the parent company about moving forward with a succession plan at that time. And lo and behold, the pandemic hit, and I just could not walk away from the company in a crisis mode. So, I didn't. I waited, I stabilized the company, did all the bad stuff that had to be done during the pandemic to stabilize the company and then get it rolling again. And then once we started coming out of it, we started expanding again and really, quite frankly, that was a lot of fun. I really enjoyed it. But the company is now in a position where I've accomplished everything I set out to accomplish. The company is financially stable. The company is growing, so it's a great time to go.
What role have travel advisors played in that success?
Travel advisors account for well over 90% of our business. We're not going to change that business model. They're important. They're good people. Their average transaction with us is much higher. So, we will continue to partner with travel advisors going forward.
You know, during the pandemic — when we had the time — we installed technology to identify home-based travel advisors and independent contractors. And today, we are tracking more than 50,000 home-based travel advisors and independent contractors who transact business with us today. That is a huge change for us. When we saw those numbers come in, we went, “Oh, my God, this is much bigger than we thought.”
And I think a lot of that was the result of the pandemic. A lot of people closed offices and had to go home and just remain there because they could run their business profitably from home. But now they're staying home. And we’re seeing those registrations with us increase monthly. There are million-dollar producers working at home.
What do you see ahead for travel advisors?
They have a very bright future. Ever since I came into this industry, and certainly, since the late 1990s, people have been predicting the demise of travel advisors. They predicted travel advisors would go down; no one needs to use a travel advisor. But I think the pandemic was a glaring reminder of how much help and how much assistance and professionalism a travel advisor could provide. And for that reason, I think they have a very bright future. I think the industry is moving to attract new people. And I think there's a very bright future. I don't ever see a day where we don't have travel advisors.
