"How am I doing?" Jason Liberty asks Richard Fain while reflecting on Royal Caribbean's past, present and future

In:
19 Aug 2025
By: 
Matt Hochberg

How does Royal Caribbean's top executive measure up to its past CEO?

Jason Liberty, Left. Richard Fain, right

A special event was held on Royal Caribbean's Star of the Seas last week where Royal Caribbean Group CEO Jason Liberty sat down for a public chat with his predecessor Richard Fain.

Mr. Liberty started off the event with a playful question: "It was about 20 years ago, almost to the day, that Richard hired me. So how am I doing?"

Without missing a beat, Fain quipped back: "You’re asking that about four years too late."

Fain and Liberty during the event

It drew a laugh from the audience, and set the tone for a reflection on where Royal Caribbean Group is headed.

Mr. Fain plainly said after the answer is in the results.

“If you look at the share price, employee satisfaction, the popularity and ratings on our cruises," Fain said with a smile, "apparently you’re doing a good job."

"It's the people"

Michael Bayley with a crew member

Richard Fain lead Royal Caribbean for 33 years, and his legacy encompasses taking the company from cruise line to cruise giant.

Mr. Fain believes the secret to Royal Caribbean's success was never just about ships or flashy innovations. 

"It’s the people, it’s the people, it’s the people," he said. "Royal Caribbean has always attracted, promoted and dealt with the best and that has never left."

Having the right people to make their aspirations work is something Mr. Liberty agreed with.

"We’re surrounded by some of the greatest talent that walks on the planet, not just because they’re talented, but because they’re passionate," Liberty added.

A legacy that began in 1988

Old photos of Richard fain

Richard Fain began working at Royal Caribbean in 1988, but he never imagined where the company would go and become in the decades since.

Under Mr. Fain's tenure, Royal Caribbean went from a cruise line with a handful of ships to a market leader with dozens of ships all over the world.

"It was hard for me to imagine it today. It’s so different than what we expected. But the one thing that hasn’t changed was to be a cut above and to be more than just a cruise line, but to be part of the vacation market."

Under his leadership, the age of the megaships was introduced and it redefined what a cruise vacation would encompass.

Mr. Liberty gave credit to Fain for the years of dedication that lead Royal Caribbean's growth, "The culture of this company is really rooted in the culture that Richard built. The amount of pride to see his flowers bloom must be exceptional."

More talk of Project Discovery

Vision of the Seas docked

During the question and answer session, a travel agent asked about plans for a smaller cruise ship design and Mr. Liberty touched on the rumored plans.

Liberty acknowledged that the company is also investing in "Project Discovery," a new class of slightly smaller ships designed to deliver the same signature Royal Caribbean experiences at a more approachable scale.

"There's also an opportunity to build ships that have a lot of the same amenities and activities, but on a slightly smaller platform," he said.

He admitted it's still in the "dream engine" phase, but more to come, "hopefully relatively soon."

Fain added that size has never been the point: "It wasn't a team fixated on large or small. It was a team that could bring magic to whatever size it was."

City tours are in the past

Icon of the Seas

A really interesting discussion centered around their vision for the future.

Mr. Liberty had a bold statement about how people want to explore the world, "The time of city tours, I think, is of the past," he said. 

"The time of experience building with your friends and family is where we are today, and I think where we’re going to be tomorrow."

Raft slide on Icon of the Seas

He's alluding to the idea that going to a city simply to sightsee isn't as engaging from a memory making family vacation as a cruise can be in that regard.

"Vacation experiences have to be something that you want to brag about on social media or things that you’ll build legacies for a lifetime," Liberty added


Matt started Royal Caribbean Blog in 2010 as a place to share his passion for all things Royal Caribbean with readers. He oversees all the writers at Royal Caribbean Blog, and writes a great deal of content on a daily basis.  He has become one of the foremost experts on a Royal Caribbean cruise.

Over the years, he has reached Pinnacle Club status with Royal Caribbean's customer loyalty program.

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