Podcast Summary: How Leaders Lead with David Novak

Episode #266: Richard Fain, Former CEO of Royal Caribbean Group – Push Past Comfortable
Date: November 20, 2025
Guest: Richard Fain

Episode Overview

This episode of “How Leaders Lead with David Novak” invites legendary cruise executive Richard Fain, former CEO of Royal Caribbean Group, to reflect on 33 years of innovation and bold leadership. Fain and Novak discuss organizational culture, the power of words, taking big risks, and how to turn a people-centered vision into UFB (Unf***ing Believable) experiences. Richard opens up about his personal journey, his leadership lessons, and how he continuously inspired (and was inspired by) his teams to push past comfortable, both in calm seas and through unprecedented crises like COVID-19.

Key Discussion Points & Insights

1. First Encounters With “Wow”

[00:33] Richard Fain:

• Fain’s life-changing first cruise with Royal Caribbean (at founder Ed Stefan’s insistence).
  • “The thing that blew us away was the people. They were so spectacular, they were passionate, they were innovative. It was just terrific. And I think that was probably one of the more defining moments of my career.”
• Early misconceptions about cruising.
  • “I had a view that…cruising is good, but I’m too sophisticated for that. …And it was amazing just how wrong I was.” [01:25]

2. Building Culture Through UFB—Unf***ing Believable

[02:19] Richard Fain:

• The origin of “UFB,” a phrase that drove their internal dialogue on innovation.
  • “Somebody came up and said, oh, this should really be unbelievable. …So it was un. Effing believable. …The question when we would meet is, hey, that’s pretty good…but is it UFB? Is it truly unbelievable?”
• The role of language and symbolism in company culture.
  • On project names: “The project needed to be aspirational. …We call it Project Eagle, and people wanted to soar like an eagle.” [03:48]

3. Innovation By Debate and Inclusion

[06:17] Richard Fain:

• True innovation comes from open, passionate discussion and rewarding healthy debate.
  • “People who argue are rewarded…We say, you know, that was really good. You made a really good point. You were wrong, but you made a really good point.” [07:43]
• Devil’s advocacy is embraced.
  • “Devil’s advocate becomes sort of a nice word. It’s a compliment, not an insult.”

4. Risk-Taking & Iconic “Big Toys”

[08:35] The Blimp Story:

• A “childhood dream” – putting a tethered blimp on a cruise ship for guests.
  • Fain recounts being afraid of heights, the adventure of the trial, and the punchline:
    • “The captain got a call from the Swedish Air Force. ‘Your blimp is in our airspace. Do you mind if we shoot it down?’” [00:00, 11:10]
• Lesson: Innovate boldly, accept failure, laugh at the missteps.

[05:03] Cutting a Ship in Half:

• Early leadership risk: physically expanding ships by cutting them and inserting new sections.
  • “I still don’t understand the engineering, but the guests were fine with it. It gave us economies of scale. It was a dream.”

5. Vision: Competing Beyond Cruises

[11:34] Richard Fain:

• On growth from niche market to industry leader:
  • “We were going to be a competitive force in the vacation market, not just cruise. That’s been very successful.”
• The “sexy stuff” vs. “the basics.” True wow is in the experience, not just the flashy features.
  • “Most of the time it’s small things. …It’s saying ‘good morning’ in a pleasant way. …Let me show you where it is.” [13:08]

6. Bringing Leadership Home

[14:44] On Family:

• Fain calls his wife his first mentor and credits his family for grounding him.
  • “I don’t have any confidences from my wife…She would say, ‘Did you really mean to talk like that?’ I would know this was a time when I should call somebody back and reset the conversation.” [15:39]
• On blending leadership at work and home:
  • “It is a question of working together, aligning, seeing the world in the same way and moving towards a common goal.” [16:41]

7. Evolution of Culture

[20:11] Ed Stefan’s Founding Culture:

• Fain inherited a culture of excellence and pushed for continual, intentional improvement.
  • “It’s not one great epiphany. It is a continual, every single day living that you believe.” [21:42]
• The “do it right or don’t do it” approach, exemplified in choosing real ice for ship skating rinks.
  • “If you’re going to do something, do it right.” [24:03]

8. The Rule of Thirds: Innovating with Intent

[37:20] Fain’s Rule of Thirds:

• Balancing tradition, evolution, and revolution on every new ship.
  • “One third, one third, one third. …We don’t want a new ship that is all revolutionary. …What do we have that people really love? Let’s give them that.”
  • “Then…make it just a little bit better…and then throw in some wacko ideas.”
  • Examples: ice skating rink, surf simulator, skydiving simulator.

9. Courage Through Crisis: COVID Era

[39:28] Facing Pandemic Shutdown:

• Recalls instant drop to zero revenue and what it taught about leadership in crisis.
  • “It was March 13th of 2020…and all of a sudden, revenues ceased. …The idea of zero revenue had never crossed our thought process.”
  • “Our mantra was: our objective here is to come out of this strong.”
• Decisions: keeping ships in ‘warm layup’ and investing in relationships with crew, bankers, and travel advisors.
• Restart: Deeply emotional return to sailing.
  • “[The crew] said, when we start operating tomorrow, these people are going to have the best cruise in their lives.” [42:52]

10. The Power and Risk of AI

[45:23] On AI’s Promise and Peril:

• “AI…allows us to be more responsive, to understand more about what people want. …it’s really going to be transformational.”
• Cautions about losing the personal touch, and need for intentionality.
  • “Before, we would take weeks to think something through. Now we tend to put it into AI and get an answer in 72 seconds.” [46:19]
  • “It's too late for [just experimenting]. We have to be using it…because only by using it do you truly understand it.” [48:27]

11. Lessons in Leadership

[49:41] Reflection:

• “The biggest lesson for me was don’t look back. There’s no forward progress without screwing up. …If you spend time obsessing about your mistakes…you’ll become so risk averse that you won’t do the things that are necessary to make you successful.”

Notable Quotes & Memorable Moments

The Power of Language:

• “Is it UFB? Is it truly unbelievable?” – Richard Fain [02:19]
• “I do believe in the power of words. I do believe in the power of symbolism.” – Richard Fain [31:10]
• “If you can pick the right words, they stand out. They break through the clutter.” – David Novak [61:02]

On Debate and Inclusion:

• “People who argue are rewarded for it…You made a really good point. You were wrong, but you made a really good point.” – Richard Fain [07:43]
• “Devil’s advocate becomes a compliment, not an insult.” – Richard Fain [07:43]

On Risk:

• “You can’t innovate without taking risks. …There just has to be a confidence that you know enough about your customers…” – Richard Fain [24:30]
• “Either do it right or don’t do it.” – Richard Fain [21:42, 24:03]
• “There’s no forward progress without screwing up.” – Richard Fain [49:41]

On Passion, People, and Privilege:

• “It’s the people. It’s the people. It’s the people.” – Richard Fain [26:52]
• “Love what you do, or don’t do it.” – Richard Fain [58:45]
• “It is such a privilege.” – Richard Fain [55:51]

On Resilience Through Crisis:

• “Our mantra was: our objective here is to come out of this strong.” – Richard Fain [39:28]

On Letting Others Lead:

• “Everybody needs to bring you along, too. …It really is a symbiotic relationship.” – Richard Fain [28:51]

On Adoption of AI:

• “It’s too late for just experimenting. We have to be using it because only by using it do you truly understand it.” – Richard Fain [48:27]

Timestamps for Key Segments

• [00:33] – Richard’s first cruise ‘wow’ moment
• [02:19] – Origin and impact of “UFB”
• [05:03] – The story of cutting a cruise ship in half
• [06:17] – Fostering debate and innovation culture
• [08:35] – The blimp story and bold experiments
• [11:34] – Vision for Royal Caribbean as a travel leader
• [13:08] – Delivering the ‘wow’: Basics and details
• [14:44] – Family as leadership foundation
• [20:11] – Company’s founding and continuous improvement
• [21:42] – Real ice skating rinks: Doing it right
• [24:30] – Taking risks and betting on mega-ships
• [28:51] – Bringing people (and being brought) along
• [31:10] – How “Delivering the Wow” became a rallying cry
• [37:20] – The Rule of Thirds in innovation
• [39:28] – Covid, zero revenue and the “restart”
• [42:52] – Emotional first restart after pandemic
• [45:23] – The potential and peril of AI for Royal Caribbean
• [49:41] – Biggest leadership lesson: No forward progress without mistakes
• [50:37] – Lightning round (personal insights)
• [54:31] – The tradition of champagne bottles and ship godmothers

Debrief & Tangible Leadership Takeaways

1. Make the Culture Tangible

• Use bold, memorable language (UFB) as rallying cries.
• Embed language into daily processes to set expectations and behaviors.

2. Embrace Debate

• Reward healthy conflict and devil's advocacy, fostering an inclusive environment for new ideas.

3. Innovate with Structure

• Use the “Rule of Thirds”: preserve loved traditions, evolve what works, and inject revolutionary ideas.

4. Balance Risk and Research

• Take bold bets, but compensate risk with thorough study, feedback, and alignment.

5. Lead with and Through People

• Invite bottom-up and top-down inspiration—“bring others with you,” and let them take you with them.

6. Crisis as Culture Test

• Double down on long-term goals, not just survival, in adversity.
• Maintain relationships across crews, advisors, and partners.

7. Adapt and Lead Technological Change

• Be intentional and proactive with adopting transformative tools (like AI); use rather than just discuss them.

8. Keep It Personal and Human

• Value small gestures as much as the grand “wows.”
• Share credit and stay grounded in gratitude and legacy.

Final Advice from Richard Fain

“Love what you do, or don’t do it.” [58:45]
“There is no forward progress without screwing up.” [49:41]

This episode distills decades of leadership wisdom, mixing big, bold innovation with humility, warmth, humor, and infectious enthusiasm. Whether you’re running a company, a team, or your own life, Richard Fain’s lessons—on the power of people, debate, and never settling for less than UFB—will help you push past comfortable and chart a course toward legendary leadership.