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Success Story with Scott D. Clary

Richard Fain - Royal Caribbean Chairman | How Culture Took Us from $550M to $90 Billion

Success Story with Scott D. Clary

Success Story Media

Business, Education, Self-improvement, How To

4.6326 Ratings

🗓️ 28 October 2025

⏱️ 75 minutes

🧾️ Download transcript

Summary

➡️ Join 321,000 people who read my free weekly newsletter: https://newsletter.scottdclary.com   ➡️ Like The Podcast? Leave A Rating: https://ratethispodcast.com/successstory Richard D. Fain led Royal Caribbean Group as CEO from 1988, growing it from a $550 million company into a $90 billion cruise industry giant. A Berkeley and Wharton grad, he's known for pioneering revolutionary ship designs and sustainability initiatives that changed how the world cruises. His culture-driven leadership style built one of the most innovative and successful companies in global travel. He now serves as Chairman of the Board.   ➡️ Show Links https://www.linkedin.com/in/richardfain/    ➡️ Podcast Sponsors Hubspot - https://hubspot.com/   ShipStation - https://www.shipstation.com/ (Code: SuccessStory) Square - https://square.com/go/success  SurveyMonkey - https://www.surveymonkey.com/scott  Monarch Money - https://www.monarchmoney.com (Code: Success) Claude - https://claude.ai/success  Incogni - https://incogni.com/success (Code: Success) Huel - https://huel.com/scott (Code: scott) Think Big, Buy Small Podcast - https://link.chtbl.com/B2cH36AX?sid=SuccessStory  NetSuite — https://netsuite.com/scottclary/  Indeed - https://indeed.com/clary   ➡️ Talking Points 00:00 – Intro 01:28 – Why Richard Fain Can’t Retire 02:44 – 33 Years as a Cruise Industry CEO 04:55 – The Death of Long-Term Thinking 06:36 – The Inflection Point That Changed Everything 08:18 – Building Culture with Intention 12:35 – Leading Under Pressure Without Losing Culture 15:32 – Vision vs. Intentionality: What’s the Difference? 18:17 – Hiring the Right People for the Mission 21:09 – Alignment Over Consensus 23:46 – Sponsor Break 28:21 – Killing Ego While Leading with Purpose 30:17 – Driving Results Without Burning Out Your Team 35:47 – The CEO’s Decision-Making Framework 38:11 – How to Create True Innovation 42:52 – Inside Royal Caribbean’s ‘Culture of WOW’ 46:28 – Sponsor Break 49:21 – Getting Your People to Go the Extra Mile 52:59 – Turning Products into Culture Statements 1:01:35 – Fear Makes People Stupid 1:06:04 – How to Pass the Torch the Right Way 1:12:16 – Lessons from Richard Fain’s Book 1:13:31 – The Most Important Lesson for His Kids

Transcript

Click on a timestamp to play from that location

0:00.0

Why are you failing at retirement?

0:02.0

I thought life was going to be so simple and so quiet. It seemed to be involved in so many things. This feels very good. All those people who say that retirement is difficult, nonsense. It's just choose the things you want to do and do them. He was handed the wheel of a modest cruise line and transformed it into a global travel empire with fleets that dared to dream bigger than the horizon.

0:21.1

Richard Fain, the man who reimagined what a cruise could be.

0:24.4

The most important thing I had was good luck.

0:27.0

I was in the right place at the right time.

0:29.0

When I had good luck and was in the right place at the right time, I worked hard to take advantage of.

0:34.0

If all you do is what you did, then you're not going to get anything different.

0:37.9

A vision is almost like saying I have a hope. The vision is important, but it also needs how am I going

0:43.4

to get there and what am I going to do to make that happen. Introducing megaships, pioneering

0:48.7

experiences, and building a culture obsessed with good enough isn't good enough. For over three

0:53.7

decades,

0:54.3

he steered through storms, innovation, and entire industry revolutions. Particularly if you're on a

0:59.8

longer term course, keep in mind the longer term and accept that there are going to be bad things

1:06.2

that happen along the way and don't look back, accept them, but it isn't going to take me off of my path.

1:12.6

It will make your life both more fun and more successful.

1:28.3

Why are you failing at retirement? That's my wife's line.

1:31.3

I don't know.

1:33.3

I thought life was going to be so simple and so quiet, and yet I seem to be involved in so many things that I'm having trouble doing all that I want to be doing. But I must say,

1:46.0

this is, this is, this feels very good. I'm feeling I get to do things I like to do. I get to

1:52.8

choose when to do them. So I'm busier than I want to be, but I'm enjoying what I'm doing.

1:58.0

I love that. So I think that by the way, for all people that are super ambitious, I think it is very hard to actually retire and to actually turn off. No, it isn't. No. That's, you know, I've heard that from so many people and it's nonsense. This is the best thing I've done. It's just, it's so much fun. I get to spend more time with my family,

2:19.3

but I also get to do the things that I love to do. So I had the best job in the world.

...

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