Success Story with Scott D. Clary

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

October 28, 2025

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  • Retirement for highly ambitious leaders is often misunderstood, as choosing what you love to do makes the transition enjoyable rather than difficult. 
  • Long-term thinking is essential for success, especially in public companies, and requires continuous dialogue and defense against short-term pressures. 
  • Culture is not inherent; it requires intentionality, constant discussion, and leading by example to permeate an organization, as demonstrated by Royal Caribbean's 'Culture of WOW'. 
  • Acting out of fear focuses attention too narrowly on the short term, causing leaders to make poor decisions and miss long-term opportunities. 
  • During crises like 9/11 and COVID-19, over-communicating the 'North Star' vision is crucial to instill confidence and prevent employees from succumbing to external fear and making suboptimal decisions. 
  • Successful leadership succession requires selecting an extraordinary leader, ensuring the supporting team is strong, and the predecessor must resist second-guessing the new leader's unique approach, viewing their success as their own. 

Segments

Richard Fain’s Retirement View
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(00:01:16)
  • Key Takeaway: Retirement is easy for ambitious people if they choose activities they enjoy.
  • Summary: Richard Fain rejects the notion that retirement is difficult for the ambitious, stating it is simple: choose the things you want to do and do them. He enjoyed his 33 years as CEO, working with wonderful people, but now enjoys a different, chosen kind of life. He emphasizes that one should not accept the premise that retirement is hard or that there won’t be enough to do.
Longevity and Long-Term Thinking
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(00:04:00)
  • Key Takeaway: Thirty-three years as CEO allowed for seeing long-term results and building on past successes and failures.
  • Summary: A long tenure allows leaders to complete more work and observe the tangible results of their strategies, both good and bad. Short-term thinking, driven by quarterly pressures in public companies, is a strong force against longevity. Success in long-term endeavors requires having mentors and an environment that supports a multi-year perspective.
Culture as Intentional Catalyst
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(00:08:17)
  • Key Takeaway: Culture requires intentional, daily work and cannot be assumed as inherent DNA.
  • Summary: Culture translates into business metrics when it is pursued with intentionality, not just assumed. Intentionality means constantly discussing, focusing on, and demonstrating desired cultural traits like integrity or excellence through leadership actions. This intentional focus ensures that all levels, including the board, align on the organization’s North Star.
Decision Framework and Alignment
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(00:13:34)
  • Key Takeaway: Alignment requires clear, unambiguous direction, contrasting with consensus which leads to watered-down outcomes.
  • Summary: Every decision must pass through a shared framework or lens to maintain intentionality across thousands of daily choices. Consensus often results in ‘creeping crud’—a series of small compromises that dilute the original clear direction. True alignment is achieved when all voices are heard and respected, but the final path forward is clear and uncompromising.
Creating Psychological Safety
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(00:21:02)
  • Key Takeaway: Rewarding innovative thinking and encouraging devil’s advocacy prevents groupthink and fosters psychological safety.
  • Summary: The process of reaching the right answer involves robust discussion where people feel safe to challenge the status quo. When employees are rewarded with kudos or promotion for innovative thinking, they feel empowered to bring up dissenting views. This dynamic competition of ideas, rather than seeking consensus, leads to better outcomes.
Vision Versus Continuous Improvement
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(00:38:07)
  • Key Takeaway: Continuous improvement focuses on upward trends toward a North Star, unlike perfectionism which seeks an unattainable perfect answer.
  • Summary: The North Star serves as a constant direction but is an unreachable goal, making continuous improvement the practical focus. Continuous improvement is energizing because it celebrates making things better now, rather than criticizing past work as ‘bad.’ Striving for excellence means accepting there is no perfect answer, only perpetual betterment.
Innovation Through Calculated Bets
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(00:42:29)
  • Key Takeaway: True innovation requires a structured approach to calculated risks alongside meeting known customer desires.
  • Summary: Royal Caribbean intentionally structures new ship development with segments for traditional, evolutionary, and revolutionary features. This framework allows for trying completely new concepts, like the ice skating rink, without abandoning proven elements that guests expect. Betting against innovation is riskier than making carefully gauged, expensive bets, as stagnation prevents reaching the goal of being the best vacation provider.
Defining the Culture of WOW
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(00:46:52)
  • Key Takeaway: The ‘Culture of WOW’ is defined by employees consistently going above and beyond in their roles, even in logistics.
  • Summary: The ‘WOW’ standard was adopted to guide employees to deliver something special, exemplified by crew members taking guests to shops instead of just giving directions. This concept extends beyond customer-facing roles; logistics personnel solved complex supply chain issues over successive years to improve onboard service. Employees often view these extra efforts as standard procedure, which reinforces the culture through peer example.
Navigating Zero Revenue Crisis
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(01:03:32)
  • Key Takeaway: Overcoming extreme crisis requires rejecting victimhood and focusing leadership confidence on emerging stronger.
  • Summary: During the 18-month zero-revenue period, the leadership team rejected victimhood, focusing instead on how to emerge from the pandemic strong and vibrant. The team’s long tenure and shared culture were crucial assets in maintaining confidence and alignment. Personal coping mechanisms, like eating chocolate, helped leaders demonstrate the necessary confidence to the organization and partners.
Passing the Torch Lessons
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(01:12:27)
  • Key Takeaway: Successful CEO transition hinges on the successor being an extraordinary leader and the predecessor accepting that second-guessing the new leader’s methods is detrimental.
  • Summary: The success of Richard Fain’s transition to Jason Liberty was largely due to Liberty being an inspirational and knowledgeable leader, supported by a strong team and culture. A critical lesson learned is that the predecessor must avoid second-guessing, recognizing that the successor will be different but effective in their own right. The former CEO finds pride in the new leadership’s success, mirroring the satisfaction of seeing one’s children succeed independently.
Book Promotion and Proceeds
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(01:17:46)
  • Key Takeaway: Proceeds from Richard Fain’s book, ‘Delivering the WOW Culture as a Catalyst for Lasting Success,’ benefit a scholarship fund for Royal Caribbean employees’ children.
  • Summary: The book, ‘Delivering the WOW Culture as a Catalyst for Lasting Success,’ is available for pre-order and purchase wherever books are sold. Fain emphasizes that education is important, and he directs all proceeds from his book to a scholarship fund supporting the families of Royal Caribbean employees. The book covers key ideas that helped Royal Caribbean grow during his tenure.
Core Lessons for Success
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(01:18:58)
  • Key Takeaway: Lasting success requires a dual focus on prioritizing people and maintaining a long-term thinking perspective, resisting short-term societal calibration.
  • Summary: The two most important lessons are the focus on people—who drive success—and the importance of long-term thinking, as CEO decisions rarely show impact within 12 to 24 months. Society is currently calibrated too heavily toward short-term results, making long-term vision difficult to maintain. Leaders must train themselves to accept short-term setbacks as distractions that do not alter the long-term path.
Advice to Younger Self
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(01:20:02)
  • Key Takeaway: The most vital advice for life success is to maintain focus on the long-term course and accept inevitable negative events without letting them derail the established path.
  • Summary: Richard Fain’s advice to his younger self was to ask his wife, Colleen, for her hand in marriage earlier. The most important wisdom to pass to his children is not to let short-term issues bother them or cause them to look back. By accepting bad things as distractions that won’t change the three-to-five-year plan, life becomes both more fun and more successful.