You don’t have to command a cruise ship (or a boardroom) to lead with purpose. On this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug welcome Richard Fain, longtime chairman and former CEO of Royal Caribbean Group, for a conversation that’s not about corporate leadership… but about life leadership.

Richard shares timeless lessons he learned from decades steering one of the world’s most innovative companies—lessons that apply just as powerfully to parenting, coaching your kid’s soccer team, running a PTA fundraiser, or simply trying to create more joy at home. You’ll hear how to dream bigger about your own life, build a culture of kindness and excellence in small groups, and turn the ordinary moments around you into opportunities to “deliver the WOW.”

Of course, this wouldn’t be the basement without a few money detours. The crew also breaks down new 401(k) rules and annuity updates, debates whether tax flexibility beats fancy planning, and celebrates Doug’s birthday with trivia, laughter, and a few movie reviews along the way.

By the end, you’ll walk away inspired to bring a little more vision, creativity, and generosity into every corner of your world. No cruise ship required.

What You’ll Learn

How to lead from wherever you are: Richard’s lessons on building strong teams, communities, and families. No corner office needed.

Turning the ordinary into extraordinary: Simple ways to “deliver the WOW” at home, work, or anywhere people count on you.

Dreaming bigger about your life: Why bold vision isn’t just for CEOs; it’s for anyone looking to create meaning and momentum.

Financial updates you can use: New 401(k) rules, annuity insights, and practical tips to strengthen your plan.

The lighter side of leadership: Trivia, birthday celebrations, and a few fun detours (because we can’t resist).

Questions for the Basement

What’s one way you could “deliver the WOW” in your own life this week?

Who’s a leader in your everyday world (at home, work, or your community) who’s made an impact on you?

How can dreaming a little bigger change the way you approach your next financial or personal goal?

FULL SHOW NOTES: https://stackingbenjamins.com/better-money-habits-with-richard-fain-1748

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201

Enjoy!

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