2438 - When Rerouting a Cruise Ship Becomes a Lesson in Leadership and Accountability with Anthony Reeves

5 Jun 2026 · 20 min · 7 chapters

Ask about this episode

Ask anything about it. ChatGPT or Claude reads this page and answers with the times it was said.

Connect VO and ask about every podcast you hear, including the moments you saved. Add to ChatGPT · Add to Claude

In short

Leadership and accountability through “discomfort” and owning mistakes, using the example of Virgin Cruise Lines rerouting a ship and building trust via transparency. Anthony Reeves argues that great companies embrace productive discomfort (process/product decisions) while avoiding discomfort caused by unfair treatment of people, and that growth requires making mistakes rather than being “perfect” all the time.

Guest background

Anthony Reeves, “outback kid to global boardrooms,” keynote speaker, former executive at Amazon and other companies, author of Eat the Donkey.

Key claims

Discomfort drives innovation; trust is built when leaders pause, admit error, and correct course; ease and perfectionism block growth; public-company quarterly pressure limits experimentation.

Notable examples

Virgin Cruise rerouting due to weather and openly “falling on the sword”; Amazon interview question about wrong assumptions; Starbucks protecting its “third spot” identity; Southwest refusing premium fluff; Washington Mutual’s risky home-loan strategy; AI/“legalese” reducing human authenticity.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Endurance Sports and Golf: A Shift in Focus

1:26 to 4:16

Anthony shares his transition from endurance sports to golf and the mental challenges involved.

“Before we get into your superpowers, the work that you do, I always love hearing what high-level leaders do for fun when they are not at work.”

The Concept of Discomfort in Leadership

4:16 to 6:36

Discussion on discomfort as a necessary element for growth in leadership and organizations.

“Well, from that, Anthony, to talking about Eat the Donkey, it's a manifesto against average.”

Staying True to Company Values

6:36 to 9:26

Examples of companies maintaining their core values amidst discomfort and challenges.

“I got to deal with people that are being unfair, unkind or something like that, whatever, you know, the specific complaint that might be, you know, stimulating those feelings of discomfort.”

Trust and Accountability in Leadership

9:26 to 13:02

Exploring how accountability and trust are essential in leadership through the example of Virgin Cruises.

“One thing you were talking about is, you know, kind of, you're talking about the, I'm sure the virgin cruise boondoggle here.”

The Importance of Authenticity

13:02 to 14:00

Discussion on the need for authenticity in communication and leadership in the digital age.

“Or, you know, I get this, you know, but when everything comes through so sanitized and legally approved by the attorneys, it's just nothing but legal speak.”

The Challenge of Perfectionism in Leadership

14:00 to 15:46

Explore the pressures CEOs face in a culture that prioritizes perfection, stifling innovation.

“as opposed to they go into robo, you know, legalese mode, which is the opposite of that.”

Insights from Anthony Reeves on Business Growth

15:47 to 17:41

Learn from Anthony's experiences and his new book, offering insights into business decisions and growth strategies.

“When folks go to your website, it's anthonyreeves.co.”
Hear the part that matters, and keep it.Open this episode in VO. Double tap your headphones to save a moment as you listen.
Get VO free

Transcript

Automatic transcript. May contain errors.

0:03Welcome to the Thoughtful Entrepreneur. If you're committed to growing your business by serving audiences with generosity and real expertise, you're in the right place. This is a daily 15-minute show featuring leaders who believe real impact comes from generosity, not hype, which means as a listener, you're going to get the good stuff. In fact, we created podverified.com to give thoughtful leaders like you free tools to show up better on podcast stages like this one. That includes your free podverified score, free podverified guest training, a free media kit builder, and so much more. It's the first ecosystem of its kind built by podcasters who genuinely want to help guests thrive and grow in podcasting.

0:46Visit podverified.com if you'd like to be featured as a future guest. I'm Josh Elledge. Let's get into it. With us right now, Anthony Reeves. Anthony, you are known as the outback kid to global boardrooms. You are the number one selling author of a book that's getting some pretty good traction. It's called Eat the Donkey. It's got great reviews. Anthony, you're a keynote speaker. You're a former executive with Amazon and a number of other places. and you help companies keep their foundations and communicate. Well, it's great to have you, Anthony. Thank you for joining us. It's amazing to be here, Josh.

1:26Thank you very much. Before we get into your superpowers, the work that you do, I always love hearing what high-level leaders do for fun when they are not at work. What have you been into lately? So, Josh, I think one of the areas that I cover in the book a little bit, but not a lot is I did a lot of endurance sports really from my late teens through to roughly 40 45 years old and endurance sports takes a lot of time a lot of dedication and the ability to zone out like you've got to go into that boredom state and the repetition state so I've gone the opposite direction I've started to pick up golf and golf does need that intense short period of focus time and I'm not good at that.

2:08So it's something I'm learning to enjoy. When you say that intense, short moment of focus, describe what's going on in your brain right now and why that's something that you're working through. Like, how can you, how would you describe that? When you stand in the tee box and there's three other people standing, watching you hit a ball, is a very different mechanism to having someone who's just used to the repetition and I'm used to the cadence of running or used to the cadence of riding or swimming. And it's just the repetition side of it. Golf is not like that. So for me, the mental ability of jumping up and doing something that's very different is what I'm talking about is how do I truly, truly focus immensely on the details for a very, very short period of time?

2:59And it is hard. And I don't know how players that are on the circuit do it consistently because it is hard to do. Wow. Is it about, is it more about kind of turning off all of the distractions or is it just, again, you just got that laser focus on the ball and the club in your hands. I'm just trying to, I don't golf. I live on a golf course, but I hardly ever play. I go to the driving range from time to time, but I'm not very good. But, you know, just I'm curious, like, are there anchors that you use to focus on? So as a newer golfer, for me, the ability to switch off my mind is something that I've never had to truly do before.

3:45I've enjoyed boredom and enjoyed staring at windows. But switching off that sharp period is there's no phones ringing. Everyone goes quiet, almost like the birds stop twittering. And you're zoned in on that one thing. And you might say, this time I'm going to focus on keeping my left arm straight. I'm going to focus on this. And it allows you just to have that one thing on your mind in such a short period of time. And it is very new to me. I'm suffering through it. But I enjoy that discomfort of learning something new. Well, from that, Anthony, to talking about Eat the Donkey, it's a manifesto against average.

4:26Read it at your own risk. It's why great companies embrace discomfort. Okay, can't wait to hear about this. Anthony, mind give us a quick overview of your work? And I'm sure, by the way, that there's some parallels, both to the endurance sports that you've done and also the focus that we're talking about that you're experiencing right now with golf. But tell us about Eat the Donkey. Thanks, Josh. I think the hard thing for me is I grew up in a very isolated environment where the nearest gas station or petrol station might have been a thousand kilometers away. And you learn to just keep moving forward.

5:04And you learn to know if you haven't eaten that day, you've got to go fish or catch something, or you need to sort of find that progress the way to move forward. And I've had that mentality all the way through my life. And as I started to grow through the ranks in marketing and go through the ranks in advertising, and I realized that the biggest problem that people have is actually discomfort. and they struggle and as a society as people as humans we love comfort like we we have seats that keep us warm in our vehicles and we we like working from home but that that doesn't get as progress and great companies like like an airbnb or an amazon or lvmh they actually build mechanisms into their system to enhance discomfort and they'd allow that to really happen they don't talk about it openly, but they make sure that discomfort happens and your end of year performance reviews are based on how many innovations you did.

5:59Not whether the innovations worked, but whether you innovated as you go through. And one of Jeff's biggest questions that he ever talked about was, tell me about something you invented. Now, he doesn't care whether it's the new phone or a new vehicle. It could be something really tiny, but he's looking for that mindset and how to remain uncomfortable and progressing forward at all times. And the parallels from discomfort in the outback and discomfort of the boardroom are absolutely parallel to each other. And survival mechanisms in both is absolutely critical. Wow. So as leaders, I would not think that when I think about the discomfort of my teammates or folks that I might be responsible for, I think as a leader, I don't want a whole lot of discomfort for them because then they get, you know, then they get frustrated and they're like, I don't like coming to work.

6:57It's too hard here. I got to deal with people that are being unfair, unkind or something like that, whatever, you know, the specific complaint that might be, you know, stimulating those feelings of discomfort. I don't generally like the idea of discomfort at work. I would like to do better at this. Anthony, help me out. Yeah, there's a great, there's a tension point there. There's a difference between discomfort in the process and the operational procedure and the products versus discomfort in the people. And there are two different areas there. And I do want to chat about ESAT or employment satisfaction surveys because I'm not a fan of them personally.

7:38Really? No. But I'll tell you why in a second. But when I talk about discomfort, I think about the important decisions that you will make as a company to keep you to your foundational core of who you are. So take, for example, Starbucks. We all know Starbucks coffee, and they brew a very average cup of coffee, and they're okay with that. now are they a coffee shop or are they in the business of being that third spot between office and work and if they are a coffee shop as opposed to selling coffee they've got to remain that coffee shop experience and how do they make sure that everything pushes back to that and they have these revenue opportunities over here that they could go chase but they're going to keep coming back to the core of who they really are as a company and they've got to fight for that every single day.

8:30I think another great example is Southwest Airlines. Now, I believe that Southwest is probably one of the most profitable airlines that have ever been around. For 47 years outside the pandemic, they've made money. Now, they're really, really good at getting people from A to B, but they're actually horrible at everything else. You have to line up. There's 20 sections of where you can go to until recently you you couldn't choose your seat but they fought to be that low cost airline at every single point now they could have gone and chased you know the premium dollar or gone and chased the the executive money and business class they refused to do that and they stayed who they are as a company and they really fought to be really known for that foundational thing of we're good at a to b we're not good at that fluff in the middle and that's where that discomfort really comes in.

9:26It's fighting for who you are as a person or as a company. You are a good follow on LinkedIn. One thing you were talking about is, you know, kind of, you're talking about the, I'm sure the virgin cruise boondoggle here. Do you mind maybe just, yeah, yeah. Do you, I don't know if you want to mention kind of like Like what happened now? They responded and take on that. Recently, Virgin Cruise Lines had the unfortunate situation where they had to divert a cruise ship from one port to the next. And it wasn't going from, you know, Goldstone to a place in Florida. It was shipping people all the way up north, up the northeast coast.

10:09And the passengers did not know this until a few days beforehand. And it's a really, really, really bad situation for the passengers. Because of weather, right? I mean, we've had that happen before, but this was a major rerouting. Instead of Bermuda, they went to Canada. That's a little surprising. Yeah, the weather's probably not quite as good up in Canada at that time of the year. Though, what Virgin did really well in this case is they totally fell on the sword. And that is an incredibly uncomfortable thing to do, is they fell on the sword and made every apology possible that they could. and they made sure that not just the customers knew about it, but the greater world knew about like, we made a mistake, we fell on it.

10:55And I love the way their PR angle and PR team took that open, took that honesty approach to what actually happened and the mistake that happened. One of the best questions I've ever been taught for an interview in my life is focused on that and is focused on the trust that's built when you do make a mistake. Now, Virgin made a mistake with weather enforced and the trust was built through that by owning up to it. So the interview questions, Amazon has a lot of leadership principles and one of the interview questions goes back to the word trust. And they talk a lot about, you know, tell me about a time, of course, tell me about a time, Josh, when you were about to walk into a client presentation and you had all the numbers and you had all the facts and you had everything you need, like everything you need to make a great sale or a great pitch or a great connection with that customer.

11:50Five minutes before the presentation, you realize that your assumptions were wrong and what you were going to present was totally incorrect. What did you do? Wow. Now, in an interview is when Amazon asked that question. So in an interview situation, you have two choices. You can say, I went ahead and I presented the information and it went over really well and the client loved it and they bought whatever it was I was marketing. Or you could say, I put a pause on the presentation. I humbly apologize to the client that we weren't ready. We need another 36 hours or 24 hours to get ready. And the question is not about the mistake you made.

12:33The question is more about the trust that you build. The fact that you have the ability to say, I got it wrong. I'm not going to do it again, et cetera. And I feel that's very, very much the same as Virgin, where they made a monumental mistake because of the weather, etc. But they built an immense amount of trust, whereas I'm going to go on a cruise now and have a choice between Norwegian and Virgin and Holland America. I would trust Virgin more now because of that. Yes. Agreed. Agreed. You know, and as leaders, too, you know, and that's so refreshing to see that, I think, especially in the age of social media, you know, when they try to like, you know, they turn it into a joke or hide it or just, you know, they're not up front.

13:18Or, you know, I get this, you know, but when everything comes through so sanitized and legally approved by the attorneys, it's just nothing but legal speak. That's such a turnoff, too. It makes me want to wave my hand in front of the leader's face and like, man, am I talking to a real person right now? I feel like I just lost you. We all make mistakes. And I think that there's something that's endearing, you know, because we feel, I think it's easy for us to feel someone else's discomfort. and for them to acknowledge that discomfort openly, I think it's like we feel it in ourselves and like we try to, you know, what would we do if we were in that position as opposed to they go into robo, you know, legalese mode, which is the opposite of that.

14:09Yeah, you know, there's a great saying about human frailty and it's a wonderful thing to have this frailty about us where we do make mistakes and we do things that are silly or stupid or kind of dumb in a way. And with AI now, AI is so perfect. And I'm not saying the images, but the copy of the words that loses any sense of personality or any sense of who you are. And one of the things I do talk a lot about is as a company, I really feel sorry for CEOs at the moment that are of public companies. I feel horrible for CEOs of public companies at the moment because every quarter they have to report to their bosses, which is the share market, of what they did last quarter and where they trimmed money or where they didn't trim money, et cetera.

14:59And don't get me wrong, they have massive golden handshakes and parachutes and all that. At the same time though, invention and innovation and exploration is going to help the company grow into the future. But that's where you trim and that's where you trim money. And the fact that they can't explore as much as they did before and they have to have this short-term approach is very, very scary, I think, for a lot of CEOs where they can't make mistakes and their teams can't make mistakes and growth happens from mistakes. And the biggest threat we find now to companies not growing is ease, and that's caused by being too perfect.

15:38And so how is companies or how is people are supposed to grow when we're expected to be perfect every single day. Yeah. Well, Anthony, again, congratulations on your new book. It's called Eat the Donkey. I just downloaded it. It's on my Kindle right now. Can't wait to dig into it. When folks go to your website, it's anthonyreeves.co. We've got the direct link there. I know you do workshops, um obviously do keynotes uh there's the book um but but uh what would you recommend uh folks that are listening to our conversation what and they want more anthony reeves in their lives what would you recommend they do i'm i'm always happy to have a conversation chat with people is i i believe in in giving back to what i was given now i i truly understand that i had a lot of great people in my life that really helped get me through some hard times and tough times and they nurture me through and I can be a very, my strainedness comes out quite often with my swearing.

16:39So I have to curtail that, but you're getting in touch and just have a read of the book and think about it from your company point of view. And there's some, one of the things that I, that I tried to do in the book is make sure it was gave some really clear and hard examples when a company went one way over another way. And we spoke a lot about a little bit about earlier, about Southwest Airlines and Starbucks. There's another one in there that's an example where I was deeply involved in Washington Mutual Bank in 2003 to 2007 and areas like that. And Washington Mutual Bank or WAMU was founded after the great Seattle fire happened and it was really about the people's bank.

17:21But there came a pivotal moment in the company's life when they started selling home loans to people that couldn't afford those home loans. and they were the biggest bank collapse for the 2008 sort of financial crisis. And take the lessons from those companies and think about it from your business point of view is are you making the right decisions for yourself and not just selling something off? And I do believe in growing slow and that way you grew up a longevity in business and you're going to stay around a lot longer. That also means if you want an exit strategy, you're not a whale, you haven't grown too fast and then selling off.

17:59You're really about that long-term and the long-term is what it's all about. And from Amazon, we didn't believe in short-term revenue. We would sacrifice short-term revenue over long-term gain. And I've taken that lesson and just think about how Amazon keep exploring with that long-term point of view, but definitely get in touch. There's a great workshop in there about Amazon itself and how to think in a very Amazonian way. I love it. Love it. That's all at anthonyreeves.co, including your new book, Eat the Donkey, which you can get on Amazon Kindle, paperback and hardcover. So, Anthony, great conversation.

18:38Thank you so much for joining us. Thank you, Josh. I really appreciate it.

18:45Thanks for listening to The Thoughtful Entrepreneur. If your goal is to grow your business, increase revenue and build authority without gimmicks, this show is designed for you. Each episode gives you practical insight from leaders who have turned trust and credibility into real business results. If you value short, thoughtful conversations that respect your time, make sure you're subscribed. We publish daily 15-minute episodes focused on growth that actually compounds. And if you're interested in being a guest or you want to turn podcast appearances into measurable business growth, visit podverified.com.

19:21You can start for free with your pod verified score, along with free podcast guest training and a free media kit builder. These tools are built to help you get booked on better shows, deliver stronger interviews and convert audience trust into revenue. No more desperate sales. You truly can enjoy all the business you like by generously sharing your wisdom. Everything we offer is built by podcasters for guests with a focus on trust, organic growth, and long-term business success. Thanks again for spending your time with us. I'll see you next time.

From the publisher
Architectural Friction: Engineering Corporate Innovation Through Productive Discomfort with Anthony Reeves

In a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Anthony Reeves, an elite international keynote speaker, growth consultant, and author of Eat the Donkey, to dismantle the hidden operational liabilities of corporate complacency. Anthony, whose background spans intense ultra-endurance sports like Ultraman to driving high-stakes team strategy within Amazon's leadership ecosystem, argues that convenience is the ultimate enemy of enterprise scale. This conversation serves as an essential manual for middle-market founders and executive teams looking to build high-performance cultures, showing how institutionalizing deliberate operational friction can shield an organization from stagnation and unlock sustainable corporate growth.

The Strategy of Stretch: Structuring Vulnerability and Governance for Enterprise Scale

The primary threat to long-term market authority is rarely an external competitor, but rather an internal slide into institutional comfort and short-term operational thinking. Anthony Reeves explains that when a business attempts to over-engineer convenience and eliminate all administrative friction, it naturally dulls the creative drive and risk-taking capacity of its workforce. Elite multinational enterprises—such as Amazon, Airbnb, and LVMH—combat this stagnation by intentionally embedding productive discomfort directly into their talent metrics and core performance reviews. Instead of evaluating managers solely on safe, predictable output, these organizations systematically reward teams that push boundaries and test unproven hypotheses. When a company normalizes failure as a key data point in the innovation pipeline, it strips away the perfection paralysis that stalls product development, transforming calculated risk from an existential threat into a highly predictable revenue driver.

To sustain this high-yield operational velocity without causing employee burnout or talent attrition, leadership must establish a culture anchored in absolute transparency and foundational alignment. When structural disruptions inevitably occur, companies often make the mistake of deploying sanitized, risk-averse public relations scripts that destroy trust with both clients and internal stakeholders. True market differentiation is achieved when executives possess the psychological safety to publicly own corporate mistakes, a practice modeled directly by Amazon's leadership principles. By treating unexpected errors as transparent opportunities for optimization, leaders build deep organizational resilience. This vulnerability must be paired with an unyielding commitment to the enterprise's "foundational focus"—the core mission and values that define the brand—ensuring that the business aggressively rejects short-term, trend-chasing distractions that do not map to its long-term enterprise value.

Transitioning an organization out of complacency requires a corporate architect who can precisely differentiate between productive growth discomfort and destructive operational chaos. Through specialized consulting frameworks and strategic keynote sessions, Anthony assists leadership teams in auditing their current workflows to identify where compliance has replaced creativity. This systems-driven alignment demands that corporate metrics shift toward tracking long-term structural milestones rather than immediate quarterly micro-gains. By designing clear accountability guardrails and providing continuous executive development, founders can safely guide their teams through the discomfort of rapid market shifts. Ultimately, market dominance belongs to the enterprises that treat stress not as a crisis to be managed, but as the primary catalyst required to scale impact and maintain premium authority across their entire industry vertical.

About Anthony Reeves

Anthony Reeves is a globally recognized keynote speaker, growth consultant, and the author of Eat the Donkey. Drawing from an extraordinary background in world-class ultra-endurance sports—including completing Ultraman and Ironman competitions—and extensive leadership experience within Amazon, Anthony specializes in the mechanics of human and corporate optimization. He serves as a trusted advisor to executives, helping them design high-accountability workplace cultures that embrace strategic challenge to drive breakthrough innovation.

About anthonyreeves.co

anthonyreeves.co is the primary digital advisory hub for Anthony Reeves’s global consulting and speaking practice. The platform provides mid-market corporations, enterprise leaders, and event organizers with direct access to custom corporate training modules, organizational alignment workshops, and leadership development resources. Through data-driven diagnostics and culture-shifting frameworks, anthonyreeves.co equips modern executive teams with the systems engineering required to reject mediocrity and manage complex operational scale.

Links Mentioned in This Episode


Key Episode Highlights

  • The Complacency Trap: Why over-engineering comfort within corporate processes dulls innovation and introduces long-term vulnerability into your business.
  • Institutionalizing Discomfort: Emulating Amazon’s framework of rewarding employees based on their willingness to invent and take risks rather than just executing safe results.
  • The Power of Foundational Focus: Examining how brands like Starbucks and Southwest Airlines maintain long-term market control by ruthlessly saying no to trend-chasing distractions.
  • The ROI of Executive Vulnerability: Building intense customer and employee loyalty by openly owning corporate mistakes instead of relying on sanitized corporate scripts.
  • Productive vs. Destructive Friction: Training management tiers to balance intense structural challenges with robust psychological safety guardrails.

Conclusion

The conversation with Anthony Reeves highlights that corporate excellence is an intentional architecture built on the edge of the comfort zone. By deploying rigorous performance governance, fiercely protecting the organization’s core mission, and treating failure as a mandatory component of growth, business leaders can transform a stagnant operation into an agile, self-sustaining corporate asset.

More from The Thoughtful Entrepreneur

🎙️ Want to be featured on The Thoughtful Entrepreneur? Get your voice in front of 50K+ listeners. 👉 Schedule your guest spot here »

🤝 Consultant doing 6+ figures? Let’s introduce you to your next big client, partner, or referral source. 👉 See how here »

📡 Thinking of launching your own podcast? We’ve built over 250 shows for leaders who land dream guests weekly. 👉 See the system here »

🚨 What’s Your PodVerified Score? Find out how you rank as a podcast guest — and get matched with hosts who actually want you. 👉 View the platform »

📬 Subscribe to The Thoughtful Entrepreneur New episodes daily to fuel your impact, visibility, and influence. Thanks for listening — now go build something extraordinary!

To discover more strategies for scaling your impact and growing your authority, explore the resources available at UpMyInfluence.com. If you are a founder or executive with a story to share, we’d love to hear from you—click here to apply as a guest on The Thoughtful Entrepreneur Podcast!

More from The Thoughtful Entrepreneur

All 987 episodes
2438 - When Rerouting a Cruise Ship Becomes a Lesson in Leadership and Accountability with Anthony ReevesThe Thoughtful Entrepreneur · 20 min
Listen in VO