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Travis
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Dr. Yana Warner
Thanks Travis having us.
Travis
So I want to start off with talking about the book first off just so we can we can get that out of the way here and make sure that make sure everybody goes and picks up a copy of this. Phil, tell me exactly why this book was super was something that was relevant enough to release right now. Why, why, why now? Why the timing?
Phil Le Brun
Well, Yana and I through our own careers and then working at AWS and talking to so many customers and even understanding how Amazon works, we we've pattern of mistakes time and time again. We've made all of these mistakes too as we've led these huge transformations and they're soul destroying and as we talked to more and more leaders and as we became a little bit more experienced ourselves, we just found there was a better, more human way for organizations and the human beings in those organizations to change. And a lot of those patterns were repeated across industries and geographies. So part of our job at the end of the day is to help leaders make their own new novel mistakes, not the same mistakes others have made. And that's where the idea of the book came from.
Travis
Yana, can you talk into the speed of change? Is, has there been an increase in the speed of change with new technology and AI?
Dr. Yana Warner
100%. And, and through our jobs, we're at the forefront advising and talking to and sharing thoughts and advice with our largest customers, Fortune 500 and public sector companies. And we see an unprecedented rate of change. AI the speed of AI. If we, if AI stopped developing now, it would still take five years for companies to catch up to what the possibilities and opportunities are. It's just developing faster. So there's no more roadmap. Nobody has a plan or experience what to do and how to do it. This is a time where people need to learn to do constant change and quicker and quicker, learn what works and what doesn't work. And the companies currently aren't set up to do that and therefore lose a lot of money or leave a lot of money on the table.
Travis
Where did the term the octopus organization come from?
Phil Le Brun
Phil Yana, you probably need to answer this. You were the genesis of it.
Travis
Perfect.
Dr. Yana Warner
It's my fault, Travis. We saw this awesome movie that won an Oscar called My Octopus Teacher and we learned that 2/3 of an octopus's neurons or intelligence is in its arms. So they can act independently, but also together with its brain. Also it can play piano. I mean, how cool is that? Not that you need that for an organization, but yeah, the idea of this distributed intelligence and tapping into all the wonderful, smart, intelligent people and organizations much more than these traditional hierarchical organizations do. That's kind of the metaphor we picked. Say, become more octopus.
Travis
Phil, I'm curious. The if there is a difference, what the differences would be working as the CIO of McDonald's versus working with AWS executives in residence. Is there? Are there is. Do you, do you view your role as being static between those two wildly different organizations? Or has it been a little bit different being part of a massive technology company versus a fast food restaurant?
Phil Le Brun
It's been different, but I don't think in the obvious way. So McDonald's very operational role. You had projects, you had to understand the customer, build stuff for customers, get it out to as many restaurants as possible, then support it. And it's quite an arduous job being a CIO because there's always something that needs attention, let alone budgets and governance and people and the subs like the privilege of the role we have at the moment is yes, we're part of a large technology company, but we try and run it as the world's largest startup. So there's lots of decentralized teams. It's a very curious organization in terms of it encourages people to be curious about things and ask questions, come up with a hypothesis, and gives us a lot of autonomy to actually explore new ideas, which is very much attuned to what we wrote about in the book. But I love that fact that we're constantly pushed to think a little bit differently because it's very easy in organizations to just ride the status quo. Change feels hard, it feels risky. The reality is if you don't change, that's riskier. So I love the fact we're learning constantly and we're pushed in a great cultural way to think about bigger ideas and how to experiment out ways to get there.
Travis
Yana, can you tell us a little bit more what an executive in residence at AWS would be responsible for doing?
Dr. Yana Warner
I feel like I have the most wonderful job in the world right now and I appreciate it because I had jobs that were not wonderful at all. And so I get to share my battle scars and madness and mistakes I've made and learned and see elsewhere made like Phil said with all these big companies and we get to speak to executives, to leaders at the front line driving and leading large scale change, introduction of AI, new products, new markets and have the conversations and help them kind of X peer to peer in a very trusted way. What, what helps, what we see work, what doesn't. We get to create beautiful books out of that and advice and keynotes and talks and with the, with the idea of helping become a bit more octopus. So I've got an absolute wonderful job and meet the most incredible people across industries and continents who are hungry to drive change.
Travis
Phil how, how would, how does a company like Amazon view the disruption that AI is bringing? Like how do you, how do you, how do you enact something
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Travis
That's this game changing on a level when you have the just sheer volume of employees and business that's going on at something like Amazon.
Phil Le Brun
Yeah, it's an interesting. I think that's part of the challenge I think most organizations have. They think about I need to change the entire organization quickly. And this technology is a threat. I think we view it a bit differently. It's a bit like electricity. There's this opportunity. We don't quite always know what it is, but we know there's something magic in this technology. So firstly, we give as many people in the organization access to the technology as possible and the skills and the opportunity to practice those skills and then we set them free with it. Just fall in love with an outcome. So fall in love not, not with a solution AI, but a problem to solve for the customers. Go experiment with the technology and do that at broad reach within the organization. So as many people experimenting with as many ideas as possible. And yes, there may be some duplication, but isn't it better to be able to have everyone been able to realize a vision and try and try and fix a customer problem than waiting for a governance meeting to give permission to one team or the other? So we actually have a formula that says two is greater than zero. And what we mean by that is we'd prefer two teams or 10 teams to go off and solve the same problem rather than every team waiting for permission to go and solve the problem or for one of those teams to be given the bath and to go solve that particular problem. So, yes, it's a big organization, but there's a massive opportunity here. And, and our expectation is everyone's technology literate too. Not because we're a technology company, but just like you'd expect any leader to understand finance or leadership, the same should be true with technology in the future.
Travis
Yana, you mentioned the implementation of AI across across Amazon. I'm really curious, with companies of this size, do you guys use like a lot of the regular or I guess popular AI tools that are out there, or is Amazon constantly developing its own internal AI tools to protect data and security information, things like that?
Dr. Yana Warner
It's a mix of both. So we have partnerships with large organizations that we work with that are developing different models and we have collaborations using and sharing those models to our customers. We don't mandate single tools that our customer use or that we use. And we of course also develop our own tools. So things like we have a bedrock, we have Kiro. So there are certain tools that we develop as aws, but we really Think about what our customer needs. And then we develop these tools based on the customer needs that appear. So it's a mix of both, and it's making sure that we get the best of what's out there and that what the best is right now continuously changes. And that's why also, we don't lock in the customers that work with us so they can keep getting the best of what's out there.
Travis
Tell me a little bit, Yana, about your relationship with Harvard Business Review. How did that come about? How did you start writing for them?
Dr. Yana Warner
That's absolutely awesome. We had this mad idea for the book and met people who worked with Harvard before. And at some point I met an incredible woman who's written these incredible books. They now get turned into Netflix series, and she's on the board of an incredible company. And she, I put my big girl pants on and just walked up to her and said, we have this idea. Would you listen to me for five minutes? And she was kind enough to listen, and she made introduction to the most wonderful editor we could ever ask for. And it's like a romantic love story where he said, I picked you. I loved the octopus idea. And he was like the Michelangelo. He saw like this piece of marble, and he helped us chisel out a beautiful book. And we got so much support, they asked us to write for their journal as well, and it landed so well. Then we got wonderful feedback, and they're now asking us to come back again and do talks for them. And we met the incredible professor, Linda Hill, who humbly has a photo of shaking Nelson Mandela's hand in her office. She's professor at hbs, Leadership professor. She worked with people like the Pixar CEO at Catmull and others, and such a humble woman. And she looks at innovation at C scale. So this universe is this wonderful universe of incredible people just keeps unfolding in front of us, and they seem to see something in us as practitioners to share some crazy stories of what we see and what we've done.
Travis
Yeah, well, that's what I like about books like this, is that they're being, I, I, I like to see the practitioners write more rather than simply the philosophers. And, and there's value in both, obviously. But I, I like, I like the practitioner manuals a little bit better from people who are kind of in the trenches on a daily basis. Phil, I'm curious when, like, with, with putting this book out there, what is your core intention? Who is the person that you had in mind while you were writing this book? And what do you hope that they gain from it?
Phil Le Brun
The audience is quite broad. Originally we thought about folks on the board of directors, the C Suite. The C suite minus one. But frankly, what we're finding as we talk to more and more customers is this is anyone who wants to be or considers themselves a leader. And you can be a leader of yourself. It's not restricted to a particular title. What we wanted to get out of it is simply to get away from these soul destroying. These soul destroying transformation projects which suck the life out of everyone, which is done to people and give everyone the opportunity to make their own job, their career, their lives better as well as an organization. So it's really what we've learned very quickly is this is not a good way to earn money and retire quickly. But it is.
Travis
Wait, wait, wait. Hold the phone, hold the phone.
Phil Le Brun
I know, I know, Disappointing. But I think it's been a brilliant opportunity for us to start to build community and conversation around. There's gotta be a different way to these soul destroying transformations. 70 to 90% of them don't see the value intended. And we've known that figure for decades. And yet what do we do Next year we run another soul destroying multimillion dollar transformation.
Dr. Yana Warner
We've noticed really interesting, Travis. We as an experiment we turned the book into an agentic advisor, an octopus that can speak to you and help you. And we observed alpha testers using it and there are people in the mid management who are so sick of how things are stuck and difficult. They ran to the octopus advisor called Otto and share that. It's like almost social psychology. It's a, it's a therapy session. It's quite interesting. It tells you a lot about what's going on in our workplaces.
Travis
You guys have both obviously had incredible careers in multiple facets. A lot of younger people listen to this show and are obviously hoping for that. It's called Travis makes Money because we found that there's not enough emphasis on people earning more money. Most of the emphasis goes at least from finance advice, personal finance advice, investment advice. Most of the advice goes toward cutting expenses and budgeting and saving money and Putting away your $100 a month in your 401k plan and crossing your fingers that it compound interest, works in your favor and all this other stuff. And our goal is more to bring awareness to the idea that look, all of that is fine and good and yes you need financial discipline, yes you need a budget, yes you need to set up for the future. But also if you're worried about spending $73 a month on Starbucks coffee, then you're probably focusing on the wrong lever here. And we need to focus now on your ability to go out and make more money and earn more and build a successful career. I'm curious from both of your perspectives and we'll start with Phil and then we'll move to you. Yana, what would be your advice to a young person who is at the precipice of making some big career decisions? How would you advise them to. To move forward in the. In the current economy and corporate landscape?
Phil Le Brun
What's worked for me is to be continually curious and not to lose that over my career. I started on the shop floor in a McDonald's, literally cooking hamburgers. And there's always whatever the job.
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Phil Le Brun
There's always an element of joy, an element of interest, something you can be curious about, something you go and say, maybe if I do this a bit differently, some magic will happen. So taking ownership of the opportunity you have, finding something in that, whatever that opportunity is, to experiment, to have a voice, to ask questions. We train people to have answers, not ask questions. And yet the best leaders we meet, at whatever level of the organization, they continually ask questions because they don't know they have all of the answers. And frankly, people like answering questions too. So be curious, be a lifelong learner. It's. It's got me to where I am today. A lot of it's serendipity too.
Travis
Sure, sure. Yeah. There's always a little bit of luck and timing mixed into the equation. Of course, some things that are outside of our control. But you seemingly did a great job with the things that were under your control. Real quick, Yana, before I have you answer that, Phil, can you tell me like the timeline for you? Like you said, you started working at a McDonald's flipping burgers and then you became CIO. What was that time frame?
Phil Le Brun
I was, I was a 16 year old crew kid earning some pocket money while I was at school. I worked at McDonald's while I was at university. I left briefly and went into banking. Decided that was not for me and came back. And, you know, I saw some folks get promoted a lot faster than me, but sometimes they just then plateaued and found jobs that had a great title and they didn't enjoy. And I. I sort of chased things, which interested me, and it took me a little bit longer. I guess. In reality, it was about. From shop floor to being a CIO about 25 years.
Travis
That was directly in the McDonald's organization for the most part.
Phil Le Brun
Yes. Yeah, I took a bit of a detour into. Into banking and then came back. But actually, I mean, company that size, we. We talk about the downsides of large companies. A company the size of McDonald's with something like 2.2 million employees, if you can't find something curious and interesting to tackle, you're probably not looking hard enough. I had the opportunity to do that.
Travis
Now, I love that story, man, because we talk a lot about those types of things here on the show. And what I love is that it's just wherever your feet are planted, take full advantage of that opportunity. Even if you think that it seemed like being a burger flipper at McDonald's for whatever reason tends to be like the job that people throw out as the bottom of the barrel type of a thing. You know what I'm saying? Like, whenever they use an example of like, well, it's not like I'm flipping burgers at McDonald's, it's for. For some reason the thing that gets vilified the most. But that's why I love. That's why I want you to answer that, because I love to hear the story of like, yeah, that's also that. That also can be an amazing opportunity if you view it as an amazing opportunity and you're willing to go the extra mile and take full advantage of whatever opportunities at your fingertips, because you never know what can come from it.
Phil Le Brun
Absolutely. I don't know if the fact is still true, but it wasn't that long ago where McDonald's had created more millionaires than any other company on the planet. You know, crew members became franchised owners or corporate officers or went on to do big things. But there's a lot of opportunity in pretty much any role out there. And I think it's just a case of looking hard for that and being prepared to take ownership for your own career and learning.
Travis
Love it. Yana, same question. What would be your advice to the young person who wants to have a fruitful career?
Dr. Yana Warner
Well, what I've done is I've said yes to a lot of things. When people offered me suggestions and ideas, I said yes. I briefly interrupted my studies. I said yes to supporting a startup. I learned so much there. I was reporting into the founders, did a successful exit, bought by hp. I then said yes to staying at a university and doing a PhD and just because they had a scholarship and offered it to me, I just said yes. And I learned how to learn how to study and how to live across the world. I said yes to offering to start a new university in Dubai. I said yes to a job that I wasn't sure I should be doing, going into banking. I said yes to a lot of things. And that is I love this Steve Jobs speech where he says my career is a connection of strange dots. And that's exactly for me. From startup to academia to banking to aws, it's a strange connection of dots because I said yes to a lot of things. And again that's this thread of curiosity and I met incredible people and all of this made me maybe, I hope more I'm still have corners but more rounded than I was.
Travis
Yeah, you can only connect the dots when you look backwards is I think what you said there. Yeah, it's the success is a spiral staircase, you know what I mean? You can't, you can only see the next step and then you look back and you can join up all those dots together. What do, what do you, what do you guys do for like anything outside of work? Like what it's seemingly for, for people in your position, you're obviously very, very proud of the work you do. You love the work that you do. What do, what do you, each of you do for like unplugging and getting out and you know, having a little bit of me time or fun time. What, what, what's like hobbies and stuff like that? Bill?
Phil Le Brun
Well, I mean firstly, the thing I've learned through the process of writing with Yana is I have way more time than she does. I've come to really appreciate what it's like to raise a family, write a book, have a full time job, which I see Yana do just brilliantly. Things I do, I like to build. A lot of the stuff we do is knowledge work. I like to build stuff whether it's wood, metal, 3D, plastics. I built, my God kids chess sets out of wood and Star wars characters because you can see something. And I still, I still code for fun. And then, you know, building sort of extends into cooking. So I love to cook. It's a, it's a great way of relaxing, I find.
Travis
What. What's your favorite thing to cook?
Phil Le Brun
Oh, it's typically Indian, but I like to experiment.
Travis
No kidding.
Phil Le Brun
Mainly Asian.
Travis
Okay. Okay, Yana, same question.
Dr. Yana Warner
I have two awesome children, and I love spending every minute I can with them. They are so curious. I learned more most octopus facts from them. My son's just learning to build mechanical things and code from the awesome Mark Rober crunch labs, of course. And my daughter is the most curious human you've ever met. She loves to cook. She's only 12, and she cooks better than. Better than Phil, maybe. I don't know.
Travis
I was going to say cook off. Cook off. There's only one way.
Dr. Yana Warner
We love to travel because kids learn early that different cultures do things, things differently. And there isn't a right or wrong. It's just different. And it makes them very curious and excited about the world. So they're becoming little world people. And we look forward to the next place where we're going in summer.
Travis
Last question for you both. Again, you both are touching so many different things. You. You do so many different things. What is it about what you do that you enjoy doing the most? If you could eliminate everything else that you do from your plate and only choose one thing to do, what would that one thing be?
Phil Le Brun
That's a. That's really hard. It's a great question because we talk a lot about relentlessly focusing on things. I love the fact we get to think, but turning that into action in a way that the thing that gives me greatest pleasure in the job is seeing or hearing from one executive, one leader. One leader to be after a session with them, saying, maybe there's something I can do differently. Maybe I do have the right to go and try something without asking for permission. So just changing people's mental models, that gives me so much pleasure.
Dr. Yana Warner
Jana, I think there's a reason we wrote the book together, because you just said what I was thinking. My favorite sentence has become. It's so old, and I never got it. Where there's a will, there's a way. And when we can help someone change the way they look at the world and they have this aha moment. And from there, everything just falls like a positive card. How it's not a negative. Dominoes. That's the. That's so rewarding, and it's wonderful. And it unlocks companies, other people's careers under this leader, with this leader. It's the most amazing thing when you. When you can give someone this insight and they can turn it into something new.
Travis
The Octopus Organization. If you're listening right now, go, go pick up a copy of this book before you forget about it. If you're driving, just pull over. You know, be safe about it. But go pick up a copy right now. You forget and I know that you will not regret that. Jana Phil, thank you so much for taking the time to join me on the show. I know you're both very, very busy people and you do not take your time for granted. Where else can people go to to learn more from both of you besides just the book?
Phil Le Brun
Phil, if you go to theoctopusorganization.com there's material on there, even experiments you can run in your workplace tomorrow if you want. And secondly, you know, go read the reviews and ideally lead a leave a review on Amazon.com too, because that really helps people understand what's working, what isn't working, and how excited people are that there may be a better way of of transforming the workplace.
Travis
Theoctopusorganization.com for all the extra goodies, as well as the book itself. Guys, thank you again for taking the time. Everybody else listening. Remember, money only solves your money problems. But it's usually easier to solve the rest of your problems when you got some money in the bank. So let's start there. Here on the Travis Makes Money podcast. Thanks for tuning in, everybody. We'll catch you next time. Peace.
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Host: Travis Chappell
Guests: Dr. Yana Werner & Phil LeBrun
Air Date: May 27, 2026
This engaging episode of Travis Makes Money dives into how individuals and organizations can thrive in an age of rapid technological disruption, emphasizing the importance of adaptability, curiosity, and distributed leadership. Travis is joined by Dr. Yana Werner and Phil LeBrun — both senior leaders at Amazon Web Services (AWS) and co-authors of The Octopus Organization. Together, they explore organizational change, career growth, AI innovation, and the human-centric strategies needed to navigate the modern business landscape.
(02:47) Dr. Yana Werner:
“The speed of AI... if AI stopped developing now, it would still take five years for companies to catch up to what the possibilities and opportunities are.”
(04:00) Dr. Yana Werner:
“The idea of this distributed intelligence... that’s kind of the metaphor we picked. Say, become more octopus.”
(08:43) Phil LeBrun:
"We actually have a formula that says two is greater than zero..."
(12:48) Phil LeBrun:
“What we wanted to get out of it is... to get away from these soul destroying transformation projects.”
(15:52) Phil LeBrun:
“What's worked for me is to be continually curious and not to lose that over my career. I started... literally cooking hamburgers.”
(19:52) Dr. Yana Werner:
“I've said yes to a lot of things... my career is a connection of strange dots.”
(22:21) Phil LeBrun:
“I like to build... I still code for fun... I love to cook. It’s a great way of relaxing.”
(23:36) Phil LeBrun:
“Seeing or hearing from one executive, one leader... saying, maybe there’s something I can do differently—just changing people’s mental models, that gives me so much pleasure.”
(24:10) Dr. Yana Werner:
“When we can help someone change the way they look at the world and they have this aha moment... that's so rewarding.”
The conversation is warm, honest, and motivational, with a strong focus on practical wisdom and human empowerment. Both guests balance humility with expertise, often emphasizing curiosity, experimentation, and the value of learning from mistakes.
For listeners seeking more than traditional financial advice, this episode offers actionable strategies for personal and organizational growth in a rapidly changing world—reminding us that adaptability and distributed intelligence are the keys to unlocking success today.