How To Work Efficiently Outside The Box With Greg Cagle
7 Dec 2025 · 33 min
Dr. Gary Sanchez talks with entrepreneur and executive coach Greg Cagle about challenging the status quo and rethinking how organizations work. Cagle emphasizes thinking differently and being authentic in leadership, drawing on his experience as both an entrepreneur and coach.
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Welcome to beyond you'd why Podcast, where we go beyond just talking about your why and actually help you discover and then live your why. You see, we believe that knowing your why, that driving force behind every decision you make and every action you take, is the essential first step to really knowing yourself. It allows you to move forward faster and have a bigger impact. If you're already a fan of the show, then you know that every week we talk about one of the nine whys and then we introduce you to somebody with that why so you can see how their why has played out in their life. This show will be more powerful for you if you've already discovered your why. If you still need to do that, head over to why institute.com and discover your why today. It'll only take you about five minutes. Now let's meet today's guest.
And so this week we're going to be talking about the why of challenge. To challenge the status quo and think differently. So if this is your why, you don't believe in following the rules or drawing inside the lines. You want things to be fun and exciting and different. You rebel against the classic way of doing things. You typically have eccentric friends and eclectic taste because after all, why would you want to be normal? You love to be different, think different, and you aren't afraid to challenge virtually anyone or anything that is too conventional or too typical for your tastes. Pushing the envelope comes naturally to you. Today I've got a great guest for you. His name is Greg Cagle. Greg is a passionate advocate for authenticity, a transformational executive coach, a corporate culture consultant, an author and a speaker. Leveraging more than 25 years of of in the trenches experience in building and leading his own companies, Greg comes alongside leaders and guides companies to position them for breakthrough success in building a culture that blows away the competition. With his proven let's do this approach, Greg has served top organizations like McCormick, Planet Fitness, Steel Dynamics, Army Special Operations, and the FDA. He's worked with a wide range of industries including manufacturing, five star hospitality, technology, software, nonprofit education, higher education, financial insurance and engineering. Greg has also partnered with the John C. Maxwell Co. For many years as an executive coach, speaker, trainer and business consultant in every consulting and coaching, relationship speaking, engagement and training environment. Greg's focus is on getting innovative, creative results that empower leaders and teams from around the world to outperform the competition and achieve more than they ever believe possible in business and in life. Greg, welcome to the podcast.
Thank you. Great to be here.
Man, that was a mouthful. That's a Lot of stuff you've done.
Well, it sounds a lot more important than it really is. We'll just leave it at that.
Well, okay, so tell everybody. Now, where are you now? Where do you live? Where are you right now?
Yeah, I live in Knoxville, Tennessee now. Moved here back in 2016. So that's home base, Knoxville, home base.
Now let's go back in your life a little bit and kind of see how you got to where you are now. Where did you grow up and what were you like in high school?
Yeah, I grew up in very, very small town in the Deep south, in Mississippi, to be more accurate, and very small town. I grew up, went to high school at a very small school. And it's interesting because when I was reading my why, one of the words that it uses is rebel, and describe me perfectly from a very early age. I've always been rebellious. My grandfather told me one time, he said, you're either going to lead a biker gang or you're going to lead a great organization one day. I don't know which. And so I'm not the leader of a biker gang yet.
So what do you mean by rebellious? Give us an example what your friends have said about you and how could we tell you were rebellious?
I just never really saw the need to follow along. And it was so entrenched in me for a long. I mean, ever since I can remember. Just break the mold. Just get outside the lines. Everything just called for me to do something different and to break outside of the norms. It's always there. Always there.
Never felt like you fit in, right?
Never. No. Yeah.
So, okay, you graduate high school, I assume off to school after that. Did you go off to college?
You know, I did. I actually. I went to college for two years, and again, just being rebellious. After two years, I just kind of said, I'm ready to get away. The only reason I think I lasted two years is I was an athlete. I played basketball, so I was on a basketball scholarship, so I played ball for a couple of years, and that kind of kept me there because I'm a competitor. I love to compete, but I just couldn't take it anymore. I was ready to get out there. And even college was just too restricted for me.
Like Steve Jobs, right? So Steve Jobs, why? He has the same why as you, and he didn't last even that long.
So you might remember in a lot of Steve Jobs interviews, he used to say, he said, you know, I'm a lot like Greg Cagle. I don't know if you ever heard.
Any I did hear him say that as a now, I didn't know who that was, but now it makes a lot more sense. Okay, so you leave after two years, then what happens to you?
Yeah, so I went to work for a company and again, I was very successful. I was in sales and I turned out I was pretty good at it. But again, just had this itch to pave my own way, do my own thing. And at 28, I left and just jumped out and started my own thing. And I look back on it now, Gary, it's just absolutely one of the stupidest decisions I ever made, but it's one of the best decisions I ever made. I was too stupid to realize I shouldn't do it, but I did it. And I've just always been this guy said, I don't know exactly what I'm doing here, but I know I'm going to figure it out. And so with $7,500 and a $2,000 cash advance on a credit card, I started my first business. And that was kind of launched me out there doing my thing.
So what was that business?
It started off as a marketing company, eventually evolved into pretty much a full service ad agency. I don't know if this is true or not, but back in those days, ad agencies had a full staff of media buyers and artists and so on and so forth. I think I might have been the first ad agency that basically built up a network of those services. And I was the first front person with the client, but then subcontracted all of those services out and coordinated that and led those ad campaigns and stuff, and it turned out really, really well. We did a lot of good work for a number of years.
So how would you, looking back to those times when you're say, 26, 28 years old, how would you do as an employee? How would that work out for you? Showing up at 9, leaving at 5, doing what you're told to do?
It's one of the reasons I left my first job. I was a top producer. Sales came easy to me, but I came in when I wanted to, I left when I wanted to, and I did what I wanted to. And I remember the boss calling me in one day and he said, listen, we got to do something about you. You're supposed to be here, you know, certain time. Back then it was 8 o', clock, supposed to be here at 8 and you just come rolling in whenever you want to. And you know, we have certain rules. And with all sincerity, I just looked at him and said, why are you telling Me, this. I outsell everyone else here. Why can't you just leave me alone? And it was right then and there, I think he discovered that I wasn't right for the company, and I think I discovered I wasn't right for any company. And it just didn't fit. I'm still that way. I've tried to temper it sometimes, and I've tried to knock the rough edges off of it, but still that way.
For those that are regular listeners and know about the YF challenge, man, you are just the perfect example of what we talk about because essentially unemployable because you're not going to do what everyone else is doing. But you're amazing as a visionary, amazing as a leader, amazing as someone who's going to break new ground and do things differently. What would the world be like if there weren't people like you that pushed the limit? We wouldn't progress.
There's a lot of people that have experienced me that would like to find out what the world would look like.
Okay, all right, so now you've got an ad agency and a marketing company, and you're late 20s. How long did you do that? Or do you still have that?
No, no, I did that for a few years. And just again, this is so much my personality. I got to a point where I was kind of bored with it, and so I sold that business and moved on to other things. So over the course of my career, the marketing and ad agency, I had a technology development company that I started with a partner who I wound up marrying his daughter. That's a whole nother story. And then. And I'm still married to her, thank goodness. And I also started a bar and restaurant business at one time where we had multiple locations there, which I also did with a partner. But I have this history of building something, getting it to a point, and then becoming bored and restless and wanting to kind of move on. So that's kind of what I've always done until my last business. The last business that I did was in the real estate industry. I was in not only real estate development, but I had a brokerage firm, and we grew that one pretty big. And I had a lot of employees associated with that. That was a defining moment for me, or created a defining moment for me, because I think that was the business that was just different enough every day. And there weren't really any rules to real estate development. You could kind of make your own, and it was going before zoning boards and kind of convincing them that you had a better way or that you wanted to do a different type of development. So I think had it not been for an event, that might have been where I would have stayed. But there was this event, you probably remember it, it was late 2007, early 2008, called a financial collapse when we had the big. And real estate was the tip of the spear of that. So at the time that that happened, I was holding hundreds of millions of dollars worth of real estate at some level of development, some stage of development. And it was just like someone turned off the faucet and everything kind of collapsed. And so that kind of set in motion about two years of real pain for me trying to work through all of that. I had six different banks, all of them decided they were going to squeeze me for everything that I had. And so it was a really painful time. And working through that and trying to get on the other side of it when I did, what I real, you know, at that time is like, what do I do now? The economy was still not that great. There wasn't a whole lot that I could do in real estate, of course. And I actually did try to hire on to get a job. And to your point, it's amazing you said what you said, not hireable. Gary, I'm going to tell you, I don't know how many times I got to an interview process for a position in a company and I'm thinking to myself, I'm so qualified, I could do this in my sleep. This is going to be a no brainer, but I need a paycheck almost every time. This is what I heard they said, I just don't think you're going to fit in here. You've been on your own too long, you're not going to want to do anything that we want you to do. I just don't see you as hireable. And that was the exact words they used. And so I kind of had to reinvent myself because I knew I wasn't going to get a job. And again, that's probably one of the best things that ever happened to me was being unhirable.
And so then what did you finally end up doing?
I went back to what I knew, which was I just had this knowledge of business. I had the ability to look at something and break it down to its simplest form and say, well, here's a solution. And so that's what I did in business. It's like, here's the best way to do this or here's a better way to do this. And so what I decided to do was I said, I know business. And I also have started, built and sold several businesses. I've had tremendous success. I've also been knocked down into the valley. I've seen it all. So I think maybe I can just make myself available to other entrepreneurs and other business owners and help them along the way and get paid for it. And so that's what I started doing. Reached out to a few people, networked and was doing that and actually ran across the John Maxwell Company. They do a lot of leadership training and executive coaching for their clients. And so they asked if I wanted to do some work with some of their clients. And so we did that for quite some time. In fact, I still do a lot of work with that company. But along the way I started kind of building out my own thoughts about how to help leaders do business differently. That rebellious nature of mine, that we can do this better kind of thing. And so I started challenging leaders and saying, hey, you know, there's a better way. Or I would challenge leaders, even in the coaching aspect and say, you're looking at this all wrong. Have you ever looked at this? And I just published a few months ago, it just came out. That whole book was a two year project for me. And it was. That's what it was about. It was kind of me challenging my why Challenging leaders to look at a different way of doing business. So that's kind of where we are today.
You are the perfect person to do that. So Greg's why is challenge right? To challenge the status quo and think differently. How he does that is by making sense out of complex and challenging things. And ultimately what he brings is a way to contribute, add value, have an impact in the lives of others. And that is the perfect yos for what you're doing. You get people to think differently. Do you find that most people put themselves in their own box?
Absolutely, I do. In fact, I challenged organizations to think about this, particularly the top leaders. I said, I want you to think about your organization, what you reward, and how you communicate with your organization or the people within your organization. Are you, without realizing it, building a box that says if you're going to be successful here, this is what you need to look like. And then I challenge them to look at themselves and say, have you built your own box in the book that I'm referring to? Actually, one of the statements that I make in that book is that most business leaders, they evaluate new ideas through the lens of their experience and their knowledge. Now think about this for a second. So if every idea that I look at is through the lens of my experience and my knowledge and what I know to be successful. What chance does that idea have of ever making it? In my mind, very little. In fact, there's a great story about Western Union. Back in the day, they were one of the top communication companies in the United States. And this guy, you might have heard of him, named Alexander Graham Bell came along and he invented this communication tool called the telephone. And he didn't have the ability really to do much with it financially. So he goes to the best communication company on the planet and he offers to sell them his patents. And it's interesting because the CEO at that time was quoted as saying, what would this company ever do with an electronic toy? Now, I don't need to tell you, would you rather own stock in AT&T right now or would you rather own stock in Western Union? But the bottom line there is, this is the way a lot of business leaders think. They take a look at what they know is the current reality of success in their industry or whatever it is they're leading. And everything needs to begin to make sense to that. That's why Steve Jobs was such an innovative, brilliant leader, because he never looked at things that way. And so yeah, I do believe, I believe leaders put themselves in a box and I believe they put the people within the organization a box. And I believe they create these decision making filters called experience and knowledge, which really we could relabel as the status quo. Right. And that's how their people begin to make decisions. And then they wonder why someone out innovates them or why they become irrelevant over time. That was a long answer to a very short question. I'm sorry about that. No, I got random.
That was really good. You know what I would love, and I don't know if you can do this, but take us into your mind as to what happens to you. What do you see? You go into a company now and you see status quo. What happens internally in your brain? Like how do you see all these things outside the box? How are you able to. It's probably almost instantly right where you can say, well, they're just stuck here. What happens to you when you walk into a business like that?
That's a great question. I'm not sure that I can give you a great answer, but I'll do the best I can. When I first started in this, what I'm doing now, which is coming in as a third outside perspective or third party coming into an organization to try to help figure out what's Going on, the first thing I always do is I just, I want to get to the root of the problem. I want to know, hey, what is the problem? And here's what's interesting. A lot of the time, maybe even 50% or more, what I am told is the problem, almost never is the problem. And what I mean by that is what they're really doing is they're telling me what the problem is from their perspective and the way that they've already designed themselves to think, and the way they think is the way that they encourage their employees to think. And so I go in with the idea almost always that what they think the problem is, it's not going to be that. That's the first thing that I do. And then once I discovered that the problem truly isn't what they thought it was, or even if it's what they think it is, it doesn't exist as a problem the way they think that it got there. And so either way, I'm just always looking for to totally break their model of thinking first. In fact, when I talk about organizational culture, I define it as the way the organization thinks, acts and interacts, or the people. And so I almost always look to disrupt their thinking because if I can disrupt their thinking, then their behaviors are going to change. And if their behaviors change, outcomes begin to change. And that's really where I really coach leaders is what is the thinking we need to have here. And by the way, you can't determine what the thinking needs to be if you can't really understand what it is you're doing. Because businesses basically perform on three business functions. They're either executing on strategy or they're navigating some kind of crisis or some adversity that's hit them, or they're trying to capture an opportunity. Well, each one of those three requires something different from the organization. And if that's not built into your culture, you're going to fail. And in one of those three, a lot of organizations are built really well for executing strategy, but they're not built very well for navigating crisis or adversity, or they're not built well to agile enough to capture opportunity when it presents itself. And so what I try to help leaders understand is there's all three of those are important for the long term sustainable success of your organization. Let's build that into your culture. And the way we build that into your culture is defining how do we want to think, how do we want to act, and how are we expected to interact with ourselves. And Our customers, if we can define that, become clear on it, then we understand how to create something different. If I'm navigating crisis, for example, that's going to require adaptability. Here we are on the other side of COVID right now. Some companies are on the other side of COVID Some never made it because they had to be able to adapt the way they did business in order to navigate that crisis or that adversity. So how do you need to think to be adaptable? And so what I began to get leaders to do is get away from, depart from that knowledge and experience that is so comfortable for you. Get out of what you know in search of what you need to know, what you should know. And that's uncomfortable. It means you have to be vulnerable. And something I learned, that's easy for me. In fact, I actually enjoy doing that and do it unasked or unprompted. But it took me a long time, Gary, to figure out most people aren't wired that way, so they have to have some sort of stimulus to say, listen, you can always go back to what you know. Why don't we just jump out of that for a moment? Why don't we just get out here in the unfamiliar waters of what we don't know and see if we can discover something really significant.
I could see that being scary for a lot of people, but exciting for a lot of people. And the ones that are ready are probably just ready, right?
I'm really glad you said that because one of the first things I have to tell people, I am not for everyone. Because, Gary, just to your point, look, if you're not ready to be challenged, if you're not ready for me to shake you out of your familiar comfort zone of all your knowledge and experience where you get to be the smartest person in the room, I'm not for you. In fact, 80% of the people, the companies and organizations that come to me, 80% of them, I never work and wind up working with. And I'm looking for that 20% that, to your point, is ready or at least willing. They may not be ready yet. I'll help them get ready, but at least they're willing to venture out. So, yeah, you're right.
And you are the perfect person for that. And you've lived it, you've seen it, you've experienced it. You've hit the highs, you've hit the lows. You've been the hero and you've been the goat. I'm sure the amount of experience that you have Is invaluable, I'm sure.
Yeah. I mean, it's. You mentioned it when you were introducing me in the trenches. I mean, I know as an entrepreneur, in everything I ever did, I started from scratch. So it's not like I went out and raised invested capital and bought a business or anything like that. Everything I did was started from scratch, which again, fits my personality because I'm going to do it the way I want to do it anyway. But I know what it's like to lay awake on Tuesday night thinking about, how are you going to make payroll on Friday? I know what it's like when the bank note is due and you got a choice. Do I. Do I pay my payroll taxes? Do I pay my bank note? I mean, I've gone through all of that. I also know what it's like to be on the top of the mountain and. And really own the industry that you're in or what you're trying to do and be nervous about, hey, can we stay here? And what do we do to stay here? And how much do we need to innovate and how much do we need to stay the same? And all of those questions. So, yeah, it's, it's. I've got all the scars that go with that, and I tell people all the time what qualifies me. I mean, I. I just told you earlier in this interview, I didn't finish college. I don't have a sophisticated degree. I didn't go to high school, Ivy League school. What I tell people what qualifies me to do, what I do is I have failed at everything you can fail. I've made every decision that you can make that was wrong. And I've still been successful as a result of it. I suffered a lot of pain. I've got a lot of scars. And that's really what qualifies me to sit down and work with a business leader, because I just been there.
Yeah, it probably sets their mind at ease that, man, this guy's not perfect. And I don't have to try to be perfect because he already knows what it's like if it's not perfect, because he's lived it. So I can tell him anything.
I'm. Gosh, I'm so glad you said that, Gary. One of my biggest challenges when I'm working with a leader is they take on this responsibility. I don't know who told them they were supposed to, but they take on this responsibility that supposed to always know the right direction to go, always know the answer to the question. Always have the vision that's needed to always we solve the problems. And what I tell them is, and you've probably heard this before, but I say, look, if you're the smartest person in the room, you're either in the wrong room or you're the wrong person for the room. And what I also try to help leaders understand is quit carrying so much of that and understand that the leader's job is to extract the brilliance of the collective. The best leaders I know understand the real brilliance of an organization lies within the collective of the people. And if I can be a genuinely curious leader where I interact with my people and I'm looking for their perspective, their understanding of things, what they see that I don't see, what they touch that I don't touch, and relieve myself of the responsibility of always having. Having to have all the answers, that's when great things happen. I love that.
Now, on another note, so my wife has your why? So I know. Yes. So I know what it's like to be married to you. And so I have a lot of sympathy for your wife.
And hey, Gary. So, Gary, let's have some fun with this. And I know your audience will benefit from this. So what have you recognized as, like, the biggest challenge of a relationship with. With someone, with this. Why? Where do you struggle? I know there's tons of benefits because you're still married, so there's a benefits. What makes it tough for you? Where do you struggle?
Unpredictability. I mean, you just cannot count on anything to be typical. You can't count on what, your expectations. Not a chance they're going to be met because they're going to go in another direction for sure. I mean, logically, I struggle sometimes to just follow along. Like now, how did we come to this decision?
And I don't know if your wife would say the same thing.
Can you share a story or can you give us an example? Do I dare ask?
Oh, of course. I mean. Well, I'll give you a real simple example. We'll get in the car to go home. Let's say we're together at an event that we go to a lot. And she'll say to me, well, let's take a different way home. I'm like, we're just trying to get to home right now. I just want to get home. I know, but let's go a different way. I'm like, why would I want to go a different way? I just want to get from here to there to go to bed. I know, but we Always do it this way. Let's see. Let's go a different way. It might be more fun or it's just different. I'm like, no, I'm not looking for that right now. So it's like, no. But in her mind, it makes total sense to find a different way. In my mind, it's like, I want the best way. I just want to get home the fastest way. Does that make sense?
Yeah, absolutely. I'm laughing because I know exactly. Guilty is charged.
But it's a lot of fun when fun is needed and wanted, when you're needing something predictable, consistent, not likely it's going to be that way. So that's been my life so far. So I would love to spend some time with your wife and swap stories because I think it would be a fun time. And you and my wife, Right?
Yeah. Well, I think what I'm going to do when we finish here, I'm going to actually have my wife do the assessment because I'd like to know why I'm married to.
Yeah.
So here's something that's been interesting and don't let your wife know this yet, but you can get back to me on this. It's fascinating how often people with the why of challenge are married to people with the why of better way, which is my why. And I don't know why that happens that way. But so many people, so many of my friends that guys that have the why of a better way are married to gals that have the why of challenge and vice versa. So it'll be interesting to see what your wife is, because they're very similar. Better way thinking, finding a better way and challenging the status quo, I mean, are very similar. They're both outside the box. But challenge wants things fun and different and interesting and better way wants things outside the box. But it has to be better. Not just different. Has to be better.
Gary, you just hit on something. I'll tell you a quick story. So in the beginning, you know, in the early days when I started my first business, I wanted some cheap employment employees. So my wife was the perfect one, Right? So this is serious. On two different occasions, we tried to work together, right? It just made sense. We got the same alignment of goals and, you know, I can trust her and so on and so forth. It never worked. And it never worked for one reason. You just hit on it. I would ask her, say, look, can you see that this gets done and can you handle this and can you do this? And she always would come back. Well, I think there's a better way to do that. I'm like, I'm not looking for a better way right now. I'm looking for efficiency. We got to go right now. It's time. We got to go. No, no, no. We can do better. And so it would ultimately wind up in an argument. And finally we just, we realized we cannot work together. It's just not going to work. Now, we probably could. We probably could in the normal workplace where you've got two different wise like that, they would probably work together and complement each other, but unfortunately for us, we're married. And so all of that goes into we just couldn't work together. Yeah.
Well, Greg, hey, last question for you.
Yes, sir?
What's the best piece of advice you've ever gotten or the best piece of advice you've ever given?
Okay, I knew you were going to ask this question, so I had to give some thought about it. It turns out the best advice I've ever gotten is the same that I've given, which is. I'll explain. That guy told me one time when I was really down and out about something that I was doing with a large group of people, and I just felt like they hated me. And I remember expressing it to him. He was a little bit older than me and he was a lot smarter than me. And he said something that stayed with me. He said, you need to remember something. You are not for everyone, and you weren't even created to be. And I thought about that and it just was such a relief. I found myself telling people all the time after that, be authentic. Be who you are. The world needs you. And I actually wrote a book one time called be Weird. And I told everybody, you're weird. You're weird. Embrace your weirdness. Be that weird. Because if you don't, there's a hole in the universe with your name on it never gets filled. And that frees you up to understand. Look, I might not be for you, Gary, but that's okay because someone else is. But I'm going to be right for someone else, and that's what I need to worry about. Just be me. So that's the best advice I ever had.
Yeah, my wife always talks about that once she discovered her why is challenge. It's kind of given her such peace because she's like, hey, you know what? I am okay. I'm okay being me. I can just be me. And that's good enough. And I don't have to try to be somebody else or like somebody else. So here's an interesting Thing about the why of challenge is that people with this why, if they look at their why as a curse, they medicate and try to get away from themselves and are very unsuccessful. But if they look at their why as a gift, they do amazing things. They expand the horizon, you know, Steve Jobs, Herb Kelleher, Richard Branson. They have the courage to do things the rest of us wouldn't do. And so they bring amazing things into the world like I'm sure you've done in many cases and are going to continue to do so. Greg, thank you so much for being here today. Really enjoyed connecting and talking with you, and I look forward to following you. Tell us the name of your book.
Yeah, the name of the book is called the Four Dimensions of Culture and the Leaders who Shape It. And so it's really about understanding what culture is and how your leadership shapes culture. Just came out. It's on Amazon, Barnes and Noble, all those.
Well, I guess then before we leave, what prompted you to write that book?
It was, interestingly enough, to challenge leaders. Look at running your business differently. Business leaders tend to operate and lead from where the light is. I can look at a report. I can see what my revenue projections say. I can see what my profit margin says. I can see where my brand opportunities and all of that. And they try to lead from there. And what I'm trying to get them to understand is, look, it's culture. Culture leads. In your absence, Culture executed on. Focus on that and understand it deeply. And when you do, you're going to lead differently. And I feel so blessed because we've gotten this out there, this message now recently, over the past couple years, and we're seeing some significant transformations in the way business leaders lead and ultimately how their organizations do business. It's really, really exciting. I love it.
I'm going to have to get it now because culture is a big thing. You've got to have the right culture. In your case, it'll be to think differently, right?
Yep.
So very good, Greg. Thank you so much for taking the time to be here. Great to meet you and I look forward to following your book and following you.
Thank you. Thank you very much.
I really hope you enjoyed today's episode and that through today's guest, you heard how important it is to know your why and how impactful it can be in your life and the lives of those around you. Be sure to head over to whyinstitute.com and discover your why today. Remember, the more you know about yourself, the more you'll know about others. I'm Dr. Gary Sanchez, and I'll see you on the next episode.
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