Transcript of Why Playing It Safe Is the Riskiest Thing a Founder Can Do (The Jeff Bezos Principle Nobody Applies) New

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00:00:00

Most people think Amazon won because Jeff Bezos got lucky. He didn't. He followed a system, and he wrote it down for over 20 years in every single letter he sent his shareholders. My guest today, Steve Anderson, read all of them. Then he pulled out 14 growth principles that explain how a company that lost money for a decade became one of the most valuable on Earth. We get into the one most founders get wrong. Bezos called it unwarranted risk aversion, the idea that playing it safe is the most dangerous move you can make. We talk failure as a strategy, obsession over the customer, and why Bezos ended every letter the same way. It is always day one. If you are building something and you feel stuck, this one is for you. Let's unlock it.

00:01:00

So Steve, welcome to the show. I know you spent many years, I mean, I'm going to say your whole life discovering, but many years looking at Jeff Bezos and really what he did and how he's accomplished, I mean, so much. I know you wrote this book called "The Bezos Letters." I'm looking here on Amazon, thousands of reviews. Bestselling book. I mean, I'm so excited to jump in and see what you're about. Well, thank you.

00:01:31

I am too. And thanks for having me on the show.

00:01:35

So, for everyone listening, just even just right now, tell us a little bit of like who you are and how did you even come to this idea or how did you find this concept?

00:01:44

So, I will start off by saying I stumbled into it. My background is the insurance industry. Spent my career there early on selling insurance to individuals and to businesses. Kind of midway through that, I got intrigued with the technology piece. So, agents using websites and all of that, and I kind of lived through all of those technology changes from the internet to websites to social media to et cetera, and now certainly AI. But along the way, I was consulting with insurance agents, and I think we all realize that technology continues to develop really rapidly, more so now than ever, I would say. But even 20 years ago, it seemed fast. And so I started this idea of thinking about this idea that the biggest risk businesses face is actually not taking enough risk. Sitting back, "Let me wait a few years. I don't know if this internet is going to be anything. Let me just—" And at that time, you could do that. Certainly, today, much, much harder. So, I started looking at companies in general and something I did pretty effectively, I would say, is look outside the insurance industry for ideas and trends and where things are going.

00:03:13

Because the insurance industry tends to be very conservative and slow to adopt. So looked at companies that had once been very successful and were gone, out of business, and companies that had been successful and continue to be successful, and trying to understand what's the difference, why one company did this and the other company wasn't able to. During that research, came across Amazon. Had sort of heard and read maybe one or two of the letters to shareholders that Jeff Bezos wrote about Amazon, but got started getting deeper. And at one point, read every letter that he had published to that point, probably through that— at this point, it was probably 2017— and read them one after the other as a narrative and realized there were trends that he talked about in the letters. And really, the trends that caught my attention were how he grew Amazon and how Amazon was able to be successful and continue to be successful. So, that's the kind of what the hook that got me. And then, I had this brilliant idea to create a lead gen, right? Here's some great takeaways from Jeff Bezos. I don't even know if he was a billionaire at that point, probably, but obviously successful.

00:04:41

Amazon continues to grow. Here's some things you can learn wherever you are in your business journey, from startup to 50 employees to 500 employees, et cetera. And fortune— so I created a one-page executive summary of all the letters to that point. Fortunately, my wife is in the book publishing business. And so, I was pretty excited about this. I thought, this is really interesting to me. And I showed it to her and she looked at it and said, "This isn't a lead gen. This isn't a giveaway. This is a book." And so, that moment was actually my "oh, shit" moment, which was, "Oh, I don't know how to write a book." And she sort of said, "Well, I do." 'You come up with the ideas, we'll work on this together.' And so that was the start of a probably year and a half to 2-year process of actually figuring out what the principles would be, how they apply, research, and all of that kind of stuff that went into the manuscript. And I said, I accidentally stepped into it. I had no conception of what it would become and has become. You mentioned bestseller, Wall Street Journal, USA Today, debuted on their bestseller list, and it's been translated into 21 languages.

00:06:07

And as you said, you know, lots of reviews. And I still am sort of surprised, you know, why me? There are a lot of smart people in the world, but I had the right combination. And I think one of the hooks that's different about this book is that view of risk, right? So the insurance industry is all about reducing risk, mitigating risk, transferring risk. And I was saying, you need to take more risk. Very counterintuitive, certainly for me and the industry, but I think for people in general who often are very risk-averse. And there's a phrase Bezos uses that I still like a lot, which is unwarranted risk aversion. Right. So anyway, well, you can wind me up. I can keep going. So you're going to have to interrupt me.

00:07:03

So, yeah, I don't think it's— anyway, I think it's very important. So unwarranted risk aversion, I think, is what you said. Well, yes. I mean, let's start there. Like, what did that mean to Jeff Bezos? Where did that— like, how did you even find that in all these letters. So just to recap, because I just want everyone to understand, you went and researched and found, I don't even know how you find this, but you found every letter Jeff Bezos wrote to the shareholders, to the board. And you then got, I'm going to say you got deep into it and really analyzed and studied these letters and started seeing trends. And started seeing what, what was actually going on as, as Jeff was writing these. And you can see probably the evolution of the company of what he was writing. So you, you kind of went deep into that and then built a book around it called The Bezos Letters. And from The Bezos Letters, there came, I believe, 14 business principles or 14 Jeff—

00:08:07

Well, I call them growth principles. Yeah, 14 growth principles on how Bezos grew Amazon to what it is today. And I think, again, I always try and emphasize, regardless of where you are in business, these are principles that are principles, which means they're long-term. They're not kind of flash-in-the-pan marketing hacks and things like that, but they are principles. And the more I talk to business owners of all sizes, it resonates with people. Now, they're not all easy to implement. And that's part of the work that goes into it. But if you feel stuck as a business owner, if you're growing but not enough, or these are ideas that can help you get unstuck is the way I would say it.

00:09:05

Back to my question of the first, I don't know if that was a principle or not, but you were talking about not having the fear and being able to be a little, like, you know, go in and be unwarranted risk-adverse, I think is what you said. Yep. Was that a principle or is that something that you kind of saw within the letters and saw within the company?

00:09:27

Well, so I would say first, I saw it in the letters. How it shows up is from the very beginning. So the first letter he wrote when Amazon went public was 1997, and he had kind of 3 main sections, uh, in that letter. And some of the principles grew out of that, but one of the, the common threads throughout the letters and started from the very beginning was this idea that And he, Bezos, knew we needed to experiment in order to invent on behalf of the customer. And those words, experimentation and invention, and on behalf of the customer are really kind of key ideas. What he said was, is that if you're going to experiment, you're gonna fail., right? Because if you know the experiment's going to work, it's not an experiment. So, you have to, as a business owner, be willing to suffer the failures to find the wins. So, that idea became my first principle, which I call encourage successful failure. Okay. So, the structure or the framework is 4 cycles: test, build, accelerate, and scale. And the principles fit into those 4 cycles. And that's just a way to— 14's a lot, and we debated a lot about, is it too many, and all of that.

00:11:09

But that framework is a way to kind of grasp, you know, what principle affects you during what phase. Of your business. And I believe those 4 phases every business is going through all the time. If they're a 5,000-employee business or a 5-employee business, they look different, but they're still the same. They're testing an idea, they're building on the successful results, they're accelerating the growth, and then they're scaling. Okay. And then starting over again. And it could be different departments, different regions, you know, etc. So, yeah, so I got to answer your question. That whole idea of experimentation and failure is one of the principles, and that's how I put it together.

00:11:59

I mean, it makes sense when you hear it, but it's sometimes, I think, as business owners, marketers, 'cause I mean, the amount of testing that you even have to do as a marketer, but I mean, just saying even as a project builder, whatever it might be in the scope of business, is, yeah, I get it's hard to test because there's a lot of failure that's going to come from it. But Bezos was basically saying, we're going to fail before we succeed. You're on this board, get ready, which I love because it's also setting him up as well as why is this not happening? You know, it's like, hey, and they get— they got to buy in and they got to trust. And, you know, I'm sure they've had more. I know they've had trillions of dollars of failures before they've had their, you know, their successes. So That's interesting. So test, test. He said it in 1997. We are going to basically test. We're going to trial. We're going to keep figuring it out. What I love at the end, you said something was either for the customer or by the customer. It was, or like to support the customer.

00:12:56

So customer was always kind of the forefront is in his mind.

00:13:00

Yeah. And that's another principle, which when Bezos talked about it in the '97 letter, he said, we will obsess over customers. And so my principle, growth, is obsess over customers. And, you know, this was an interesting principle because most businesses go, well, I take care of my customers, or I have good customer service, or I've mapped out a good customer journey. But there's a different flavor or connotation when you talk about obsess over customers.. And I don't see many businesses obsessing over customers. Now, if you're listening to this and you're buying from Amazon, there's a reason. And that reason is they obsess over customers, meaning they're always looking for lower prices. They're always trying faster delivery and they're always building more selection. And those are 3 customer pillars that Amazon has put in place and continues to grow. But this whole idea of obsessing And it can have negative connotations, right? If someone's obsessive, they've gone too far. But can you go too far when you're taking care of the customer? I don't think you can, right?

00:14:16

I think that there is— I don't think there is a line for that, truly. And it's interesting because you said they're always looking, they're always trying to build. But I think there's also— I could be wrong, but they're also retaining. And what I mean by that is You ever try to return something with Amazon? Mm-hmm. You ever had a hard time doing it? Not often. Never for me. I mean, I returned, I had a, I've returned one product that was bought like 2 years ago and then they sent it again and it broke a year later and they let me return that product. And then they finally said, you know what? Let's just give you the full refund back. Yeah. I used the product for like 3 years and I was willing to buy a new product, but just— and it wasn't— it was like $150 thing. But I guess what, the next day I bought more things off Amazon. I actually try to find products that you'd buy on a normal regular website on Amazon because I know the refund policy and the, the process to refund is going to be the easiest there is.

00:15:23

So, and I think that's a point too. I mean, in my mind, that always goes to how much friction do you have currently as a business owner with your customers? What do you make them jump through? What hoops? That's all friction. Amazon is obsessive over removing friction, and that's just what you described.

00:15:43

So I wanna ask, I, I kind of wanna go deeper here because I, I want, we are gonna learn more about the principles, but I kind of wanna go deeper in the, the psychology, if you picked up any, like, what was he really saying? What was he really thinking? Were there moments when you were reading letters that seemed more panicky or more, let's say, less on the vision and more maybe about not— like, was there times that he deviated from what the mission was, maybe because it was lack of resources or lack of money or things were happening in the economy and he was just trying to save the company before it exploded? Or were the letters always just the same tone?

00:16:20

No, they weren't. And when you say that, I'm thinking it's the 2001 or 2002 letter when the internet bubble burst and Amazon stock went, and I can't quote the numbers, I'd have to look them up, but something like $81 a share to $6. And he started his letter with, "Ouch, it's been a brutal year." So, I think he was on it. Again, he's CEO of a growing large publicly traded company. There are parameters around that. And at the same time, I always felt like he was being him, real, or being who he is. I think he was pretty optimistic. I think he had an interesting innate ability to look into the future. And really, two examples of that. One is just seeing the internet. So, the whole origin story with Amazon is he was a financial analyst in New York City and kept hearing about internet and how fast its use was growing. And He started asking himself the question, could it be used to sell stuff? And he said, yes, it will be. And so another example is, I think it's probably '98 or '99 letters, again, an early letter, when he talks about how slow the internet is and that bandwidth was a constraint on Amazon, right?

00:18:02

Because it took time for the web page to load. They had to be conscious of how many images, right? All the stuff that had to happen to, speed up the time. But he also said, and today is the worst it's ever going to be. So again, there's acknowledging problems to overcome and being realistic about what they could do. But he was always, he literally was always thinking multiple years or decades ahead. The second example of that is his space company, Blue Origin. He started that in 2001. He had a long-term vision. In fact, he was valedictorian of his high school class in Miami, and his valedictorian speech was how manufacturing would be moved to space so people could come back to the Earth as a national park. And visit. You know, I mean, again, so long-term vision and the willingness to continue to step by step move toward that vision. Now look at Blue Origin, right? Again, reusable rockets and, you know, interesting competition there between Musk and Bezos and all of that. But now Amazon, you know, is launching satellites and has created what is now called Amazon LEO. LEO, which for low Earth orbit satellite constellations for high-speed internet communication.

00:19:39

That's how they've been working on that for years. So that's that line. So one of my principles, and I can't remember, oh, there it is. It's in the build cycle. It's called apply long-term thinking, right? As you're building, you need to have the conviction of what you think is right or what's going to be happening and be willing to continue really to suffer not just losses, but suffer— what's the right word I want to use?

00:20:09

Well, I was going to say suffer through the pain of not just the external of the people saying it won't work, this and that, but the pain of the internal. Being able to set your vision and believe in a vision so big and so bright that other people can't see it and still stay on the lane.

00:20:28

To go through it. You know, at one point, at one point, I think it was Bloomberg had a cover, Amazon Bomb, right? That was during the, you know, dot-com era. But still, I mean, people, naysayers saying this will never work. You've got to have something to keep that going. And for him, it really was long-term thinking.

00:20:51

I think there's a little bit of, you know, some people might call it psycho or sociopath. There's definitely something that these, these guys have for sure that just they're relentless. They know it's like they don't even— if we don't know them, right? We don't know their personal journeys. But it feels like doesn't even matter what the journey is, they will just find a way to pursue and keep building no matter what happens. And I mean, yeah, it's like anybody can sit here and go, it's quite remarkable what Jeff Bezos has done. And with Amazon. I mean, it's amazing. And I know they just, I feel like that company's just starting. I was told, I'm not sure if this was correct, but I was told this like many years ago that like one of the goals or the missions is, can you buy something from Amazon and have it delivered at your house faster than it would take you to get in your car, drive to the store and come back? And that was, I don't know if that's still one of their goals or not, but like, I would not be surprised. I mean, people are talking about— I would not be surprised in the next probably year, I would say year for sure, two drones are going to be dropping off my packages.

00:22:00

Well, and yes, I totally agree with that. And that's another example of a long-term vision. I mean, they've been working on drones for a long, long time, you know, and people were, you know, a normal business would have given up a long time ago. Yeah, it's just really— You know, and so having that vision and that long-term goal, fast delivery and faster— I mean, keep pushing that edge, and they keep pushing that. And again, that's— and this is an example where principles stand on their own and they interact with one another. So that's long-term thinking, that's obsess over customers, That's leveraging time with technology. I mean, it's a number of principles that are interacting there that create that environment that can be successful.

00:22:56

So, let me ask this question. As you were going through all these letters and you came up with the 14 principles, which were the 1 or 2 that really stood out for you that you're like, "I knew this had to be in the book." this was one of the game changers. What was that principle and how did you come to it?

00:23:18

There are a couple that come to mind. I think first we've talked about the encourage successful failure. Quick story on where that came from. It definitely was intertwined with experimentation and Bezos was a big believer in experimenting. And one of the things, actually, a friend of mine, who did an early read of the manuscript. And he came back with, on that principle, he came back with, you know, employees aren't afraid of failure, but they are afraid of the consequences of failure. And that holds companies back because they won't experiment, they won't try something new, they won't because they're afraid. They're afraid their career is going to get hit, they're going to get fired, they're going to, you know, et cetera, et cetera. So that was one, and that phrase literally came from the Apollo— the— oh, I just forgot the director's name. Hang on a second. Apollo 13 movie at the very end. So I'm a space nut, have been forever. So I love space stuff. And watching at the very end of that movie, Ron Howard's movie, thank you. Apollo 13, really good movie. And at the very end, Tom Hanks, who's playing the commander Jim Lovell, is stepping off the helicopter onto the deck of the Iwo Jima.

00:24:45

And he's narrating in the background, "Our mission, Apollo 13, became known as NASA's most successful failure. We didn't make it to the moon, but we got all 3 astronauts back alive." Mm-hmm. And that to me encapsulates the definition of a successful failure. Okay. Right. So that, I mean, that you learn. So that's one. Yeah.

00:25:09

So another way of saying that, just from my perspective, is there's learning to be like every failure, there's a lot to be learned. And actually in every failure is just getting you closer to the win. Correct. You don't get closer to the win without the trial, without the error, without the consequences, and most probably without the failure. Right, exactly.

00:25:30

I think another, we talked to obsess over customers, so I won't go into that one again. The other one that resonates with me and a little story behind it is in the Accelerate cycle, it's called make complexity simple. Mm-hmm. And so we talked some about that, right? Just about returns can be, most places it's complex for the customer, certainly at Amazon, It's less so. So they make complexity simple. That came from a, um, I was listening to NPR radio interviewing when Amazon bought a company called PillPack, which was a pharmacy company, that mail-order pharmacy company that specialized in patients who had multiple medications per day. And they created a process to package in a little plastic Yep, you know, little plastic by date and by time, morning, noon, 12, I mean, whatever.

00:26:30

And then just pop them up beneath the mat.

00:26:32

And then you just opened them and take them. You didn't have to use the pill boxes and all of that kind of stuff. So Amazon bought them. One of their first forays into that, you know, pharmacy, healthcare, et cetera. One of the CEOs of the established pharmacy company, I think it was Walgreens, but I'd again have to look that up again. He was being interviewed and was asked about, you know, how does this affect you for, you know, Amazon getting into the pharmacy business? And there's been, there had been a bit of a trend of kind of the Amazon effect, right? And the CEO said, yeah, I'm not really worried about Amazon because it's more complex than they realize. And I thought, I literally said, I remember this, I said out loud in my car, I was alone, but I said, that's what Amazon does. As they make complexity simple. And so again, how do I say this? Experience. I mean, how I kind of put these ideas together ended up with, you know, the book and then the framework of the Growth Principles.

00:27:41

From the letters. Now, we've talked a lot about what was in those letters, you know, and there's 4. We don't wanna give all the principles away. That's the whole point. You gotta get the book to really get the principles. But was there things that you saw in the letters, even maybe going through the journey of Bill Bill in the book where we're not talking like that didn't maybe make the book that maybe should have made the book and or things that you saw with those letters that like, what was he not saying? I think we talked about this before the show. I was like, I want to understand like, what was he not saying in these letters? Because these letters, again, I'm assuming just for the audience, like you're writing letters to a board where at this point You know, I'm going to assume Amazon's losing multiple, multiple millions. If you don't understand, like Amazon was losing multiple millions of dollars a month.

00:28:31

Yeah, especially, especially the first 10, 10, 15 years.

00:28:35

Profit was negative, like negative. And how are you writing and what are you writing to these people who are still dumping in money? The board that they're— they have the pressure from everyone else. And you have one guy that's still sitting on the vision. Like, what was he not saying in those letters?

00:28:54

Indirectly? Um, a couple things come to mind, and he, he ended up addressing them later. So let me— and I think what's coming to mind is, um, employees, and really more specifically fulfillment center employees, the warehouse workers. Uh, lots of stories of what's the right word, tough working conditions, their drivers not being able to take breaks, uh, you know, things like that. Um, and early on, even in that, I think the '98 letter, he talked about the importance of employ— you know, employees and hiring the right employees in order for Amazon to be successful. But he also said, this is a tough place to work. We have a vision. And, and here's how he phrased it: we are building something great, something we can tell our grandchildren about. Part of that translated into pushing for faster. And maybe not— certainly early on, maybe not taking as much time or effort or thought into how do we better treat our warehouse employees. Now, they, they— I think because of pushback, uh, responding to some of that, they actually, um— so Amazon had 14 leadership principles that are different than my growth principles, but there's some overlap.

00:30:44

But they added 2 more just before he steps aside as CEO. And they, you know, one of them was, will be the Amazon will be the best and safest place for an employee to work in the world. So that, and again, for them, leadership principles are core to who the organization is. So, that was a different focus. I think there's still legacy kind of thoughts. I mean, one of the pushbacks I get talking about the book is, "Yeah, but he treats his employees like crap." Well, that's what I was thinking.

00:31:21

I didn't want to say it, but from my understanding, they're actually not the greatest working conditions. They're actually unsafe working conditions. And I know there's safety regulations that are different in North America to other countries as well. And he can only control so much in those safety— as a business owner, he can only control so much at that level. But from my understanding, it wasn't actually, the safest and most fruitful place to work.

00:31:46

And I'm gonna go back to customer obsession because that's one of the things you have to be aware of. If you're obsessing over customers and speed is the measure of that obsession, then you're gonna push employees harder and harder and harder. And employ— warehouse employees get healthcare on day one. They have what's called Career Choice. So they— Amazon will pay— now used to be 90%, now it's 100% of tuition for, um, schooling. I'll say that. And, and it doesn't have to— yeah, it doesn't have to be related to their job. It could be they'll pay for a nursing degree. Hmm, interesting. Right? So yeah, and again, that emphasis on safety. And again, this is sort of the interesting— because the other piece to this is their continued work on robotics. So they are replacing— okay, the very first fulfillment center I went, I was, did a tour of, walked into, when you clicked buy, an employee in a fulfillment center got a notice on a handheld device, go to aisle 23, shelf 8, section 3B, and pull this. They had a cart with a yellow bin that they walked up and down miles and miles of these aisles in a fulfillment center of probably at least a million square feet, and they were walking and doing that.

00:33:43

That has been replaced by robots. So, they no longer have that position. Now, they're getting, "Well, you're putting people out of work." But people are also complaining, "Well, it's unsafe to work." I mean, so it's an interesting counter, you know, working of, yes, we're trying to be safer and we wanna be faster.

00:34:07

Here's the thing with that, 'cause I think we're getting into a little bit of a different topic, but the reality is, 'cause I've gone all in, on AI. Someone asked me the other day, what does that mean, all in? I mean all in. Whatever I do, it's through AI. How I think is, how can AI do this? Because whether, whether you believe it or not, this thing isn't coming and going. This thing is here, and it's here to take over. It is here to take over your job. It's here to take over your business. It's here to take over civilization. It really is. So for me, Eric Hoffer— I don't want to bush this, but Eric Hoffer, had one of the best quotes and he said, "In times of change, the learners will inherit the earth while the learned find themselves beautifully equipped to live in a world that no longer exists." And we are in that change right now. So, I look at it and go, you can either fight it, argue it, and think it's not coming. The same people who once said, You don't need a website. Well, guess what? No, you're right.

00:35:11

You were right. You're right. You don't need a website today. Today you don't need one. But guess what? And it's gonna be the same with AI. So that's just the reality. But I hope that with AI, those jobs are gonna be replaced and 10 more jobs might be created. And you know, that's the opportunity.

00:35:27

Well, and I, you know, again, having now decades of watching some of this stuff, yes, jobs are going. Away. And I absolutely am convinced new jobs that we can't even imagine right now are being created. And actually, mentioning AI, when we first started, we talked about analyzing the letters and all of that. And I almost popped up and said, "And I didn't even have AI to do that. I had to do that myself." I mean, can you imagine though, like what your 2.0 book would be?

00:36:00

Having all those letters and I like to like and here's the reality. I like to say you're the smartest guy in the room and you got the team full of smartest people. And I'll tell you something, you know, smarter than all those people combined. AI. And I guarantee you, AI can look at all those letters and pull some crazy stuff out of there that we wouldn't even be able to think. And that's just the power of it. But here's the cool part. Are you the guy who's using the AI in that way to pull out that information? Or are you the person who's sitting around and saying, oh, I not going to work and I'm just going to write this on my own, you know, etc., etc. But yeah, I can't imagine you— the amount of work you guys would have done and detailed you would have and letters you would have had to pull to read those and actually come up with all that. That, that goes without saying. I mean, what a, what a, what a great thing you did, I would say. What, what, like, I mean, awesome. Like, I mean, this book's obviously doing as successful it is for a reason, uh, and I love it.

00:36:55

The Bezos Letters. So as we come to an end here, I know I'm looking on Amazon, but where else can people get this book? I'm going to say people need this book. We've talked about like one or two of the principles. There's 14 principles here. If you're in business, you're in marketing, I'm going to say even probably in life, there's 14 principles that Jeff Bezos has kind of lived by, I would say, directly or indirectly to create Amazon. So if you want a life like that, follow the principles, get the book, where can they find the principles in the book?

00:37:28

So, obviously, the book itself and it's all formats, physical, digital, and audio available on Amazon. The book website is thebezosletters.com. And there's some additional information there on helping, little workbooks and some things like that to help actually. I was really, tried to be very intentional about not just having the ideas, but how can we actually do something with it? And so, and interestingly, Bezos is building an AI company right now.

00:38:05

Oh, I'm sure they, I mean, they all are, right?

00:38:08

And it's really, he's focusing on manufacturing and how AI can help manufacturers, you know,, being streamlined, etc., etc.?

00:38:20

Well, I think it's already happening. I know that they're working on robots right now. They put them in, I believe, I forgot what it was, it was like the BMW plant, and they put that same robot into like a food manufacturing plant, and the robot did the job of like 10 employees more efficiently, more effective. And I mean, that's the scary thing, right? Like, that's the jobs, you know, robots and AI is going to take over. I got one deep question for you. And only because I know you studied these letters and you must have gotten deep into the psychology of Jeff himself. So let me ask you this, knowing what you learned from those letters and the principles and everything you saw, all the triumphs, the ups and downs, if Jeff was sitting there with his son, and his son asked him, "Daddy, what's one thing I need to know about business and life?" What do you think Jeff would be saying to his son?

00:39:20

There's so many things I think he would say. I think I would distill it down to don't be afraid to experiment. Have a long-term vision, understand where you want to go, and believe it's always day one. So we didn't talk about that principle. That's the last one. But he ended every single letter he wrote with some version of, it's still day one, it's always day one. And, and day one is a mindset. Of the excitement when you first opened the doors to your business, whatever that looked like for you, that excitement of helping customers, having something to do, you know, that. And Amazon's been described as the world's largest startup. Mm-hmm. Because that mindset of we still have a lot to learn. And I don't think we have time for the whole story, but I want to give you one piece. He, at an all-hands meeting in Seattle 10 years ago now, he had a question from an employee in the audience. He had talked about company update and opened it up for questions. The question was, Jeff, what is— because of that day one, that's very common. 'Jeff, what does day 2 look like?' And he kind of chuckled and he said, 'I think I know the answer to this question.

00:41:00

Day 2 is stasis, followed by irrelevance, followed by excruciating painful decline, followed by death.' Wow. And that's why it's always day 1. So you think about those companies that once were very successful, And he later— and they actually told that story in one, in the 2016 letter. And he said it could take 20 years for that process, but once it starts, it's really hard to reverse. And he said— and this is, I want to tie into a little what you said earlier about AI— he said there are 4 things that I think will help fend off Day 2. I won't go through all of them. But the one is eager adoption of external trends. And he identified 10 years ago, machine learning and artificial intelligence as one of those trends. So again, looking ahead, not being afraid, having an understanding of experimentation and trying, and move it forward. I think there'd be some version of that conversation to his son. I love it.

00:42:23

Well, Steve, thanks so much for showing up and being here with us. And for those, those, for those of you that want to learn more, it's The Bezos Letters. All you got to do is go to Amazon and put in The Bezos Letters and you can't miss it. Thank you so much.

Episode description

Most business owners think risk is the enemy. The man who decoded Jeff Bezos found the opposite. The instinct to wait, to protect what you have, to move only when the path is certain feels responsible. It is the exact behavior that kills companies slowly enough that no one notices until it is too late. This episode names the thing nobody wants to say out loud: caution is not safety. It is a slow-motion decline you mistake for stability. Steve Anderson, author of The Bezos Letters, spent his career in one of the most risk-averse industries on earth: insurance. Then he read every shareholder letter Jeff Bezos ever wrote, start to finish, as a single narrative. What he found became a Wall Street Journal and USA Today bestseller translated into 21 languages, and a set of 14 growth principles that explain how Amazon went from burning millions to dominating the planet. Kayvon pushes past the surface. They get into what Bezos was actually saying to a board watching the company lose money for over a decade, and what he was not saying. The conversation moves through the principle of unwarranted risk aversion, the discipline of obsessing over customers until friction disappears, and why Amazon wins by making complexity simple while competitors assume that complexity protects them. Then it sharpens. Bezos ended every letter the same way: it is always Day One. When an employee asked him what Day Two looked like, his answer was stasis, then irrelevance, then painful decline, then death. That single idea reframes how a founder should think about success itself, because the companies most at risk are usually the ones that already won. This is for founders, operators, and executives who are growing but feel stuck below their ceiling. For the people building something real who suspect their own caution is the thing holding it back. If you want motivation, this is the wrong room. If you want the operating logic behind one of the most valuable companies in history, stay. The conversation also covers what most business owners get wrong about experimentation, why failure is the price of invention rather than the absence of it, how customer obsession can quietly turn into pressure that costs you elsewhere, and where AI fits into the same pattern Bezos identified years before it became obvious. Eager adoption of external trends was on his short list for surviving Day Two long before machine learning was a headline. Topics Covered: Why unwarranted risk aversion is the real threat to a growing business How reading every Bezos letter revealed 14 repeatable growth principles The test, build, accelerate, scale framework and where most founders stall Customer obsession as a system for removing friction, not a slogan The hidden cost of customer obsession on the people doing the work Making complexity simple as a competitive weapon The Day One mindset and why Day Two means decline Where AI sits inside Bezos's logic of adopting external trends early Looking to dive deeper into these conversations and connect with our host and guest? Follow Steve Anderson:  Instagram Facebook LinkedIn X Buy The Bezos Letters on Amazon  Learn More Follow Kayvon: Instagram Facebook LinkedIn TikTok     Want to go deeper with Kayvon? Subscribe to the newsletter Book a discovery call Get your Revenue Engine Scorecard™️ Hire the right salespeople