Writing the Book(s) on Amazon with Brad Stone

Author and Senior Executive Editor, Bloomberg Technology

Brad Stone is the author of four books, including Amazon Unbound: Jeff Bezos and the Invention of a Global Empire,published by Simon & Schuster in May 2021. It traces the transformation of Amazon into one of the largest and most feared companies of the world and the accompanying emergence of Jeff Bezos as the richest man alive. Brad is also the author of The Everything Store: Jeff Bezos and the Age of Amazon, which chronicled the foundational early years of the company and its founder. The book, a New York Times and Wall Street Journal bestseller, was translated into more than 35 languages and won the 2013 Financial Times/Goldman Sachs Business Book of the Year Award. In 2017, he also published The Upstarts: Uber, Airbnb, and the Battle for the New Silicon Valley.

Brad is Senior Executive Editor for Global Technology at Bloomberg News

where he oversees a team of 65 reporters and editors that covers high-tech companies, startups, cyber security and internet trends around the world. Over the last ten years, as a writer for Bloomberg Businessweek, he’s authored over two dozen cover stories on companies such as Apple, Google, Amazon, Softbank, Twitter, Facebook and the Chinese internet juggernauts Didi, Tencent and Baidu. He’s a regular contributor to Bloomberg’s technology newsletter Fully Charged, and to the daily Bloomberg TV news program, Bloomberg Technology. He was previously a San Francisco-based correspondent for The New York Times and Newsweek. A graduate of Columbia University, he is originally

from Cleveland, Ohio and lives in the San Francisco Bay Area with his wife

and three daughters

Announcer: Hello, and welcome to Screaming in the Cloud with your host, Chief Cloud Economist at The Duckbill Group, Corey Quinn. This weekly show features conversations with people doing interesting work in the world of cloud, thoughtful commentary on the state of the technical world, and ridiculous titles for which Corey refuses to apologize. This is Screaming in the Cloud.

Corey: This episode is sponsored in part by Thinkst. This is going to take a minute to explain, so bear with me. I linked against an early version of their tool, canarytokens.org in the very early days of my newsletter, and what it does is relatively simple and straightforward. It winds up embedding credentials, files, that sort of thing in various parts of your environment, wherever you want to; it gives you fake AWS API credentials, for example. And the only thing that these things do is alert you whenever someone attempts to use those things. It’s an awesome approach. I’ve used something similar for years. Check them out. But wait, there’s more. They also have an enterprise option that you should be very much aware of canary.tools. You can take a look at this, but what it does is it provides an enterprise approach to drive these things throughout your entire environment. You can get a physical device that hangs out on your network and impersonates whatever you want to. When it gets Nmap scanned, or someone attempts to log into it, or access files on it, you get instant alerts. It’s awesome. If you don’t do something like this, you’re likely to find out that you’ve gotten breached, the hard way. Take a look at this. It’s one of those few things that I look at and say, “Wow, that is an amazing idea. I love it.” That’s canarytokens.org and canary.tools. The first one is free. The second one is enterprise-y. Take a look. I’m a big fan of this. More from them in the coming weeks.

Corey: This episode is sponsored in part by VMware. Because let’s face it, the past year hasn’t been kind to our AWS bills, or honestly any cloud bills. The pandemic had a bunch of impacts: it forced us to move workloads to the cloud sooner than we would have otherwise, we saw strange patterns such as user traffic drops off but infrastructure spend doesn’t. What do you do about it? Well, the CloudLIVE 2021 virtual conference is your chance to connect with people wrestling with the same type of thing, be they practitioners, vendors in the space, leaders of thought—ahem, ahem—and get some behind the scenes look into various ways different companies are handling this. Hosted by CloudHealth by VMware on May 20, the CloudLIVE 2021 conference will be 100% virtual and 100% free to attend, so you really have no excuses for missing out on this opportunity to deal with people who care about cloud bills. Visit cloudlive.com/coreyto learn more and save your virtual seat today. That’s cloud L-I-V-E slash Corey. C-O-R-E-Y. Drop the E, we’re all in trouble. My thanks to VMware for sponsoring this ridiculous episode.

Corey: Welcome to Screaming in the Cloud. I’m Corey Quinn. Sometimes people tell me that I should write a book about Amazon. And that sounds awful. But to be sure, today, my guest is Brad Stone, someone who has written not one, but two books about Amazon, one of which coming out on May 11th, or as most of you will know while listening to this, today. Brad, thanks for joining me.

Brad: Corey, thanks for having me.

Corey: So, what on earth would inspire you to not just write a book about one of what is in many ways an incredibly secretive company, but then to go back and do it again?

Brad: Yeah. I’m a glutton for punishment. And Corey, my hair right now is completely white way before it should be, and I think that Amazon might be responsible for some of that. So, as you contemplate your own project, consider that this company—will you already know: it can age you. They are sometimes resistant to scrutiny.

So, to answer your question, I set out to write The Everything Store back in 2011, and this was a much smaller company. It was a cute little tiny internet company of about $100 billion in market value. And poor, impoverished Jeff Bezos maybe had, I’d be guessing maybe $50 billion.

So anyway, it was a much different time. And that was a great experience. The company was kind of flowering as the book came out. And to my surprise, it was embraced not by Bezos or the management team, who maybe we’ll talk about didn’t love it, but by Amazon employees, and customers, and competitors, and prospective employees. And I was really proud of it that this had become a kind of definitive account of the early years of the company.

And then a funny thing happened. The little cute little internet company became a juggernaut, a $1.5 trillion market cap. Bezos is the wealthiest guy in the world now with a $200 billion fortune, and Alexa, and the rise of AWS, and the Go store, and incursions into India and Mexico and other countries, I mean, so much had changed, and my definitive history felt a little out of date. And so back in 2017—also a different world, Bezos is a happily married man; he’s the CEO of Amazon, Amazon’s headquarters are in Seattle only—I set out to research and write Amazon Unbound. And as I was writing the story, yeah, just, like, the ground kept shifting under my feet.

Corey: Not a lot changes in the big sphere. I mean, one of the things that Bezos said is, “Oh, what’s going to be different in 10 years? I think the better question is, ‘what’s going to not be different in 10 years?’” but watching the company shift, watching it grow, just from the outside has been a real wild ride, I’ve got to say. And I restrict myself primarily to the AWS parts because well, there’s too much to cover if you go far beyond that, and two, it’s a very different place with very different challenges around it.

I viewed The Everything Store when it came out and I read that, almost like it was a biography of Jeff Bezos himself. And in some respects, Amazon Unbound feels like it hews in that direction as well, but it also goes beyond that. How do you approach separating out the story of Amazon from the story of Jeff Bezos?

Brad: Yeah, you’re putting your finger on almost the core challenge, and the adjoining challenge, which is how do you create a narrative, a linear story? Often readers want a chronological story out of a miasma of overlapping events, and initiatives, and challenges. Amazon’s really decentralized; everything is happening at once. Bezos is close to some things, he was very close to Alexa. He is really distant from other things.

Andy Jassy for years had a lot of independence to run AWS. So, how do you tell that story, and then keep Bezos in the center? I mean, Andy Jassy and Jeff Wilke and everyone, I mean, those are great business people. Not necessarily dynamic personalities as, Corey, you know well, but people want to read about Jeff Bezos. He is a larger-than-life figure.

He’s a pioneer. He’s an innovator. He’s controversial. And so the challenge all along is to, kind of, keep him in the center. And so that’s just, like, a writing challenge. It’s a narrative challenge.

And the lucky thing is that Amazon does tend to orbit around Jeff Bezos’s brain. And so in all the storytelling, even the AWS bits of the book, which we can talk about, as an author, you can always bring Bezos back just by following the facts. You’ll eventually get, in the evolution of any story, to an S Team meeting, or to an acquisition discussion where Jeff had an impact, said something insightful, walked out of a meeting, raise the bar, had impossibly high standards. So, the last thing I’ll say is, because Amazon’s so decentralized, when you write these books you have to talk to a lot of people. And then you get all the pieces of the puzzle, and you start to assemble them, and the challenge as a writer is to, kind of, keep Bezos, your main character in the lens at all times, never let him drift too far out.

Corey: One of the things that I learned from it was just the way that Bezos apparently talks to his senior executives, as far as, “I will invest in this project, more than you might think I would.” I guess I’ve never really heard of a budget meeting talking about, “I”—in the first person—“Will invest.” Like, that is what happens, but for some reason the business books never put it quite that starkly or frame it quite that way. But in hindsight, it made a lot of things of my own understanding of Amazon fall into place. That makes sense.

Brad: He’s got a lot of levers, ways in which he’ll back a new initiative or express his support. And one of them is simply how he spends his time. So, with Alexa in the early years, he would meet once or twice a week with that team. But another lever is just the amount of investment. And oftentimes teams will come to him—the India team is a great example—they’ll come to the S Team with a budget, and they’ll list out their priorities and their goals for the coming year, and he’ll say, “You know, you’re thinking about this all wrong. Don’t constrain yourself. Tell us what the goals are, tell us what the opportunity is, then we’ll figure out how much it costs.”

And his mindset is like you can kind of break up opportunity into two categories: one are the land grabs, the big immediate opportunities where he will go all out, and India was a great example of that, I think the failed fire phone was another example, Prime Video, he doesn’t cap the investment, he wants to win. And then there are the more greenfield opportunities that he thinks he can go slower on and groceries for a long time was in that category. And there the budgets might be more constrained. The other example is the much older businesses, just like the retail business. That’s 20 years old—I have a chapter about that—and the advertising business, and he recognized that the retail business wasn’t profitable and it was depending on advertising as a crutch, and he blew it up because he thinks that those older divisions shouldn’t require investment; they should be able to stand on their own.

Corey: One quote you had as well, that just really resonated with me, as far as basically my entire ethos of how I make fun of Amazon is—and I’m going to read the excerpt here. My apologies. You have to listen to your own words being read back toward you—

Brad: [laugh].

Corey: These were typically Amazonian names: geeky, obscure, and endlessly debated inside AWS since—according to an early AWS exec—Bezos had once mused, “You know, the name is about 3% of what matters, but sometimes 3% is the difference between winning and losing.” And I just want to call that out because I don’t think I’ve ever seen an AWS exec ever admit that names might be even 3% worth of important. Looking at how terrible some of their service names are, I would say that 3% might be an aspirational target for their worldview.

Brad: [laugh]. Let me throw this back at you, Corey. Have you ever figured out why certain AWS services are Amazon and why others are AWS?

Corey: I did. I got to sit down—in the before times—with then the VP of Global Marketing, Ariel Kelman—who’s now Oracle’s Chief Marketing Officer—and Jeff Barr. And the direction that they took that in was that if you could use an AWS service without getting into the AWS weeds of a bunch of other services, then it was called Amazon whatever. Amazon S3, for example, as a primitive service doesn’t need a bunch of other AWS services hooked into it, so that gets the Amazon moniker. Whereas if you’re dealing with a service that requires the integration of a whole bunch of AWS in the weeds stuff—

Brad: Mmm, right.

Corey: —then it’s AWS. For example, AWS Systems Manager is useless without a whole bunch of other Amazon services. And they say they don’t get it perfectly right all the time, but that is the direction that it’s gone in. And for better or worse, I still have to look a lot of them up myself because I don’t care nearly as much as their branding people do.

Brad: Right. Well, I’ll tell you in the chapter about AWS, that quote comes up when the team is contemplating the names of the databases. And they do go into long debates, and I remember talking to Charlie Bell about the search for Redshift, and they go back and forth on it, and the funny thing about that one was, of course, Oracle interpreted it as a competitive slight. Its corporate color, I guess, being red, which he intended it more as a physics term. But yeah, when they were launching Aurora and Redshift, they contemplated those names quite a bit. And I don’t know if it’s 3%. I don’t know if it does matter, but certainly, those services have become really important to a lot of businesses.

Corey: Oh, yeah. And once you name something, it’s really hard to rename it. And AWS does view for—better or worse—APIs as a promise, so when you build something and presented a certain way, they’re never going to turn it off. Our grandkids are going to have to deal with some of these decisions once they get into computers. That’s a problem.

And I understand the ethos behind it, but again, it’s easy to make fun of names; it’s an accessible thing because let’s be very real here, a lot of what AWS does is incredibly inaccessible to people who don’t live in this space. But naming is something that everyone can get behind making fun of.

Brad: Absolutely. Yep. And [laugh] it’s perhaps why they spend a lot of time on it because they know that this is going to be the shingle that they hang out to the world. I don’t know that they’re anticipating your ridicule, but it’s obviously key to the marketing process for them.

Corey: Some of the more aware ones do. But that’s a different topic for a different time. One question I have for you that I wrestle with myself is I’ve been spending the last four years or so basically studying AWS all the time. And there’s a lot of things they get right; there’s a lot of things that they get wrong. But for better or worse, it’s very difficult not to come away from an in-depth study with an appreciation for an awful lot of the things that they do. At least for me.

I’m not saying that I fall in love with the company and will excuse them their wrongs; I absolutely do not do that. But it is hard, bordering on impossible for me, to not come away with a deep respect for a lot of the things that they do and clearly believe. How do you feel about that? Looking at Amazon, do you come away with this with, “Ooh. Remind me to never to become a Prime member and get rid of everything with an Amazon logo in my house,” versus the you’re about to wind up wondering if they can hire you for some esoteric role? Where do you fall on that spectrum?

Brad: I think I’m probably with you. I come away with an admiration. And look, I mean, let me say upfront, I am a Prime member. I have a Alexas in my home, probably more than my wife and kids are comfortable with. We watch Prime Video, we have Prime Video.

We order from Amazon all the time, we ordered from Whole Foods. I’m an Amazon customer, and so part of my appreciation comes from, like all other customers, the fact that Amazon uniquely restores time to our lives rather than extracts it. I wouldn’t say that about the social networks, right? You know, those can be time-wasters. Amazon’s a great efficiency machine.

But in terms of my journalism, you know, now two books and this big in-depth study in Amazon Unbound, and you have to admire what they have built. I mean, a historic American institution that has not only changed our economic reality, in ways good and bad but over the last year and a half, in the pandemic was among the few institutions that functioned properly and served as a kind of lifeline. And there is a critique in Amazon Unbound and we can talk about it, but it’s hard to come away—I think you said it well—it’s hard to come away after studying this company and studying the top executives, and how Jeff Bezos, thinks and how he has conceived products without real admiration for what they have built over the last 25 years.

Corey: Well, let’s get into your critique of Amazon. What do you think is, from what you’ve seen with all of the years of research you put into this company, what’s the worst thing about them?

Brad: Well, that’s a good way to put it, Corey. [laugh]. Let me—

Corey: [laugh]. It’s like, talk about a target-rich opportunity. Like, “Oh, wow. It’s like my children. I can’t stand any of them. How in the world could I pick just one?” But give it a shot.

Brad: Right. Well, let me start this way, which is I often will listen to their critiques from Amazon critics—and I’m sure you might feel this way as well—and just think, like, “Do they get it?” They’ll argue that Amazon exercised its size and might to buy the companies that led to Alexa. As I write in the Alexa chapter, that’s not true at all. They bought a couple of small companies, and those executives were all horrified at what Amazon was trying to do, and then they made it work.

Or the critics will say, “Fifty percent or more of internet users start their product searches on Amazon. Amazon has lock-in.” That’s not true either. Lock-in on the internet is only as strong as a browser window that remains open. And you could always go find a competitor or search on a search engine.

So, I find at least some of the public criticism to be a little specious. And often, these are people that complained about Walmart for ten years. And now Amazon’s the big, bad boogeyman.

Corey: Oh, I still know people who refuse to do business with Walmart but buy a bunch of stuff from Amazon, and I’m looking at these things going, any complaints you have about Walmart are very difficult to avoid mapping to Amazon.

Brad: Here’s maybe the distillation of the critique that’s an Amazon Unbound. We make fun of Facebook for, “Move fast and break things.” And they broke things, including, potentially, our democracy. When you look at the creation of the Amazon Marketplace, Jeff wanted a leader who can answer the question, “How would you bring a million sellers into the Amazon Marketplace?” And what that tells you is he wanted to create a system, a self-service system, where you could funnel sellers the world over into the system and sell immediately.

And that happened, and a lot of those sellers, there was no friction, and many of them came from the Wild West of Chinese eCommerce. And you had—inevitably because there were no guardrails—you had fraud and counterfeit, and all sorts of lawsuits and damage. Amazon moved fast and broke things. And then subsequently tried to clean it up. And if you look at the emergence of the Amazon supply chain and the logistics division, the vans that now crawl our streets, or the semi-trailers on our highways, or the planes.

Amazon moved fast there, too. And the first innings of that game were all about hiring contractors, not employees, getting them on the road with a minimum of guidance. And people died. There were accidents. You know, there weren’t just drivers flinging packages into our front yards, or going to the bathroom on somebody’s porch.

That happened, but there were also accidents and costs. And so I think some of the critique is that Amazon, despite its profession that it focuses only on customers, is also very competitor-aware and competitor-driven, and they move fast, often to kind of get ahead of competitors, and they build the systems and they’re often self-service systems, and they avoid employment where it’s possible, and the result have been costs to society, the cost of moving quickly. And then on the back-end when there are lawsuits, Amazon attempts to either evade responsibility or settle cases, and then hide those from the public. And I think that is at the heart of what I show in a couple of ways in Amazon Unbound. And it’s not just Amazon; it’s very typical right now of corporate America and particularly tech companies.

And part of it is the state of the laws and regulations that allow the companies to get away with it, and really restrict the rights of plaintiffs, of people who are wronged from extracting significant penalties from these companies and really changing their behavior.

Corey: Which makes perfect sense. I have the luxury of not having to think about that by having a mental division and hopefully one day a real division between AWS and Amazon’s retail arm. For me at least, the thing I always had an issue with was their treatment of staff in many respects. It is well known that in the FAANG constellation of tech companies, Facebook, Amazon, Apple, Netflix, and Google, apparently, it’s an acronym and it’s cutesy. People in tech think they’re funny.

But the problem is that Amazon’s compensation is significantly below that. One thing I loved in your book was that you do a breakdown of how those base salaries work, how most of it is stock-based and with a back-loaded vesting and the rest, and looking through the somewhat lengthy excerpt—but I will not read your own words to you this time—it more or less completely confirms what I said in my exposé of this, which means if we’re wrong, we’re both wrong. And we’ve—and people have been very convincing and very unified across the board. We’re clearly not wrong. It’s nice to at least get external confirmation of some of the things that I stumble over.

Brad: But I think this is all part of the same thing. What I described as the move fast and break things mentality, often in a race with competition, and your issues about the quality, the tenor of work, and the compensation schemes, I think maybe and this might have been a more elegant answer to your question, we can wrap it all up under the mantle of empathy. And I think it probably starts with the founder and soon-to-be-former CEO. And look, I mean, an epic business figure, a builder, an inventor, but when you lay out the hierarchy of qualities, and attributes, and strengths, maybe empathy with the plight of others wasn’t near the top. And when it comes to the treatment of the workforce, and the white-collar employees, and the compensation schemes, and how they’re very specifically designed to make people uncomfortable, to keep them running fast, to churn them out if they don’t cut it, and the same thing in the workforce, and then the big-scale systems and marketplace and logistics—look, maybe empathy is a drag, and not having it can be a business accelerant, and I think that’s what we’re talking about, right?

That some of these systems seem a little inhumane, and maybe to their credit, when Amazon recognizes that—or when Jeff has recognized it00, he’s course-corrected a little bit. But I think it’s all part of that same bundle. And maybe perversely, it’s one of the reasons why Amazon has succeeded so much.

Corey: I think that it’s hard to argue against the idea of culture flowing from the top. And every anecdote I’ve ever heard about Jeff Bezos, never having met the man myself, is always filtered through someone else; in many cases, you. But there are a lot of anecdotes from folks inside Amazon, folks outside Amazon, et cetera, and I think that no one could make a serious argument that he is not fearsomely intelligent, penetratingly insightful, and profoundly gifted in a whole bunch of different ways. People like to say, “Well, he started Amazon with several $100,000 and loan from his parents, so he’s not really in any ways a self-made anything.” Well, no one is self-made. Let’s be very clear on that.

But getting a few $100,000 to invest in a business, especially these days, is not that high of a stumbling block for an awful lot of folks similarly situated. He has had outsized success based upon where he started and where he wound up ending now. But not a single story that I’ve ever heard about him makes me think, yeah, that’s the kind of guy I want to be friends with. That’s the kind of guy I want to invite to a backyard barbecue and hang out with, and trade stories about our respective kids, and just basically have a social conversation with. Even a business conversation doesn’t feel like it would be particularly warm or compelling.

It would be educational, don’t get me wrong, but he doesn’t strike me as someone who really understands empathy in any meaningful sense. I’m sure he has those aspects to him. I’m sure he has a warm, wonderful relationship with his kids, presumably because they still speak to him, but none of that ever leaks through into his public or corporate persona.

Brad: Mmm, partially agree, partially disagree. I mean, certainly maybe the warmth you’re right on, but this is someone who’s incredibly charismatic, who is incredibly smart, who thinks really deeply about the future, and has intense personal opinions about current events. And getting a beer with him—which I have not done—with sound fantastic. Kicking back at the fireplace at his ranch in Texas, [laugh] to me, I’m sure it’s tremendously entertaining to talk to him. But when it comes to folks like us, Corey, I have a feeling it’s not going to happen, whether you want to or not.

He’s also incredibly guarded around the jackals of the media, so perhaps it doesn’t make a difference one way or another. But, yeah, you’re right. I mean, he’s all business at work. And it is interesting that the turnover in the executive ranks, even among the veterans right now, is pretty high. And I don’t know, I mean, I think Amazon goes through people in a way, maybe a little less on the AWS side. You would know that better than me. But—

Corey: Yes and no. There’s been some turnover there that you can also pretty easily write down to internal political drama—for lack of a better term—palace intrigue. For lack of a better term. When, for example, Adam Selipsky is going to be the new CEO of AWS as Andy Jesse ascends to be the CEO of all Amazon—the everything CEO as it were. And that has absolutely got to have rubbed some people in unpleasant ways.

Let’s be realistic here about what this shows: he quit AWS to go be the CEO of Tableau, and now he’s coming back to run AWS. Clearly, the way to get ahead there is to quit. And that might not be the message they’re intending to send, but that’s something that people can look at and take away, that leaving a company doesn’t mean you can’t boomerang and go back there at a higher level in the future.

Brad: Right.

Corey: And that might be what people are waking up to because it used to be a culture of once you’re out, you’re out. Clearly not the case anymore. They were passed over for a promotion they wanted, “Well, okay, I’m going to go talk to another company. Oh, my God, they’re paying people in yachts.” And it becomes, at some level, time for something new.

I don’t begrudge people who decide to stay; I don’t begrudge people who decide to leave, but one of my big thrusts for a long time has been understand the trade-offs of either one of those decisions and what the other side looks like so you go into it with your eyes open. And I feel like, on some level, a lot of folks there didn’t necessarily feel that they could have their eyes open in the way that they can now.

Brad: Mm-hm. Interesting. Yeah. Selipsky coming back, I never thought about that, sends a strong message. And Amazon wants builders, and operators, and entrepreneurial thinking at the top and in the S Team. And the fact that Andy had a experienced leadership team at AWS and then went outside it for the CEO could be interpreted as pretty demotivating for that team. Now, they’ve all worked with Adam before, and I’ve met him and he seems like a great guy so maybe there are no hard feelings, but—

Corey: I never have. He left a few months before I started this place. So, it—I get the sense that he knew I was coming and said, “Well, better get out of here. This isn’t going to go well at all.”

Brad: [laugh]. I actually went to interview him for this book, and I sat in his office at Tableau thinking, “Okay, here’s a former AWS guy,” and I got to tell you, he was really on script and didn’t say anything bad, and I thought, “Okay, well, that wasn’t the best use of my time.” He was great to meet, and it was an interesting conversation, but the goss he did not deliver. And so when I saw that he got this job, I thought, well, he’s smart. He smartly didn’t burn any bridges, at least with me.

Corey: This episode is sponsored in part by our friends at ChaosSearch., you could run Elasticsearch or Elastic Cloud—or OpenSearch as they’re calling it now—or a self-hosted ELK stack. But why? ChaosSearch gives you the same API you’ve come to know and tolerate, along with unlimited data retention and no data movement. Just throw your data into S3 and proceed from there as you would expect. This is great for IT operations folks, for app performance monitoring, cybersecurity. If you’re using Elasticsearch, consider not running Elasticsearch. They’re also available now in the AWS marketplace if you’d prefer not to go direct and have half of whatever you pay them count towards your EDB commitment. Discover what companies like HubSpot, Klarna, Equifax, Armor Security, and Blackboard already have. To learn more, visit chaossearch.io and tell them I sent you just so you can see them facepalm, yet again.

Corey: No. And it’s pretty clear that you don’t get to rise to those levels without being incredibly disciplined with respect to message. I don’t pity Andy Jesse’s new job wherein a key portion of the job description is going to be testifying before Congress. Without going into details, I’ve been in situations where I’ve gotten to ask him questions before in a real-time Q&A environment, and my real question hidden behind the question was, “How long can I knock him off of his prepared talking points?” Because I—

Brad: Good luck. [laugh].

Corey: Yeah. I got the answer: about two and a half seconds, which honestly was a little bit longer than I thought I would get. But yeah, incredibly disciplined and incredibly insightful, penetrating answers, but they always go right back to talking points. And that’s what you have to do at that level. I’ve heard stories—it may have been from your book—that Andy and Adam were both still friendly after Adam’s departure, they would still hang out socially and clearly, relationships are still being maintained, if oh, by the way, you’re going to be my successor. It’s kind of neat. I’m curious to see how this plays out once that transition goes into effect.

Brad: Yeah, it’ll be interesting. And then also, Andy’s grand homecoming to the other parts of the business. He started in the retail organization. He was Jeff’s shadow. He ran the marketing department at very early Amazon.

He’s been in all those meetings over the years, but he’s also been very focused on AWS. So, I would imagine there’s a learning curve as he gets back into the details of the other 75% of Amazon.

Corey: It turns out that part of the business has likely changed in the last 15 years, just a smidgen when every person you knew over there is now 10,000 people. There was an anecdote in your book that early on in those days, Andy Jesse was almost let go as part of a layoff or a restructuring, and Jeff Bezos personally saved his job. How solid is that?

Brad: Oh, that is solid. An S Team member told me that, who was Andy’s boss at the time. And the story was, in the late 90s—I hope I remember this right—there was a purge of the marketing department. Jeff always thought that marketing—in the early days marketing was purely satisfying customers, so why do we need all these people? And there was a purge of the marketing department back when Amazon was trying to right-size the ship and get profitable and survive the dotcom bust.

And Jeff intervened in the layoffs and said, “Not Andy. He’s one of the most—yeah, highest ceiling folks we have.” And he made him his first full-time shadow. Oh, and that comes right from an S Team member. I won’t say the name because I can’t remember if that was on or off the record.

But yeah, it was super interesting. You know what? I’ve always wondered how good of a identifier of talent and character is Bezos. And he has some weaknesses there. I mean, obviously, in his personal life, he certainly didn’t identify Lauren Sánchez’s brother as the threat that he became.

You know, I tell the story in the book of the horrific story of the CEO of Amazon Mexico, who Jeff interviewed, and they hired and then later ended up what appears to be hiring an assassin to kill his wife. I tell the story in the book. It’s a horrible story. So, not to lay that at the feet of Jeff Bezos, of course, but he often I think, moves quickly. And I actually have a quote from a friend of his in the book saying, “It’s better to not be kind of paranoid, and the”—sort of—I can’t remember what the quote is.

It’s to trust people rather than be paranoid about everyone. And if you trust someone wrongly, then you of course-correct. With Andy, though, he somehow had an intuitive sense that this guy was very high potential, and that’s pretty impressive.

Corey: You’re never going to bet a thousand. There’s always going to be people that slip through the cracks. But learning who these people are and getting different angles on them is always interesting. Every once in a while—and maybe I’m completely wrong on this, but never having spent time one on one with Andy Jassy, I have to rely on other folks and different anecdotes, most of them, I can’t disclose the source of, but every time that I wind up hearing about these stories, and maybe I’m projecting here, but there are aspects of him where it seems like there is a genuinely nice person in there who is worried, on some level, that people are going to find out that he’s a nice person.

Brad: [laugh]. I think he is. He’s extraordinarily nice. He seems like a regular guy, and what’s sort of impressive is that obviously he’s extraordinarily wealthy now, and unlike, let’s say Bezos, who’s obviously much more wealthy, but who, who really has leaned into that lifestyle, my sense is Andy does not. He’s still—I don’t know if he’s on the corporate jet yet, but at least until recently he wasn’t, and he presents humbly. I don’t know if he’s still getting as close from wherever, [unintelligible 00:32:50] or Nordstroms.

Corey: He might be, but it is clear that he’s having them tailored because fit is something—I spent a lot of time in better years focusing on sartorial attention, and wherever he’s sourcing them from aside, they fit well.

Brad: Okay, well, they didn’t always. Right?

Corey: No. He’s, he’s… there’s been a lot of changes over the past decade. He is either discovered a hidden wellspring of being one of the best naturally talented speakers on the planet, or he’s gone through some coaching to improve in those areas. Not that he was bad at the start, but now he’s compelling.

Brad: Okay. Well, now we’re talking about his clothes and his speaking style. But—

Corey: Let’s be very honest here. If he were a woman, we would have been talking about that as the beginning topic of this. It’s on some level—

Brad: Or we wouldn’t have because we’d know it’s improper these days.

Corey: We would like to hope. But I am absolutely willing to turn it back around.

Brad: [laugh]. Anyway.

Corey: So, I’m curious, going back a little bit to criticisms here, Amazon has been criticized roundly by regulators and Congress and the rest—folks on both sides of the aisle—for a variety of things. What do you see is being the fair criticisms versus the unfair criticisms?

Brad: Well, I mean, I think we covered some of the unfair ones. But there’s one criticism that Amazon uses AWS to subsidize other parts of the business. I don’t know how you feel about that, but until recently at least, my reading of the balance sheet was that the enormous profits of AWS were primarily going to buy more AWS. They were investing in capital assets and building more data centers.

Corey: Via a series of capital leases because cash flow is king in how they drive those things there. Oh, yeah.

Brad: Right. Yeah. You know, and I illustrate in the book how when it did become apparent that retail was leaning on advertising, Jeff didn’t accept that. He wanted retail to stand on its own, and it led to some layoffs and fiercer negotiations with brands, higher fees for sellers. Advertising is the free cash flow that goes in Prime movies, and TV shows, and Alexa, and stuff we probably don’t know about.

So, this idea that Amazon is sort of improperly funneling money between the divisions to undercut competitors on price, I think we could put that in the unfair bucket. In the fair bucket, those are the things that we can all look at and just go, “Okay, that feels a little wrong.” So, for an example, the private brand strategy. Now, of course, every supermarket and drugstore is going to line their shelves with store brands. But when you go to an Amazon search results page these days, and they are pockmarked with Amazon brands, and Whole Foods brands, and then sponsored listings, the pay-to-play highest bidder wins.

And then we now know that, at least for a couple of years, Amazon managers, private label managers were kind of peeking at the third-party data to figure out what was selling and what they should introduce is a private Amazon brand. It just feels a little creepy that Amazon as the everything store is so different than your normal Costco or your drugstore. The shelves are endless; Amazon has the data, access to the data, and the way that they’re parlaying their valuable real estate and the data at their disposal to figure out what to launch, it just feels a little wrong. And it’s a small part of their business, but I think it’s one where they’re vulnerable. The other thing is, in the book, I tried to figure out how can I take the gauge of third-party sellers?

There’s so many disgruntled voices, but do they really speak for everyone? And so instead of going to the enemies, I went to every third-party seller that had been mentioned in Jeff Bezos’s shareholder letters over the past decade. And these were the allies. These were the success stories that Bezos was touting in his sacrosanct investor letter, and almost to a one, they had all become disgruntled. And so the way in which the rules of the marketplace change, the way that the fees go up, and the difficulty that sellers often have in getting a person or a guiding hand at Amazon to help them with those changes, that kind of feels wrong.

And I think that maybe that’s not a source of regulation, but it could be a source of disruptive competition. If somebody can figure out how to create a marketplace that caters to sellers a little better with lower fees, then they could do to Amazon with Amazon years ago did to eBay. And considering that Marketplace is now a preponderance of sales more than even retail on amazon.com, that can end up hurting the company.

Corey: Yeah, at some point, you need to continue growing things, and you’ve run out of genuinely helpful ways, and in turn in start to have to modify customer behavior in order to continue doing things, or expand into brand new markets. We saw the AWS bleeding over into Alexa as an example of that. And I think there’s a lot of interesting things still to come in spaces like that. It’s interesting watching how the Alexa ecosystem has evolved. There’s still some very basic usability bugs that drive me nuts, but at the same token, it’s not something that I think we’re going to see radically changing the world the next five years. It feels like a hobby, but also a lucrative one, and keeps people continuing to feed into the Amazon ecosystem. Do you see that playing out differently?

Brad: Wait, with Alexa?

Brad: Absolutely.

Brad: Yeah. I agree with you. I mean, it feels like there was more promise in the early years, and that maybe they’ve hit a little bit of a wall in terms of the AI and the natural language understanding. It feels like the ecosystem that they tried to build, the app store-like ecosystem of third-party skills makers, that hasn’t crystallized in the way we hoped—in the way they hoped. And then some of these new devices like the glasses or the wristband that have Alexa feel, just, strange, right?

Like, I’m not putting Alexa on my face. And those haven’t done as well. And so yeah, I think they pioneered a category: Alexa plays music and answers basic queries really well, and yet it hasn’t quite been conversational in the way that I think Jeff Bezos had hoped in the early days. I don’t know if it’s a profitable business now. I mean, they make a lot of money on the hardware, but the team is huge.

I think it was, like, 10,000 people the last I checked. And the R&D costs are quite large. And they’re continuing to try to improve the AI, so I think Jeff Bezos talks about the seeds, and then the main businesses, and I don’t think Alexa has graduated yet. I think there’s still a little bit of a question mark.

Corey: It’s one of those things that we remain to see. One last thing that I wanted to highlight and thank you for, was that when you wrote the original book, The Everything Store, Andy Jassy wrote a one-star review. It went into some depth about all the things that, from his perspective, you got wrong, were unfair about, et cetera.

And that can be played off as a lot of different things, but you can almost set that aside for a minute and look at it as the really only time in recent memory that Andy Jassy has sat down and written something, clearly himself, and then posted it publicly. He writes a lot—Amazon has a writing culture—but they don’t sign their six-pagers. It’s very difficult to figure out where one person starts and one person stops. This shows that he is a gifted writer in many respects, and I don’t think we have another writing sample from him to compare it to.

Brad: So, Corey, you’re saying I should be honored by his one-star review of The Everything Store?

Corey: Oh, absolutely.

Brad: [laugh].

Corey: He, he just ignores me. You actually got a response.

Brad: I got a response. Well.

Corey: And we’ll put a link to that review in the [show notes 00:40:10] because of course we will.

Brad: Yes, thank you. Do you—remember, other Amazon executives also left one-star reviews. And Jeff’s wife, and now ex-wife Mackenzie left a one-star review. And it was a part of a, I think a little bit of a reflexive reaction and campaign that Jeff himself orchestrated at my—this was understanding now, in retrospect. After the book came out, he didn’t like it.

He didn’t like aspects of his family life that were represented in the book, and he asked members of the S Team to leave bad reviews. And not all of them did, and Andy did. So, you wonder why he’s CEO now. No, I’m kidding about that. But you know what?

It ended up, kind of perversely, even though that was uncomfortable in the moment, ended up being good for the first book. And I’ve seen Andy subsequently, and no hard feelings. I don’t quite remember what his review said. Didn’t it, strangely, like, quote a movie or something like that?

Corey: I recall that it did. It went in a bunch of different directions, and at the end—it ended with, “Well, maybe someday he’ll write the actual story. And I’m not trying to bait anyone into doing it, but this book isn’t it.” Well, in the absence of factual corrections, that’s what we go with. That is also a very Amazonian thing. They don’t tell their own story, but they’re super quick to correct the record—

Brad: Yeah.

Corey: —after someone says a thing.

Brad: But I don’t recall him making many specific claims of anything I got wrong. But why don’t we hope that there’s a sequel review for Amazon Unbound? I will look forward to that from Andy.

Corey: I absolutely hope so. It’s one of those things that we just really, I guess, hope goes in a positive direction. Now, I will say I don’t try to do any reviews that are all positive. And that’s true. There’s one thing that you wrote that I vehemently disagree with.

Brad: Okay, let’s hear it.

Corey: Former Distinguished Engineer and VP at AWS, Tim Bray, who resigned on conscientious objector grounds, more or less, has been a guest on the show, and I have to say, you did him dirty. You described him—

Brad: How did I—what did I do? Mm-hm.

Corey: Oh, I quote, “Bray, a fedora-wearing software developer”—which is true, but still is evocative in an unpleasant way—“And one of the creators of the influential web programming language, XML”—which is true, but talk about bringing up someone’s demons to haunt them. Oh, my starts.

Brad: [laugh]. But wait. How is the fedora-wearing pejorative?

Corey: Oh, it has a whole implication series of, and entire subculture of the gamer types, people who are misogynist, et cetera. It winds up being an unfair characterization—

Brad: But he does wear a fedora.

Corey: He does. And he can pull it off. He has also mentioned that he is well into retirement age, and it was a different era when he wore one. But that’s not something that people often will associate with him. It’s—

Brad: I’m so naive. You’re referring to things that I do not understand what the implication was that I made. But—

Corey: Oh, spend more time with the children of Reddit. You’ll catch on quickly.

Brad: [laugh]. I try, I try not to do that. But thank you, Corey.

Corey: Of course. So, thank you so much for taking the time to go through what you’ve written. I’m looking forward to seeing the reaction once the book is published widely. Where can people buy it? There’s an easy answer, of course, of Amazon itself, but is there somewhere you would prefer them to shop?

Brad: Well, everyone can make their own decisions. I flattered if anyone decides to pick up the book. But of course, there is always their independent bookstore. On sale now.

Corey: Excellent. And we will, of course, throw a link to the book in the [show notes 00:43:31]. Brad, thank you so much for taking the time to speak with me. I really appreciate it.

Brad: Corey, it’s been a pleasure. Thank you.

Corey: Brad Stone, author of Amazon Unbound: Jeff Bezos and the Invention of a Global Empire, on sale now wherever fine books are sold—and crappy ones, too. I’m Cloud Economist Corey Quinn, and this is Screaming in the Cloud. If you’ve enjoyed this podcast, please leave a five-star review on your podcast platform of choice, whereas if you’ve hated this podcast, please leave a five-star review on your podcast platform of choice and then a multi-paragraph, very long screed telling me exactly what I got wrong.

Corey: If your AWS bill keeps rising and your blood pressure is doing the same, then you need The Duckbill Group. We help companies fix their AWS bill by making it smaller and less horrifying. The Duckbill Group works for you, not AWS. We tailor recommendations to your business and we get to the point. Visit duckbillgroup.com to get started.

Announcer: This has been a HumblePod production. Stay humble.