Still Day One: How Amazon Thinks Small For Unstoppable Business Growth (And You Should Too) with Steve Anderson

What if failure wasn’t the opposite of success but part of the plan? Discover how Amazon’s strategy of ‘successful failure’ might be the boldest business growth mindset you haven’t tried yet.

📌What’s covered:

• The overlooked risk that’s killing more businesses than failure itself
• Why customer obsession is more powerful (and dangerous) than customer focus
• The real meaning of “Day One” thinking—and what happens when you slip into Day Two
• How to test bold ideas without reckless risk (most startups get this wrong)
• The Amazon leadership habit that forces deep thinking—and how you can steal it

Steve Anderson is an expert in strategic risk and business growth. Drawing on decades of experience in the insurance industry, he wrote The Bezos Letters: 14 Principles to Grow Your Business Like Amazon, which has become a Wall Street Journal, USA Today, and international bestseller. With hundreds of thousands of followers, Steve has been handpicked by LinkedIn as one of the world's most influential thought leaders.

🌐Learn more at  https://www.thebezosletters.com/

Download additional material that helps you apply the principles revealed in the book.

🎁 Try out the Bezos Chat Bot  https://bezos.ifyoucouldask.com/

🤝Connect with Steve https://www.linkedin.com/in/stevetn/

🌟Join the WAITLIST for The Faithful Founders Collective at https://reinventing-perspectives.kit.com/231f666d82

💛 Thank you for listening in! 😀

P.S. Don’t forget to leave a review! Much appreciated.

Transcript

[00:00:00] I started asking the question is the biggest risk they face, actually not taking enough risk. That led me on a journey. Jeff Bezos started in the garage of the house in Bellevue, Washington, on his hands and knees, taking books, people at order online, putting 'em in a package, and then driving them to the post office.

He started like everybody else first. One of the core mindsets at Amazon is obsess over customers. Understanding the customer's wants, needs and desires so deeply that we can, and I'm using his words now, invent on behalf of the customer. Principle number 14 is believe. It's always day one. It's a concept.

It's that feeling you have the first day you open your doors for business, whether they're virtual doors or whether they're physical doors. And that excitement you have, you're serving your customers.

[00:01:00]

Priscilla: Welcome to the Entrepreneur's Kitchen. Today I have an amazing guest for you. I have Steve Anderson, influential thought leader, a strategic risk expert, and he is also the bestselling author of the book, the Bezos Letters. So Steve, please tell us how did all of this start?

Steve: A bit of a long story that I'll try and shorten. I've been in the insurance industry for a long time, the last 35 years, helping insurance agents here in the us with technology, right?

So internet and social platforms and all kinds of different things. And we all know technology continues to develop really rapidly. And so I started asking the question is the biggest risk they face actually not taking enough risk? Because with technology we know that it's harder [00:02:00] and harder to wait and see.

Used to be able to do that 25 years ago, you can't do that anymore. That led me on a journey of really researching companies that. Were successful at some point and are literally gone. And companies that have been successful and continue to be successful, and I wanted to try and find out why.

That's when I came across Amazon and the letters to shareholders that Jeff Bezos wrote. So Amazon went public in 1997. He started writing his first letter at 1997 and then wrote every year a letter up until he stepped aside as CEO in 2020. And so reading those letters I realized that there are threads that went through the letters and I read 'em all in order.

And I thought, there's a lot of really good information here on how he grew Amazon. What did he do? And again, most shareholder [00:03:00] letters from CEOs aren't very interesting, frankly, and his definitely was to me. And I put 'em in the same category as Warren Buffett or some of the others that we pay attention to.

So it was , that idea that I created what I call a lead gen, right? PDF giveaway of. An executive summary, one page of each of the letters that I had read. Fortunately, my wife is in the book publishing business, and so I showed it to her and she said, no, this is not a lead gen. This is a book.

And so that started another journey of, okay, how do we take these ideas and actually put 'em in a book? And that book was published in, as you mentioned, as the Bezos letters. That's a quick background. Obviously a lot more kind of into making that work and having it happen. But yeah, and I don't know why somebody else didn't do it, so there you go.

Priscilla: , You actually said why people didn't do it because usually the [00:04:00] CEO letter you browse it. It's nothing to spend time thinking about typically.

Steve: Yep. That's right. And again, the letters typically are touting the company and how great they are and what they did this year and read all of that. And Bezos did some of that but I think what grabbed my attention is the fact that he talked a lot about how he did it and how Amazon did it.

And those were the principles that I talk about in the book that I think apply to any business. Certainly insurance agents, but. A broader category of businesses, literally startups to larger organizations can learn from these principles and think about how to incorporate them within their organizations.

Priscilla: Yeah, truly brilliant. How he took something that people don't pay much attention to and used to really communicate to his shareholders. Because typically when you don't do that, , you have people waiting for earnings reports and [00:05:00] analysts result.

People are just in and out because they don't have a sense of what is really the direction and what is going on, . That's absolutely interesting.

Steve: As I said, it certainly caught my attention, 

Priscilla: We're glad it caught your attention and you wrote the book. You always say it's day one, and I know this is one of the principles. Why do you think that Jeff Bezos anchored Amazon's mindset on that phrase? It's always day one, and then you speak about , what day two looks like.

.

Steve: Yeah. I'll give a little context to that. So there are a total of 14 principles in the book, and that's a lot. And we knew that, but. Each one is important in its own way. I categorize the principles into four cycles, test, build, accelerate, and scale. And the last principle, number 14, as you mentioned, is believe.

It's always day one. From the very first shareholder letter in 1997, Bezos talked about it's day one for the internet. Now, [00:06:00] remember, 1997, it literally was day one for the internet. Nobody really knew what it was or how it could be used, or people were still saying it's not gonna work, or all of those things.

By the way, there's some corollaries to today with that kind of thought process, but. What he said in the letter is it's day one for the internet and for amazon.com if we execute well. And so he ended up by design, I think ending every single letter that he wrote with some form of, it's still day one.

It's always day one. And even in the 2019 letter, in the midst of the pandemic he said, even with the challenges we face is still day one. It's a concept. It's that feeling you have the first day you open your doors for business, whether they're virtual doors or whether they're physical doors, and that excitement you have, you're serving your [00:07:00] customers.

How do you maintain that within an organization? And I've been fascinated how Amazon continues to maintain that idea. In fact, the current CEO Andy Chassis. Said, I think last year or year before is we wanna be known as the world's largest startup. That's that idea of day one. So day two, that's a interesting, so 2016 letter, Bezos writes about an all hands meeting in Seattle.

So a couple thousand employees there, a quarterly common meeting. Here's the state of the company, here's our direction, here's what we're thinking. At the end, it's open for questions. And so he had some questions on cards in his hand, and he looked at the next one. He smiled and he said, I think I might know the answer to this.

And the question was, Jeff, what does day two look like? He answered the question, and he wrote about this in the [00:08:00] 2016 letter. He said, day two is stasis followed by irrelevance. Followed by excruciating painful decline followed by death.

And that's why it's always day one. And that resonates with me because in my research of those companies that were once very successful, and literally are gone bankrupt, not around, you can trace that progression in their business.

They got stuck on what got them there, but not what could keep them going. And if I may, Bezos asked the question how do you fend off day two? It's really hard.

And he said, I think there are four things and I hopefully I can remember all of four.

First is customer obsession. That's something that's really core at Amazon and is a principle. The second is a skeptical view of proxy. So a proxy [00:09:00] is a process or procedure, which you need, but a process and procedure that doesn't continue to serve the customer. And so have a skeptical view of those and be willing to change.

Third. Is eager adoption of external trends, and he even identified in 2016 one of those trends which he called machine learning, which as we know now was a precursor to the generative AI that we have right now. Those were some of the earlier days to it, and then the final of the four. Is high velocity decision making.

And again, that's another principle that I have in the book. That is, as companies get bigger, they tend to slow down decision making 'cause they add layers to the process. And when you add layers to the decision making process you slow down growth. And that starts a day [00:10:00] two process.

Priscilla: Oh my, so much you've said in there., Too many good things , i'm gonna take you back a little bit because you talked about obsess over the customer. And a lot of people say we're customer focused, but clearly there's a distinction. 

Steve: , so I love this idea because you're right, every business knows they need to take care of the customer. And again, customer focus, customer journey, customer service, right? All those things. We talk about customers, but Bezos, in the first 1997 letter, use the term obsess at Amazon, we will obsess over customers and that just caught me.

Because you don't hear that word used very often in business. Certainly, and it has some negative connotations, right? When you say someone's obsessed over something, they're like going too far, but. If you're taking care of the customer, can you go too far? And that is still to this day. One [00:11:00] of the core mindsets at Amazon is obsess over customers.

And what Bezos talks about is . Understanding the customer's wants, needs and desires so deeply that we can, and I'm using his words now, invent on behalf of the customer and think about Amazon's history. Think about all the things they brought to the marketplace, things that people didn't know they couldn't live without.

Kindle Alexa. Echo devices, right? Shipments, arriving in hours, not days. All of that. Literally comes out of obsessing over customers getting faster. And Amazon has really, to this day, three pillars for customers. Wide selection, the everything store low prices, not always the lowest, but consistently low prices.

People know they're gonna get a good price and fast delivery. What Bezos said was, I can't imagine a [00:12:00] day where a customer will want less selection, higher prices, and slower delivery. So they're focused on obsessing to improve each of those three pillars.

Priscilla: Yeah. Thank you for making that clear because I think people say, but we are customer focused, but are you obsessed?

Steve: and I would say customer focus absolutely could be.

But there's a different level when you obsess over customers. It's a different way of looking at how, and the way I like to phrase it is, how do you remove friction between you and the customer? So , what are the points? And I would say most businesses do not understand where in their customer journey customers stop or get irritated or something doesn't work right.

Or you've been on a website and you filled out all your carts and all of a sudden it's gone and Right. All those things. Amazon is obsessively [00:13:00] focused on improving every one of those. Some would consider minor little steps, but those minor little things add up to a, most people, I think would agree. An extraordinary customer experience at Amazon.

Priscilla: Yeah. I think so. Thinking of the startup owner who is listening to this and thinking, gosh, where do I start? With, implementing, for example, the customer obsession or with the testing and at what point am I just taking in too much risk when I'm not sure exactly what to do, 

Steve: so a couple thoughts come to mind. One is I always like to remind people that Jeff Bezos started in the garage of the house in Bellevue, Washington, on his hands and knees taking books. People had order online, putting 'em in a package, and then driving them to the post office. He started like everybody else first.

So remember that I think second the startup. [00:14:00] Solopreneur, that first kind of step of an idea actually may have an advantage over a large corporation. 'cause the large corporation is so entrenched in what they've always done. They have a really hard time of thinking about doing something different.

I think third, your idea of risk. How do I gauge and I can hear people thinking if they're listening to this saying, yeah, but Amazon's got billions. They don't have to worry about it. One, they didn't always have billions. Two, they took risk seriously. And the first principle in my cycle arena is called Encourage successful failure.

Now, again, you don't normally hear those two words together, right? Successful failure, what in the world is that? But Bezos said, if we're gonna obsess over customers, we have got to experiment with new things and things that we may not know how to do. And if you're going to experiment, you're going to fail because if you're experimenting and you know it's gonna work, it's not an [00:15:00] experiment. we have to keep going. We have to keep testing 'cause it's not always gonna work the first time. And in too many companies, employees are afraid of failure because of the consequences. Not because they're afraid of it, but if you build a culture that allows experimentation and testing

that can bring all kinds of creativity out. I will also say Amazon is intolerant of incompetence. So this is not just, who cares? Let's figure it out. This is strategic, this is thoughtful. This is, thinking through all the potential problems even before you start, and that's how you reduce the risk of the experiment and. What can you learn from the experiment that you can carry forward into the next one or into a next product or into a next department? And so absolutely it's strategic and [00:16:00] intentional. In fact, in the book I call Jeff Bezos the Master of Risk because of how he uses risk strategically to grow 

Priscilla: I like that you broaden the fact that this is not just, Hey, that sounds great. Let's try that. And if we fail, 'cause sometimes that's the impression people get and, 

Steve: that's not how Amazon does it. They are very rigorous in how they go about this process. So it's not, who cares? Not at all. And, I agree. I think people may hear that thinking, oh, I guess it doesn't matter. But it really does.

Priscilla: I'm glad you painted that picture of how Jeff started in the garage, probably less glamorous than people who will listen to this. I'm sure you're sitting at a beautiful desk somewhere a lot less glamorous than the people listening and people are thinking, okay, from that point of sending books in the mail to the point of having this, mind that could craft these [00:17:00] letters with the intention to communicate where the vision was going. You wonder what happened in between there or where people get lost or where people can find inspiration in that.

Steve: a couple things come to mind. One is I'm very impressed with. How good a writer Jeff Bezos is. , That comes through the letters all the time. The way he phrases things, how he thinks about things, and that's the culture at Amazon. Quick story, 2004 Bezos sent an email to his senior leadership team and said, no longer will we allow PowerPoint presentations in any meeting.

Instead, the person calling the meeting or who needs the decision will write a maximum six page memo. So physically writing out, by the way, that is one of those risk mitigation techniques because when you have to write something out, [00:18:00] you have to think deeper. He says, people hide behind PowerPoint bullet points.

They haven't thought through everything, and if you have to write it out in a narrative, then you have spent the time thinking deeply about what it is that you want to do. Here's the other thing that's still, I think, unique. I don't know of any other company that's doing this. Those memos are not passed out or sent out before the meeting.

They are passed out at the meeting and. Everybody reads the memo together like Study Hall and Bezos said Executives are busy. They will say, , they've read it or we'll get to it. They won't. So we're gonna carve out time at the meeting. So literally everybody's on the same page. So that idea again, of the successful failure that's an [00:19:00] example of how these principles stand on their own and they interact with one another.

That's maybe some of the magic at Amazon and why they continue to be growing and not even, I just say surviving. That's not true at all. They're growing and they're thriving.

Priscilla: Oh, I actually do not know that much about the culture it makes sense. So many times everyone who has an idea wants to have a meeting. Everyone who just saw something that they think is interesting, wants to have a meeting and it just ends up being meeting for the sake of meeting and waste everybody's time.

Steve: Literally today I was doing some consulting with a company and did a survey and , one of the questions was, if you could change one thing at the company, what would it be?

And I said, it feels like there are meetings for meeting's sakes, and I don't know when people actually get work done. If I could change something, it would be people could opt out of attending a meeting and or they'd have to write a six page memo. I didn't go into all of that explanation, but [00:20:00] if you're gonna call a meeting and you have to write a six page memo , it is for sure.

You're gonna make sure that meeting is important, right? And something's gonna get accomplished.

Priscilla: No, absolutely. You can tell that it was a culture of people thinking deeply if Jeff Bezos were building Amazon today in 2025, knowing what you know and the depth of which you know it, what do you think he would do differently?

Or do you think he would do anything differently?

Steve: I'm pretty sure some of the mechanics might be different, but I don't know that the philosophy. And the culture would be that different. And Priscilla, your question is prompted 'cause I was just reading today.

So Jeff Bezos stepped aside as CEO in 2020. Andy Jassy, who was CEO of Amazon Web Services, stepped into the CEO role of Amazon overall, and he released a memo today that he had sent to employees [00:21:00] talking about ai. The fact that Amazon is going all in on generative ai, the AI tools, right agents all those kinds of things.

And he said, being forthright and upfront, it's likely that we will have reduced workforce as a result of these changes. And he also said, and in support of who our customers. Continuing to obsess over how we can improve their experience with Amazon. So I think some of the technology that Amazon is.

Helping to build and using internally for their customers. That might be a nuance, that would change how things were done. But I will tell you, I've been to three different fulfillment centers. The latest one was just a couple of months ago. And it was their latest generation of fulfillment centers.

So this [00:22:00] is where , all the stuff is stored and when you click buy, somebody picks it off a shelf, puts it in a box and ships it out, and it gets to your, front door , in amazing, fast time. But this fulfillment center, I won't say entirely, but it was significantly run by robots.

That did the work instead of people. And I think those are some of the things that invention, right? So Amazon's continuing to invent new ways to get fast delivery. New ways to lower prices and new ways to have a wider selection. And that's part of the core of what they do. That's what I think any business can start thinking about.

How can we do that? How can we emulate that? And you don't have to copy it, figure out your own way of doing that type of thing. What works for your business, for your customers, for the [00:23:00] marketplace where you are? But be informed by some of the principles that have worked at Amazon.

Priscilla: Oh, absolutely. Maintaining the guiding principles that he put forward, and just now applying technology to do it better. Day one. Still day one.

Steve: Still day one. Exactly. You got it.

Priscilla: You spoke about the four key growth cycles . .

Steve: Businesses are going through these cycles all the time, whether as a business or as a department or a region, but people are always testing new ideas or should be. If they're not, that's an indicator of something. They're building on those ideas.

The successful ones, they're accelerating that growth and then as they get bigger, they're. Scaling and figuring out how do we keep that core as we scale. That's still one of my amazing questions or thoughts or things. With Amazon, they have over 1,000,003 employees worldwide. How do you keep that culture with [00:24:00] that kind of workforce and dispersed literally across the world?

And I think that's a testament to being thoughtful and being persistent in keeping to your core of who you are as a company.

Priscilla: Absolutely. Wow. I think everybody should read the Bezos letters

Steve: I do too, but I'm a little prejudiced on that. Doesn't mean I'm wrong, but.

Priscilla: You sure sold me. And I hope you sold a lot of people. Tell me, Steve, what's exciting for you personally as you look to the future in the marketplace as well?

Steve: So I will say generative ai came across that a couple, two and a half years ago now, I think. And the way I describe it is I've gone pretty deep down the rabbit hole. And I consider myself an AI student. I think there are very few experts, so I don't consider myself one. And I'm doing a lot more work.

As I said, the company I'm consulting with is advising them on their AI strategy. It's giving me a lot to continue to think about and work [00:25:00] on and keep me busy, which all is good.

Priscilla: I did notice you said you're a student of ai. And I thought very interesting. It's still an area where very few people understand where is this going? What does this mean for me? How can I, take advantage of this? Like you said, it's a lot like the internet day one, and I wonder like what similarities or maybe the way people should think about it if they're thinking internet day one, AI day one.

Steve: so the way I think about it and actually. , I would recommend go to Amazon or just Google, Andy Jassy AI memo, you should be able to pull it up.

It's on Amazon's site under their, press releases, et cetera. It's pretty long. He talks about the impact of AI within Amazon. And I'm not quoting it '. But he said something close to generative AI will be more impactful than the internet was in the mid to late nineties, [00:26:00] and we know what happened there.

I think the generative AI impact is faster and things are changing significantly faster than with the internet, but I do believe that I was gonna say as important, I think it's more important as a technology. I think we need to learn how to use it and how to incorporate it and what it can do and what it can't do.

And I also don't believe it's going to be sentient. It's ones and zeros. It's a computer program. It's a pretty amazing one, but we need to learn how to use it and. Maintain our humanity and use it., The way I describe it, use it as a thought partner. It is pretty amazing at helping you think deeply about things.

So I'm an advocate. , I think it's pretty fun actually.

Priscilla: You phrased it well as a thinking partner to think deeper and we understood the success of Amazon if we boil it down to think deeply about [00:27:00] things. Is there something you wanted me to ask you that I did not ask

Steve: There are so many principles we could talk about for a very long time that I know we don't have time for. I do think the customer obsession, successful failure, believe it's always day one, are some of the core principles that if people take a look at that that can be really helpful.

We got a good core picture I think of what Amazon has done and will continue to do. And again. It's not about Amazon, but it's about the principles they have and how that can apply to your own business.

So I would suggest you think deeply about that.

Priscilla: Thank you, Steve. To the audience, if you could go to the bezos letters.com. I will link that in the description below. Steve, are you active online? Where can people follow you?

Steve: My primary platform is LinkedIn. Typically Steve Anderson either insurance or Steve Anderson Bezos, and you can find information there.

And if you let me know you listened I'd be happy to connect with you. And Priscilla, I haven't done this [00:28:00]before, so this is an experiment, right? I have created a chatbot, trained on the book and other interviews with Jeff Bezos, and I call it, jeff Bezos. And so we'll put this in the show note.

I'll give you, I'll send you the link, but it's Bezos BS period. If you could ask. And obviously no spaces. So if Bezos period, if you could ask.com and you'll be able to ask questions of Jeff Bezos, ask him about the six page memo, ask him about the day one, ask him about successful failure. You'll get responses based on the trainings of the book manuscript, as well as a number of other documents, including all the shareholder letters.

Priscilla: Wow.

Steve: , That's my experiment with the AI stuff. So

Priscilla: Excited for that. Please do jump on that. I know I will. I'm excited to do that. Thank [00:29:00] you so much, Steve. It's been a pleasure and thank you for your time and sharing your

Steve: Priscilla. I enjoyed the conversation. Thank you so much.

Priscilla: Thank you.