Top Three Lessons from Working with Jeff Bezos for 23 Years at Amazon

Glad to be here. Thanks for having me.

Yeah, it was twenty three years. You know, I came straight out of grad school and worked up from that to be CEO of the consumer business was a hell of a ride. And I did. I learned a lot. And when I think about the things that, you know, a lot of has been published about Amazon and about the way Amazon operates and runs its business. But I think, you know, some of the things that I think have been really important to me over time is this idea of giving people an opportunity to stretch beyond what they think is possible.

When I think about the the career I had, much of why I had it is because people, you know, let me do things that I had no business doing and had a high probability of failing at, but then ended up finding a way to be successful. I think people too often put limits on what they think their people are capable of out of fear of overstretching them in some way.

Well, some would say, you know, this is a fulfillment center, and we’re picking and packing boxes, and there’s a very clear defined process on how to do it. It needs to be done the same way every time and in order to be safe for the employee and high quality for the customer. And you you really don’t want to, like, be going crazy experimentation on that every day and throwing big risk at that. The other is a big new project. You know, it’s a thing that you wanna try.

It’s a thing you wanna build. It’s not existential to the today. It’s optimistic for the future. And those are great places to invest in people. You know, you just set a big audacious goal for what’s possible and let them go off and run.

One, I measure on progression. So I look at it as how far down the path did we get. Almost no matter where you’re gonna miss a number of goals. Almost no matter what you set them Like, if you say, I wanna go a 100 yards, most of the time, at least some percentage of the time, ten, fifteen, five, you’re gonna come short of a 100. If you say, we’re gonna go a 150 yards, you may miss the 150 yards by, you know, 30% of the time or even 40 of the time, but you’re far more likely to have a 100% over a 100 yards.

Your net gain of stretching farther is much better than setting something you think is a more realistic target. The key is, you know, you can’t beat everybody up over, you know, not achieving those big hairy goals. Now if you set a 150 yard goal and you go 50, then that’s different. Usually, the people you take bets on, my experience has been that people take bets on get much closer to that unless something really goes sideways. And probably at least half the time, they go further than the one fifty.

anecdote that’s interesting. What I find to be most consistent is that the three biggest traits, and maybe in order, they’re simplifiers, they have great grip, and they’re smart.

Well, there’s people on your team where you’re like, hey. I’ve got this idea, and it’s gonna sound nutty. And I’m gonna tell you, we’re gonna do this, that, or the other. We’re gonna go to the moon next week. And there’s the one person who starts and goes through a an hour long all the things that are gonna go wrong in very complicated ways of every little nuance that could happen of why that’s the dumbest idea you’ve ever had in your life. And then there’s the other person who’s like, well, that’s kinda crazy, but this could work and that could work and that could work.

This thing over here is gonna be super hard, so we’d need to get somebody to figure that out. It’s the difference between the people who find ways not to do things oftentimes and people who find ways to do things. Like, they separate the hard from the easy. Like, almost all the problems that you think are too complicated to do are like 90% things that aren’t too complicated to do and 10% of the thing is. And they quickly shed the 90 and they know exactly what to go to, where the real innovation or the real hard piece lives, and that’s where they spend all their time.

How do you test for grit? It’s like increasing pressure. You basically start at one level of load. If you can handle it, then you get more, and then you get more. Strange one,

My favorite hires, I’m a little afraid that they’re gonna be way better than hires I feel best about are the ones I feel the most nervous about being additive to helping them. You know, like, this person is gonna make me have to work harder because they’re gonna be challenging. And I think too many people look for somebody who’s gonna do what they’re told. You know, they want somebody who’s gonna fill the job of the now. And what I want is somebody who’s gonna fill the job gonna be the job three years from now or five years from now, and that is going to be, you know, very unhappy if their world is just me telling them what to do on a regular basis.

I think the world tends to think of Jeff as like Moses coming down from the mountain with 10 commandments and is like, shazam. Here is what we shall and it’s not like that. I think what Jeff is good is particularly skilled at. Well, I mean, he’s brilliant. Table stakes is like he’s just a brilliant guy. But he is one of the best simplifiers, if not the best simplifiers I’ve ever met, which is he can context shift incredibly well. You can have a meeting, you know, this hour on AWS, the next hour on consumer business, the next hour on labor, and be perfectly in the mode in the moment, which a lot of people have trouble doing.

And he can quickly sort out the 90% that isn’t hard, that he doesn’t need to worry about because somebody will figure out, and he can very quickly narrow down to the 10% or whatever it is, the the small slice that requires sort of his level of intellect or senior level intellect to figure out how to solve and what’s most important. So he’s hyper efficient with the time that he spends because he doesn’t waste time on the stuff that’s easy.

First, I do the things that will get me fired, and second, I do the things that get me promoted. So, like, I want a straight up prioritization mechanism. Do the promotion list last.

I’ve made lots of wrong decisions over time. I think my batting average is pretty good, but I’ve certainly struck out plenty of times. I personally don’t mind any of the, like, mistakes I’ve made, the ones where we did something and screwed it up. The ones that linger with me are the ones where we didn’t do it, where, you know, my gut was we should have done this thing and overthought it, or I was too cautious, and I didn’t do it. It’s the errors of omission to me ring much louder than the ones where I did it wrong.

And if I think about the things that we omitted, like, think we were late getting to the ultra fast shipping piece when we were at Amazon. And I think some of that was a decent amount of that was probably on me. And looking at the cost and the you know, there’s there’s not a real feasible, like, one hour delivery profitable bot despite all the subsidized funding processes to the contrary. There’s not a lot of great profitable models for that. And so I was always like, well, this isn’t gonna make it.

But the piece I didn’t put enough weight in was how much doing the effort actually sent a message to customers about the company and velocity. And so I think I held us back from that. We launched, you know, Prime Now. We were late to it, I think, because in part because I was conservative on this isn’t gonna work long term.

Sometimes, you know, there are a lot of people who say they do things really, really fast, but that’s really a small subset of what gets done. But it’s a marketing messaging. Customers start to believe, you know, have a perception of speed about you as a company. And there was a period of time there where, you know, I mean, two day was like, you can get anything you want in the world basically in two days or less, and, like, nobody was really competitive with it. And then all of a sudden, there were all these companies that were like, well, two days for boomers.

Like, I’m gonna get it to you in, you know, fifteen minutes. And that was where all the VC money went. It’s where all the eyeballs went. And because of that, it made two day the impression of two day slow. And because we didn’t have the other offer, I feel like it made customers think we weren’t on the cutting edge anymore.

In my personal opinion, yes. The closest I think it gets to working as a model is if you can get to subscription and ad. You you knock a like, just product cogs and margin with delivery cost. It’s very hard to get the density you need. If you’re paying net averaging $20.25 dollars an hour for a delivery or an hour for somebody who’s doing deliveries in The US, You know, you really need to net, you know, five or six deliveries an hour to get good scaled costs there.

It takes a lot of scale, takes a lot of density to make that happen. And so in order to economically make it work, you know, there’s companies who do it. Right? But they did there’s a lot of ads. There’s a tremendous amount of fees. My kids love Chick fil A, and they get $30 Chick fil A sandwich and fries on a regular basis by the time you pay the fees and the delivery fees and the tip. It’s an expensive proposition.

I think it’s gonna vary by company. It’s gonna kinda depend. People who will make it will have tremendous scale and have customers who are sort of inelastic in spend and can eat the fees and the subscription fees and the convenience and time are worth more than their money, or they actually value that. They actually put a financial value on their time and have done some sort of trade off. And the people without scale just won’t make it. They’ll go away.

Well, she said it’s about time, in all honesty. I consider it a sign I married the right woman, which is probably the most important decision I’ve ever made. But I was in a place where I just wasn’t happy with what I was doing. I love the people I was working with. It’s an incredible problem, but I had moved into a role where mostly I was a bureaucrat in a lot of ways. You know, I was basically talking to government and PR and managing my boss, and I was not in a place where I was spending my time building.

Amazon’s still a builder, you know, oriented company, but I personally was not in a place where I was getting to do that anymore. And I didn’t start at Amazon with the intention of having a 2,000,000 person workforce running one of the largest companies in the world. It wasn’t my plan. I like working closely with the team and getting into the creative work and building, and so I wanted to go do that again. That’s where I get a lot of joy.

I think

started changing for me a lot probably around 2015 or ’16 when I took over leading the global ops team around 2011 or so in there, sort of a big elbow in the curve around two thousand ten, eleven, twelve, where FBA growth really took off, the Fulfilled by Amazon, where third party merchants were moving their products into the company, really took off in that time period. And so we grew a lot over the next decade. And so we were an enormous operating company by 2015 or ’16.

We were starting to build out transportation networks. It really became to a place to where my life became much more about delegating and managing a lot of global issues and less about building.

You really already know if you’re customer centric in a very, very hard moment where you’re faced with doing something that the customer would like, but it’s gonna cost you a lot of money that you really, really, really don’t wanna spend. And that’s when you discover whether you’re customer centric. And Amazon was that or is that. And we’re gonna make Flexport that. That’s how we operate today, and that’s how we’re gonna build the culture.

as a damage or a return. For many customers right now, if you get an item, you say it’s damaged, as soon as it registers that you printed the labels to the back, we’re giving you your money back. That’s expensive, and there’s fraud in that, but it’s super positive for the customer from an Amazon perspective to be able to drive that efficiently. From a Flexport standpoint, we’ve had the same thing. Like, you know, hey, this trailer got held up at the port for some duration of time.

You know, a typical forwarder would say, well, it doesn’t matter why or how we’re gonna send you a bill for that. You know, we’re looking at that and saying, hey, these days of this, you know, we really should have gotten it out that we’re not gonna bill the customer for that. That’s on us. That’s our operational defect we need to resolve going forward. It’s really these tension points to where you could choose, and the customer probably wouldn’t know the difference or it would be equal to what competitors do.

But you know you can do something substantively better for the customer, but it’s gonna cost you money. What have you not taken to Flexport that either did or didn’t work? I think, you when I look at cultural history for me, I think, I mean, Amazon is a fairly intense place. You know, Amazon, I think you’re as good as you what you did yesterday kind of thing. There’s not a lot of longitudinal stickiness in that way. And I’d like to think that what we’re bringing is the intensity for customer, the intensity for process with a little more empathetic and a little more collaborative type of approach to engaging together.

You earn trust in people, and you earn trust in customer. And, you know, it’s easy to to say something or make a promise and not live up to it sometimes. Flexport right now has got a very aggressive road map of products we’re building for late twenty three and ’24, and we’re going out. We haven’t always historically delivered them, but we’ve put the pieces in place. And we’re going out and telling customers, this product is coming in ’23 and ’24. And if you’ll sign up to be part of this and be part of helping us develop it, you’re gonna get this.

Those are hard promises because there are a lot of work, and there’s a lot of dependencies between here and there. But if you deliver on it, you earn an immense amount of trust. You get a lot of credit for committing to deliver something that they know requires a lot of work, and then when you actually do it, just following through on doing what you mean, meaning what you say is where trust is built. And the more you’re willing to lean out on that for people and for customers, the more trust you build.

I think people, like, emotionalize it too much. It’s less about trust and more about ramping up on knowledge and experience. You know, it just becomes a bit of, like, hey. We’ve been doing this for a long time. You’ve been doing this for now two days. If you don’t have all the keys to the car and the house yet, it’s just because you’ve been here for two days. We hired you, which, by the way, is like among the most trusting things you can do is to hire somebody and give them a big role.

And sometimes people conflate ramping into things with trust, and I think that’s just a bad sort of misnomer. But for me, whoever starts on my team starts with trust. I assume you’re gonna be great, and I assume you’re gonna have all positive intent in what you do, and and my job is to help you be successful.

I think of it as especially at big c suite jobs or big executive jobs. I think there’s a lot of mutual trust and mutual accountability in that hiring decision. I’m placing a big bet that you’re gonna come in and do the things you need to do to deliver in the company, and you’re placing a bet that I’m gonna support you, and then I’m gonna live up to my end of the deal with help and support and resources and guidance and whatever is needed to enable you to be successful.

And it’s a two way street, especially at a senior level, because those are marriages in my view. Those aren’t short term hires. You’re hiring somebody that’s gonna decide who these big teams are for the company. Have you

And especially younger in my career, I was less patient. Maybe didn’t have enough appreciation for some degree didn’t have enough appreciation for sort of the impact of broader life in the moment, but with the whole person and not just who they were were early in my career. I think that was, you know, learning to understand who people were as a whole person in and out of the office and how those things interplay with their performance was important.

Yeah. We’re not a family because we’re all here to do a job, and we have a set of roles and responsibilities. You have to deliver on performance. You know, it is a team. I think that’s a much better way of framing it. Doesn’t mean that you don’t have personal relationships with people. Family is family. There’s no getting no getting out of your fam. It’s permanent. Jobs aren’t permanent.

My preference is to hire internally. If the talent is available and matches the need, but in fast growth environment, I was in Amazon and, like, we’re in at Flexport, you often have to intersperse more senior external talent. The people who grew up internally don’t have exposure to the business you’re becoming. And so you need to hire some people from the outside who understand the business you’re becoming to help teach everybody that’s being developed underneath. The external talent is really coming in to teach the people who are developing internally something that the fastest path to learn is by having somebody who’s already seen it be present to model that behavior and help give them guidance on how to how to lead in that new way.

I like to hire entry level jobs out right out of college. You haven’t learned any bad behavior. You haven’t gone to a company that’s not very good at things and learned a bunch of foundational elements that are wrong culturally in our world. And so where we have opportunities to do it, I really like hiring people who are, like, day one in their career because you have more attrition in that because people are still discovering themselves and discovering what they wanna do. You hire somebody out of college in the Flexport, they’re a Flexport.

They’re here for ten years. That’s their tried and true Flexport employee, and they know the culture. They’re part of building it. You know, there’s no better evangelist for it, and they learn what we’re all about. You’re not bringing in some other company’s culture with them.

It was a great opportunistic moment, and we had kind of viewed it as not particularly a land rush in this year. And so we were gonna start a team later in 2023 to build that when we started having conversations with Shopify about the idea that they were gonna sell or they were looking to potentially sell Shopify Logistics and Deliverr.

It went something like that. I mean, Tobi knows Ryan because they invested in our round in early twenty two. And so Ryan and Tobi have a relationship, and so he reached out and said, hey. We’re thinking about this. We think you all might be an interested party in this. Would you be? Ryan and I talked and agreed we would be, and we started engaging in conversation. It made a ton of sense for us to acquire. We viewed it as a it would be a a pretty effective acquisition and accelerant to our overall plan.

And getting to be Shopify’s preferred logistics provider or official logistics provider and provider for shop promise is a great thing for us as a company and gives us, you know, just that much more access to help merchants and sellers even faster than you’d planned.

My own experience, the thing that, you is waiting too long to hit the ground running and to just make the moves to integrate. Harish and team are a great group, and the team from Shopify is a great group, but they’re Flexport people now. We’re all gonna be one team. I wanna get through that quickly, and I think folks should be excited about the journey we’re gonna be on and part of the new company they’re part of. But if they’re not, it’s okay. Like, it’s fine.

I’d rather than decide that sooner rather than later, and I’d rather more quickly all become part of one team than drag it out and try to tiptoe around which company’s what and try to be overly sensitive about everything when the only thing that really matters is we need to go build stuff for customers.

Well, I mean, we want everybody to stay. We try to convince people that it’s the right thing, and here’s why it’s a good thing. And but if it’s not for you, it’s okay. No hard feelings. Not everything is for everybody. There are lots and lots and lots of places to work in the and you should find the one that makes you happy. And if it’s not us, it’s okay.

Well, I wish I could say I’ve always done that, but I don’t think that’s true. You know, there’s certainly been moments where I’ve been out of balance on that.

For me, it’s been about like, Leanne and I, we’re on the same journey together. Like, we recognize that, you know, I’m not successful without her. She’s not successful without me. We accept that about each other, and we want the same things. We we’re on the same journey in life. Our base desires are aligned. Then you gotta figure out how do you balance the time and the commitment. That answer is different for every person. I’ve always said I could only be good at two things, and, you know, that’s work and my family, and sometimes I’m not even good at two things because one takes place over the other.

The key I found is just becoming more and more aware of what I’m doing with my time. More and more realizing I think the older I get, I recognize that the only thing of true value I have is time. And so I become much more protective of it than I was, you know, a decade ago. As a result, I structurally reserve in my calendar and with my assistant, making sure that I have, you know, more structural basis for spending the time in the places that matter to me and that can have the most impact.

It’s like the simplicity thing. I only have a limited amount of time, so I wanna spend it on the 10% that gets the maximum impact between my job, my kids, and my wife. And, hopefully, all those things make me happy too.

COVID. When I think about the twenty twenty and twenty one of Amazon, we doubled the size basically of the entire operating footprint for Amazon in eighteen months. And everything that’s happened with employees and sort of trying to keep people safe and, I mean, that two years of COVID, I think for everybody that was in operations at Amazon was, like, a decade. It’s like a weird sadistic blur at this point.

I wish that I was that sophisticated in my thought and language in those moments. For me, it’s just always been try to be as open in communication as we can be, except that I screw up a lot and, you know, we’re heading on the same journey. It’s like everything else to just try to be committed to try to make it better tomorrow than it was yesterday. I wish it was like that clear, but you when you’re in the shit, you often don’t realize that you’re in the shit.

Even if you’re working till 11:00 at night, you don’t you kinda don’t even recognize that you’re doing it to a degree or that you don’t recognize that you’re not engaging. You don’t because you’re in the shit.

Well, this will really turn into a therapy session for you. I it’s good. I like it. Let me let me see if I can help You know, here’s the way I put it. I’m a better leader and partner to my teams. When I’m at full patience and where I have clarity of thought and I am in that condition best when my home life is also in balance, at least a respectably good way. And so if the choice is that the company and the team can have me, you know, and I’m unwilling to sacrifice my family, it’s too important to me.

It’s a piece that I view as a requirement for me being happy. And so it becomes a decision, which is does the company want me in that capacity? You get this much of me, and you get me in a healthy, happy state, and then my family gets the other part, or you can have none of me. And the sum of me, I think, is better than the none of me. And I suspect the same is true for you, that in a well rounded you state, you’re better than when maniacally focused.

I suspect that it’s true that the company and the people you work with would be better off with some of you than none of you, and that some of you is still better than the replacement. Like because I also view it as like, well, who would do this if I didn’t do it? And would they be better than me right now with what time I spend? I mean, I still think I spend a lot of time with with what time I spend. Would they be better than me?

And if they would, then I should go. Then they should take that job. And I would do that and feel fine about it, but I don’t think that’s true today. So I feel very imbalanced on that. And I suspect it’s similar for you. I

I think mostly it just made me more patient. One, I think you see yourself in your kids. Like, you see your behaviors in your children. Like, you know, they don’t fall far from the tree. You see some stuff and you’re like, oh, you said that’s annoying. I should stop doing that. And you just learn to be patient with people because you can’t with their kids. Like, what are you gonna do? It’s also very humbling. Nothing keeps you humbling like wiping somebody’s butt. I wiped a lot of butt, lot of poop in my house.

So, like, I’ve I’ve done a lot. It keeps you humble, and that’s help. You know? I mean, it just keeps you connected to the real world. Right. People are a composition of everything in their life, their kids, their family, their work, and all those things make them great and come in and out of challenges and good stuff. And I think I just have a deeper appreciation of the whole person having now have kids.

Well, I I’m only 11 and eight, so I can only speak to that part of it. And I can just say that the hardest part for me is that, you know, there’s never anybody in your life that you’re more willing to go crush somebody into a million bits for hurting someone than when they hurt your child in some way. And it’s like a different level of anxiety and a different level of protective sort of instinct, if you will. And it it helps at least for me, it helped soften me, I think, in a bunch of ways and helped me think about, you know, the whole person.

And I thought about the world in a different place after that. Because when something goes bad, you’re only as happy as your happiest child is a is a pretty common phrase that I hear a lot, and it’s pretty darn true.

I would be more present wherever I was, whenever I was there over time. It’s very easy to fool yourself that you are present when you’re not. Kids become good truth tellers at that. They’re like, dad, you’ve been on your phone the whole time you’ve been sitting. You start to recognize things you’re doing that you didn’t realize you’re doing. So I think presence is so important to people, whether it’s people at work or people at home or your kids. And I wish I had learned to be more present with everyone I was with in the moment.

Like, the phone was, like, the worst. So largely, it’s like trying to be very conscious of what am I doing with my phone at this moment while I’m engaging with this person. I I had an Apple Watch for a while I was trying to wear because I was trying to do sleep tracking stuff. And I realized that, like, it was making me not present because you would engage me in, like, lots of very different ways. And so I just stopped where? Because it’s, like, a distraction.

Yeah. We talk about it a lot. My wife and I both come from backgrounds that certainly look nothing like the lives we have today, and it’s a challenge. We have two two rules in our house, which is basically do the best you can and don’t be an asshole. And so we want to like our kids when they’re 30. I don’t want my kids to be assholes. I want my sons to be happy, polite, good to people, caring, empathetic, well rounded human. And if they do that and they don’t wanna go to Harvard, I don’t care.

I was a terrible student in life. I mean, I hated school. School was the most boring pedestrian, like, check the box. I hated it. I did terrible right up until I had to be good at it. And then I did really good in grad school and went to Amazon. I’m personally not a big believer that, like, you need to go to Harvard to be successful in the universe. And so I mostly want my kids to be curious and learn and be nice, well rounded humans. I wanna like them.

I wanna wanna have dinner. I wanna live to when they’re 30, and I wanna be able to have dinner with them and enjoy it. What about flying private? There is a lot of people who sort of say they sacrifice their own, like I view it as I would work really hard. I’m not a flying coach so that my kids can learn to respect coach, but they’ve now learned to have societal responsibility, and they do things, you know, with school and other things to help and to learn those skills.

If you’re very wealthy and flying coach, your kids still know you’re very wealthy.

My kids are fully aware that if they want to enjoy this lifestyle after they leave the house, they’re gonna have to figure out how to work. If you teach them to be good people and respect others, whether, you know, it’s the person at the bank teller or the drugstore or the grocery store or the person who is doing whatever or, you know, the waiter at the restaurant and whether or not it’s a CEO who’s coming over the house for dinner, They’ve gotta learn that all those people are phenomenal people, and they gotta treat them all with dignity and respect and that they have responsibility to the communities they live in.

Then, you know, kind of the rest, I think, they’ll figure out.

Okay.

I can’t remember the name of the book right now, but it was in when I was in high school, I was in band, and I was really fortunate that my high school band director, this guy named Bert Creswell, was a big leadership guy, and he did leadership books. And we did every year these big leadership sessions where you, like, learn how to be a leader in high school, and it was a gift. And I remember one of the exercises he did, and this is so corny and cheesy, but I remember it like it was freaking yesterday.

He had this pink heart. So you can imagine, like, 200 high school kids threw his pink heart. He folded in half, and he’s like, you’re a jerk. You know, you’re ugly. You’re blah. Like, he pulls off all these pieces of it, and then he starts apologizing and taping it all back together. And he holds it up and he’s like, it’s back it’s a hard still, but it’s not the same. And so, like, there’s a lot of leadership training and then this moment of realizing that, like, you can say all the things you want and do all the things you want, but apology after you’ve done it, it’s still never the same.

So you best not do it in the first place.

Single biggest bet is probably where I went to school because I didn’t know where Auburn was when I went there, moving to Delaware with my later to be wife, and then, you know, maybe leaving Amazon. What’s the kindest thing anyone’s ever done for you? Honestly, I think coming to work for me. I view it as a gift. The people on my team right now could be anywhere on the planet. Most all of them can be running their own company if they wanted to be. They’re brilliant, creative, fun people, and they took a leap to come do this crazy ride with me, and there’s not much more they could give me than that.

And I take it as a gift, and I view it as a lot of responsibility as a result.

Quite honestly, I grew up in a way where I didn’t care about school, I just wanted to work. My mother passed away when I was a junior in high school, and my dad passed away when I was in grad school. And it was very painful to lose your parents early, but I don’t think I would be who I am had I not gone through that. I tell my kids a lot, I hope I don’t need to die for them to feel the need to be really successful over time.

But it was very painful, but transformative in a way that I think shaped my independence and self reliance and desire to succeed in a very powerful way early in life.

Oh, that would be fun. Lockheed Martin or, like, some weird defense. I wanna go to a defense contractor where I can get into all the deep, most secret government files and access and just go crazy for a little while.

Well, I think we’re gonna be sitting down in 2028 saying, you know, a massive portion of the world’s goods move on Flexport’s technology stack and that there’s been a massive amount of waste taken out of the environmental footprint of the world and how small business is growing faster than it’s ever grown before because it has the ability to be competitive in ways that cost that it’s never been able to be competitive. And how many people are part of the Flexport universe?

Happy to do it. If you need some follow-up on your relationship advice, I’m happy to have follow-up sessions with you for nominal price.