The DNA of Unicorn Leaders with Ann Hiatt – EP 180

Justin Donald: Hey, Ann. Welcome to the show.

 

Ann Hiatt: Thanks for having me, Justin.

 

Justin Donald: Oh, it's fun to see you here. By the way, it's really cool that we're able to do this from across the world. You and I, we just had a chance to meet in person at South by Southwest but you're in Spain right now, right? You live in Spain?

 

Ann Hiatt: I am. I've just got over the Austin jet lag, actually.

 

Justin Donald: It's a lot different these days. I remember I used to get over it. You know, people would talk about jet lag. I'm like, "Give me a break. I'm fine.” Now, I feel it.

 

Ann Hiatt: No. Over 40, no. It's a different ballgame.

 

Justin Donald: It is a totally different ballgame. So, there is so much cool stuff that I want to get into. Big shout out to my dear friend and your friend, Brad Johnson. He had you on his show, which if you're unfamiliar with it, it's Do Business Do Life, to those of you listening in, but incredible guy, incredible company called Triad, incredible podcast, and one of my closest friends in the world.

 

Ann Hiatt: Yeah. That was a really fun conversation. Yeah.

 

Justin Donald: He's so good at what he does. He's a master of his craft and he basically gave you as high of an endorsement and high of praise as anyone he has ever introduced me to, Ann.

 

Ann Hiatt: Oh, wow. That's really, really nice. I'm sure that's a decidedly high bar on his part so that's flattering.

 

Justin Donald: Yeah. It was fun meeting you in person. You had a book signing at South by Southwest. You spoke at South by Southwest, which is a huge honor. Last year, I had the privilege and honor of the same and being a South by Southwest investor judge, which is fun, but the ecosystem is just incredible. I mean, it's abuzz. It's ten days of just so much stuff. I'm curious if this was your first South By and what you thought of it.

 

Ann Hiatt: Yeah. I too am a huge fan. This is actually my fifth time speaking at South by Southwest.

 

Justin Donald: Good for you. Yeah. You’re a regular.

 

Ann Hiatt: Yeah. I feel really, really lucky because it's a community that means a lot to me. The first couple of times I went, I've probably been about ten times in total because my bosses or people I worked with were speaking. And so, I kind of came along to staff or to help or just to tag along for fun. And then I started the old-fashioned way, submitted through PanelPicker and was chosen by the community to speak. So, the first two times, that's how I spoke. And then after that, I have an amazing contact there that we curate something very special. It's always a bespoke presentation that I get for the very first time at South By. So, this is my third time as a featured speaker that way.

 

Justin Donald: Well, and your message this last time was quite the incredible message and, yeah, bespoke is an understatement here. You talked about the DNA of unicorn leaders because you've had the luxury and privilege not only of working with and for and side by side many of them but, two, because of that proximity, having access to all kinds of other incredible entrepreneurs, right?

 

Ann Hiatt: True. My career was something that has exceeded my wildest imagination. It took on a life of its own but, yeah, I've worked directly for three major CEOs who are household names. We can get into that. And then now, yeah, I have consulting clients, CEOs of rapidly scaling organizations literally across five continents. So, I've had the incredible privilege of the depth and breadth of getting to know tech giants in a way that many people don't experience in their everyday lives. It’s been fun.

 

Justin Donald: Yeah. That's really cool. Yeah, we'll have to get into that because I'd love to figure out and learn from you on just takeaways, lessons, keys from each of these behemoths. Before we even dig into that, I thought it would be fun to talk about the path that you thought you were going to go on versus how on earth you ended up where you are today because you were going to be a professor, right?

 

Ann Hiatt: Yeah. That was plan A. I thought the most fun I could imagine having at work was a job where you got to read and write books for a living. I was a very studious child. It just sounded like incredible fun. My parents always have put a high value onto education. I'm the oldest of seven kids, five girls and two boys, and all of us conversations growing up were always about when you go to school, when you go to university, not if. And so, those seeds were planted early. So, yeah, I plan to do a PhD and become a professor. And, yeah, life took me on a different path than that.

 

Justin Donald: Where would you have taught? What was your goal? You had to be thinking somewhere.

 

Ann Hiatt: I mean, oh, so my dream program, my PhD program was at UC Berkeley in California, and I actually got into that program. And, yeah, really, really enjoyed that environment. It was a huge, I mean, I didn't know it was actually preparing me for my career in tech but it really was a huge education in asking the right questions and leaning into your curiosities and just digging, like not ten levels deeper, but like a hundred, a thousand levels deeper than the normal person would with the questions that you ask and the things you investigate. I have this photo of me after my first semester in my PhD stacked up with the books on the floor were literally taller than me, and they were in four different languages. So, that was just my first semester.

 

So, it was just learning to process massive amounts of information as quickly as possible. And not only that, but try and extract something unique or insightful, or to contribute to this conversation that's been going on long before I sat down in that room and is surely continuing now. So, that was an incredible prime for me for what came next in my career.

 

Justin Donald: Well, I love that. It's a tough school to get into. Most people don't. I can assure you I wasn't getting into it. I've done well but from an academic standpoint, I didn't stand a chance at any of the big names.

 

Ann Hiatt: I didn't think I did either, honestly. I've been in public school my entire life, elementary, junior high, high school, and even undergrad. I went to University of Washington in Seattle, where I grew up. So, it’s public all the way, including my PhD even though Berkeley is a top-ten U.S. university. Yeah. I’m one of the few people at Google who has ever been to a university of anything. Yeah. They're all the Stanford, Harvard, MIT guys. But, yeah, university of all the way.

 

Justin Donald: That's hysterical. I'm the same product of the public school system. I turned out alright at least by most people's accounts. And, yeah, it's great to see that you could penetrate kind of like the upper echelons of Silicon Valley, the tech startups.

 

Ann Hiatt: Snuck in.

 

Justin Donald: I mean, I guess, at what point is it not a startup and more of a behemoth? But what a cool experience getting to work with and for Jeff Bezos, first and foremost, right? And then if memory serves me correctly, from there, was it, Marissa Mayer?

 

Ann Hiatt: Correct.

 

Justin Donald: And then Eric Schmidt?

 

Ann Hiatt: Yes.

 

Justin Donald: So, you went Amazon, you went Yahoo, you went Google. And Eric, by the way, his resume is incredible because he not only ran as the CEO, he not only ran…

 

Ann Hiatt: Sun, Novell, and then Google.

 

Justin Donald: That's right. Yeah. And Alphabet, right? Moved up the ranks into an executive chairman. So, I just saw him speak at Abundance360 literally, last week.

 

Ann Hiatt: Oh, you've seen him more recently than I have. Oh, I'm jealous.

 

Justin Donald: Yeah. He's awesome.

 

Ann Hiatt: Yeah. He is the best.

 

Justin Donald: So, I would love to hear like how you landed that. And in fact, you open your book. I've got your book here, which great read. Everyone needs to read this. And mine's actually personally signed by you, so it's even more special. But it says, "To bet on yourself,” and you wrote in here for me to bet on myself and I feel like my career is exactly that, so I appreciate that. But the first thing you mention in this book is how you almost killed Jeff Bezos, and then somehow you went on to do great things and helped build an incredible company.

 

Ann Hiatt: It's true. It's true. I did nearly kill Jeff Bezos. And that is a nice teaser opening line to a longer story. But, yeah, I grew up in Seattle. I was actually, I'm an Air Force brat. So, my dad was a fighter pilot. He flew F-4 fighter jets during my childhood. But then he retired from the military and went to law school and ended up settling in Seattle. And my parents were both born and raised on farms and so moving to Seattle felt like a really big city to them, even though it's not that big. So, they decided to buy a house in Redmond, Washington, not anticipating the way in which that decision would literally change the course of my life because they moved there in 1985, which is the year that Microsoft announced that is their global headquarters, and everything has changed since.

 

Like, we had this huge plot of land. Our neighbors had horses. If you've ever been to Redmond, Washington, it resembles nothing like that now. But, yeah, I started working in tech very unintentionally, just kind of grew up around me, and I got swept up in it. So, my very first job ever at 16 years old was working at a five-person startup founded by two brothers who had just graduated from Harvard Business School. And, yeah, I went to undergrad. I studied international studies. I graduated immediately after the dot-com bust. So, the entire economy of Seattle had really disappeared.

 

And that actually was one of the greatest, most serendipitous moments in time for me possible because had that not happened, I wouldn't have ended up applying at Amazon, but I did. We can get into the long version of the story if you want, but to accelerate it, yeah, it took me nine months to get that job. I did three rounds of interviews and the final interview was with Jeff Bezos himself, and he hired me on the spot. So, my very first big girl job was working directly for Jeff Bezos in the foundational years of Amazon. This was in I got hired in 2002, so we weren't yet profitable. We were just breaking out into new product categories, you know, beyond books.

 

I was there just after he had created Super Saver Shipping. I was there for the launches into Japan, launched into the categories of sporting goods and jewelry and beauty. It was that early that we were just making it up as we went. And it was the Wild Wild West of the internet but that was definitely my executive education.

 

Justin Donald: That's incredible. And to land that job, to actually interview with the man himself is so cool. Now, everyone listening wants to learn more about that but I'm going to do the unfathomable because I want to go back to your dad. Your dad actually marks a really important point in time and really kind of is infamous in the fact that he plays a key role in a movie that is one of my all-time favorite. I've probably watched Top Gun more than any other movie. I can likely quote a third to a half of that movie. I've watched it that many times, but your dad was actually Goose. That's what that whole character was based around, right? So, we'll get back into all the business stuff but you got to tell us a little bit about that.

 

Ann Hiatt: This is my true claim to fame. Who cares about Jeff Bezos and Eric Schmidt, right? Like, my dad is Goose. No, it's true. So, I was born, literally, on the Air Force base in Tampa, Florida, MacDill Air Force Base. And then about a year later, my dad was transferred to Alaska. And so, I spent the rest of his military career based in Alaska. He was all over the place. He was like in Korea and all kinds of secret missions we didn't know about because this was during the détente period of what became the end of the Cold War. So, my dad's responsibility in his squadron, they were patrolling the airspace between the US and Russia.

 

And so, it was during that time that there was a, yeah, movie studio that was going to do a movie about pilots, and they wanted to listen to cockpit recordings of how pilots actually talk to each other because they've got their own shorthand and lingo, and the way that they give quick commands and keep everyone kind of organized and synchronized. And so, the movie studio got permission to listen to that, and they ended up just adopting all of the call signs for the pilots they listened to. And my dad is Goose and I grew up with Iceman and Maverick and all those guys who are now infamous.

 

I actually didn't see the movie for the first time until I was in college. I was probably 19 or 20 before I saw it for the first time because my dad actually didn't love it originally. So, first, he didn't love that when they finalized the movie script, they came to the Air Force and asked for their approval, and they didn't love the way that the pilots were portrayed. And so, they kind of withdrew their permission to call them Air Force pilots but the Navy had no such reservations. They were like, "We don't care. That's fine.” So, they became Navy pilots. So, one, he was upset that it was Navy and not Air Force because they've got a little friendly rivalry there.

 

Second was he hated that they made him a navigator. He was not a navigator. His F-4 Phantom fighter jet didn't even have a back seat. So, he was not a backseater. He was a fighter pilot. And third, he didn't love that they killed him. He died at the end of that movie. However, he did really, really like that they preserved the character of Goose as a good family man and that he very much is so. He liked that they kept that element of his character.

 

Justin Donald: Yeah. That's incredible. Did you see the second one, Top Gun 2?

 

Ann Hiatt: I did. Yeah, I did. My family actually rented out a theater. My dad actually has mantle cell lymphoma right now, so he can't be out and exposed to a lot of people but for his birthday, which happened to be right around the launch of that movie, they rented out a theater and just my parents and my siblings went to watch it together. I'm so jealous to miss that.

 

Justin Donald: That is cool.

 

Ann Hiatt: Yeah. Very cool.

 

Justin Donald: What a neat experience.

 

Ann Hiatt: And then my brothers had to fight over who the successor actually was based on, which of my brothers.

 

Justin Donald: That's funny. Well, you're the oldest. So, maybe there's a world where it could have been you. Maybe if the film was recorded years later.

 

Ann Hiatt: Yeah. There was a case to be made there. Yeah. I've actually been in a fighter jet once and the blue angel who was flying me was very impressed. He tried to make me black out. No such luck. Did not black out, did not throw up. I loved it. My mom always says I have jet fuel in my blood. And I think, yeah.

 

Justin Donald: That's incredible. Oh, good for you. Well, not only do you have all kinds of cool personal stories, you've got all these cool professional stories, but we've got to hear the story of how you almost killed Jeff. I mean, Jeff Bezos, I guess, you thought maybe you were going to get fired. He figured, "You know what? You are the real deal. We need to not only keep you here. We got to put you out more critical things.” So, let's hear about this.

 

Ann Hiatt: Yeah. It remains the worst professional day of my life. I hope never to break this record but it was just a couple of months into my employment at Amazon. It was actually the very first project that Jeff ever gave me directly after being hired. He came to my desk and had this white piece of paper with just long series of numbers on it, and he dropped it on my desk and he said, "Ann, I have these five locations I need to go to next week. We've got Tuesday, Wednesday, and Thursday,” and he just kind of walked away. And I was like, "What is this?” Because it wasn't addresses. It turns out to be GPS coordinates. So, my Air Force brat military background came in handy and I figured that out.

 

So, I plotted it out, and I determined that it was actually impossible for him to visit all these locations. It was way too spread out in West Texas. It was just impossible. There weren't runways. We couldn't move the jet that we were chartering. They were too far apart to drive. So, I went to my manager, John, and I told him that, and he didn't even look up. He just said, "Well, no is not an answer.” And so, back to my desk being like, "Okay. I can't make these places closer to each other and I can't bend space and time.” So, I thought, "Okay. What's in between car and plane?” And so, I decided to hire a helicopter.

 

So, I asked John that. He's like, "Great. Do that.” I'm 20 years old. I didn't have a helicopter in my Rolodex. I had no idea what I was doing. So, I figured it out through the jet charter company that we were working with at the time and hired my first helicopter. And I was super nervous about all the logistics. I had no idea what I was doing, but Jeff went on that trip and loved it. He came back like a kid on Christmas morning, super excited. He'd narrowed it down to two properties. He wanted to go back the next week and finalize it and decide which one to buy. At this point in my Amazon career, I am rightfully terrified of my job that I've been hired for because I had no experience in tech. I didn't understand the lingo. I didn't know who we were talking about. Everything in tech is acronyms. It's like learning a foreign language.

 

So, I kept a notebook on the side of my desk every day, would write down all those terms, acronyms, people, all the things I didn't know. And I would come in an hour or so earlier than everyone else to do my homework. And just kind of there was no Google. This is how old I am. There was no - like Google wasn't a thing yet. So, I just had to read newspapers and books and articles and everything they mentioned, everything I could get my hands on. So, I was at my desk. I was the only one in the building. It was very early in the morning when my desk phone rang and it was the charter pilots for the jet, and they had never called me before.

 

They said, "Ann, we don't want to alarm you,” and of course, I'm instantly very, very alarmed. They say, "But there's been a helicopter crash in the area, and we don't know if it's him. Like, don't panic but it's just one of those emergency automatic beacons. Like, if it crashes, this goes off.” So, I think to myself, “I've just killed Jeff Bezos.” Like, what do you do when you've… Because at the time, again, we are not yet profitable. All of the value of the company is based on faith in this single human, that faith in Jeff Bezos to invent the future. All of our investors had lost trillions of dollars overnight in the dot-com bust. Jeff, for all of them, was the last investment standing. And I thought it was very, very possible all that had just gone up in smoke.

 

So, I think what do you do if you've just killed Jeff Bezos? So, I decided, okay, we need to get the board of directors.

 

Justin Donald: Who’s next in line?

 

Ann Hiatt: Exactly. Who is the successor? We had no successor at the time. So, I guess, okay.

 

Justin Donald: Classic early-day startup, right?

 

Ann Hiatt: Early days.

 

Justin Donald: We don't know what's going to happen if someone gets hit by a bus, let alone dies in a helicopter.

 

Ann Hiatt: No. He did solve for that very quickly afterwards but, yeah, there was no clear. So, I organized my very first ever board of directors call. They had no idea who I was because I'd only been there for two months and I was like 19 years old. They didn't need to be talking to me. But we did an emergency board call. And then while my manager, John, was getting them together and they were preparing statements for if it was him, if it wasn't him, if he was dead, if he was injured, all the possible scenarios, what are we going to do, I had the job of finding him and finding out, is this him? What's the status of things?

 

So, again, pre-Google Maps, I had to just through an old school map figure out where the hospitals would be and where they might have taken him. And I started calling hospitals and eventually, I found him, patched me through. I got him talking to the board of directors. And then when he finished that call, he asked to speak with me. And, yes, I thought he was going to fire me. I really thought I'd done something wrong. But no, he said the kindest words that have ever been said to me professionally and he said, "Ann, I hear you're really good under pressure.” And he probably said something after that, I think I blacked out.

 

I was so relieved that he was okay and that he wasn't upset with me, and that I had done the right thing, that he was happy with how I had handled it. And, yeah, that was a turning point that changed the course of my career from then on because, one, he no longer saw me as this 20-year-old who had no business having this job but more importantly, it changed how I saw myself. I knew I could trust myself. I could keep an even head. I could keep my cool. I could gather my experts and put together an action plan even in the worst possible of situations.

 

And so, in the future, if I ever felt intimidated or had those moments of terror of like I have no idea how to do what I've just been assigned, which happens every day in early tech, it became like my mantra. I was like, "Well, it's not a helicopter crash, so I'll figure it out. I can trust myself.” And everything changed from then. Yeah. He threw me on insane projects that were far outside of my job description just because he could trust me.

 

Justin Donald: That is so cool. I'm reading the book right now about Twitter and Elon taking over.

 

Ann Hiatt: Such a good book.

 

Justin Donald: It's so good. Ben Mezrich’s one of my favorite authors out there and so it's interesting because one of the unassuming women in the organization that I think most people, most of the higher-ups in that current organization kind of didn't think much of her, that she was disposable, probably, and she ends up moving up to basically become Elon's right-hand woman. And so, it's cool hearing your story and your ascension in a similar way, although much more traumatic, I must say.

 

Ann Hiatt: It was traumatic. That's for sure.

 

Justin Donald: So, what would you say are some of the best lessons or a few of the best lessons that you learned from Jeff and maybe why he has been able to accomplish what he has with Amazon? You've got an inside scoop like no one else.

 

Ann Hiatt: Yeah. We could be here for a very, very long time for me to do justice to that, answering that question but there are some favorite takeaways that I have. The first is around the team that he assembled. He was very, very careful, especially in those early days of who he brought on board. He, in fact, when I got into my dream PhD program and left Amazon and was going to California, we interviewed what felt like hundreds of people to replace me. And he just rejected all of them. My PhD was starting, and I couldn't change the date of grad school, and I was panicked because I wanted to have months of prepping my successor to take over.

 

And I went back to him and I chose my top three candidates, and I said, "Would you reconsider any of them?” And he was just almost offended that I even asked him that question. And he told me what is now my mantra in hiring, which is, “I will only hire people I have to hold back, not push forward.” That's how he summarized the people he needed around him, especially in the early days. He needed people who were full of ideas, insatiably curious, very, very smart learners, and could teach themselves to do anything because we couldn't hire for the skill set we needed because no one had ever done it before.

 

No one had ever invented his fulfillment center systems or the predictive modeling around how are we going to stock inventory and where and how to make that actually not cost prohibitive to do what became Amazon Prime and things. We had to invent systems, physical technological systems that never existed before. So, he just needed to hire people who were really, really smart and loved to push a boulder up the hill in really creative ways. And so, that is probably the thing that I reflect on the most is the incredible people that I was privileged to learn around, especially at the foundational years of my career.

 

And one of my favorite examples of that is I think it was just like a month or two before I started Amazon, Jeff created this new role that he titled The Shadow and the Shadow’s role was to be at his side at all times, like in every meeting, copied on every email, on every flight, like literally at his side. It was a rotational role. And the very first person to hold that role was Andy Jassy, who now 19 years later became Jeff's successor as CEO of Amazon. Andy came on board as The Shadow and he is the model I use for the rest of my career.

 

He's the reason why I've paired not only with the three CEOs that I work directly for, but also now, in the way I approach my consulting is he was there to ask the right questions, poke holes in all their favorite ideas, help them see around blind corners, and to really anticipate the data they're going to need to really accelerate their decision making and help them get to the right answers faster. He wasn't there to provide the answers. He was there as the catalyst for these brilliant minds to accelerate their effectiveness. And I just watched everything Andy did and tried to replicate that, educating myself, doing my homework, writing my opinions in the way he did, speaking to executives in the way that he did.

 

He was the master at what at Google we call TLDR as the Too Long Didn't Read executive summaries. It's the few things that he chose to highlight for Jeff were the most important things that needed his attention. And so, yeah, that was really pivotal for me as well. And then if I had to choose other qualities, I would say it would come as no surprise to hear that his vision is just unmatched. He had such a gift for knowing where tech was moving. But I think more importantly than that, he was exceptionally capable of keeping his eye in the long-term win. He was never tempted to do the short-term win, which would have made complete sense because all of our shareholders wanted a return on their investment, finally.

 

And he never took on projects that would only take a two to three-year horizon. His sweet spot was really around a seven-year horizon, and that's why he always looks like he has a crystal ball into the future is because he wasn't tempted by the easy wins or the low-hanging fruit which many entrepreneurs can be distracted by. He refused to optimize for that. He was always optimizing for the long term. So, I mean, it's hard to do justice to that question in just like a couple of minutes, but those are my favorite highlights, I think.

 

Justin Donald: Well, I think you crushed that. I mean, I love this whole idea of a shadow. And I mean, talk about how to really get someone good. You know, it's through immersive training. It's through a true, like for me at least, I know I learned best through some sort of immersion. Like, if I go to an event, if I did something one hour a week for ten weeks, I'm going to learn way less than if I just went and jumped in for ten hours in one or two days, right?

 

Ann Hiatt: It was an incredible executive training program. You're right. And he rotated that like Colin Bryar was shadow number two and he wrote this incredible book called Working Backwards where he documents literally every processes that we developed working together for how to run an executive office, how to run an innovative organization. Jeff called it Day One. He always wanted to stay in that Day One startup mindset and never rest on his laurels. And that's the other half of the shadow’s job was. Yes, it was an incredible executive training ground because when Colin or all the other shadows graduated, they could ask the questions that Jeff would ask. When he's not in the room, they would make the decision he would make when he's not there anymore.

 

But equally important was what it did for Jeff. It kept him from falling in love with all his own ideas or really he not only tolerated but he demanded that it was someone's full-time job to keep him in check and make sure that he had looked at things from every angle and kept him from getting lazy or just repeating patterns. And everyone won in that. And that is something that I don't see many CEOs doing, but the ones who are truly remarkable have some kind of mentor, volley partner, intellectual sparring partner at their side.

 

Justin Donald: And someone like I admire anyone that puts people in their path, that their job is to question their decisions or to say no to them or to just try and course correct because most founders, most people that start big companies are huge thinkers. But you can't just be a big thinker. You need the other people around that can actually make it a reality and you need some practicality, right? What's too big right now versus what's too big ten years from now? Those are totally different. So, why leave? You know, you seem like you're on a great trajectory up.

 

Ann Hiatt: I know. Finally making money.

 

Justin Donald: Right.

 

Ann Hiatt: I left because I got into my PhD program. That's the only reason. Probably the most expensive PhD in history maybe given where I left at Amazon when we were finally profitable and my stock was starting to have value, and then the years I missed at Google also while I was doing it, but yeah, I left because I honestly thought I was going to do plan A. I loved what I learned from Jeff. I knew it had changed my brain, my approach to life, my curiosity. It was an incredible privilege. But, yeah, I got into Berkeley and I wanted to continue my education that way, but it didn't work out that way. And I got recruited mid-program by Google who heard I was in town.

 

Justin Donald: Yeah. So, let's talk about that. So, you abandon this goal, this dream from a very prestigious university to go pursue something that at the end of the story, you can say, "Hey, that was the right choice,” because the experience you got there had to dwarf whatever it would have been at Berkeley. But, talk us through that.

 

Ann Hiatt: It was a really hard decision. Yeah. Looking back now, it feels super obvious that that was the right decision but it was gut-wrenching. And I'm not a very emotional person but it was like I cried my last day I was at Amazon. I cried when I resigned from my PhD program at Berkeley. But honestly, Jeff is the one who really gave me the courage to make these hard decisions because he very famously accounts when he had the idea of Amazon and he went to his boss and pitched in the idea and his boss said, "Well, that sounds like a great idea for someone who doesn't already have an amazing job.”

 

Because Jeff was the youngest ever promoted hedge fund VP in the history of that company. What's the name of the company? I just can't. It's flying in on my brain. But anyway, and his bosses, I mean, he had all the money, all the power, all the influence he could possibly want. But he calls it his regret minimization principle. And Jeff had a conversation with himself where he thought, "Okay. At the end of my life, am I going to regret having tried this and failed? Or would I regret more not having tried?” And he decided, “I wanted to give it a shot. I would regret more not having tried.” So, I think of that regret minimization principle very, very regularly still now, 20 years later, after working for him because that is game-changing.

 

I find that the things that haunt me most are not my mistakes of commission. They're my mistakes of omission. The time I wasn't brave enough to sign up for something or raise my hand in a meeting or volunteer for a project because I was intimidated by, I don't know, my lack of experience that other people in the room or something, those are the things that haunt me most. Not when I raise my hand and kind of stumbled my way through something or maybe failed very publicly at something because goodness knows that happened. But, yeah, I so regret minimization was what made me brave enough to give a chance and go to Google.

 

Justin Donald: Yeah. D. E. Shaw?

 

Ann Hiatt: D. E. Shaw. Thank you. It's driving me nuts. Yes.

 

Justin Donald: Yeah. I was thinking, I'm like, I'm going to think of it. I'm going to remember.

 

Ann Hiatt: Yeah. Thank you.

 

Justin Donald: So, okay, now you have an opportunity to work at Google and really, in short order, kind of move into a position that didn't exist in tech companies. Right?

 

Ann Hiatt: That's true. Yeah. My first three years there, I worked for Marissa Mayer, who was the VP of Product, of Search Products. That just meant we were in charge of making cool stuff. Other people had to figure out how to monetize it, but we were just there to fulfill the mission of the company, which was to organize the world's information and make it universally useful and accessible. That was what we did every day. It was really fun. We invented Maps, we invented Chat, we invented all this kind of like image search. The earliest inklings of artificial intelligence were really what we were working on together.

 

Then, yeah, I caught the attention of Eric Schmidt, who is still CEO of Google at the time and he brought me into his office. He recruited me away from Marissa. She was not too pleased about that but then she ended up getting her dream job of being a CEO herself and went to Yahoo! Yeah. Once I was in Eric's office, the first three years I worked for him, he was CEO. And I really learned to fully appreciate his very, very unique management style because he had this very difficult job, which was it wasn't his company. He was there to fulfill the mission of our co-founders, Larry and Sergey, and he did so incredibly artfully.

 

He has a very different personality from the other execs I had worked for before but, yeah, we ended up working together for almost exactly a decade. So, after three years, he transitioned from being CEO and became the first-ever Executive Chairman of Google. He'd never been a full-time chairman before. Google never had one before. So, he was really inventing himself. And we spent a full year, we did a listening tour, visited 40-plus Google offices. We met with heads of state and lawmakers and researchers and universities and everyone we could to see where did tech need us most. What problems could we uniquely solve?

 

In the end of that year, we had a full job spec, but at the same time, I needed to evolve in order to possibly help him accomplish that very, very big mission. Because back then, I mean, and even mostly now, when you move from CEO to chairman, it's kind of semi-retirement normally. And Eric laughed at me and he was like, "No, I'm going to 10X my output.” And I was like, “Eric, that's impossible. We're already working so hard.” But he did. And so, I needed to up my game similarly. And so, I created a role that had never existed before that was inspired, one, by how I'd seen Andy Jassy and Colin Bryar be shadows to Jeff Bezos but also for my friends in the policy world because we were doing so much work with governments.

 

We were working with the Obama administration at the time, and I saw this role called Chief of Staff that was really this right-hand thought partner, really basically fulfilling that shadow responsibility to their executives. And I thought, "This is what he needs. He needs someone to be that voice in his ear, to be that sparring partner to be.” And that's a terrifying job. I mean, I’m almost inarguably among the smartest people in the entire world. Like, to be his intellectual sparring partner is terrifying. But I knew that's what he needed in order to fulfill his mission and what the company and what tech in general needed from us most.

 

So, yeah, I created this job that had never existed before, and it actually took me three years to get HR to approve it. So, I was really doing it without the official authority or title to do so but it was the greatest privilege and continuation of my business education possible.

 

Justin Donald: It’s incredible. Well, you talk about how smart and how much of an outlier Eric Schmidt is. And I think it's also evident in the success that he's had. I mean, if you look at the wealthiest people in the world, it's almost always founders, almost always, right? You've got a few others that may make the list. Maybe to the far back of the 500, you might get some real estate types. But it's generally not hired guns, right? Executive C-suite. So, he's one of the highest-earning C-suite, I think, ever. And based on where he's finished up, I mean, he could write a textbook on being the CEO, being the chairman in a way that no one else probably can.

 

Ann Hiatt: It's wildly unique. He came into a partnership between Larry and Sergey that was really, really unique. He saw their vision and they rightfully were mature enough. I mean, they started Google in their dorm room at Stanford at they were like 25 in their PhD programs. And they really, to their full credit, they realized they needed to stay in that zone of genius. They were inventing something that never existed before. I mean, there was others, right? There was Yahoo was the number one. There was others. They were number three when I joined in 2006. But they knew that they needed somebody who knew how to run the day-to-day, who had that playbook already.

 

And Eric had been CEO of Sun and Novell and he had been tested by fire like those were not easy jobs. He had had some huge setbacks and he had recovered really well. And they bonded over some things, not only professionally but also personally. They really, really clicked very, very well together. So, yeah, Eric became this incredible catalyst for their crazy ideas. And Google became dominant. I don't think Larry or Sergey would argue because of Eric's guidance and helping them really fulfill their mission.

 

Justin Donald: That's incredible. I mean, if memory serves me correctly because I love studying this stuff, I love figuring out what makes people tick and where people are in their financial world, that's kind of what I do, but I think he has like a $25 billion net worth, which you look at like some of the most successful founders out there and there are very few ahead of him.

 

Ann Hiatt: Oh, yeah.

 

Justin Donald: It really just speaks volumes to what he is able to do and how differentiated he is, how he's kind of in a league of his own.

 

Ann Hiatt: No question. Yeah. He’s exceptional.

 

Justin Donald: What are some of like the greatest takeaways and lessons learned from him? I mean, he has to have so much wisdom that you've been able to glean over the years.

 

Ann Hiatt: Yeah. He is the executive I spent most of my career with. Like I said, it was just under ten years that I work side by side with him quite literally, like 18 hours a day for a full decade

 

Justin Donald: And he wrote an incredibly kind and, I mean, just warm and complimentary foreword in your book.

 

Ann Hiatt: Yeah. That really touched my heart. That gave me, I got all misty-eyed reading it because I, of course, volunteered to, “Yeah. Let me give you some ideas, some bullet points,” just to make it really easy for him to write the foreword because it was already so generous of him to agree to do that. And he wrote every word himself.

 

Justin Donald: That’s so cool.

 

Ann Hiatt: Yeah, it's really, really sweet of him. Yeah. We did a lot together. Like, we have been through some of the wildest moments of tech. And, gosh, it's again really hard to kind of distill what I learned over a decade of mentorship and absorbing best practices. But among my favorite things about Eric is really first thing that comes up in my brain is his curiosity. I share in the book that he had this plaque on his desk at Google that said, "If at all possible, say yes.” And that mantra isn't about overfilling your calendar or taking everything onto your plate or being a pushover. It's the opposite, actually. It's keeping space in your day, in your mind for curiosities, keeping open opportunities for serendipity and discovering new things.

 

Eric got invited to all kinds of crazy stuff, and he would always lean towards the thing that he understood the least because he was always just trying to expand his understanding. And a big part of my job was helping him connect with the world's greatest thinkers who had expertise different than his own. And so, my favorite things that I did were really trying to be this gathering point of assembling these people, and that way we could fulfill our job of anticipating where tech was going and the problems that we could solve. But he is an insatiably curious human. And that was really important in his role as CEO and also as chairman because often the path forward was very unclear.

 

It wasn't like we were choosing between good and bad or black and white. We were choosing between like complete unknowns into the future. And he's very professorial in the way that he runs a meeting. He’ll kind of sit back. He's often the quietest voice in the room, and then right at the right moment, he'll just do this summary statement that pulls the silver thread, the bing, bing, bing, all the data and everything that we've been debating just kind of falls into path. And he did a great job of also doing that for our founders when they were just kind of workshop things out loud and just brainstorm. He would help them make sense of all of their ideas and pull it into a game plan.

 

And so, I think his curiosity really came through in his ability to do that. Not only did he have playbooks from his past experiences, but he was pivoting them and adapting them into new unknowns. So, his curiosity, one, made every day very fun because I never knew what was going to happen. And, two, it helped me embrace the unknown and not be intimidated by it, but to be really excited by possibilities. He also taught me one of my favorite things that I pass on to my consulting clients, which is to treat all your decisions like experiments. It's not like a one-and-done and you move on and you never reexamine. He was constantly setting up parameters of like, "What do we expect the consequences of this to be?” I now call them my green light indicators and red light indicators.

 

When my CEO consulting clients are making a really big decision that feels very intimidating, especially when you're at the scale-up stage and you don't have money to burn, you don't have time to burn, you really need to get it right, I helped them set them up these small, controlled experiments where you can say, "Okay. If this really big decision that we're making is correct, we would expect to see X, Y, and Z happening. If it's incorrect, we'll see A, B, and C happening.” And that really helped us put in some guardrails and then know we have these indicators of like, "Okay. It's working. Full speed ahead. Let's 10X this.” Or, “Whoop. Okay. We've got a red light here. Let's do a small pivot. Let's look at our data again and then off we go.”

 

And I really learned that from him. He's exceptionally good at setting up these controlled systems for experimentation that really accelerate your success in a way that other people, I think, that's one of the biggest misunderstandings is about moonshot thinking, is around that because they kind of treat them, Jeff called them one-way doors and two-way doors. It's actually false that most of your decisions are one-way doors that you can't come back from. Often it’s a two-way door so that means just move as fast as possible and watch for those red light, green light indicators of if you need to circle back.

 

Justin Donald: That's good. I love that. And you know, in his foreword, he basically talked about what was important to him that he sees in you. One of those is excellence without ego, which I could not agree with more. And our whole Lifestyle Investor community is based on that fundamental that if someone has a big ego, if they've already arrived, I don't care how successful they are, they're never going to get in because that's not who we want to be around. And then he also says you're a force multiplier. So, you've worked with people that are big-time force multipliers with excellence, without ego. What a great compliment to be paid to you.

Ann Hiatt: I can’t think of anything that would mean more to me for him to say. Probably one of the most commonly asked questions I get when I’m in conferences or speaking places is what are the common denominators between these super performers that I’ve worked for and with. And it consistently surprises people, the first word I use is humility. Because when you think of all these jacked space cowboy CEOs on the covers of all these financial magazines and stuff, humility isn’t the first word that comes. But that’s how they got there. Unquestionably, like, including Jeff Bezos, the shadow is a great example of that. They are humble first. They question themselves first. They’re curious. It’s impossible to bruise their egos because they are just– I think it’s hard because they really, really care.

 

To your point, like incredible wealth often does come from founders and founders. This is their baby. There’s nothing more personal to them than what they’re trying to put out in the world or the change they’re trying to make in the world. But the only way you’re successful in the long run is if you have the humility to listen, to gather the right voices, to test your own theories, to be willing to be wrong, and to just stand up again and take it over again. There’s an interview with Marc Andreessen I listened to recently, who’s founder of Andreessen Horowitz, one of the most successful VC firms in the world. And one of his founders told him, it’s kind of like learning to like the taste of your own blood, which is truly a horrible thing to say. But being a founder is kind of like that, you kind of have to be willing to get punched in the face over and over and over again, and you just learn to see it as an indicator of like, I showed up again today. It’s kind of like that, unfortunately. It’s painful.

 

People think at Silicon Valley, we celebrate this thing called failure and we don’t care and it doesn’t bother us. That’s 100% incorrect. It hurts deeply and personally every single time. But being willing, having the mission matters so much to you that you would take that kind of brutal schedule and scrutiny and questioning and risk taking, it comes from really being aligned with a passion and a purpose that matters more to you than your own individual comfort.

 

Justin Donald: Yeah, that’s so good. Now, I’m not sure if humility is one of the five characteristics of a unicorn leader. I think it is. But I’m curious if there’s another one or two that you want to share. We don’t have to share them all, because I want people to have to go seek out your work and figure some things out.

 

Ann Hiatt: Yeah, so my talk at South by Southwest about the traits of a unicorn leader, my main goal there with that talk was to dispel the myths that keep people from participating or feeling like they belong in that crowd. And as I’m looking at how quickly tech is evolving, especially right now with the incredible possibilities being unlocked by artificial intelligence in general, intelligence, we need more people participating, not less. So, my goal in that talk was really to help people see that they belong there and not only they belong there, but we need you to do it.

 

Yeah, so one of my favorite things, we talk about some of the expected things like intelligence or bold risk taking, yes, our core characteristics. But then I eased the listeners into some concepts that I thought they might find really challenging to the myths they have built up in their head of effective leaders. And one of those I discussed was openness. Openness is the willingness to take data and decision and feedback and ideas from multiple sources, which we’ve kind of talked about here on this podcast, but it’s also about gathering the right teams around you, being humble.

 

Being one of the other characteristics is low neuroticism. That’s probably counter to whatever a CEO you’re imagining in your head right now, who’s surely on the front cover of a New York Times or something today, they probably seem very neurotic. But what I mean by low neuroticism is they’re people who keep their standards impossibly high over long periods of time. They’re able to take very complex goals, break it down into manageable steps, and make progress incrementally, step by step, slowly.

 

I know that on the outside, it looks like they have these crystal ball, glimpses into the future that the rest of us, it’s some kind of divine plan that’s been gifted to them in one whole chunk of like, they can see how they’re getting from today to this incredible success of future. No. I’ve been in those rooms. That’s not once been true, ever. But having a low, neurotic approach to your work is really about appreciating the incremental nature of what you’re trying to do and really re-examining your best practices. And that’s, again, why you need a world-class team around you. That’s why you need to lean into these moments of discomfort, where you have to be willing to take risks, even if it’s going to hurt when it doesn’t go right for the first 10, 20, 100 times. Yeah, I think some of those traits are a little surprising, but openness and low neuroticism at the heart of that, that really is humility.

 

Justin Donald: That’s incredible. I love hearing that. I like hearing how you’re distilling things down that, maybe contrary to popular belief. Now, I’m curious, why move out of Silicon Valley? Why move to Spain? When and, like, how long have you been there? And why was this the move?

 

Ann Hiatt: Oh, to me, it still feels insane that I did have. The short version of it is I married a Spaniard. So, my husband is Spanish and I live here. He was born 10 minutes from where we’re recording this right now. And it was at a time…

 

Justin Donald: That’s near Valencia?

 

Ann Hiatt: Yeah. I live just an hour outside of Valencia. The Mediterranean is two blocks that way behind me. It’s pretty great.

 

Justin Donald: That’s so cool.

 

Ann Hiatt: Yeah. So, I met him around a time when I was thinking of what was coming next. I’d been at Google for around 10 years when we met, and I was really looking for my next challenge. And actually, my last year at Google, I was in London, embedded with the DeepMind team, which is now very famous because– but back then, no one was talking about artificial intelligence, but DeepMind was Google’s first investment into that. And I was sitting with the London team here trying to utilize that. And we were really rolling out this vision of how it was going to be integrated into all of the products and offerings and really looking for ways to disrupt ourselves in anticipation of this new capability.

 

And so, in the end of that experiment of me being in London and working in, but I think I was in five different offices that year, I decided my challenge had to be outside of my very, very comfort zone of my Google family. And so, I made the really hard decision to leave. And so, I thought, okay, it was around the time I got engaged. So, I thought, why not just fully uproot myself, take a bit of a break, reinvent, see what the challenges are? What do I want to do next in my career? And not knowing that the pandemic was coming one year later, yeah, so I’ve been in Spain for five, almost six years now. And I started consulting very unintentionally.

 

When I decided to leave Google, Eric Schmidt has a personal VC called Innovation Endeavors. And a lot of his portfolio CEOs who had known me for a long time asked me to kind of, “Hey, could you come on board for this? Or could I get your advice on that?” And before I knew it, I had a full consulting list and a waiting list. And now, yeah, I have CEOs literally across five continents working with me. And I focus on the wonderful problems that come with rapid growth in scale, specifically around people and operational systems, because that’s what I ran at both Amazon and Google. And so, I try and pay for those playbooks and help my CEOs avoid some of the mistakes that we made and really accelerate from the learnings that we had. But there’s no one size fits all solution. So, again, I just try and play that role of asking the right questions, looking at their data, helping them see around some blind corners, and trying to accelerate their decision making and effectiveness as fast as possible.

 

Justin Donald: Oh, I love it. That’s awesome. And I love that you’re in business for yourself, working with the people that you really enjoy being around the most, and you’re doing it on your terms. You’re working with who you want, you’re working where you want and how you want, and living where you want, I think that’s incredible. And before we hopped on air here, we were talking about how I just got back from Mexico City because our Lifestyle Investor community, we did this epic trip for our mastermind where it’s white glove from start to finish and really nice. And I shared that itinerary with you.

 

But what I didn’t tell you is our fall, white glove trip is to Spain. And we’re going to be going to all the top Michelin-rated restaurants in Barcelona. We’re taking a private jet from there to San Sebastian, hitting up all the Michelin star restaurants there and we’re going to Bilbao.

 

Ann Hiatt: It’s so good. Okay, so you’re not coming in my neighborhood. I live in a very small town, but we have six Michelin star restaurants like within. I could literally walk to from where I live right now. So, yes, I want that itinerary. I have FOMO already. I’m really excited about your deal. Yeah, you’re going to love it. I’ve been to many of those restaurants. I’m sure you’re going to.

 

Justin Donald: Oh, I can’t wait. I’ll share it with you.

 

Ann Hiatt: Yeah, please. Okay, now I’m going to, like, stalk you.

 

Justin Donald: Well, I was going to say, maybe if timing is right, we can work it out and you could join us for part of it.

 

Ann Hiatt: Yes, please.

 

Justin Donald: I mean, I would imagine that most of the people, if not all of the people on the trip, are likely right fit clients for you anyway, since we’ve got about 130 members in our mastermind and over 50 of them have exited their companies and the other large majority are running their own business. And the ones that exit often start new businesses.

 

Ann Hiatt: Yeah. Oh, so much synergy there.

 

Justin Donald: I know.

 

Ann Hiatt: Just a short train right away, you’re going to be in my backyard. That’s crazy.

 

Justin Donald: No kidding. Well, this has been so fun. You are just a blast to get to know. You’ve got so much life wisdom and just great stories, great, real utilizable information. So, thank you so much. Where can our audience learn more about you?

 

Ann Hiatt: Yeah, I am very active on LinkedIn. I post three or four articles every week aimed at these entrepreneurs. I take whatever the big theme is for my consulting clients, and I literally share those best practices with as many people as possible. My personal mission is to democratize success and get more people participating at this level. So, I try and give away as much content as possible for free. That’s also why I wrote Bet on Yourself, my book. So, aside from LinkedIn, also my website, which is my name, Ann Hiatt, A-N-N H-I-A-T-T. I also have a lot of free resources, downloads, videos, and things that are linked there. So, another good place to get to know each other.

 

Justin Donald: Oh, I love it. Well, you and I definitely are in alignment on democratizing the ability to build wealth, create success, live life on your terms. And for me, it’s just helping people buy their time back so they can really spend it with the people that matter most and doing the things that have the most fulfillment, the most impact, bring the most joy. And so, yeah, I could see a lot of cool synergies between the two of us.

 

And I like ending every episode, asking our audience a simple question. And that question is this to those of you watching, to those of you listening, what’s one step you can take today to move towards financial freedom and move towards a life that you truly desire, one that’s on your terms, so not a life by default like most people live, but rather a life by design? Think about one thing you took away from Ann today. And what’s that thing that you can implement today to move forward? Thanks so much. And we’ll catch you next week.