Thirty Minute Mentors Podcast Transcript: Former PayPal and Intuit CEO Bill Harris

I recently interviewed former PayPal and Intuit CEO Bill Harris on my podcast, Thirty Minute Mentors. Here is a transcript of our interview:

Adam: Our guest today was the leader of two of America's most successful technology companies. Bill Harris was the CEO of Intuit and was the CEO of PayPal. Bill was also the founding CEO of Personal Capital, which was acquired for a billion dollars, and is the founding CEO of Evergreen Money. Bill, thank you for joining us.

Bill: Hey, great to be here. Thank you.

Adam: You grew up in Boston, and from a very early age, you were really interested in business. You started a mutual fund when you were 13. You started a number of different ventures, a lawn mowing business, a tennis business. You wound up going to a pretty good business school in the Boston area.

Bill: Second behind UCLA, of course.

Adam: That's what we tell ourselves. Yeah. You can convince yourself of anything. Yeah. Can you take listeners back to your early days? What early experiences and lessons shaped your worldview and shaped the trajectory of your success?

Bill: Well, if you really want to go back to the very beginning, it was my dad. I mean, I love my mom. She was nurturant and marvelous, and she gave me so much of hopefully what I am today. But in terms of what drives me, it all came from my father. He was a remarkable guy. He was an orthopedic surgeon, but he was also an inventor and a researcher. And I mean, one of the cool things, you know, the way that you understand what the impact and influence of a CATA mission is. You look at the peer-reviewed journals and then you count the number of citations of somebody's work in other people's work. And they looked at the medical world for a period of 20 years. He had 100,000 citations, twice as much as anybody else in his field. And he was an inventor. That's the main thing. He invented equipment. He invented prostheses. He invented medications. He was involved in inventing some new materials with some people at MIT. He was a ball of fire. That's what I learned from. And so I tried to do the same thing. I tried to go do things. And I loved school and did pretty well, but it wasn't doing it. And so that's what I really sparked to.

Adam: Was there a single lesson that you take away from your dad that has stuck with you through all these years?

Bill: Yeah. He was just always eye on the ball, and actually more so than me. We're very similar in many ways. He was driven by discipline. I mean, he was up at 5.30 every morning. He was out the door at 6.30. He knew exactly where he'd left his keys and wallets, and he scooped them up on the way out. He did grand rounds at 7 a.m. And then an entire schedule. He was home at 11 and Monday, Wednesday, Friday. He was home at 7 in order to have dinner with the kids on Tuesday and Thursday. He's just driven by discipline. I'm very similar, except I'm driven by enthusiasm. I just get ideas in my head and I can't shake them.

Adam: Discipline and enthusiasm, two essential elements to success in whatever it is that you want to pursue in your career, whatever it is you want to pursue in your life. What were the keys to excelling in your career and what can anyone do to rise within their career?

Bill: Well, a couple of things, maybe. One is what we've been talking about, just having internal enthusiasm, a little discipline, or maybe in my case, it's less discipline because I'm not terribly disciplined, but it's persistence. I just won't give up. That comes naturally to me. What does not come naturally to me, but is probably even more powerful is finding ways to extend that to other people. And so motivate others, build teams, do all that kind of thing. And I'm not a good role model for that because I'm too much of a do-it-yourself kind of person. But I've tried to learn it and the earliest opportunity I had was as a senior in college. I got a job at a magazine. I was in Northern Vermont. I got a job at a magazine in Boston and I thought this was great because I interned my junior summer. So I was working there in summer and they said, hey, listen, this is great. Let's give you a job and you can work through the year. I said, well, I can't do that. I've got my college here. And they said, oh, you know, don't let your schooling get in the way of your education. And I said, all right. And so what I did was I went back to Middlebury College in Northern Vermont every two weeks because I had a senior seminar. Everything else, I skipped the lectures and I just read the books and then came back for the exams. And, you know, managed to get through, but more importantly, got this incredible year of experience working for this magazine. But the trick was that I had signed up to be a freshman, I think they call them resident assistants in a freshman dorm, an older person who's supposed to keep the dorm under control. And I didn't know how it's going to do that, but I went up before the first class and you know how you can tell in a group of people who are the leaders or the influencers or whatever. I mean, they just stand out. And so I grabbed a couple of those people and I brought them together. I said, all right, the administration thinks you need a nursemaid. I think you don't. So I'm leaving and we'll see how you do. And if you don't do well, I'm going to have to come back. And so it was the best-behaved dorm on campus. And the reason was that I wasn't there and that I gave them the responsibility.

Adam: There's a lot to unpack in that story, but something that you mentioned, when you look at a group of people, you know who in that group is the leader. What do you believe are the key characteristics of a great leader and what can anyone do to be a great leader?

Bill: Well, the starting point is that you've got to have the moxie to step into that role. And most people don't. Most people, they're a little bashful or lethargic is not the right word, but not terribly engaged perhaps. But the first thing is you got to have the gumption to go step into it. However, if you just barge your way in and start to try to dominate everything, people will turn you off. And so you have to engage in a way that is not thumping your chest and instead is trying to draw other people out and then trying to see the people who are similarly ready to engage and bring them out and start to build something that is more than just what you're saying, it's what the group is saying. And then what you'll find is, I mean, you just watch it a little while, you'll find that maybe there's 20 or 25% of the people who become the natural folk that everyone else looks to and listens to.

Adam: A couple of words that you didn't use, but that are implicit in what you just shared. The importance of listening, the importance of observing. All great leaders have great EQ.

Bill: I wouldn't quite say all, I think certainly most, but there are some leaders out there who are completely clueless about anyone but themselves. And it's a shame because they will stunt their capabilities by making it all about themselves. And I have to say, me personally, this is the area that I need to work most on. I love the sound of my own voice and I have to remember, shut up Bill, listen.

Adam: Great leaders have great EQ, but to your point, not all leaders are great leaders. There are plenty of leaders out there who are bad leaders. Toxic leadership is a real thing, and there are plenty of leaders out there who might have the potential to be great leaders but aren't there yet. I'm a big believer that many of us are born with characteristics that allow us to have the potential to be great leaders, but leadership is a skill just like data science, software development, accounting. It's something that every single one of us has to learn, has to work on, has to develop, has to improve. You're not born there.

Bill: I get that and I agree. It is partly innate. You're starting with some natural capabilities and then yes, I think it's right. You've got to learn, you've got to study, you've got to watch and you've got to practice it and fail and learn from that.

Adam: Was there a key failure along the way for you that allowed you to grow, transform, become a significantly better leader?

Bill: Yes. And it's when I learned what I think is the most important thing I've ever learned in my life on the professional side. I went to a good school and going out and went to a good company and then went up through the ranks and over time in a couple of different jobs, different places, but ultimately ended up at age 40 or late thirties running a public company, was into it, running a public company with 5,000 employees. And I wasn't very good at it. Because what I really wanted to do was be a product person. And so I was always diving into the product things and saying my thing and then leaving. Classic swooping or helicopter behavior. And meanwhile, I was really not good at the large-scale administrative responsibilities of being a public company CEO. And so I basically failed. I mean, not quite, but it wasn't the job for me. And so ultimately I left. Where did I go? I went to PayPal with Elon Musk and Peter Thiel and David Sachs and all those guys. And that was a pretty wild ride. But the reason I went was that it was getting back into the environment that I really love, which was the chaos of starting a company and then just having to figure out what to do. So what did I learn? I spent the first 40 years of my life thinking that I knew what I wanted to do and knew what you needed to do in order to get there. And I thought that I was a business person and what do you do? Well, you get greater responsibility and ultimately run a big company or something like that. And what I realized is, whoa, I am not good at that. And that was the most important realization I've made in my entire career because it is much more important to understand what you're not good at than what you're good at. It's easy to understand what you're good at and you get reinforcement every day. But understanding and admitting to yourself what you're not good at, then first of all, you can go now with understanding, find those situations where you really can excel, and most importantly, Find people to do it with you who are good at what you are not good at. And so for instance, at Personal Capital, there's a fellow named Jay Shah. I was CEO, he was Chief Operating Officer. And I was all ideas and let's go try this and that. And he was all, let's make the trains run on time. And as a team, we were great. And ultimately when I left, he took over the company and he's done a lot of great things since, but it was only because I understood that I wasn't good at that and I needed somebody as a partner who was, that made Personal Capital successful.

Adam: There's so much there that you shared which I absolutely love. Know thyself, self-awareness essential to success as a leader, essential to success period. As important as it is to know what you're great at and that's critical. It can be at times more important to know what you're bad at and that comes down to being intellectually honest. Possessing humility, one of the key characteristics of the most successful leaders, not being afraid to say, I don't know everything. In fact, I don't know most things. I'm good at some things, but we're all bad at most things. And like most people, I'm bad at most things. And until you can get to that place, until you can admit that you're not great at everything, you're not great at most things. Identifying what you're not great at allows you to get to a place where you can then surround yourself with people who can compliment you. You can understand who are those people who you need to bring on to your team to surround yourself with, much in the way that you were able to find the right business partner who complimented you.

Bill: Well, it was the most important thing that I learned.

Adam: Another thing that you shared, which I love, the importance of understanding what your own definition of success is. What does success mean to you? What does winning mean to you? You thought that success meant becoming the CEO of a huge brand name company. But once you reach that milestone, you realize that you had the wrong definition of success because that wasn't bringing you happiness, fulfillment. That wasn't allowing you to do what you were great at, what you were best at. And once you understood what success really meant for you, not what success might mean for a classmate of yours at Harvard Business School, but for you, success had a different definition. And once you were able to understand that, it allowed you to pivot in the right direction for you.

Bill: Yeah, it's kind of interesting because there's been two transferences in my life, the major influence on thinking what I should be doing. I started out all through my educational years and probably for a period of time thereafter. Fundamentally, I was doing what I thought my father wanted me to do, do well. He didn't care whether I was a doctor or a lawyer, he was a doctor, but he wanted me to be Good. Try. And actually, it doesn't even care if it was good, but just try. Get out there and do your best in it. So that was the first phase. The second phase was that I think I just transferred that notion to, rather than doing what I thought my father wanted me to do, transferred it to doing what I thought society wanted me to do. In other words, okay, I'm a well-educated person. I'm going to go into business and I'm going to work up the ladder at good companies and do all that stuff. And finally, my third transference was to try to do what I wanted to do. And that came with at the same point as understanding what I was not good at, but the wrinkle was understanding what I wanted to do.

Adam: I love that. Once you're able to shift from focusing on doing what is expected of you, whether it's trying to fulfill the expectations of a parent, of a friend, of whatever you believe society thinks you should be doing, to focusing on what is right for you. You can then get to that place where you're able to be at your very best, where you're able to attain real meaningful breakthrough success, not just on paper, but in actuality. No one needs anyone else to tell them whether or not they're attaining real meaningful success. We know that. All we need is our own internal monitor to understand that every single one of us gets it, understands it, and when you're focused on doing what's right for you, you're going to get there.

Bill: Yeah. Well, you mentioned what do we want? What makes us happy? So I'm 68 now, but in most ways, I feel like I'm top of my game, better than ever. And I've still got energy and I've got so many experiences that are distilled into pattern recognition. So what are the two things that I really love? At the end of the day, if I look back at the day. What makes me feel good? The first one is ideas. I'm very much an idea guy. Whether anything ever happens with the idea, whether even it's a good idea, I get consumed by ideas, new things. The second is mastery. When I can go home at the end of the day, and I don't care what it is, but feel like I did a good job, boy, I killed that one. And it doesn't matter if it's writing a business plan or mowing the grass. Mowing the grass, it's so satisfying if you really take it seriously and trim first and then do the horizontal back and forth and make sure that you haven't hit the flowers. If you really think about it, if you really are conscious that you are doing a job and then take pride in that job and then you do it, that to me is the definition of happiness.

Adam: You mentioned your dad, obviously a key influence in your life, perhaps the most important influence in your life. Your dad, an incredibly successful inventor, innovation in your DNA. You've been an innovator throughout your career. You're driven by ideas. Ideas bring you happiness, bring you fulfillment. What are the keys to driving innovation and how can anyone get to a place where they're at their most innovative?

Bill: So I'm not sure in all walks of life, but let's narrow it down to what I know, which is in business. And particularly I've been in the tech business and even the financial technology, some financial and cybersecurity business for some time. Started, I think nine different companies at this point. So what does it take? Some people think it's the ability, the willingness to take risks. Because you're going out and start something or joining an early company or joining a new project or something like that. There's risk. There's financial risk. How am I going to be able to pay the mortgage? And what if I get fired? There's financial risk. There's career risk. There's all these things. And so what a lot of people in Silicon Valley will tell you is, well, you have to be willing to be bold and go take the risk and go do it. And that's true. But far more important is being comfortable in ambiguity. Because when you start something, when you go into something, and I don't care whether you're starting a company or a new job or a new project or whatever it is, you just don't know. And particularly in starting a new company, which is what I've been doing, you're making it up. There is no playbook. You're making the playbook up as you go along. And so you just don't know when you come to work every morning, what is it going to be? What are we going to do? How's it going to work? And that is an intense form of ambiguity. And you live with it. You're just drenched in it because you just don't know. And it's something that most people, all people, including myself, are inherently uncomfortable with. We like to know, when are we going to get up? What are we going to do? Where are we going to go? What are we going to do during the day? When are we going to go home? How it's all going to work? What we're responsible for? What success is? we're not comfortable, we're not naturally comfortable with ambiguity. And that, I think getting comfortable with the fact that you just don't know is one of the keys to innovation because that allows you then to think about multiple things. I don't know. So what about A, B, C, or D?

Adam: How can one become more comfortable in ambiguity? And how can leaders create an environment where the people who they lead are ultimately comfortable in ambiguity?

Bill: Well, from your point of view, from an individual point of view, what do you have to do? You have to get out of your comfort zone and that's a willful act often. Sometimes it's something that happens to you, but at least in the business world, it's something that you do to yourself. You decide that you're going to go venture out. In terms of what you as a leader can do, and again, I don't claim any special powers in this realm. In fact, it's one of the things I really need to learn to do better. But I think the most important thing you can do as a leader is encourage effort over results in some places. I mean, everywhere you go in business, they say effort doesn't count. What are the results? You're responsible for the results. In this instance, you got to flip that around and you got to say, listen, I'm not hyper-focused on the results. I'm focused on you taking the risks, thinking about it, trying something new, and I'm not going to slit your throat if it doesn't work.

Adam: I like that a lot. I've interviewed so many of the most successful leaders and have asked so many of them about this topic, how to foster innovation. And a key theme that I've heard over and over and over again is you have to create an environment where your people are not afraid to fail. Your people are not afraid to make mistakes. And by encouraging effort over results, that's a great way to do it. Something that you and I were chatting about off the air by teaching work over the years at UCLA and students who've taken my classes over the years tend to fall into one of two categories. They're either students who are drawn to my classes because I'm teaching about leadership and teamwork and those are topics they're interested in. But more often than not, they're actually students who are pushing their comfort zone by taking my classes because they're not that familiar with leadership, teamwork, qualitative skills. This isn't their area of comfort. Exactly what you shared, Bill, is what I try to convey to my students. Effort over results. What I care most about is your effort. What I care most about is that you're engaged. If you're engaged, if you're showing up to class and you're asking questions, you care, this matters to you, that's a lot more important to me than whether you got the question right, whether your English is perfect, whether your answer is this or that. I want to see effort. And I think every good leader would say the same thing.

Bill: Yeah. Boy, I agree. And it's very different in an educational setting as in the real world. In an educational setting, it's learning skills and then demonstrating that you have learned those skills. And when you hit the world after, whenever it is you leave the academe, It's just about, are you willing to take it to the nth level? Do you have the persistence? Do you have the resilience? That's a great word, resilience. And the people who do will run circles ultimately around people who have very strong skill sets, but don't have the energy and the engagement and in some instances, the courage and the grit to make it work. There's another thing. Which is hiring. My mantra on hiring, and I don't always get this right, but my mantra is I don't hire for experience and knowledge. I hire for attitude and aptitude. Because if you've got somebody who's good, who's driven, who can figure things out and combines that with the attitude that I'm going to break through that wall no matter what. And by the way, I'm going to be somebody who brings other people along because ultimately that's the only way to truly be successful is to not just motivate yourself, but motivate the team. If you find somebody who's got attitude and aptitude, they can do anything. And sure, for the first six months, somebody with the experience and skillset is going to do far better. By the time 12 months roll around and 24 months, and then 10 years with an organization, oh my God, somebody with attitude and aptitude is going to far outpace everyone else.

Adam: Could not agree with you more. I love the words you shared. Resilience, grit, attitude, aptitude, skill set, experience. Anyone can develop a skill set. Anyone can develop experience, but only a subset of people possess resilience, grit, a winning attitude, a winning mindset. Those are the people you want on your team. You made reference to your time as CEO of PayPal. You mentioned a couple of the people who you were in the trenches with, Elon Musk, Peter Thiel, David Sachs. What were the best lessons you learned from your experience as CEO of PayPal and what lessons did you learn from your time leading and leading with interesting characters, with interesting personalities, and interesting size egos?

Bill: Well, there were probably four or five of us. Not a single one of us had an ego that would fit in large gymnasium. It was a bloodbath. It didn't last that long because we ultimately sold the company to eBay. But it was wild. We went from zero to a million customers in six months. And okay, that might not seem like that successful, but today, sure, people do that. This was now 25 years ago, and nobody knew what the internet was. And zero to a million customers, holy moly. But internally, and perhaps one of the reasons for our success, it was a zoo. I mean, it was a fist of cuffs every morning. Every single one of us thought we were CEO. So many people grabbing for the wheel and we careened back and forth. But in that chaos, we had willingness or ability or whatever, lucky to just try a bunch of new things all the time. And 10% of them hit. Then we go, oh, look at that. Okay, let's do it. So, I would not say that it was any kind of a team environment that I would suggest to anyone because it was, I won't call it toxic, but it was unproductive in many ways. However, what did I learn from the individuals? From Elon, I learned boldness. I have never met somebody who is willing to go so far, so confidently, to the extent that everybody around him, including myself, thought he was nuts. But he would just say, I can do this. And oftentimes he could. From Peter Thiel, he is the personification of a contrarian. he would just take anything and everything, not just within our little business, but in the world, politically, economically, socially, whatever. And whatever idea he came across, he would just instinctively believe the opposite. And again, that was mostly dysfunctional, but on occasion, man, he was right. And he was willing to just go not only against the crowd but dramatically and aggressively against the crowd. So to the extent that I learned anything from just watching people and watching people like Peter Thiel and Elon, it was those two things.

Adam: Bill, what can anyone listening to this conversation do to become more successful personally and professionally?

Bill: I guess I would just go back to what in my life were the keys. First of all, understand what you're good at, what you're not good at. and then chase the things you're good at and cope with the things you're not by coping, meaning find it elsewhere. Very interesting. There is this wisdom in Silicon Valley. It's something that people say. I don't know if it really is true, but they say that a third of the successful entrepreneurs in Silicon Valley are dyslexic. And I'm a little dyslexic as well, but I don't attribute that to my career. You know, you ask why, why would dyslexic people be potentially so good at starting companies and doing this kind of thing? The thought is that when you are dyslexic, as you were coming up through the educational system, and my son was exactly like this, he was quite dyslexic, still is. And as he was coming up through the educational system, he had to rely on others. And so he had to build a team and he had to cope with things that he was not good at. And he's a wildly smart guy. He's now studying for his PhD in quantum mechanics and condensed matter and all these things. Wildly smart, but he couldn't read. And so he had to have people help him and machines that helped him and all that. And so he developed this coping skill and the skill at enlisting other people to help him with the things that he was not good at. And I think that's a bigger lesson. I'll tell you the one thing, a little anecdote. At one point, I don't think he was more than 12 or something. And after dinner, he was up doing his homework. Then he came rushing down and he was at the stage where he jumped on the kitchen counter and was walking back and forth on the kitchen counter, you know, just having fun. And he's going, I've got a game. I've got a game. All right, everybody. Now I've got some questions I'm going to ask you and whoever gets the answer first wins. And he started giving us a little bit of math problems and whatever. And after about six of these things, he jumped off the counter and started running upstairs. And he said, thanks a lot. You just did my homework. And so it was a really cool example of he was struggling with the homework. And so what did he do? He figured out a way to get help.

Adam: I love that bill. Thank you for all the great advice and thank you for being a part of 30 minute mentors.

Bill: Hey, my pleasure. Let's do it again.


Adam Mendler is an entrepreneur, writer, speaker, educator, and nationally recognized authority on leadership. Adam is the creator and host of the business and leadership podcast Thirty Minute Mentors, where he goes one on one with America's most successful people - Fortune 500 CEOs, founders of household name companies, Hall of Fame and Olympic gold medal-winning athletes, political and military leaders - for intimate half-hour conversations each week. A top leadership speaker, Adam draws upon his insights building and leading businesses and interviewing hundreds of America's top leaders as a top keynote speaker to businesses, universities, and non-profit organizations. Adam has written extensively on leadership and related topics, having authored over 70 articles published in major media outlets including Forbes, Inc. and HuffPost, and has conducted more than 500 one on one interviews with America’s top leaders through his collective media projects. Adam teaches graduate-level courses on leadership at UCLA and is an advisor to numerous companies and leaders. A Los Angeles native, Adam is a lifelong Angels fan and an avid backgammon player.

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