Autodesk is the massive public software company at the heart of designing almost everything around you, from cars to buildings to video games. CEO Andrew Anagnost talks with host Jeff Berman about why he first joined a “rebel” group at the company, how he battled for the top job, and why he thinks leading with empathy is smart business.
About Andrew
- CEO of Autodesk since 2017; member of Autodesk Board of Directors
- Led Autodesk's SaaS business model transition as CMO and strategy SVP
- 29-year Autodesk veteran across product, marketing, biz dev, and development
- Ph.D. from Stanford after overcoming a high school dropout start
- Joined HubSpot's Board of Directors in 2023
Table of Contents:
- How mentors changed the course of his life
- Why start-ups teach speed and range fast
- What rebel teams need inside big companies
- How Andrew Anagnost became the CEO of Autodesk
- How to decide what to cut or keep
- Why AI must fit real industry workflows
- Why empathy and courage belong together
- Episode Takeaways
Transcript:
From high school dropout to CEO
Note: Transcripts are automatically generated from episode audio, and are not fully corrected for spelling, grammar, and formatting.
ANDREW ANAGNOST: I think we are the product of the people who lift us up. I really believe that. I never believe this bullcrap, “Oh, I did this all myself.”
JEFF BERMAN: Who do you want behind you: the one who believes in your mission or the one you paid to be there, the mercenary? You want the one who believes in your mission.
ANAGNOST: Try a startup while you’re young.
BERMAN: Why do you tell people that?
ANAGNOST: You learn a set of skills that is really hard to learn in a larger company because everybody’s being so careful. All that’s stripped away in a startup. You’re just trying to survive, and you’re trying to make it happen.
BERMAN: This is Masters of Scale. I’m Jeff Berman, your host. With us today is Andrew Anagnost, the CEO of Autodesk. While you may not be familiar with the company itself, you’re definitely familiar with what the company does because pretty much everything you’re looking at in the real world, their software helped make. Welcome to Masters of Scale.
ANAGNOST: Thank you. We like to talk about Autodesk as the biggest tech company nobody’s heard of. Everything that you see in the world — the cars on the roads, the bridges you drive over, the machines you see, your phone, the buildings — is built and designed using our software.
Copy LinkHow mentors changed the course of his life
BERMAN: I’m keen to get into the story of how you joined the company, became CEO, and are leading it through this era, but I want to go way back because we were learning before we started recording that you and I have more than a few things in common. One of them is neither of us was our best self as a teenager.
ANAGNOST: No, I was not my best self.
BERMAN: What were your teen years like?
ANAGNOST: My teen years were a little rough, all right? As I progressed and got into high school, I essentially started numbing myself.
For lack of a better word, I self-medicated. I just went off the rails, and I dropped out of high school for a while and ended up in the wrong places. I was never a violent kid. The only person I really ever hurt was myself.
I was the only high school dropout who would show up for trigonometry class, sometimes under the influence of something. One day, one of the teachers came up to me and said, “You know what? You can ruin your life all you want, but you’re not going to ruin the rest of the people’s lives in this room. Get the hell out of my class.” I remember it to this day. I can see his face in my mind. I can feel his breath. In the moment, I just laughed at him. It didn’t stick with me then, but he was very brave, this teacher.
I remember, not that long later, when I was expelled and got into a very serious car accident, I almost killed the passenger in the car. I was handcuffed. I was on the ground in a gravel driveway, pinned down. I was injured. And his voice just banged through my head. I’ve never forgotten him: Mr. Carrington. Hello, Mr. Carrington, if you’re still alive out there. Most people who drop out of high school, get expelled, and have problems don’t end up going to graduate school at Stanford. So in that respect, I’m kind of a statistical anomaly. But it’s because of people like that I met along the way, people who saw that I had potential and I was just pissing it away.
BERMAN: Wait, Andrew, what happened between being face down, handcuffed in the gravel, having already had the experience with Mr. Carrington trying to get you back on the right track, and getting all the way to Stanford and to us sitting here today?
ANAGNOST: That moment was pretty seminal in my life. Actually having almost hurt someone, I think you sit there and reflect and go, “What am I doing?” It really was a switch moment. Voices like that kind of propelled me forward. I got into the local Cal State. I worked my way through that program. I fought to get internships. I had professors along the way who told me, “Look, you have potential.” They believed in me.
I believe that you have to work hard. You do make your own luck in some ways, but it’s kind of a fool’s errand to think that your environment hasn’t, in some way, either pulled you down or pushed you up. I was fortunate that some of these people really believed in me, and I was not going to let them down.
BERMAN: There’s something really profound about the there but for the grace of God in this.
ANAGNOST: Yeah.
BERMAN: How incredible that you had people who stepped in for you and helped you get on track.
ANAGNOST: I did, including the judge who chewed me out in juvenile court. Look, I think we are the product of the people who lift us up. I really believe that. My life experience has taught me that. I never believe this bullcrap that I hear out there about, “Oh, I did this all myself.” The most important people in your life tell you what you need to hear, not what you want to hear.
Copy LinkWhy start-ups teach speed and range fast
BERMAN: So you get through this. You get to Stanford. You get your Ph.D. You don’t go into academia.
ANAGNOST: No, I don’t.
BERMAN: How do you end up at Autodesk?
ANAGNOST: I actually went to a start-up. It was a deep-technology startup in Boston, and I spent almost five years there, which was a magical experience. I tell young people that you should try a start-up while you’re young.
BERMAN: Why do you tell people that?
ANAGNOST: When you’re at a startup, you learn a little of everything very quickly. A startup has very little hierarchy, and if there is any hierarchy, most people ignore it. You make decisions very quickly. You learn the value of speed and of arguing things out in a kind of Socratic way, where the ideas have to be challenged, not the people. And you learn a set of skills that is really hard to learn in a larger company because everybody’s being so careful in a larger company, or they’re being so political. All of that is stripped away in a start-up. You’re just trying to survive, and you’re trying to make it happen. So that journey from zero to $10 million is so educational.
BERMAN: And from zero to 30 or 50 people or so, you kind of know everything happening in the company.
ANAGNOST: You know everything.
BERMAN: Right?
ANAGNOST: Everybody knows everything. You know exactly who to go to to get something done, and you know how to get your relationships in place. You also know that you can cut through the BS. Of course, it teaches you some things that do not translate to a large-company environment. This high-speed connection that you have in a startup, where you’ve been sitting there late at night eating with these people and you can call BS on them and they do not feel bad, does not translate.
I was actually recruited out of this company by Autodesk. But the funny thing was, I met the woman who would become my wife, and she wanted to move to California.
BERMAN: Oh, wow.
ANAGNOST: We were working for competing software companies.
BERMAN: Huh.
ANAGNOST: Can you believe that?
BERMAN: Wow.
ANAGNOST: Yeah. The only reason I took the job, though, is because it was on a team that was trying to fight against this company that I had actually partnered with at my start-up. I thought, “Oh, yeah, they’re terrible. We should build a product that defeats them.”
So I got a little excited about that. But let’s face it, I thought it was a stepping stone to something else. It turns out that when I got there, I really liked being on this counterculture team that I was working with, a rebellious team in terms of rebelling against the primary culture in the company.
Copy LinkWhat rebel teams need inside big companies
BERMAN: How big was Autodesk at the time?
ANAGNOST: Less than 1,000 employees.
BERMAN: OK, but still not an early-stage startup.
ANAGNOST: Not an early-stage startup.
BERMAN: You’re relatively scaled.
ANAGNOST: Big enough to have a well-established culture and well-established norms.
BERMAN: And most companies at that scale with a well-established culture and norms may say they want a rebel group. They may say they want the innovator, but generally it does not go so well.
ANAGNOST: Carol Bartz did this, OK? Carol Bartz set up this team. We were butting up against the big, established part of the company that was really built on top of the core product that the company started with, which was called AutoCAD, the name that most people know.
It was kind of an exciting period. I learned a lot about how you operate and how you use the edge, but then soften the edge over time, through that experience. Carol Bartz showed me the importance of commercial discipline, the rigor associated with that, and the need to have accountability in getting things to customers in order to scale, because I knew zero to 10 pretty well.
Ten to 100 I did not know very well, right?
BERMAN: Yeah.
ANAGNOST: She was really influential on me, and I look back at her in positive ways. I always like to say I’m the product of two dysfunctional parents, and they both have the initials CB. One was Carol Bartz. One was Carl Bass. Totally different people, OK? Both CEOs that I reported to.
BERMAN: Yeah.
ANAGNOST: Carol was much more on the commercial side, Carl on the respect for innovation, respect for the customers’ processes, and what they do. Each of them taught me something. Each of them taught me what to do and what not to do in many ways.
BERMAN: What did Carol and Carl do to allow a rebellious group inside the company not just to function, but to flourish?
ANAGNOST: Carol only allowed a small number of these, like one.
She had a good sense for who could push things and who could not, and she supported them. Carl, on the other hand, would create hundreds of these. He let them pop up everywhere, to the point that it would stress the company’s ability to execute. Carl’s style was much more, “Let 1,000 flowers bloom,” and maybe never prune a single flower.
BERMAN: Wow. It’s almost like working at two different companies, with leadership that different.
ANAGNOST: Absolutely.
ANAGNOST: Very different companies.
BERMAN: Yeah.
ANAGNOST: Even the company that I run now, Autodesk, is somewhat different, but it learned from both of those companies. I’d like to think that because we can scale new businesses, because we’re very passionate about killing our own businesses and products, and because that is a cultural norm in the company, I’ve done a decent job. But I owe it to that experience and that arc.
BERMAN: I want to come back to the norm of killing your own businesses when you need to.
ANAGNOST: Yeah.
Copy LinkHow Andrew Anagnost became the CEO of Autodesk
BERMAN: But I do want to hear about the journey to CEO, because you weren’t given the job outright. You had to really fight for it. Will you tell us about the process that started with a co-CEO arrangement and led to you becoming the sole CEO?
ANAGNOST: When they started the succession planning, before the activist came into the company and ultimately led to the co-CEO scenario, I opted myself out of the succession process.
BERMAN: Why?
ANAGNOST: Because I just never saw myself that way.
ANAGNOST: For some reason, I looked at that job and said, “Well, then you don’t have any fun anymore,” which might actually be true. It was only as the activist process progressed that there was someone from the old culture in the mix, there was me from the newer culture, the inside outsider, and then there was the threat of an outsider. As I watched the plot evolve, it was very clear to anyone that the culture norm wasn’t going to get the job. More and more, I just said, “Okay, that means an outsider, and I love this company.” That’s when I said, “I’m putting my name in. I want to try for this job.” And that’s how I ended up in the situation where they pitted the old-timer against me in the co-CEO role, and for six months, no decisions were made at the company.
BERMAN: Why did they do that? I mean, it’s not exactly a model that’s likely to work unless you are deeply partnered.
ANAGNOST: It works much better at smaller companies than it would ever work at a large company, right?
BERMAN: Yeah.
ANAGNOST: I think they did it because they were afraid of disrupting the current culture of the company. I think they were creating theater.
ANAGNOST: It was about making sure we assessed everything. They were really buying themselves time to get through the process. It was awkward for both of us, and it wasn’t a great time. And like I said, for six months, no major strategic decisions were made at the company.
BERMAN: And were daggers out? Were you all basically trying to kill each other? What was it like?
ANAGNOST: No, we weren’t like that. At least, I can speak for myself: I wasn’t like that. I knew intuitively that the job was probably going to go to me, not necessarily because I was more deserving or anything like that, but because I was the inside outsider.
ANAGNOST: And I think that’s what people wanted at that point. And frankly, it’s probably what the company needed.
ANAGNOST: They needed a separation from the Carl era. They needed to move forward. And I think they wanted to do it in as gentle a way as they possibly could and visibly make it look like it was a fair process. You’d have to ask them, right?
BERMAN: Yeah.
ANAGNOST: But it wasn’t great. It wasn’t a fun time.
BERMAN: When you became the sole CEO, what was job one on day one?
ANAGNOST: I fundamentally believe that you’ve got to have a guess at what the future is. You’ve got to have a guess, and then you have to have the fortitude and the strength to pay attention when your guess is wrong and correct it. So I pulled out a lot of flowers that I thought were weeds. A couple of real flowers got pulled out in the process, and I had to dig out of that over time. That was move number one. And believe it or not, I shifted money to the back office, which is a very odd thing to do.
BERMAN: Wow, yeah.
ANAGNOST: And here’s why I did it. You might not know this, but I was the one who led the subscription transition at Autodesk and started fixing the back office and trying to get it into a position where it could scale in an era where we have SaaS products. That was the first thing I did.
BERMAN: Well, it sounds like, Andrew, what you saw was that you had a foundation that wouldn’t support the skyscraper you were trying to build.
ANAGNOST: I could build the best products in the world right now, and I couldn’t get them out to the customer. I certainly couldn’t get them to new customers. The next thing I did was make a couple of large acquisitions for Autodesk to scale the construction business because I believed firmly that in the world of hyperautomation we were heading into, just being a design software company, which is what we were back then, wasn’t going to be enough.
We had to be a design-and-make software company. We had to extend ourselves across the process. So I went big on trying to do that, and that was the next thing I did as I progressed through my early days as CEO. That was quite successful. We scaled the business. It was hard. We had to overspend, but we scaled it.
BERMAN: Did you have the right team, or did you also have to overhaul your leadership team?
ANAGNOST: I think three-quarters of the leadership team either left on their own or were asked to leave.
BERMAN: That’s a lot of change for a big, scaled company.
ANAGNOST: It was a lot of change. Some of these were good people. They just weren’t the right fit for what I was trying to do.
BERMAN: How did you manage the communication to the rest of the team as they were seeing this changeover at the top of the company: “No, no, no, no, this is actually good. This is where we’re going”?
ANAGNOST: I overcommunicated a lot. I spent a lot of time explaining why. I told the why story over and over again.
And I gave elements of the what and left some of the what to everybody else to challenge and engage with. But I spent a lot of time talking about the why to the company. And let’s face it: in a company like this, half were for me, and half were for the other guy.
BERMAN: Sure.
ANAGNOST: Was it exactly 50-50? Who knows? It was pretty close. So I had to earn not only the trust of the other half, but I had to prove myself to the half that was for me: “Were you the right person?” So I had to be a whole-company leader. Unlike some of the leadership we have today, but I won’t digress down those avenues. I had to be a whole-company leader.
BERMAN: You’re welcome to digress anywhere you want to go.
ANAGNOST: I think if you really want to be effective, you have to prevent thrashing.
When you pander to one extreme or the other in a company, in a society, or anything, you thrash back and forth. You have this illusion of progress, but you don’t. What you’re doing is burning calories, wasting energy, wasting money, and wasting time. So I had to make sure that I didn’t thrash the company.
So I worked hard to win over the people who saw some of their darlings depart, and I worked hard to bring some of the people who were with me over to the other side. I cross-pollinated a little bit, and I didn’t punish people for what side of the fence they stood on. But I had to earn trust. Let’s be very clear here. And I didn’t have much time to do it. You have to earn that trust in the first one or two years because when you’re asking the company to sacrifice, especially when you do a big RIF of darling projects and send them off, people aren’t your fans at that point. They’re questioning you. So it was hard work telling the company the why over and over again and then actually delivering some success.
Copy LinkHow to decide what to cut or keep
BERMAN: I want to drill in also to this decision to kill businesses, to pluck weeds that may actually have been flowers, because I can imagine there are some people who are like, “Awesome. Finally, we’re making these decisions,” whatever.
ANAGNOST: Yes.
BERMAN: But I have to bet there are a lot of people who are like, “But wait, that’s my baby.”
ANAGNOST: “You’re killing innovation.”
BERMAN: Yeah.
ANAGNOST: Yes.
BERMAN: So I guess two parts: One, what was your process for making that decision? And then how did you manage the human emotion behind the attachment to some of the projects you were killing?
ANAGNOST: The process had a few simple tests, OK? I’m a big believer that a few simple rules set you free. And the tests were these: Do we have a right to win?
Is there something special about Autodesk, the markets we serve, or what we do that gives us some kind of right to win? The other thing I asked was how adjacent it was to our current business, or how far away it was. What’s the distance from our business? The reason I asked that question is because the farther something is from your business, the harder it is for you to get to it over a period of time and build it, because usually what you want to do is hops. But if you take a big leap, sometimes you leap too far. So adjacency was the other test that I did. And then the third one was: Do I have the team? Do I have the right product vision and the things associated with that? A bunch of things quickly were like, “Nope, nope, nope.”
One or two of them, I got wrong, and I live with that. I still make a joke out of it because I’m still digging out of the hole. If you’re right 70 percent of the time, you’re killing it, OK? You’re just killing it.
BERMAN: Yeah.
ANAGNOST: So that’s the process I took to decide what stays and what goes.
BERMAN: The hop-versus-leap idea has one exception: if you think your entire business is about to hit a wall. Think about the Netflix transition.
ANAGNOST: Yes.
BERMAN: As an example, which, OK, it’s illogical, but that was more of a leap than a hop.
ANAGNOST: That was a leap.
BERMAN: Right. The hop philosophy makes a ton of sense. When do you have to take the leap?
ANAGNOST: When there are paradigm shifts, OK? There are differences between leaping into a new technology, which I think you have to do when your business is threatened, and leaping into a completely new market, where even an acquisition might stress the organization beyond its limits. We leap into technologies at Autodesk. We hop into adjacencies.
So far, so good. We were on AI quite early, so we leaped into the technology, trying not to be too early.
BERMAN: Yeah.
ANAGNOST: You know the balance, right? Too early, you spend too much money. Too late, and you spend too much money and have no success.
Copy LinkWhy AI must fit real industry workflows
BERMAN: Where are you in your AI transformation, and where do you see it going?
ANAGNOST: First off, let’s talk about why it’s so important, OK? We have a massive capacity problem in the built world. In the civil, building, and construction world, we need to build a lot. We all know the housing problems in California. We all understand it’s not just a technology problem.
BERMAN: Nope.
ANAGNOST: It’s an ecosystem problem. But technology can help the ecosystem because one thing that’s really broken about how you build civil infrastructure, buildings, and homes is that it’s a fragmented ecosystem with highly competing people who like to sue each other, and there’s no traceability or accountability. Nothing any manufacturer would ever accept.
Now, on manufacturing, which we’re also in, highly automated factories are the future. That’s the only way the U.S. is going to be competitive in building things on U.S. soil, so you have to move to super automation there. I’d like to bring some of this discipline of transparency from manufacturing to the building world. I just wanted to characterize the capacity problem we have in the industry.
So where are we on our AI journey? We have been working really hard to automate the design process and converge it with the making process, either construction or manufacturing. So we use AI as project intelligence, or a brain in the middle, that helps you make decisions about design that are informed by what it takes to construct or manufacture something, or make decisions about construction or manufacturing that inform the design.
We connect those things and automate them as much as we possibly can. This is something we’ve been working toward for eight or nine years. We call it convergence: the convergence of design and make, the convergence of construction and manufacturing, the convergence of digital and physical worlds. This is what we call it internally.
I’d say on our journey, we’ve made huge progress. We’ve got AI under everything. We built our own custom AI models off data that we have from our customers. It’s controversial with our customers. We’re super transparent with our customers, though, about what we’re doing.
BERMAN: Why is it controversial with your customers?
ANAGNOST: Because they ask, “Are you training other people on my IP to do what I do, my special sauce?” And what we tell people is this: “If we do that, you’re going to be able to opt out of that training. We will erase your data from that training set.” But that’s not what we’re doing right now. What we’re doing is training for productivity.
We’re doing it by using the data to train our own custom models that are high-speed, high-performance, and also using the context of what they’re doing to help them get better answers. And everybody says, “Well, aren’t the large language models going to replace that world?” I think there are a couple of things that we all have to pay attention to here. “Probably right” is wrong in our business. “Probably right” ends up with machines that don’t work, and that’s something we can’t afford. That’s why we need custom models that are more precise. Precision matters in our world.
The other thing is, context matters a lot. When you’re moving in a design process, or you’re moving from design to construction, so much information gets lost. The other thing that’s really important, and we’ll learn this over time, and I think this is going to be the zeitgeist for the next year or two, is that it’s expensive to use a horizontal tool to solve vertical problems.
BERMAN: Say more.
ANAGNOST: When you have a tool that’s trained on large amounts of data with a lot of complex interconnections, and it has to go through complex cycles, and you have to design a series of prompts to get the right answer, you are burning a lot of compute to get there. However, if a tool is maybe a smaller model that’s designed to specifically solve a particular problem, and you don’t have to engage in a lot of prompts because the tool already knows what you’re trying to accomplish, the ability to deliver precision, speed, and total cost of ownership is going to define vertical software in the future with AI.
BERMAN: I’m curious, in this moment where perhaps the war for top-tier talent is more vicious, more competitive, more difficult than it has ever been, especially in Silicon Valley, how are you winning? How are you getting people to Autodesk?
ANAGNOST: Say you’re out in a war and you’re fighting a tough battle, all right? You’re trying to get up the hill. You’re under intense enemy attack, and you look behind you, hoping your team is behind you. Who do you want behind you: the one who believes in your mission, or the one you paid to be there, the mercenary? You want the one who believes in your mission. The mercenary is fickle and will change their mind very rapidly.
Sorry I used a war analogy, but it’s helpful. There are a lot of mercenaries out there, and there are a lot of people who think, “I’m so amazing, and I’m worth this ten million dollar check out of nowhere.” And you know what? Go chase those people. Go chase them. Go chase the prima donnas. Go chase the people who will go to the highest bidder. Chase them. Go at it all day.
I find in my world, and at Autodesk, you find the people who love the problem. God, how many times have I been recruited out of the company? I love what our customers do. I love the ecosystem I serve. I go home every night thinking I do something that’s useful to the world. I don’t go home thinking I screwed up teenagers’ minds. I don’t go home thinking I screwed up the whole publishing industry. I don’t go home with any of those feelings. I go home feeling like I’m doing something important. I’ll take ten of those over a hundred of those other people. It’s that simple.
BERMAN: I was at Web Summit Portugal last year, and I walked offstage. The question that was asked was, “What is the leadership skill that’s going to be most important in this next era?” And my reflexive answer, the answer I gave, was empathy.
ANAGNOST: Yes. It’s not in vogue right now, though it is.
BERMAN: It’s not in vogue right now.
ANAGNOST: Yeah.
Copy LinkWhy empathy and courage belong together
BERMAN: You talk about empathy. You practice empathy. You have a core set of leadership beliefs where empathy is central to it. How does that manifest? How do you lead that way? Why?
ANAGNOST: Yes.
BERMAN: Beliefs where empathy is central to it. How does that manifest? How do you lead that way? Why?
ANAGNOST: Look, I think these people who are saying that empathy is a weakness don’t understand empathy. They get a lot of airtime. They suck a lot of air out of the room because they’re successful. I would argue they’re just one trick ahead of their next trick or mistake, but that’s another argument for another day. Look, I operate from an ethos: courage, scholarship, and empathy. The two anchors, courage and empathy, actually lever off each other. I think, per some of the discussions we have had previously, you have to have the courage to attack your own business, okay? Cannibals are much feared, but rarely seen in the wild. If you talk to sales forces, “Cannibals are everywhere. They’re gonna get ya,” all right? But you rarely encounter them. You also have to have the courage to tell people what they need to hear, not what they want to hear. But you also have to have the courage to say, “I don’t know.”
BERMAN: Yeah.
ANAGNOST: So the counterbalance to courage: courage without empathy is just meanness and nastiness. You have to know how your courageous act is going to land with particular audiences, because if you want those people behind you, and you want them moving with you when the world tacks left or right, and you want them to stick around when things get hard, you’ve got to know what the impact is. And it doesn’t mean you stop. Empathy’s not sympathy. It’s something very different. It’s going, “I know this is going to hurt for you, and I understand that. Let me tell you why I’m doing it, and let me tell you what I’ll do about it in the future.” That’s what empathy is, right? Empathy is the way you glue courage to an outcome, and I think anybody who thinks it’s other than that is just confused. And I don’t think you can lead, especially large organizations, without knowing what the ramifications of your actions are. My life has taught me that every action you take has ramifications for somebody else, and if you do not understand it, it will blow back on you in some way, or you will cause damage that you do not understand. You will harm people and you will harm your objectives.
I think empathy is a superpower. I think you have to use it wisely. You don’t tip into sympathy. You don’t let it paralyze you. The reason I glue it together with scholarship is you always have to learn enough to know what you’re going into. I have a wood plaque up in my office. It says, “Impulsiveness is not a virtue.” And you won’t believe how many people I’ve had in my office who try to convince me impulsiveness is a virtue, and they’re confusing impulsiveness with boldness or decisiveness. Impulsiveness is action without thought. That’s what you want when you’re in a terrible, risky situation. Your life’s in danger. You want muscle memory. You want things moving. It’s where split-second decisions matter.
When you use it for, “Oh, I met my wife impulsively,” and you use it to make a decision, and you turn out married to that person for 50 years, you got lucky. You got lucky. And you don’t want to play luck on big, long decisions. You want to think, do enough scholarship to know what’s going on. You don’t want analysis paralysis, because that’s what people say: “Oh, too much thinking. That’s analysis paralysis.” Well, no thinking is stupidity, and so you want to strike the balance. That’s why I’ve always talked about this notion of courage, scholarship, and empathy, and I bookmark everything with courage and empathy because I just think you have to lead that way.
BERMAN: Well, here’s to more courage and empathy and scholarship across our world. Lord knows we need it.
ANAGNOST: Yeah, in our political system, maybe, too.
BERMAN: Well, let’s go there since you raised it before we wrap up. You’ve been public about your political views, and a lot of CEOs are unwilling or too afraid or too concerned to speak up on their beliefs. Why are you public about where you stand?
ANAGNOST: Because I care a lot about this world. I’m not beholden to any particular point of view. I’ve been a radical independent most of my life. I lean left, obviously. But I’ll take an idea from whatever side, and I’ll run with it if it’s a good idea. But the only way you find out if there are good ideas is if you act reasonably with people. So the how matters a lot in how you lead. You can’t separate the how and the what in leadership. So maybe I don’t agree with all the whats that someone says, but if I see a how that can get to better whats, I pay attention to that because I care about this country. I love this country. I’m the product of immigrants. I’m an immigrant success story in many respects, and I love the way this country has been able to pull in people from all sorts of places and then refresh itself and refresh itself.
And we’ve been in these dark places before. People forget about the 1920s. We had the postmaster general censoring mail. We’ve had dark periods in this country, and we’ve always come out of them, but they require people who get the how of how you bring people together. Right now we’re shifting into demagoguery on all sides, and that’s not going to get us out of this. So I speak up not because I might speak up on a particular issue or something. I speak up because I care about how things get done. Because if we don’t do things right, we thrash, and if we thrash, we lose.
BERMAN: I’m so grateful for you. Thank you for being on Masters of Scale.
ANAGNOST: Oh, it was a pleasure. Thanks, Jeff. This has been great.
Episode Takeaways
- Autodesk CEO Andrew Anagnost reflects on a turbulent youth and says his life changed because teachers, judges, and mentors told him hard truths and believed he could do more.
- After earning a Ph.D. at Stanford, Andrew says his early startup years taught him speed, range, and clear thinking in ways big companies rarely can.
- Inside Autodesk, he learned from very different CEOs how rebel teams can spark innovation, but only if leaders pair creative freedom with real commercial discipline.
- When Andrew fought through an awkward co-CEO succession to take the top job, he moved fast, rebuilt the leadership team, and kept repeating the why behind every hard call.
- On AI and leadership, he argues the future belongs to precise, industry-specific tools and to leaders who balance courage with empathy, not ego or impulse.