From high school dropout to CEO, with Autodesk’s Andrew Anagnost

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Meeting Andrew Anagost

2:02larger company. All that's stripped away in a startup. You're just trying to survive and you're trying to make it happen.

2:12This is Masters of Scale. I'm Jeff Berman, your host. With us today is Andrew Anagost, the CEO of Autodesk. And while you may not be familiar with the company itself, you're definitely familiar with the company does because pretty much everything that you are looking at in the real world, their software help make. Welcome to Masters of Scale. Thank you. Yeah, we like to talk about Autodesk as the biggest tech company nobody's heard of. Everything that you see in the world, the cars that you see on the roads, the bridges they drive over, the machines that you see, the phone, the buildings, it's built and designed using our software.

2:47I'm keen to get into the story of how you joined the company and became CEO and how you're leading it through this era. But I want to go way back because we were learning before we started the recording that you and I have more than a few things in common. But one of them is neither of us was our best self as a teenager. No, I was not my best self. What were your teen years like?

A troubled youth and turning points

3:11Yeah, my teen years were a little rough, all right? As I progressed through and got into high school, you know, I essentially started numbing myself and lack of a better word, I self-medicated. I just went off the rails and I dropped out of high school for a while there, ended up in the wrong places, was never a violent kid. The only person I really ever hurt was myself. You know, like I was the only high school dropout that would show up for like, you know, the trigonometry class, sometimes under the influence of something. And, you know, one day one of the teachers came up to me and he 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.

3:48Get the hell out of my class, you know? And I remember to this day, right, I can see his face in my face. I can feel his breath, right? You know, it's one of those things where at the moment I just laughed at him, didn't stick with me, but he was very brave, this teacher. And I remember not that long later when I was expelled and I got into a very serious car accident, almost killed the passenger in the car. And I was handcuffed, I was on the ground in a gravel driveway, you know, smashed down, I was injured.

4:19And, you know, his voice just banged through my head. And I've never, I've never forgotten him. Mr. Carrington, hello, Mr. Carrington, if you're still live out there. Most people that, you know, drop out of high school, get expelled, 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, actually, that I met along the way that saw that I had potential and I was just pissing it away. Wait, Andrew, what happened between the face down, handcuffed in the gravel, having already had the experience with Mr. Carrington trying to get you back on the right track, that got you all the way to Stanford and that has us sitting here today?

4:57That moment was pretty seminal in my life. Actually, having almost hurt someone, I think you just sit there and you reflect and go, what am I doing? It really was a switch moment. And it was voices like that that kind of, you know, propelled me forward. You know, I got into the local Cal State. I worked my way through that program. I fought to get into internships. I had professors along the way that told me, look, you know, you, you have potential. You know, they believed in me, you know, and I believe that you have to work hard. You do make your own luck in some ways. But, you know, 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.

5:32And I was fortunate that some of these people really believed in me and I was not going to let them down. There's something really profound about the there, but for the grace of God of this. How incredible that you had people who stepped in for you and helped you get on track. I did, including the judge that chewed me out in juvenile court. You know, look, I, I think we are the product of the people that lift us up. I really believe that my life experience has taught me that I never believe this bull crap that I hear out there about, oh, you know, I did this all myself for the most important people in your life.

6:05They tell you what you need to hear, not what you want to hear. So you get through this, you get to Stanford, you get your PhD, you don't go into academia. No, I don't. How do you end up at Autodesk?

Joining Autodesk and early leadership lessons

6:16So I actually went to a startup. It was a deep technology startup in Boston and spent almost five years at a startup, which was a magical experience. All right. I mean, I tell young people, you should try a startup while you're young. Why do you tell people that? When you're at a startup, what you do is you, you learn a little of everything very quickly. And a startup is very low hierarchy. And if there is any hierarchy, most people ignore it. And you make decisions very quickly. You learn the value of speed and arguing things out in kind of a Socratic way where the ideas got to be challenged, not the people.

6:51And 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 or all these things. All of that's stripped away in a startup. 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. Yeah. And from zero to 30, 50 people or so, you kind of know everything happening in the company. You know everything. Right. Everybody knows everything. And you know exactly who to go to to get something done.

7:21And you know how to get your relationships in place. You also know that you can cut through the BS. Now, of course, it teaches you some things that do not translate to large company environment. This high-speed connection that you have in a startup where, you know, you've been sitting there late at night eating with these people and you can call BS on them and they don't feel bad doesn't translate. So I was actually recruited out of this company by Autodesk. But the funny thing was is I met the woman who would become my wife and she wanted to move to California. Oh, wow. We were working for competing software companies.

7:52Can you believe that? Wow. Yeah. The only reason I took the job, though, is because it was in a team that was trying to fight against this company that I had actually partnered with at my startup. And I go, yeah, they're terrible. We should build a product that defeats them. And so I got a little bit excited about that. But let's face it, I thought it was a stepping stone to something else. It turns out that, you know, when I got there, I really liked being in this counterculture team that I was working with. A rebellious team in terms of rebelling against the primary culture in the company. How big was Autodesk at the time?

8:23Like less than 1,000 employees. Okay. But still not an early stage startup. Not an early stage startup. Relatively scale. Big enough to have a well-established culture and well-established norms. And most companies at that scale with well-established culture and norms, they may say they want a rebel group. They may say they want the innovator. But generally, it doesn't go so well. Carol Bartz did this. Okay. 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 poor product that the company started with, which was called AutoCAD, the name that most people know. Right? And it was kind of an exciting period.

8:55I learned a lot about how you operate and how you kind of use the edge, but then soften the edge over time through that experience. Carol Bartz, she kind of showed me the importance of commercial discipline and the rigor associated with that and the need to have accountability on getting things to customers in order to scale. Because I knew zero to 10 pretty well. 10 to 100? Well, you know, I didn't know that very well, right? She was really influential on me. And I look back at her in positive ways.

9:26I always like to say I'm the product of two dysfunctional parents, and they both have initial CB. One was Carol Bartz. One was Carl Bass. Totally different people. Okay? Both CEOs that I reported to. Carol much more on the commercial side. Carl on the, you know, respect for innovation, you know, 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. What did Carol and Carl do to allow a rebellious group inside the company not just to function but to flourish?

9:59Carol 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'd let them pop up everywhere. Wow. To the point that it would stress the company's ability to execute. Carl's style was much more let a thousand flowers bloom and maybe never prune a single flower. It's almost like working at two different companies with leaders that different. Very different companies. Yeah. Even the company that I run now is Autodesk. It's somewhat different. But it learned from both of those companies.

10:31And I'd like to think that because we can scale new businesses, because we're very passionate about killing our own businesses, killing our own products, which we are very passionate, and I think that's a cultural norm in the company, that I've done a decent job, but I owe it to the experience and the experience arc. I want to come back to the norm of killing your own businesses when you need to, but I do want to hear about the journey to CEO, because you weren't given the job outright.

Becoming sole CEO

10:58You had to really fight for it. Will you tell us about the process that started as a co-CEO and led to the lone CEO? When they started the succession planning before the activists came into the company that ultimately led to the co-CEO scenario, I opted myself out of the succession process. Why? Because I just never saw myself that way. For some reason, I looked at that job and I said, well, then you don't have any fun anymore, which might actually be true.

11:21It was only as the activist process progressed, okay? There was someone from the old culture that was up. There was me, you know, from the newer culture, the inside outsider. And then there was the threat of an outsider. And as I was looking at the plot evolving, the culture norm wasn't going to get the job. It was very clear to anyone that that wasn't going to happen. And more and more, I just said, okay, that means an outside, I love this company. And that's when I said, I'm putting my name in.

11:52I want to try for this job. And that's how I ended up in this situation where they then pitted the old timer against me in the co-CEO role. And for six months, no decisions were made at the company. Why did they do that? I mean, it's not exactly a model that's likely to work unless you are deeply partnered. Unless you're, it works much better at smaller companies than it would ever work at a large company, right? I think they did it because they were afraid of disrupting the current culture of the company. I think they were creating theater, all right?

12:23About, you know, we got to make sure that we assess all. They were buying themselves time, all right, to get through the process. And it was awkward for both of us, all right? And it wasn't a great time. Like I said, for six months, no major strategic decisions were made at the company. And were daggers out? Were you all basically trying to kill each other? No, no, we weren't like that. I mean, at least, you know, I could 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, you know, or all of those things, but because I was the inside outsider.

12:56And I think that's what people wanted at that point. And frankly, it's probably what the company needed. 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 make it look, make it visibly look like it was a fair process. You have to ask them, right? But it wasn't great. It wasn't a fun time.

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15:15When you became the sole CEO, what was job one day one? I fundamentally believe that you've got to have a guess at what the future is, okay? 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. 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. And 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.

15:51Wow, yeah. All right? And here's the reason why I did it. Because you might not know, but I was the one that led the subscription transition at Autodesk and started fixing the back office and trying to get it in a position where it can scale in an era where we have SaaS products. But that was the first thing I did. When it sounds like, Andrew, what you saw was you had a foundation that wouldn't support the skyscraper you were trying to build. I could build the best products in the world right now, and I couldn't get it out to the customer. And I certainly couldn't get it to new customers.

16:22The next thing I did was I made a couple of large acquisitions for Autodesk to scale the construction business. Because I believe firmly that in the world of hyperautomation that 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 kind of progressed through my early days as a CEO. And that was quite successful. We scaled the business. It was hard.

16:52We had to overspend, but we scaled it. Did you have the right team, or did you also have to overhaul your leadership team? I think three-quarters of the leadership team either, you know, left on their own or were asked to leave. That's a lot of change for a big, for a skilled company. It was a lot of change. And some of these were good people. They just weren't the right fit for what I was trying to do. How did you manage the communication to the rest of the team as they're seeing this changeover at the top of the company that, no, no, no, this is actually good. This is where we're going. Yeah. I over-communicated about it a lot. I spent a lot of time saying why.

17:24I 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 kind of, like, challenge, right, and engage with. But I spent a lot of time talking about the why to the company. And let's face it, I had to build trust because in a company like this, half were for me, half were for the other guy. Sure. Was it exactly 50-50? Oh, who knows? It's 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, that, you know, were you the right person?

17:55So I had to be a whole company leader, and that, unlike some of the leadership we have today, but I won't digress down these avenues, I had to be a whole company leader. You're welcome to digress anywhere you want to go. I'll go there with you. Well, you know what? I think if you really want to be effective, you have to prevent thrashing. And when you pander to one extreme or the other in a company, in a society or anything, you thrash. And you thrash back and forth, and you have this illusion of progress, but you don't. What you're doing is you're burning calories, wasting energy, wasting money, and wasting time.

18:28So I had to make sure that I didn't thrash the company. So I worked hard to win over the people that saw some of their darlings depart, and I worked hard to bring some of the people that were with me over into the other side. So 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 know, you have to earn that trust in, like, the first one or two years, because when you're asking the company to sacrifice, especially when you do a big riff of, like, darling projects, you know, and just send them off, people aren't, you know, they're not your fans right at this point.

19:07They're questioning you. So it was hard work telling the company the why over and over again, and then actually delivering some success. I want to just 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, like, we're making these decisions, whatever. Absolutely. But I have to bet there are a lot of people who are like, but wait, that's my baby. You're killing innovation. Yeah. Yeah. 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?

19:41The process had a few simple tests, okay? I'm a big believer in a few simple rules set you free. And the tests were this. 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 ask is, how adjacent is it to our current business, or how far away is it? What's the distance from our business? Now, the reason I ask that question is because the further something is away from your business, the harder it is for you to get to it over a period of time.

20:11Because usually what you want to do is do hops, but if you take a big leap, sometimes you leap too far. So how close is the 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? And, you know, a bunch of things quickly were like, nope, nope, nope, nope. One of them, two of them, I got wrong. And, you know, 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% of the time, you're killing it, okay? You're just killing it. So that's the process I took to decide what stays and what goes.

20:46The hop versus leap is one exception if you think your entire business is about to hit a wall. Like, just think about the Netflix transition. Yes. As an example, which, okay, it's illogical, but that was more of a leap than a hop. That was a leap. Right? I mean. So when we went to subscription, that was a leap. Right? The hop philosophy makes a ton of sense. When do you have to take the leap? Yeah. When there's paradigm shifts, okay? So there's 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 where it is.

21:21So we leap into technologies at Autodesk. We hop into adjacencies. And so far, so good. All right? We were on AI quite early. So we leap into the technology trying not to be too early. Yeah. You know the balance, right? Too early, you spend too much money. Too late, and you spend too much money and have no success. Where are you in your AI transformation, and where do you see it going?

AI strategy and the built world

21:46First off, let's talk about why it's so important, okay? 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 at all. Nope. 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 it's this fragmented ecosystem with highly competing people that like to sue each other

22:18and 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. So 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,

22:51either construction or manufacturing. So use AI as kind of project intelligence or a brain in the middle that kind of 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 and connect those things and automate them as much as you possibly can. This has been something that we've been working through for eight, nine years. We call it convergence, convergence of design and make, the convergence of construction and manufacturing, convergence of digital and physical worlds.

23:23This 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 of data that we have from our customers, controversial with our customers. We're super transparent with our customers, though, about what we're doing. Why is it controversial with your customers? Well, because are you training other people on my IP to do what I do in 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.

23:54We will erase your data from that training set. But that's not what we're doing right now. What we're doing is we're training for productivity. And 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 actually help them get better answers. And, you know, everybody says, well, aren't the large language models going to replace that world? I think there's 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 just something that we can't afford.

24:26That'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, it's expensive to use a horizontal tool to solve vertical problems. Say more. 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,

25:00you are burning a lot of compute to get there. However, if a tool that's maybe a smaller model that's designed to specifically solve another 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. 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,

25:32how are you winning? How are you getting people to Autodesk? 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 tense enemy attack, and you look behind you and you're hoping your team is behind you. Who do you want behind you? The one that believes in your mission or the one that you paid to be there, the mercenary? You want the one who believes in your mission. The mercenary is fickle, will change their mind very rapidly on things. Now, sorry, I used a war analogy, but it's just helpful.

26:04There's a lot of mercenaries out there, and there's a lot of people that think, I'm so amazing, you know, and I'm worth this $10 million check out of nowhere. And you know what? Go chase those people. Go chase them. Go chase the primadonnas. Go chase the people that 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 that love the problem. Oh God, how many times have I been recruited out of the company? I love what our customers do.

26:35I 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 10 of those over 100 of those other people. That simple.

Empathy and leadership philosophy

27:02I was at Web Summit Portugal last year and I walked off stage. 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. Yes. It's not in vogue right now. It's not in vogue right now. 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? Look, I think these people who are saying that empathy is a weakness don't understand empathy.

27:36They get a lot of air time. 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 of courage, scholarship, and empathy. All right? And the two anchors, courage and empathy, actually lever off each other. I think for 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. Okay? And, you know, if you talk to sales forces, cannibals are everywhere.

28:09You know, they're going to get you. 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. Yeah. Okay? So the counterbalance of 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

28:40got to know what their impact is. It doesn't mean you stop. Empathy is 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 with an outcome. And I think anybody that 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 a ramification on somebody else.

29:14And 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. So 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 can't believe how many people I've had in my office that try to convince me impulsiveness

29:45is 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 like, 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.

30:14You got lucky. All right? And you don't want to play luck on big, long-term decisions. You just want to think, do enough scholarship to know what's going on. You don't want analysis paralysis because that's what they say. Oh, too much thinking. That's analysis paralysis. Well, you know, 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. Well, here's to more courage and empathy and scholarship across our world.

30:47Lord knows we need it. Yeah, in our political system, maybe, too. 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? 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's good ideas is that you act reasonably with people.

31:21So 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 what's that someone says, but I see a how that can get to better what's. I pay attention to that because I care about this country. I love this country. You know, I'm the product of immigrants. I'm an immigrant success story in many, 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.

31:51And we've been in these dark places before. People forget about the 1920s. We had the postmaster general censoring mail. We've had dark worlds in this country. And we've always come out of them. But they require people that 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 because, not because I might speak up on a particular issue or something. I speak up because I care about how things get done.

32:22Because if we don't do things right, we thrash. And if we thrash, we lose. I'm so grateful for you. Thank you for being on Masters of Scale. Oh, it's a pleasure. Thanks, Jeff. This has been great.

32:36Thanks again to Andrew and Agnost for joining us on Masters of Scale. There is so much of this conversation that will stick with me. But perhaps the most important lesson Andrew shared is the one that he learned as a teenager. You benefit most from surrounding yourself with people who tell you what you need to hear, not what you want to hear. If you can hear the people saying the hard things, the possibilities are endless. I'm Jeff Berman. Thank you for listening.

33:17Masters of Scale is a Wait What original. Our executive producer is Eve Droh. Senior supervising producer is Tricia Bobita. Associate producer is Masha Macattanina. Video editor is Noah Wolstein. Senior talent executive is Stephanie Stern. Mixing and mastering by the audio boys Aaron Bestinelli and Brian Pugh. Original music by the legendary Ryan Holiday. Visit mastersofscale.com to find the transcript for this episode and to subscribe to our newsletter. And be sure to check out our YouTube channel.

33:49Thank you. Thank you. Thank you. Thank you. Thank you. Thank you. Thank you. Thank you. Thank you. Thank you. Thank you. Thank you.

33:55Thank you. Thank you. Thank you. Thank you. Thank you. Thank you. Thank you. Thank you. Thank you. Thank you. Thank you. Thank you. Thank you. Thank you. Thank you. Thank you. Thank you. Thank you. Thank you. Thank you. Thank you. Thank you. Thank you. Thank you. Thank you. Thank you. Thank you. Thank you.