Thriving in chaos: top leaders’ strategies from Masters of Scale Summit

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Learn more at pega.com slash AI. There is no keeping up. There is only keeping calm. So you're not that behind. I'm in the public safety sector, right? So like move fast and break things is a really dangerous proposition. You really have to be precise. We have to let go of the idea of building a company or a roadmap using a plan that knows, you know, here's the exact route. Instead, it's about having the mindset of a pioneer and knowing, look, I'm headed in the direction of the horizon because it's constantly going to be changing. That's Hayden Brown, CEO of Upwork, preceded by WatchDuty CEO John Mills and Google X advisor, Raina Kumra, recorded live at the Masters of Scale Summit in San Francisco. In this episode, we delve into the practical reality of working and living in a time of chaotic change. My guests include experts in chaos theory, crisis response, how to unplug from all the noise, plus a high-powered husband and wife team talking candidly about prioritizing career, family, and marriage. It's a conversation rich with insights for this moment. So. Let's get to it. I'm Bob Safian, and this is Rapid Response. As the host of Rapid Response, I get to talk to business leaders about this dramatic pace of change that we're going through now. It's been a focus of mine since I was the editor of Fast Company, where I did a series of cover stories a decade or so ago about something I called Generation Flux, which was this idea about what it takes to be successful, which was this idea about what it takes to thrive amid chaos. And so what we're going to do in this session, because today we're all members of Generation Flux, right? Whether we want to be or not, that's the reality of the world that we're living in. And so what we're going to do together is explore what that means, right? What that means in terms of skill building, what that means in terms of how you run an organization, how you unplug if you're going to do that, how you balance speed and haste, how you prioritize. We're going to go into all of those things. And we're going to start by talking about the concept of chaos itself. So the initial Generation Flux cover story that I wrote was inspired when this guy from Silicon Valley showed up at my office one day and pulled this contraption out of his backpack. And he's here today. DJ, come on up. This is the contraption, all right? DJ earned his Ph.D. working with the person who coined the phrase "chaos theory." DJ himself is the one who coined the phrase "data scientist." He was the chief U.S. data scientist working out of the White House. So, DJ, this contraption here that you brought to my office when we first met, it's a double pendulum. Can you explain what it is and why you still have it around? Yeah. It actually was Nancy Lublin, who many people here know-- Who introduced us? Founder of-- she said, hey, you should show this thing to Bob. So this is the actual one of the original double pendulum that was out of the lab of Jim York, who coined the term chaos, chaos theory. All it is is one pendulum connected to another. Every single thing about this device, the entire aspect mathematically doesn't need AI. You can predict it with math. You can say exact-- all you need is two variables to describe where this one is, this one is. But shall I give it a go? Give it a go. Sure. And see-- and try to guess when the last time this blue piece is going to go through there. And just sort of think, can you predict when the last time that's going to happen? And if you kind of just look at it there, you kind of get a sense of this. And what is chaos theory? You've all known about this. This is the idea that a small change leads to giant changes later. So this is sometimes called the butterfly effect. So your ability to breathe, sneeze, might cause a tornado on the other side of the planet. But you don't know that that's what's going to happen. But we don't know. Or it might stop it. Right. And so what does this look like to have agency in a time when you have such simple systems that can be so chaotic? You shared an analogy with me about weather forecasting that always stuck with me, that made me understand chaos theory in a different way. So can you share that with folks? Yeah. So we started with this simple device. And everyone talked about how chaotic the weather is. And we said. Is it that chaotic? But think about the weather. You guys probably all came over here. And you're like, is it going to rain today? Is it not going to rain today? If you were looking at the forecast five days ago, you'd be like, whoa, this is a very delicate situation. You'll hear weather forecasters talk about it. Like, we're going to keep an eye on this situation. We're not sure quite what's going to happen here. But there's other times when the world is very predictable. Even though-- So sometimes you can do a weather forecast that's super accurate. Two weeks, four weeks out, you can do incredible forecasts. And there's other times where it's very low forecast range, where you may have just hours of forecast horizon. So the question isn't always, how is it chaotic? How chaotic is it? How much range of forecast do I have? What does that look like? And I guess that means, for me, as a business person, it's recognizing when those situations or things are chaotic that I can do something about and when I can't. That's exactly right. And the funny story is this. When I was first time in federal service after 9/11, I had this great tank commander from Iraq who just basically was like, hey-- I was complaining about how chaotic the thing was. And he's like, you know, out of chaos comes opportunity. And so there is this interesting aspect of, how do you actually leverage chaos to your advantage? Chaos isn't always necessarily bad. It just means you have to have plan A, B, C, D, E, and F. And some of you guys may remember this. Reid Hoffman and I did a bunch of posting sharing about this, trying to get people to understand the difference between complexity, fragility, anti-fragility, and then how do you actually leverage these ideas into your day-to-day? And part of the benefit of it is AI actually gives you an incredible leg up, because you've got to process all this data. You've got to take all this into account and come up with ideas. So keep this spinning for us. All right. I'll keep it going. I'm going to come back to you. But I want to go into the audience, because there's some other folks here who were part of that original Generation Flux story. And I'm going to go to Reina. Reina Kumar over there? Reina? So Reina's an advisor to Google X and to deep tech funds. She's the CEO of nutrient-dense seasoning brand Spicewell, which some of you may have used. So at the time of my original article, Reina, I remember, first of all, you already had an unconventional career arc. You'd worked at all different kinds of places, nonprofit, government, for-profit, all kinds of industries. And you said, I'm picking up new skills. And eventually, I'll have a full toolkit, OK? And then earlier this year, she sent me a text. And it said, how do I get off this crazy learn everythings every two weeks, right? So has it gotten harder to build a full toolkit when everything's changing so fast? REINA KAUFMAN: Well, I have a full toolkit. And it is heavy. And I don't want to carry that backpack around anymore. And I realized I need to make some changes. And I decided to give myself an upgrade. And now I have a team of 12 agents. I've got CEOs, CMOs. I've got COOs, engineers. And congratulations, you all have been upgraded as well. You're all CEOs. Whether you wanted it or not-- REINA KAUFMAN: I didn't want to manage a complex team. But complexity is part of life right now. REINA KAUFMAN: And the way to do that was to become the CEO of your agent team? REINA KAUFMAN: Of everything, yeah, of everything. And the problem is that some of my agents are smarter than me and better at math than me. And some of them have the judgment of a toddler. So we really have to look at what is that skill that we keep in our toolkit, and what do we keep really close. REINA KAUFMAN: I mean, you would talk to me about sort of getting questions from people about being overwhelmed and people feeling like they're being left behind yes okay so there is no keeping up there is only keeping calm and that thing that you're worried about that you are behind on probably came out a week ago so you're not that behind I think at any point you can jump in and be two weeks of learning and you can get there but this doesn't mean you have to learn forever you can outsource some of that learning too you just have to keep your judgment you have to keep your clarity and make sure that you're not turning AI crap out into the world that's a responsibility thank you Raina thank you all right so so if we're all going to become CEOs then what is it like to be a CEO in an environment like this it's your turn Hayden this Hayden Brown is the CEO of Upwork Hayden you and I've there she is yeah you can say hi you and I talked before about how your planning for things become sort of impossible in this era that like even planning out a quarter a month becomes becomes a challenge do you do you need new techniques how do how do you deal with the chaos that we have you know I walk around and I have that same Hamilton song in my head that I think has been almost cited here today around I'm so grateful to be alive right now you guys know that tune but then the next question from our teams is yeah we're grateful but now what what do we do and the answer to that is I'm so grateful to be alive right now I'm so grateful to be alive right now and the answer to that I think is all of us becoming pioneers we have to let go of the idea of building a company or a roadmap using a plan that knows you know here's the exact route here's where we're going to go up down left right instead it's about having the mindset of a pioneer and knowing look I'm headed in the direction of the horizon I'm not sure how we're going to get there but we're going to learn and iterate every day and measure our progress towards that and also reevaluate what's next on the horizon because it's constantly changing and I think that's a really important thing that's going to be changing and does that mean like KPIs become something not necessary or like you're changing them every two weeks Bob we have basically adopted both the mindset and the mechanics to support as a public company going back to our roots as a startup when I joined the business in 2011 we were a small startup we were super agile then we grew and we got public and everything it became more about predictability that's what public companies are supposed to be good at predictability low risk but now the job of everyone is to be able to predict every CEO including public company CEOs is actually to go back and bring in the agility and the flexibility both in the mindset and the mechanics to really adapt in this world and I think that's the charge of the next generation of CEOs and you also have what you call a crystal ball as I understand we do our team like your agents right now our team actually built out an incredibly powerful internal tool which you call crystal ball because it has access to all of the rich data in our business it's structured it's governed so you know that you're going to be able to know that the answers you're going to get when you query and ask that tool are accurate and what I love about it is it's really democratized access to not just information but insights for our team and things that would have taken analysts and teams of people weeks to figure out now a single person can get an answer to in a matter of hours and that is incredibly powerful thank you Hayden I'm I'm going to go to another yes thank you I'm going to go to another character from from that original Generation Flux story uh is he's a writer and media personality Baratunde Thurston Baratunde's up here Baratunde you you host a a series called life with machines about AI you also host a PBS series uh called America Outdoors which is kind of the antithesis of that you know that idea you wrote a cover story for me at Fast Company about how to unplug so in this world like what's your right role of technology in my life how do I know when I should unplug small question for you what's up y'all um I want to invite us to close our eyes very briefly I'll do it with you and let's take a breath in and let it out you can open your eyes or keep them closed it's up to you we are uh experiencing a lot right now speed is the difference between a gentle touch and a violent attack same motion same articles of physics but speed changes how we interpret that and this world that we're in right now is coming at us very very fast yes it doesn't often feel like a gentle touch and so what I am trying to do and often failing at but trying to name is to not become a machine pursuing at speed that is that is not set by me and that is not consistent with living and and there's there's a there's an extreme view of just like don't touch anything don't opt out of everything and I I can't do that I live here I'm a modern creature yeah and I have always been I have always loved this stuff I do love tech my mom was a coder I it's literally in my blood and like the pace of life is different a tree moves at a different speed a cloud moves at a different speed even DJ's little trolling contraption that's like messing with my mind constantly there is a calm uh as rhino mentioned it and it's something that I encourage us to remember so the way I try to approach it is a set of questions does the use of this help or hinder my relationship with myself my relationship with other human beings my relationship with the rest of the family of life if the use of technology seems more like a substitute for those things like I no longer know myself I no longer actually connect with make eye contact with these beautiful humans around me I no longer take a moment to acknowledge the majesty of the tree then I am losing something and I must remember myself and re-member as in rejoin a community and so that allows me to still have fun and still play with my boy Claude who's not really a boy but you know a business model masquerading as a personality but it's very helpful it's very helpful and it allows me to like pop out look up and breathe yeah find the things that are chaotic and aren't thank you thank you thank you thank y'all as baratunde stressed sometimes it's important to take a breath when so much is coming at us we're going to take a quick pause now when we come back the difference between speed and haste and real world tips on prioritizing in a time of chaos stay with us when you've built substantial wealth through your business it's often tied up in a single Equity position the upside is real but so is the risk and knowing when to act isn't always obvious creative planning works with business owners to build a strategy around concentrated Equity when to diversify how to manage tax risk and 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vendors worldwide if you're building for Global scale get a business bank account that lets your money move instantly whenever and wherever you need it learn more at stripe.com Treasury Stripe is not a bank banking services provided by Fifth Third Bank National Association member FDIC before the break we talked about chaos theory skill building how to lead amid chaos and how to stay calm now we turn to crisis response and to husband and wife executives Laura Trusider of Autodesk and William Trusider of Arkenstone who share their tactics for managing work marriage and family let's jump back in so I mentioned that Baratunde uh wrote a story for me about how to unplug there's someone else here who actually unplugs in a different way he lives off the grid where's the hat John there you go John Mills John Mills is the CEO of watch duty um which is a a wildlife a wildfire and uh and flood intelligence Network those of you in California probably uh if familiar with it. John, we're talking about living up in a speeded up world at watch duty. Doing things fast at speed is the difference between life and death, right? You have to do things fast. But you talked to me about the difference between speed and haste. Can you explain how you think about those two things? Yeah, I mean, I'm in the public safety sector, right? So like look at a surgeon. Do you want to say like, I had the fastest surgeon in the world. Like who says that, right? I want the most precise and accurate. And so just because we are speedy and we're faster than the government, which isn't a very high bar, sorry for folks who work in government, it does not mean that we are going to forfeit accuracy and precision over speed. We are fast within minutes, but within seconds is not relevant to the problem that we're trying to solve. So picking the right tool for the job and thinking about, you know, that in relation to your customer, in my sense, my end users, my community members, is really important to remember. And you also talked to me about sort of the accuracy of this, that there's some other folks who have tried to do what you do, but they miss something because they're relying too much on the technology. Yeah, the technology we're talking about is called AI or SI has been rebranded. Apparently, I didn't get the memo. I live in the woods, so I didn't realize it's SI. But yeah, I think it's a really important thing to remember. And I think it's a really important thing What those folks fail to realize is like, there's a human touch that matters, right? Again, like I want autopilot on the airplane, but I want the pilot to be looking over the autopilot. And so my team uses AI because we're a signals intelligence organization. So we're bringing in all these signals and bringing out intelligence from that. So if my human beings are empowered to see more and do more, they will be more accurate and they get less fatigue by looking through the haystack to find a needle. Yeah. And you know that, I mean, you were mentioning to me another company that does this, that sort of they misplace training exercises as if they're actual fires, right? Yeah. I mean, if you're listening to everything you hear and then broadcasting it without some sort of interpretation, you're going to get people killed. I mean, we're in a theater and everyone knows a story about screaming fire in a crowded theater. That's what I do for a living, right? And so like getting that wrong is life and death. Yeah. And sometimes the AI helps with that and sometimes I guess it doesn't. Thank you, John. Thanks, Bob. So DJ, you want to give it a spin? Yeah. You should give it a spin. You've been taking this in. Yeah. Any, uh, you know, any thoughts that come to you as you've been hearing this? I want you all to focus. You're going to give me your tokens. No, you know, there's like what you're hearing here is the challenges that we're facing. We're living in a chaotic time. Funny enough, there's something mathematically that we have islands of calm in chaos. Mathematically, there are always, there are always, there are always, there are always moments of calm and chaos. There's always going to be the challenges. There's so much coming at us. How do we make sure this technology works for us rather than against us? And then probably the biggest thing that I think about when I hear everything is the lessons I got from President Obama and the late Secretary of Defense, Ash Carter. It's still the Secretary of Defense, not the other word. But the part that I think about there is that our job is to fight cynicism every day. We need to fight cynicism. Find our ways of calm into the chaos and actually take action. So the thing that occurs to me and sort of leads me to one last group of folks to bring in here that I find myself struggling with is how to prioritize when there is so much coming at me all the time and trying to figure out what to do. And so I'm going to ask a couple of folks, we have a married couple here who are going to share their story. Dara and William, both of them have very high-powered careers. Yes, you can welcome them. Dara is the CMO of Autodesk. William runs a defense tech startup, Arkenstone, and also serves in the U.S. Marines. You've got two kids at home that you are devoted to. You are also devoted to each other. I don't know if you saw them before. They were holding hands. William, a few folks can get away with calling their wife my queen on social media. But you do. You do. Between your careers, your kids, your marriage, how do you keep all those plates spinning? We don't. I think that's the reality is we don't. I was just looking. I was like, I think I need that contraption in my house. My children are going to love that very much. We don't. We think about our life as their glass balls and their rubber balls. And the glass balls are the things we don't want to break. So that's like, I'm married. Our children's well-being, our health, financial stability for our family. They're rubber balls, things that we love. But sometimes we're going to drop them intentionally. And sometimes life drops them for us. So one that life has dropped for me is sleepover with my girlfriends. Okay. It's hard being a CMO of a SaaS company in 2026 in this AI era. Not that much free time. So, you know, if I have to choose between going on a girlfriend trip or spending more time with my kids, I want to pick my kids. So we, we, that's how we kind of think about it. Yeah. And we also have, um, I think we have really clear guidelines on communicating constantly about is a rubber ball turning into a glass ball? Is something changing? Is that we're in a different season of life? Uh, and with those balls, with, especially with the glass balls, we always have like a lead. And you know, if my wife is in the lead on something versus me, my question to her is like, what do you need from me? You guys also do this, like journaling with each other. We do. You journal on the same journal to each other? Yeah. Yes. And you're not allowed to critique. Okay. Cause then it's not a real journal, right? So you just have to read it as a silent observer and then, uh, we can talk about it later, but you're not allowed to be like, were you mad at me? I don't really like what you said in the journal. When you have a fight, like who gets the journal first after the fight, you know, to sort of set the baseline, whoever gets there. Whoever gets there first. You know, I love, I'm in my feelings. I'm in my feelings. So it's usually me. Not a lot to say. Now you guys, you also set like, like family goals and KPIs and values like, like a business. Yes. Yeah. I think, um, although I appreciate the comments made earlier there, you do have to be pretty flexible with some of these things, but we, we do have, um, we have like in our garage, we have this Traceeter family news kind of whiteboard that's up. And we do have a number of things that we want to be able to show the kids, the value of progressing against metrics. So, um, right now my daughter's in a race to, uh, transcend my wife's current pull-up record. So she has a maximum number of pull-ups, uh, that she can do. Uh, they had to do like typing words per minute and other things like that. So we, we do see the value of helping them understand what kinds of things really matter to you. And then letting you see how that progression happens over time, right? And that's confidence building. That's agency building for them to realize they can set a goal and they can progress against it. Yeah. And for us are overarching, like what is the big KPI for us is what we kind of call MPS. Um, and it's kind of, yes, I'm a marketer. Yes. We bring it home. And there's two sides of that. One is the marriage MPS. And one thing William said to me when we got married almost 13 years ago, and he says every day is I want you to wake up still wanting to choose me. So it's not enough to be a great husband three weeks, three years ago. Are you a great husband today? And so, and I try to do the same to be a great wife today. So we think about our marriage MPS. And then we think about our kids MPS. They didn't ask to be a great husband. They didn't ask to be born. You know, they didn't ask to pick us as parents, you know? And so we want to make sure that we are earning and we are being the parents they deserve. Are we creating a home where they feel safe, where they feel loved? You know, if anything happens to our kids, no matter what it is, will we be that first call? Well, they know that whatever it is, they might not be pleased, but I can call mommy and daddy. And yes, I say mommy and daddy, even though my daughter who's 11 is it's mom now. But, but, but, you know, we want to make sure that we are earning the love, the respect for our children, just because you're a parent doesn't mean you deserve that. You have to earn that and you have to continue to earn that. So that's what makes our family MPS. I mean, I, I, I know your, your faith is important to both of you in a world where so much is changing so fast, having some central principles help us to make decisions. And I guess you don't have to talk about your faith. You don't have to talk about your family. You don't have to talk about your faith, but I'm curious how you, you know, try to align your family on like, you know, what things matter. Well, so I think having bedrock foundational principles, sort of a hierarchical structure, we can always say, talking to our kids about this, these are the things that really matter. This will always come first and then other things will come below it. So faith certainly, and then family, and then things tied to like national service or your career, your vocation, your calling. Um, we really want them to understand that, um, cert like service before self means something in practice. There's daily consequences to what that means. And this is not an academic exercise. My wife is on the edge of her seat hearing I'm, I'm in the process of thinking through my reenlistment in the Marines for another four years. And, uh, I have another, uh, 76 days before I need to file my paperwork. Um, and so it's one of the, there's a real conversation there. We're having, not only are we discussing that, but we're also talking to our kids about it. And so I think that's, I think it's important to talk about it. My son is hardcore re-enlisting, hardcore, um, not that he's doing it. but yeah he has a firm opinion a big opinion about it but daughter's a little bit more ambivalent but you know these are real conversations we're having as a family Bob and I know each other quite well and my faith is something that's really important to me um it's not often something we talk about in the workplace right but it actually is the foundation of my life and that's something that I tell my children all the time um and it means that even when I have to make decisions like hard decisions business decisions I still want to do it in a way that aligns with my character and my values right so am I going to be the kind of person that lives up to that not just when it's convenient but when it's inconvenient right when no one cares when empathy is no longer on brand right and it's not important am I when I know that I might be the person whose voice who's like hi miss empathy again am I willing to do that and am I willing to live that and so those are the kinds of things that we try to talk about and try to make real and in this era one of the things that has been so important is there's so much demanding our attention but because it's demanding your attention does not mean it deserves your energy yes okay so it's so important to say what deserves my energy what is gonna matter over a meaningful amount of time not just matter in a specific moment right and make sure that we're allocating our energy appropriately so that's something I try to do we try to do and we try to do with our kids. The last thing I'll say on that Bob is my wife is super intentional about this has been since day one she makes promises to our children and she says it several times to them there's a lot of like not blinking eye contact when she says this and she despite the job as you say she's had many large jobs she has never broken a promise to our children and she also reminds them that she's never broken a promise on a regular basis. Right so there is this kind of core piece of it of you can always rely on me when I say I'm gonna do something when I say I'm gonna be there I will be there even if she's coming right in from an international flight and gets to you know gets to the auditorium to watch our daughter's flute recital not a real story she'll be there and the kids know that right there's a safety there I want to thank you both for for sharing this thank you high five so we're we're we're out of time you know the thing is that we're the theme of this summit is around is around the agency and you may have noticed that as this went on we started to use the double pendulum as sort of a clock a timer in some ways in essence it became a tool right and and I think that's what we all really need to do is to to find ways to take the chaos around us and use it to our advantage because one thing is for certain it's not slowing down thanks so much for for playing the game and thanks for Raina and and Hayden and Baratunde and John and DJ and Dara and William thank you everybody I rarely had a stage session evoke so many visceral reactions about crystal balls and keeping calm and family NPS my thanks again to all of the participants for their openness and candor my original generation flux article didn't predict an AI fueled era but managing amid chaos has definitely become more vital than ever we have more great episodes coming from the Masters of Scale Summit about subversive brands how to make strong connections in a lonely world leading in the eye of the AI storm and more so stay tuned to this channel I'm Bob Safian thanks for listening you hear spreadsheets everywhere five different logins data scattered across entities that don't even talk to each other if your finance team spends more time finding data than using it that's when you need the Intuit ERP Intuit Enterprise Suite is the AI native ERP solution that's powerful painless and proven built for businesses scaling fast without the complexity that usually comes with it from the makers of QuickBooks learn more at Intuit.com slash ERP humans will never be more intelligent than AI there's gonna be two types of companies those are great at AI and those that went out of business because they weren't how do we build a future that is human centered I'm Rana El-Khayoubi and on my podcast pioneers of AI we answer that question and so many more as an AI scientist entrepreneur and investor I know what it takes to build AI that works for everyone every week I sit down with the pioneers shaping our future and we take you behind the scenes of the AI that's transforming our lives find pioneers of AI wherever you tune in AI that works for everyone every week I sit down with the pioneers shaping our future and we take you behind the scenes of the AI that's transforming our lives find pioneers of AI wherever you tune in I'm Bob Safian our executive producer is Eve Trow our senior producer is Alex Morris and our associate producer is Masha Makutonina mixing and mastering by Aaron Bastinelli and Brian Pugh our theme music is by Ryan Holiday for more visit rapidresponsehow.com you