# Navigating Chaos: AI, Agility, and Executive Leadership

**Podcast:** Masters of Scale
**Published:** 2026-11-03

## Transcript

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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 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.
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 PhD 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 US 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.
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.
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 forecasts 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 of 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's 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 and sharing about this, trying to get people to understand the difference between complexity, fragility, anti-fragility, and then how do you actually leverage this kind of 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 in account and come up with ideas.
So keep this spinning.
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 are part of that original Generation Flux story.
And I'm going to go to Reina.
Reina Kummer 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.
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?
So has it gotten harder to build a full toolkit?
when everything's changing so fast?
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, I didn't want to manage a complex team, but complexity is part of life right now.
And the way to do that was to become like the CEO of your agent team?
Of everything.
Yeah, of everything.
And, you know, 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.
I mean, you would, 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 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.
Hayden Brown is the CEO of Upwork.
Hayden, you and I have...
There she is.
Yeah, you can say hi.
You and I talked before about how your planning for things has become sort of impossible in this era.
That like even planning out a quarter, a month becomes a challenge.
Do you need new techniques?
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, 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 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 became more about predictability.
That's what public companies are supposed to be good at, predictability, low risk.
But now the job of 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 agent, Serena, our team actually built out an incredibly powerful internal tool, which we 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 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 going to go to another.
Yes.
Thank you.
I'm going to go to another character from, from that original generation flux story is, is a writer and media personality, Baratunde Thurston.
Baratunde's up here.
Baratinda, you host a series called Life with Machines about AI.
You also host a PBS series 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 the right role of technology in my life?
How do I know when I should unplug?
Small question for you.
What's up, y'all?
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 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.
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 not set by me and that is not consistent.
with living.
And there's an extreme view of just like, don't touch anything, opt out of everything.
And I can't do that.
I live here.
I'm a modern creature.
And I have fun with this stuff.
I do love tech.
My mom was a coder.
It's literally in my blood.
And 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, as Rhina 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 remember, 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, Bob.
Thank you.
Thanks, 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.
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Humans will never be more intelligent than AI.
There's going to 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 Elkawiyubi, 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.
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 Dara Trecedor of Autodesk and William Trecedor of Arkenstone, who share their tactics for managing work, marriage and family.
Let's jump back in.
So I mentioned that Baratunde 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.
which is a wildlife, a wildfire and flood intelligence network.
Those of you in California probably are 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...
Can you explain how you think about those two things?
Yeah, I mean, 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.
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 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 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 fatigued 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 the 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, yeah.
You should give it a spin.
You've been taking this in.
Any, 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.
You know, 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 moments of calm in 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...
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 Treseder and William Treseder, 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, 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, like 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 they're glass balls and they're rubber balls.
And the glass balls are the things we don't want to break.
So that's like our marriage.
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, 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 in a different season of life?
And with those balls, 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?
Because then it's not a real journal, right?
So you just have to read it as a silent observer.
And then 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 first.
Whoever gets there first.
You know, I love, I'm in my feelings.
I'm in my feelings, so it's usually me.
I got a lot to say.
Now, you guys, you also set, like, family goals and KPIs and values like a business.
Yes.
Yeah.
I think, 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, we have like in our garage, we have this Treseder 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 right now my daughter's in a race to.
transcend my wife's current pull-up record.
So she has a maximum number of pull-ups that she can do.
They had to do like typing words per minute and other things like that.
So 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, our overarching, like, what is the big KPI?
For us, it's what we kind of call our family MPS.
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 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 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 its mom now.
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 NPS.
I mean, I know 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, 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 where 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.
We really want them to understand that like service before self.
means something in practice.
There's daily consequences to what that means.
This is not an academic exercise.
My wife is on the edge of her seat hearing.
I'm in the process of thinking through my re-enlisting in the Marines for another four years.
And I have another 76 days before I need to file my paperwork.
And so it's one of the, there's a real conversation there.
We haven't, not only are we discussing that, but we're also talking to our kids about it.
My son is hardcore re-enlisting.
He is hardcore.
Hardcore.
Not that he's doing it, of course.
But yeah, he has a firm, he has 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.
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.
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.
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.
Mm-hmm.
Yes.
Okay?
So it's so important to say, what deserves my energy?
What is going to matter over a meaningful amount of time?
Not just matter in a specific moment.
Right.
And make sure that we are 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 of her children 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 going to do something, when I say I'm going to 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 sharing this.
Thank you.
High five.
We're out of time.
The theme of this summit is around 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.
And I think that's what we all really need to do, is 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 playing the game, and thanks to Raina 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.
Hey listeners, Bob here.
If you listen to Rapid Response on Masters of Scale, you may be missing half the show.
Because every Friday we release a second Rapid Response exclusively in the Rapid Response feed.
The guests and topics are just as compelling and timely, from Ford's CEO to NASA's administrator to the lessons from the Devil Wears Prada.
It takes about 10 seconds to find.
Just search Rapid Response wherever you listen to podcasts.
and hit follow to make sure you never miss an episode.
I hope to see you there.
Rapid Response is a Wait What original.
I'm Bob Safian.
Our executive producer is Eve Trow.
Our senior producer is Alex Morris, and our associate producer is Masha Macutonina.
Mixing and mastering by Aaron Bastinelli and Brian Pugh.
Our theme music is by Ryan Holiday.
For more, visit RapidResponseShow.com.