Cutting Through the Noise of a Changing World with Gayle Tzemach Lemmon

Gayle Tzemach Lemmon has spent her career moving between worlds as both an outsider and an insider, across early-stage technology company building, finance, foreign policy, politics and journalism, entrepreneurship, and emerging technology. What that’s given her is a deeply systems-level way of seeing how the world actually works, not how we wish it did.

In this conversation with Sanjeev, Gayle talks about why this moment, shaped by the forces of AI, geopolitics, and energy, is forcing a rewrite of what’s possible. She makes the case that economics and politics are inseparable, that fairness is one of the most powerful forces shaping markets today, and that homogenous thinking leads to value destruction. If you’re interested in how to think across silos, challenge conventional wisdom, communicate complexity in human language, and navigate an era where uncertainty isn’t a bug but a feature, this conversation is for you.

Sanjeev Krishnan: Gayle, welcome to the S2G podcast.

Gayle Tzemach Lemmon: Thank you. Great to be with you.

Sanjeev: One of my favorite people, you are one of the most interesting people I know. Just given your life experience and everything you’ve done and everything you’re doing right now, and areas we’ve collaborated in the past. For those people that don’t know, maybe a bit of your background. You’re obviously, I know you’re a company builder early stage and PE strategy advisor.

You’ve done a lot in foreign policy, former political reporter, investor, three-time New York Times bestseller on geopolitics, and many things. But maybe just, who are you, and how have you gotten here? The story of your life.

Gayle: Yes. No, I think, look, I have had the gift of being an outsider for a long time in a lot of different spaces, and I think that has taught me a lot about this moment, is that seeing things differently is actually a gift. I came from a single mom in PG County, Maryland. My mom worked at the phone company when there was a phone company, Sanjeev, and sold Tupperware at night and really taught me about hard work, but really about being flexible and seeing what was around corners, because I think when you have a lot of economic insecurity when you’re growing up, it teaches you to see what’s coming next because you need the next opportunity. And that has actually been the biggest gift for me because I think it just gives you a relentlessness if you’re fortunate enough to grow up with incredible role models who are able to find opportunity in adversity.

It really teaches you to always look for where is the opportunity and where is the world headed? And that sort of served me in multiple lives, across multiple sectors, as you just mentioned. And really, all with the idea always of like, how do we capture imagination to move toward the goal? How do we unlock capital?

How do we capture people’s imagination? How do we get people to buy an idea? How do we get people to buy a book? When I worked in financial services, like how do we build products that are the right products for the right customer, right? And so it’s always about thinking where is the fit with where the world is headed and what you’re offering?

And always working on how do I capture people’s imagination in a way that makes them really feel inspired and energized to make the purchase.

Sanjeev: So you graduated college. What did you do?

Gayle: I worked in news, but my first job was booking crews for the BBC.

Sanjeev: Oh wow. Okay.

Gayle: So they would need a crew, and we would give them the crew. And then I went to CBS News. Yeah. And then from CBS to ABC. That was kinda the first chapter. And that was when I covered politics, and we worked on this thing called the Note, which was one of the first political newsletters at the ABC News political unit. And then I worked for George Stephanopoulos when he launched the Sunday show.

Sanjeev: As you reflect on that part of your life and career, what are the things you take away as lessons learned or skills that you got, or perspectives that you got?

Gayle: Yeah, so I went to CNN​.com for its first presidential election, and everybody told me that was career suicide because nobody would ever get their news from that​.com thing.

Sanjeev: Yeah.

Gayle: And it really taught me that, going back to being the gift of the outsider, it’s like I wasn’t scared about going to cnn​.com ​’cause it wasn’t like I had four decades of career to worry about.

And I knew it was gonna be so hard to get an opportunity in the established world that I could go to the new media, the new technology, learn it, and then go back and transport those skills to whatever I did next. So I think that one thing is to embrace the fearlessness that I grew up with.

And the second thing is that politics trumps everything.

Sanjeev: Yeah.

Gayle: And later, working in the private sector, it was always stunning to me that people would say, ​‘Oh, but that’s just political.’ And I was like, ​‘I don’t think you understand. That’s gonna kill everything that you wanna do.’

Sanjeev: I’m gonna tie all this together as we move here, but at the risk of kind of foreshadowing, I love what you just said about politics rules everything. Based on last week’s speeches, World Economic Forum, there’s this notion that Thatcher and Reagan brought in this wave of shareholder supremacy, particularly over manager supremacy in capital markets. Though that period at some point is ending or ended in politics and geopolitics becomes…but did you anticipate when you were there that politics is gonna be a much greater portion of our lives.

It always, you can argue always has been, but it’s so endemic. Not just in culture, increasingly, in markets. And versus there was a whole debate that Thatcher and Reagan spawned, and effectively even Blair and Clinton embraced that, hey, markets are markets and politics is politics. Did you anticipate when you were in that world?

Gayle: Yes. Because I think this goes back to the people who win are the people who can see across silos.

Sanjeev: Right.

Gayle: And we’ve had a moment, and you and I have talked about this, and I know we talked about this at Summit, where there was this aberration where everybody could live in a hermetically sealed bubble, and everything could just keep going.

And people thought that was the norm, rather than the exception. I grew up in a union household. I worked for Steny Hoyer when and they said NAFTA, no. All of the Ross Perot stickers used to come in. And I never thought that you could divorce economic outcomes from the political moment.

Because at the end of the day, politics is really about the people who govern and people who are in power globally, no matter where you are in the world. And so they go to understand the moment, and as the moment changes, politics transform but they don’t ever go away.

Sanjeev: Yeah. It increasingly seems like it’s part of identity and religion almost. We’ll get into that. So you left media…

Gayle: Yes, absolutely. I think we’re in this moment of corners where it is religion. Yeah, and then I left to go to Spain on a Fulbright and to go to Germany on a Robert Bosch fellowship. And then finally, I left ABC News to go to Harvard Business School.

Sanjeev: And so you wanted to enter the world of business commerce?

Gayle: Yes. And I also believed, listen, I grew up with a lot of people who were looking for jobs. And I was fascinated by the idea of what does it take to create a job? Because I understood the dignity that work gives and the loss of dignity that being out of work immediately poisons your life, right?

I watched that firsthand with my father, and I watched it with a lot of people I grew up with, and I thought, I really wanna understand why business works the way it does, why capital flows the way it does. I understand the political piece, but I don’t understand the economics piece and the markets piece.

And so that was why business school was such a joy for me, was to learn. Now, first three months, they used verbs that were nouns and nouns that were verbs. Literally every second, I was like, wait a minute, what did they say? And then I would go back and be like, oh, that’s actually just like common sense.

It’s just a different language. And I had the privilege of already speaking different languages. So once I thought about it as a different language, then it was the same ideas. But in a different language. And I also realized there was real alpha you could generate if you take conventional wisdom from one sector and bring it to another,

Sanjeev: Yeah.

Gayle: Because things that are entirely common sense when it comes to my previous life in media were very different when I went to financial services.

So that was a real gift. But I went to business school really to understand how do you create growth? How do you manufacture hope, which is what growth does.

Sanjeev: And after business school, you went into finance?

Gayle: PIMCO. Yeah. And I was always trying to have multiple lives. I was a PIMCO for a number of years. I was in the executive office. I worked with an incredible leader, Bill Thompson, and then another incredible leader, Mohamed El-Erian, worked in emerging market product management in between, and really during the financial crisis, Washington was relevant again.

And the day of the TARP vote, one of the amazing MDs said to me, ​‘So that’s why TARP is gonna pass.’ And I was I hadn’t quite had my second cup of coffee. It starts very early in Newport Beach at the time. And so I was honest, and I said, ​‘No, there’s no way that’s gonna pass.’

Because that’s the worst vote anybody could take, right? There’s absolutely no reason why somebody would vote for TARP from the member level, right? And so everybody looked at me.

Sanjeev: To me in some ways I’m not sure we’ve fully recovered from ⁹⁄₁₁ globally, and in some ways, I don’t think we’ve fully recovered from that vote.

Gayle: I totally agree with you. And I also think that, and Mohamed would say this and this is something I thought about, we talked about, when you have socialized losses and privatized gains, it’s a deeply challenging moment that reinforces this idea of us versus them.

Sanjeev: But really, it brought to life what capitalism had evolved to, which is this notion of, do we really have capitalism or have crony capitalism? And I think that set a wave of both left right corners of this distrust of capitalism ​’cause deally you don’t have socialized losses and privatized gains. And I actually think about that a lot because if that is actual capitalism, is that what we want? 

Gayle: And I think this whole idea of fairness, you hear it in the politics today, that is a thread that runs through. And it was when I grew up with my mom was a union, CWA union household. And I remember being on picket lines with her when I was a kid. And at that point we had healthcare that was a hundred percent covered.

So my mother said, no matter how bad the job is, I always have comfort. If you need braces, it’s a hundred percent covered. And that was, I remember that to this day. How many people can say that?

Sanjeev: Yeah.

Gayle: So there is this fairness piece that keeps showing up, and that will keep showing up.

Sanjeev: Before we leave PIMCO, I’ve always thought of this James Carville quote, like, ​‘When I die, I want to come back as the bond market.’ And PIMCO was a navigator of that market for many people. Just as a niche question, I guess just for my own edification, maybe talk about for people that don’t know how influential they were in the bond market, and how maybe would you still agree with that quote? 

Gayle: Oh, look at today. I don’t think it’s any different today, Sanjeev. I truly do not think it’s any different today. The equities and the bond market are incredibly influential in this political moment. 

Sanjeev: And seem more and more correlated versus back in the day, they weren’t as correlated.

Gayle: Yeah. And I think, PIMCO, the founders were there, and it took very seriously and it continues to take very seriously its role in managing other people’s money. And I think there’s a sobriety to that and a seriousness to that and a real desire to be multidisciplinary.

It’s why somebody who came from news and then went to Harvard Business School could go and have an amazing run was because they would always say, you would go in and challenge conventional wisdom and say, look, I don’t see it that way. And here are the five reasons why. Here are the three reasons influencing that, and here are the two variables in this decision tree.

And it didn’t matter whether you had just gotten there or whether you’d been there for 10 years.

Sanjeev: But I think it’s an important life experience. Because if you look at three to 800 years of history of bond markets, particularly like 300 years, they do have an influence. And I think even the moment we are in, the spending from governments to pay unfunded liabilities or to finance aging and other things, it’s gonna have a feedback loop in places that we don’t think about. So I know the topic du jour is always equities but I do think the role of what happens to the bond market, I think it’s gonna have a particularly, we’ve gone from 3 trillion of debt to over 300 trillion of debt since Nixon got us off the gold standard.

The level of spending that governments are gonna have to do, for whatever reason, military aging, et cetera, et cetera, is not stopping. And at some point, it’s either gonna be monetized the way I imagine, or there’s a real set of unintended consequences that come including, I think, challenging assumptions around modern portfolio theory and how sort of the modern capital market and portfolio constructions work.

I don’t know if, yeah, no, I said a lot there.

Gayle: No, but think about this. Like to me, some of the themes and you and I frequently discussed this is trust, credibility, and confidence in the future.

The bond market is built on those. And the question is, what happens if you start to pull at the threads?

Sanjeev: Particularly at the 10-year, 30-year, and the longer duration stuff.

Gayle: That’s right. And that’s why I think, look, there are conversations going on about a Mar-a-Lago accord. There are conversations going on about a number of proposals that people might previously not have thought were possible. And this is a moment where you need a new imagination, right? If you take a Mad Lib and write down everything that you would write before the Mad Lib in the blank line, and then can’t happen.

You need to go back to that Mad Lib, make that whole list, and take away the T in can’t.

Sanjeev: Yeah.

Gayle: And really think through what the decision tree should include today.

Sanjeev: After PIMCO, what’d you do?

Gayle: I went to the Council on Foreign Relations. So I was at the Council on Foreign Relations, really writing a lot. I had an incredible journey at PIMCO and really left because I had a first book coming out about a teenager whose business supported her family under the Taliban. So I was going back and forth to Afghanistan from Newport.

Sanjeev: How’d you like come up with that story?

Gayle: I was there, actually, during business school. I was at BP for the summer actually, and almost went back to BP full-time. And then I went to Rwanda.

Sanjeev: Oh wow.

Gayle: For the last two weeks of the summer, to interview entrepreneurs and write about them. And I wrote this piece for the FT that was about this incredible entrepreneur who was making baskets with women whose husbands had perpetrated the genocide, and women whose husbands had been killed in the genocide.

And they were selling them at Macy’s department store in New York.

Sanjeev: Oh wow.

Gayle: It ended up being the front page of the FT’s entrepreneurship section, which they had at that time. And one of my professors at Harvard Business School said, ​‘That’s an amazing story. What do you wanna do next? We’re very supportive of this.’ And I said, ​‘If you’re gonna write about entrepreneurship, if you’re gonna look for women who own small and medium enterprises, like the story is Afghanistan.’

And I had the privilege of going there, and in the course of just scouring the city of Kabul and talking to a lot of entrepreneurs, I met this extraordinary person who had a business that had supported her neighborhood under the Taliban, and she actually became an entrepreneur because the Taliban took away every other option.

And that’s how she kept not only her family, but families all around her and her neighborhood afloat. And actually, some of the Taliban sent their daughters to work with her because they needed the money too. Back to where we started, which is that economics and politics cannot be divorced from one another.

Sanjeev: At the Council of Foreign Relations, what was your sort of focus areas? 

Gayle: Yeah. Economic development and how it intersects with geopolitics, and the role of women in economic development and how it intersects with access to capital, how hard is it to get access to capital in very tough parts of the world. Why is it that hard when it should be easy, and a place where you really need entrepreneurs who are fighting against every obstacle to build businesses that will be there the next day. Why do we make the cost of capital 27% or 23%? You couldn’t do that in Chicago.

Sanjeev: Yeah.

Gayle: And so it was writing a lot about that and basically giving the same speech 177 times and still mostly banging my head against cement, talking to people about, these are the growth engines, these are the people we need to reduce dependency, to increase growth. And these are the people fighting every single day for civility and security.

And I wanted to take it a step further and really get people to not think micro when it came to women, to try to think about the small and medium. It’s just very hard in those environments for everybody.

It doesn’t matter who you are, to start start a small, medium enterprise that grows because it’s very expensive. Capital is scarce, and capital is expensive, and frictions that exist can be daunting. So I was really trying to get roadblocks outta the way, or to use a bowling analogy, to try to get pins out of the lane for entrepreneurs.

Sanjeev: Did it give you an insight into where geopolitics was evolving? Because my notion, and going back to the statement of, I’m not sure we’ve recovered from ⁹⁄₁₁, was I’m a big believer in Hegelian Dialectics, and post ⁹⁄₁₁, it was a very much interventionist, willing to be, without a lot of debate, a financier of collective security.

And I think my sort of interpretation today was that we overextended. We effectively created a generation of folks who felt like the burden-sharing had gone too far in one direction.

And it’s created this sort of bipartisan dynamic of maybe we shouldn’t finance collective security to the extent that we do. Did you get those ruminations, or was it still more we’re in the middle of prosecuting, and no one could lose an election because of an attack, or there was not a lot of debate about the role of burden sharing in the financing of it?

Gayle: So I guess two things. One is it inspires you because you meet so many incredible people fighting against every obstacle imaginable. And people don’t live in geopolitics, people live lives, and that’s very easy to forget when you’re in DC. And I used to joke frequently that there’s much more hope in tougher places than there is in Washington.

Sanjeev: Yeah.

Gayle: And on the one hand, you had a very keen sense of the gap between the macro and the micro and the way people’s lives are lived. And on the other hand, you really did feel that afterward that the ghost of Iraq and Afghanistan hungover every decision made, and that goes far as today, right? The ghost of Iraq and Afghanistan really shaped the decisions that people are making and the collective exhaustion that a lot of people feel. And, look, less than 1% of the country fought a hundred percent of its wars for 20 years. So there’s also the exhaustion that came from those who were asked to serve.

And there’s certainly exhaustion in those who lived on the ground. But I think that it cannot be underestimated the lessons that period gave to this next generation

Sanjeev: I think rightly and wrongly, it also said, why are we doing nation-building abroad? We should do nation-building here. And then it gave an opening because I think while we were trying to do nation-building or whatever you wanna call it, potentially in Iraq or Afghanistan, the perception was, China’s focused on China and growth. Europe spends more on sort of safety nets and safeguards than necessarily military spending relative to its GDP. And so I think it gave an opening for more multipolarity, and then it gave like an introspection on the definition of unipolarity. I don’t know if you’d agree with that.

Gayle: Yeah, and I’d say two things on that. One is if you listen to Secretary Bessent’s interview with Human Events from Davos. It really gets to a lot of these conversations. You can trace a direct line. And I’ve had conversations with people who are part of the transition to this administration, really having these conversations, there is a direct line between those conflicts and the moment that we’re in.

And also this notion of fairness, the idea, and really interpreted in different ways, but the same kind of frame of underlying notion that’s informing the politics. The second piece is that you saw it on the ground, and it looked very different from the ground.

And you wanted to try to show that the economic possibility that people were fighting for, the stability that people were fighting for every single day, against all the obstacles. And so both of those truths were existing. I could see that was the political horizon that was coming.

And I think that was the one thing that really being a political reporter in my very first life, many moves back, really taught me to listen. Always have your ear to the ground. The danger is in not paying attention and imagining the world is as you wish it, versus as it is.

Sanjeev: Because I think I’m gonna tie this all together at the end, you got media and politics. You have markets and commerce. You have sort of geopolitics and people. What did you do after that?

Gayle: And then I’ve had this whole privilege of a journey to be able to write books, to work in early-stage technology, now advising a number of early-stage companies, and now really working in a visual AI company that is adding to the perception layer. And so it’s this marriage of understanding where the world was and where the world is headed, and being able to look from the outsider’s perch at both of them.

And I think, so writing books teaches you to read a room even better, right? Because every time you give a book talk, it must be like stand-up comedy is Sanjeev, where every room is different. You have the feel of where people are, where they’re going, and you really try to take a personal story and make it universal.

And I think with emerging technology, the whole idea is how do you build trust and make it relevant and useful to people’s lives? Always with trust at the center. And how do you build an enduring company that means something to people? And I think the enduring piece and the values piece is one you have to think about all the time.

Sanjeev: You brought up AI. What is your view of that word?

Gayle: Yeah. It’s become a Rorschach test, hasn’t it? It’s what everybody says.

Sanjeev: I think it’s becoming more and more under scrutiny as well.

Gayle: For sure. But this goes back to where we started the conversation. If you want to think about where this moment is, right? You think about the idea of fairness, and if you think the idea of is it more for more or more for fewer?

This all comes back to what does the economy mean for me? Then if you drive forward and you and I talk about systems investing all the time, then it goes back even one step further to what do I have to believe to make this investment make sense?

And let’s go beyond that to be alpha creating, right? Alpha inducing. And if we have this moment where people don’t feel they have a stake in growth, it becomes incredibly challenging to sell them on the vision of it.

Sanjeev: Yeah.

Gayle: I believe that AI is going to be both incredibly helpful for outsiders and that it puts the tools in everybody’s hands so the gatekeepers have transformed. And then also deeply challenging because scale is everything.

Sanjeev: It’s this bifurcation. Is it techno utopia or techno feudalism?

Gayle: Yeah. And does it have to be one or the other? Because everybody’s living in corners right now. I deeply believe that it is going to be a transformative technology that reshapes in ways that we don’t know yet, right? And that also it will be in our best interest for people to understand the why.

And if we look at what leaders need in this moment, we need iceberg language, not arugula. One of the biggest challenges we’ve had is that people have somehow taken complex as a synonym for smart.

Sanjeev: Yeah.

Gayle: And speaking in ways that,make a lot of sense at the Greenbelt High’s, or the ⁷⁄₁₁ is actually really a good idea, not just for political stability, but for economic growth.

Sanjeev: Yeah. Like it’s one of those things, it’s hard to put something on one page as opposed to 90 pages.

Gayle: Yes. Exactly. And also we have placed currency on multi-syllabic as a synonym for intellectual.

Sanjeev: So I bring this all back because why I’m so excited to always talk to you. I’d like to talk to you more, we’re both busy. And why we wanted you on our podcast and our ecosystem and to collaborate with you is to me you’re like the, your career has been the living embodiment of what of what we’re focused on and around in terms of these five pillars that we define and brand as the age of adaptation.

The world’s moving from CPU to GPU, shorthand for AI. From a unipolarity to multipolarity with geopolitical dimensions and dominoes that we don’t know fully. From an declining price of money to an unknown price of money. And then the fourth is entropy. So one, climate heating from 1.5 to something two, 2.5, and then aging. And it is my thesis, and I’m curious to hear your view on it, is these five, the cocktail, all these five are gonna change beta and alpha. We’ve talked about alpha a bunch and every sort of, I don’t know, 50 to 80 years beta changes. Do you think, I’m just curious, and you should very much feel free to disagree.

Gayle: Always.

Sanjeev: But these five and perhaps others we’re at employment where for investors, company builders, policy makers, like if you really internalize like the system level outsider view of all five of these and perhaps others, trying to underwrite your view of beta and alpha, just be careful. And I’ve obviously think beta’s gonna change and more structurally than most ICs and most sort of investment incentives allow people to do. But I don’t know, how do you react to that?

Gayle: I think that homogeneous thinking is going to lead to value destruction, right? And you really need multidisciplinary approaches. And I think you and Chuck, and Aaron talked about this on your preview of 2026, and you know that you have to be sober. And this is what I mean about the Mad Lib, right?

You need to put a blank for can’t happen. And then go back and write everything you think that can’t happen. Question every single one of them. Take the ​‘T’ off, put can happen, and then also do the thought experiment of where that leads. Because we are really in a moment of wet cement. It is not yet hardened, and we’re watching real transformations happen, I think the five that you mentioned are very much in play. And then I would also think back to, if you think that you’re moving from, the folks in asset light industries going into asset heavy industries, right? From this idea of globalization to now the nation is our heartthrob, right?

Everybody’s going back to it. Then what does that mean for resource allocation, and what does that mean for resource sovereignty, which is a huge theme that I think hasn’t been explored enough. It’s, yes, alliances will matter, but everybody thinks that they also need to do it themselves because when there is less trust on the chessboard, everybody has to make sure that they have every piece also.

Sanjeev: And I think what I’ve struggled with is like how do you tell this in a way that is iceberg versus arugula?

Gayle: Yeah.

Sanjeev: It’s just been a struggle for me to be like I believe in multidisciplinary thing. I believe in systems thinking, which is to me the art of first, second, and third order thinking applied to real things.

And then obviously what we’re trying to build is a system investing firm that underwrites this.

Gayle: And what you have built. Yeah.

Sanjeev: Yeah. And I think that’s what we continue to evolve and try to get better at every day. But like a food underwriting, a grid underwriting, a logistics supply chain, yeah, it’s about the management team that P&L, really understanding the structure, but there’s some things that you still need to pay attention to. If the 10-year is, 6% rather than three, no matter what happens, your exit multiple is gonna be impacted, ​’cause the price of money often drives multiple expansion or multiple contraction. It has nothing to do with any industry, sector, company. And so there are these larger forces that are systemic that, again, in a micro underwrite of a company that’s in the grid services industry or in supply chain, you know?

But how do we get to the iceberg of these systems issues? ​‘Cause you are an outsider, you’re a storyteller. You understand these different worlds as we’ve just come to learn. But how do we get iceberg about systems thinking and interdisciplinary thinking?

Gayle: So one thing I remember joking with my bosses at PIMCO about is, and I learned very early watching the best account managers at PIMCO is like, nobody likes to be bored. So I always start from first principles, right? What can people not be against? And nobody likes to be bored.

Sanjeev: Okay.

Gayle: So then the framing I have used for a lot of this is this whole idea, this is the age of AGE: AI, geopolitics, and energy. And get people underneath to understand that this is a trio of Grammy winners that don’t necessarily sing in harmony, but they have to work together to make some music because AI is going to determine the shape of geopolitics and it requires energy. Energy will determine geopolitical dominance, and it’s required for AI. Geopolitics will large part be shaped by AI supremacy and energy sovereignty, and security. 

And so to me it’s can you start with a framing in a prism that people can then say, okay, I get those right. I may not agree with you on all three, but it gives me a framing. And then I just go deeper and deeper using, I think, maybe that’s where growing up in PG county and going to Denny’s and getting my cheese sticks every Friday or whatever it was taught me a lot about just listening to people and how they talk. And you have to have deep respect for where people are. The reason why sometimes things are really complicated for people is people have to figure out, how am I gonna take care of my kids?

How am I gonna pay for sports? How am I gonna, I have 10 things to do between now and the time I listen to you talk about systems thinking, Gayle, that’s great, but come on. And so it’s more about…

Sanjeev: But Maslow’s hierarchy is entangled with those three things, too.

Gayle: That’s it. A hundred percent. A hundred percent. Having been in places and the privilege of being in places where energy was scarce, and electricity was almost non-existent, right? You realize its role in stability, security, and economic opportunity. And so, to go back to your question, I do think it is about meeting people where they are and framing the ideas that you’re working to communicate based on how they see the world and what folks are facing every day.

Sanjeev: So let’s move from system thinking. How many system thinking principles are being applied to investing today, in your view?

Gayle: I would ask you that question. Look, I think there are just incredibly smart people, many of whom you know and maybe I went to business school with, and a lot of people I talk to regularly. There are, but I think there’s also the hype cycle is hard to ignore, and that is why I think it’s always critical to separate noise from signal.

Always. And it’s very hard and it’s getting increasingly, and I would say exponentially harder, because the cycle is quick wins, fast returns, triple-digit alpha, and it’s hard to be sober when the champagne is flowing.

Sanjeev: Yeah.

Gayle: And so to me it is where I always come back to is who are the investors who can put the volume on zero and do their work?

And it’s why I’ve always followed Berkshire. It’s it’s why we followed people who say we build for more than the next two and a half minutes until the commercial break in old school parlance, or 15 seconds until the next video shows up in new media world.

Sanjeev: Where are we in 2026? Where are we going? We’ve obviously had a very exciting January geopolitically, even today with the Fed being announced, with Claude bot. And as we sit here on January 26^th, I feel like all of the things you just talked about geopolitics, energy, AI, just in January it feels like a year.

Gayle: It does right?

Sanjeev: So January feels like a year. Are we just gonna have more of these with those three things that you’re focused on, AI, energy, and geopolitics? Where are we going?

Gayle: Uncertainty is a feature, not a bug. And there’s a Buddhist teacher I’ve been listening to who was teaching about making friends with fear and getting comfortable with discomfort and getting comfortable with fear. And I really think that there is possibility and opportunity in upheaval. But you have to have a strong stomach, and you have to have the values that motivate you front and center.

And so it really is, to your question about investing and when you’re underwriting a company, it’s, do you have a team that has more than mono-thinking at its heart? And do you have a team that understands that real buffers have to be built in. That scenario planning, that resilience is not something that can be excluded from the model.

Sanjeev: One thing I wanna. Just ​’cause I’ve grown up in financial services, and to me a lot of financial services is CYA on the way down. It’s like, all right, everyone has an incentive structure, CYA, and the past is the future. The brand is the brand. 

Like it’s a bit of a herd mentality that structure, I believe, if you’re gonna go from the era of moderation to the era of volatility, uncertainty, CYA actually has to be bottom up, which what I mean is, at board meetings, at management team meetings, portfolio construction has never been more important.

And it’s bottom up because even something like there’s a seed stage company that was trying to figure out their supply chain, and they’re like, what’s China gonna do with X or Y, what’s the US gonna do with China? And it’s like, how do I manage inventory? And I was like, I’m reading Foreign Policy Magazine, I’m going to this. I’m like to make an inventory decision, you’re reading geopolitics? But that management team and that CEO is like I’m figuring out my working capital inventory dynamics, and geopolitics gets involved. And then even at what we do, you have to think about portfolio construction. ​‘Cause the risk that’s levered to can’t be the risk that every other company’s levered to. ​‘Cause then you’re fully levered to one set of risks in their portfolio. 

Gayle: No, for sure. And here’s my arugula reading, my read back, right? I worked an amazing CTO who would always read back to me what I had said. And I think an expansive imagination is critical to value creation.

Sanjeev: Yeah.

Gayle: And that’s what I would say was that business as usual in terms of, oh, we have a subject matter expert, and then we’re gonna bring this to market in six months and here’s our customers. No, you better be ready for everything. And you have to have modeled it out. You have to put volatility and turbulence into the model. It is not enough to say, Oh yeah, we thought about it.

Sanjeev: Inventory, working capital…

Gayle: Downside scenario planning, upside scenario planning

Sanjeev: equity, everything. Yeah.

Gayle: And it also means that storytelling is critical because it’s so noisy. And we’ve watched media face real challenges. So individual companies, voices are ever more important. The content piece of the voice, the authenticity, the trust that people have in a company that they build through what they write, through how they go out in the world, that becomes even more important because it becomes a differentiator in an ever more noisy world where mainstream media is not always going to give you the return that it might have, 15 years ago, 10 years ago, even five years ago, right?

And so portfolio construction becomes a much more expansive exercise and one that requires decision trees that go into different forests than they might have previously, but they have to be done with real discipline.

Sanjeev: This inventory question it’s very specific. I was like, you need to have a portfolio approach to this inventory decision. ​‘Cause if you just have one approach, it’s probably the cheapest from an economic perspective, but you’re gonna sacrifice some margin, but then you’re hedged if this happens or this happens.

Gayle: Your buffer could be your savior.

Sanjeev: Yeah.

Gayle: This is the world we’re in, right? Because you don’t know with policy turbulence and different countries with different policies, and potentially bilateral relationships transforming in more rapid moments than they had previously. You have to be right.

And this is what I mean, that it has to be in the model, right? The expansive thinking about the possibility set and then drill down to the rigor of what does that mean for an individual company.

Sanjeev: And this is the art and science of anti-fragile company building in the 21^st century, where volatility ends up making you outperform and not just, it’s not a cost. And that’s probably a whole other podcast that you should

Gayle: Exactly.

Sanjeev: I do think things like that will help you build fragility potential, but then at the same time, there’s some fragility to that.

So I think it’s very much an art, you’ve done so many different things. As we bring it to a close, I’ve seen a theme of outsider in a lot of what you do that’s allowed you to be a multidisciplinary systems thinker. But at the same time, simplicity and storytelling, really understanding sort of people and not just all these other sorts of esoteric and sometimes opaque things that influence people’s lives. Both known and unknown. But I wanna end this podcast with you were also an insider. You were booking guests in very

Gayle: for sure.

Sanjeev: You were

Gayle: As my great aunt used to say it’s hard to be a Fulbright scholar and a Harvard Business School graduate, and then say you’re an outsider, and yeah.

Sanjeev: Yeah. But you being an insider and with an outsider’s heart or DNA, maybe just talk a little bit about what you learned. Because I think the perception of insiders today has never been more critiqued. The sort of the elites and what’s happening on the corners.

But maybe just talk about lessons learned from being on the inside for folks, in the way that they relate to things around problem solving or the ability to kind of story tell. Like you’ve been exposed to, you’re being very humble, but a lot of people and a lot of people that have done a lot of things.

Is there a through line and lessons learned for our audience, our entrepreneurs, our management teams, our leaders, our fellow sort of travelers of the things that your mentors or things that have done less, like any sort of life lessons for people.

Gayle: Yeah, I think there’s so many. And maybe I’ll go back, and then I’ll go forward. So I think the risk with all the conversation about affordability is that it was actually the last fight.

People aren’t looking ahead to what’s next. And I think this is the next conversation is what is facing families?

Sanjeev: Yeah.

Gayle:  And how do families make it economically? And this is globally, right?

How do they get through? How do families who are working figure out how to make a life that feels like it has a stake in the system. So back to systems-level thinking, right? You have to also think about who is taking part in the system and how, and why do we keep that together, right? How do we keep that moving forward, and how do we keep shared security, stability, and prosperity?

Sanjeev: And that’s the north star of a lot of this. 

Gayle: That’s right. And then, yes, I have had the privilege of a career and really worked with people who taught me a lot, and I probably learned the most from my mom, who used to say, on a scale of major world tragedies, yours is not a three. I don’t wanna hear it. Nobody cares.

And actually, I had never talked about my family, I never talked about…My mom was sick with breast cancer when I was 10 and passed when I was 13. And when I was 11 or 12, we went to apply for food stamps because she was trying to figure out if her union job was gonna make it and what the benefits would be.

And I was so embarrassed. And the biggest thing that it taught me was that, like all these things I had been embarrassed to talk about when I was first becoming an insider, entering these rooms, actually you realize are the superpower that you have, which is you grow up in the norm of scarcity and constraint. And I think we are in this world, and you and Chuck talked about this on the podcast previewing the year, right? If you think scarcity and constraint are the norms that are going to stay, they engender a huge amount of creativity, and that was the biggest lesson I had from the people I grew up with, and the people I actually worked with afterward. And I don’t want to downplay trauma in any way. And everybody’s experience is so different. I would say, though, that adversity drives opportunity. And that ability to be resilient is a gift, right?

Sanjeev: Again, thank you again. That was a great ending.

Tonya: Thank you for tuning into the S2G podcast. If you enjoyed this episode, please subscribe, leave us a review, or share it with a friend. For more information or to connect with us, check out s2gin​vest​ments​.com.