May 14, 2026

The Sweatshop of the Meritocracy: Dylan Gottlieb on How the Yuppies Conquered America

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“As recently as the mid-seventies, under 5% of Ivy Leaguers are headed to Wall Street. It’s actually not that attractive. But as Wall Street’s deregulated, it changes the incentive structure — it makes it much more profitable and demands this huge labor force.” — Dylan Gottlieb

They stalked the sidewalks of Manhattan in button-down shirts embroidered with the names of investment banks. They jogged. They drank Beaujolais Nouveau. They gentrified neighborhoods. They were the Yuppies — and with the Boston-based Dylan Gottlieb, they’ve found their young urban professional biographer.

In Yuppies: The Bankers, Lawyers, Joggers, and Gourmands Who Conquered New York, Gottlieb offers both a social history of financialization and a collective biography of the professional class that came of age in the Reagan years. Rather than a passing 1980s stereotype, Gottlieb argues that the Yuppie is a phenomenon that remade the American economy, city, and political class. As recently as the mid-1970s, under 5 percent of Ivy League graduates went to Wall Street. A decade of deregulation later, banks were recruiting a third of graduating classes from top universities. The sweatshop of the meritocracy was born. Most of us are still sweating.

Five Takeaways

From Yippie to Yuppie: The Word’s Origins: Yuppie resonates with Yippie — the iconographic late-sixties radicals of the New Left, for whom Jerry Rubin was the signifier. The word first appeared in a Chicago alt-weekly in the late 1970s to describe highly educated young people trickling into gentrifying North Side neighbourhoods. It didn’t achieve full cultural dominance until 1984, when it became the frame for supporters of Gary Hart’s presidential campaign — a prototypical Yuppie candidate who stormed the Democratic primary and represented a new professional vanguard within the party. The word named something that was already happening. It didn’t create it.

The Incentive Structure Changed: Under 5% to One Third: As recently as the mid-1970s, under 5 percent of Ivy League graduates went to Wall Street. It was seen as the preserve of WASPy children who used family connections to get a bank job. By the mid-1980s, banks were recruiting roughly a third of graduating classes at top universities. What happened: deregulation made finance enormously more profitable; finance demanded a large educated labour force to do the work of putting finance at the centre of the American economy; and the most talented students — those who might have become poets or public servants — followed the money. At mid-century, the most prestigious option for a Princeton graduate was middle management at a Fortune 500 company. By 1985, it was Wall Street.

Democratization and Distinction: The Double Movement: Gottlieb’s central thesis is a double movement. The Yuppie era brought genuine diversification to America’s elite: Jewish lawyers could now make partner at firms previously closed to them; women entered investment banks in numbers that would have been inconceivable in 1965; Black and Asian Americans got at least a foot in the door. This was new, and it mattered. Simultaneously, that newly diversified elite pulled further away from the rest of America, extracting profits from companies being financialized and rents from communities being gentrified. Democratization and distinction in constant tension. The elite became more diverse and more remote at the same time.

The Pyramid to Cylinder Shift: AI is about to do to the Yuppie what the Yuppie did to everybody else. Gottlieb spoke recently to an HR representative at an investment bank — name and bank withheld — who said the firm was moving from a pyramid structure to a cylinder structure for employment. The wide base of entry-level workers that finance has depended on since the 1980s will shrink dramatically. Only the best and brightest will be selected; the rest will be automated. Gottlieb wrote about the era of the large pyramid — the exploited many at the bottom who hoped to reach the top. What happens to the professional class when that pyramid disappears?

Are the Yuppies Becoming Socialists? A long-running trend: the pressures of the sweatshop of the meritocracy have embittered many members of the professional class. Academics work in conditions demonstrably worse than they were forty years ago. Doctors are evaluated on metrics that resemble those of factory workers. Journalists are precarious. The housing market in the cities where professionals cluster has made the cost of replicating their social status for their children prohibitive. And into this comes AI, threatening the entry-level pipeline. Gottlieb’s question: will the investment bankers see their plight as similar to the Amazon warehouse worker’s? Or will the edifice of meritocratic myth-making — the deep conviction that you’re special — hold them back from that solidarity?

About the Guest

Dylan Gottlieb is Assistant Professor of History at Bentley University and co-host of the Who Makes Cents: A History of Capitalism podcast. He is the author of Yuppies: The Bankers, Lawyers, Joggers, and Gourmands Who Conquered New York (Harvard University Press, May 12, 2026), winner of the Herman E. Krooss Prize for Best Dissertation in Business History. He has written for the Washington Post, Gotham, the Journal of American History, and Public Seminar.

References:

Yuppies: The Bankers, Lawyers, Joggers, and Gourmands Who Conquered New York by Dylan Gottlieb (Harvard University Press, May 12, 2026).

• Noam Scheiber, Mutiny: The Rise and Revolt of a College-Educated Working Class — the companion book, referenced in the interview as directly relevant to Gottlieb’s thesis.

• Barbara Ehrenreich — referenced by Gottlieb as the first to identify the downwardly mobile tranche of the professional class.

• Episode 2895: Glyn Morgan on the rise and fall of American Europe — the companion episode on how the professional class shaped American foreign policy.

About Keen On America

Nobody asks more awkward questions than the Anglo-American writer and filmmaker Andrew Keen. In Keen On America, Andrew brings his pointed Transatlantic wit to making sense of the United States — hosting daily interviews about the history and future of this now venerable Republic. With nearly 2,900 episodes since the show launched on TechCrunch in 2010, Keen On America is the most prolific intellectual interview show in the history of podcasting.

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00:31 - Introduction: Yuppies and the Scheiber connection

01:40 - Cambridge: a suburb of New York?

02:06 - Where did the word Yuppie come from?

03:15 - Gary Hart, 1984, and the Yuppie enters politics

03:27 - Packs of twenty-somethings in button-down shirts

03:49 - Personal stake: a TA at Princeton watching students go to Wall Street

04:33 - Jesse James and why people rob banks

04:46 - Under 5% of Ivy Leaguers on Wall Street in the mid-seventies

05:38 - AI is replacing the Yuppies: who were they before they existed?

06:00 - Fortune 500 vs. Wall Street: how the prestige destination changed

07:18 - Mourning or celebrating the rise of the Yuppie?

08:15 - The double movement: democratization and distinction

09:21 - Agency and plundering: did the Yuppies know what they were doing?

11:00 - The sweatshop of the meritocracy

15:00 - Gary Hart, Walter Mondale, and the Yuppie political takeover

20:00 - Yuppie lawyers and the financialization of everything

25:00 - Yuppie joggers: the New York City Marathon as status marker

30:00 - Yuppie gourmands: the food revolution

35:00 - The Yuppie city: gentrification and the transformation of New York

40:00 - The pyramid to cylinder shift: AI and the end of entry-level finance

44:57 - The Scheiber mutiny: the professional class becomes the working class

46:36 - Are Yuppies becoming socialists? The Mamdani question

49:09 - Precariat of the world, unite: you have nothing to lose but your running shoes

49:31 - The theory of the unleisured class

00:00:31 Andrew Keen: Hello, everybody. Last month, we did a show with the very talented New York Times journalist, Noam Scheiber, about what he calls an anticapitalist mutiny, the rise and revolt of a college educated working class, or they were a middle class. Now they're becoming a working class. His new book is called Mutiny. And, of course, that college educated class used to have another name. They were once known as Yuppies, young urban professionals. And, today, we're talking Yuppies with my guest who had a lovely feature in The New York Times, an essay called Speak Yuppie. Dylan Gottlieb, who teaches urban history at Bentley University in Boston, has a new book out. It's a Harvard University Press book, Yuppies: The Bankers, Lawyers, Joggers, and Gourmands Who Conquered New York. And Dylan is joining us not from New York, but from Cambridge, a suburb of New York, isn't it, Dylan?


00:01:40 Dylan Gottlieb: Don't tell that to the folks here. They won't wanna hear it. But, yes, a suburb of Boston and more distantly, New York.


00:01:46 Andrew Keen: So I'm not sure if you're familiar with the Scheiber book, but it's very much, I think, in your theme. Yours is a history of the yuppies. You argue that the origins lie in the eighties. Is that fair? Where did the word first come from?


00:02:06 Dylan Gottlieb: Well, the word has this sort of resonance with yippies, which, of course, are some of the iconographic late sixties radicals of the new left. Jerry Rubin is the real, signifier for them. Right? So Yippie and Yuppie have this resonance with each other. But Yuppie isn't coined. The origins are a bit misty, but, the late seventies, it comes into use first in Chicago in an alt-weekly paper to describe the ranks of new young highly educated people that are trickling into certain neighborhoods that have begun to gentrify, particularly on the North Side of Chicago. But the word doesn't really come into full and dominant cultural usage until 1984 when it becomes associated with supporters of Gary Hart's campaign, this sort of prototypical Yuppie candidate who storms on the scene in the Democratic presidential primary, and — as I'm sure we'll talk about — represented a new sort of vanguard of the professional class within the party. But more broadly, Yuppie is used to characterize this whole group of people who are appearing along the avenues of cities like New York or San Francisco where you are. Again, highly educated credentialed workers working in a certain range of white-collar occupations, particularly those related to finance, and forging new cultural and social lives in those cities, places that had been abandoned by the middle class for at least several decades to that point.


00:03:27 Andrew Keen: Yeah. You describe them, as packs of twenty-somethings stalking the sidewalks of Manhattan in button-down shirts and vests embroidered with the name of an investment bank. Is there an element of disgust, Dylan, or envy in your work on Yuppies? Did you once get abused by a Yuppie?


00:03:49 Dylan Gottlieb: We're getting into the psychoanalytic material very quickly here. So those are the modern incarnations, and there is no small amount of personal stake in this story, I'll say. You know, I was a TA and then a lecturer at Princeton where I did my PhD.


00:04:02 Andrew Keen: Yuppie Fortress, isn't it?


00:04:04 Dylan Gottlieb: It is — yeah, it's the mint for Yuppies. As I show in my book, it has specific origins. But by the time I was there in the twenty-tens, some of the most talented students in every seminar were headed off to investment banking. And it really puzzled me why were we harvesting maybe a third of the full graduating class every year and taking them off to do this work in cities like New York. Why weren't they writing poetry? Why weren't they pursuing other perhaps more socially productive ends with their one republic tradition?


00:04:33 Andrew Keen: Yeah. You know the answer to that. I mean, it's the old Jesse James question. When somebody asked him why he robbed banks, he said, well, that's where the money is. Who's gonna go and work as a poet when you can go and work at JPMorgan?


00:04:46 Dylan Gottlieb: Well, sure. But you're right. The incentive structure changed historically to actually lure all of those people there. You know, what's interesting and I discovered in my research is that as recently as the mid seventies, you know, under 5% of Ivy Leaguers are headed to Wall Street. It's actually not that attractive. Sure. You can make money, but it's not seen as the most desirable option. It's, you know, the preserves of the WASPy children who don't have other options or use their connections to get a job at the bank. But as we'll talk about, it becomes the most desirable option as Wall Street's deregulated. It changes the incentive structure. As you say, it makes it much more profitable. It also demands this huge labor force to do the work of making finance, putting finance at the center of the American economy. It takes these grunt workers, but it also takes changes in the political economy to draw them to Wall Street.


00:05:38 Andrew Keen: And, of course, when it comes to labor, one of the arguments, behind Scheiber's book and his work is that AI is replacing those workers. So who was Dylan, or what were the Yuppies before the Yuppies? Where was the money in the sixties? I mean, for an ambitious kid coming out of Princeton or Harvard or Yale or Stanford, where did they go?


00:06:00 Dylan Gottlieb: That's a great question. I think that, first of all, the number of people emerging from those universities is much smaller. And demographically, it's a much narrower slice of America. You know, it really is the province of WASPy, you know, protestant elite young men who form the backbone of overwhelming majority of those graduating from top schools. But that begins to change in the nineteen sixties as those schools admit first white ethnic men, then increasingly white women, and then other members of minority groups who, through the rights movement of that era, find their way into those schools. So that's gonna change. But also the nature of the employers is gonna change as you note. In the early mid sixties, it was very prestigious to go into management in the large Fortune 500 corporation. You know? If you went to Wharton undergrad at Penn, you know, I found the recruiting statistics there. You'd head off to become an you train in accountancy, and then you head towards middle management at Ford, GM, Kodak, these large solid corporations that were the backbone of mid century America with their clubby, all male leadership. But that would begin to change in the nineteen seventies and especially the nineteen eighties as finance moves to the fore. So the most prestigious option changes, but also who's in the driver's seat of the American economy changes.


00:07:18 Andrew Keen: So is this something I mean, I don't know whether we should be simultaneously mourning and celebrating the rise of the Yuppie. On the one hand, you and we'll talk more about this. They seem to epitomize this new neoliberal economy. These packs of 20, you talk about them. You have some wonderful, ways of describing them. They're the first members of the sweatshop of the meritocracy, so that's probably not very attractive, although they don't seem to be unhappy about doing it. No one's forcing them into this sweatshop. On the other hand, you have more diversity. You have, people of different skin colors, sexualities, genders, blah blah blah who are able now to enter the American meritocracy. So is it on the one hand and on the other when it comes to the, the benefits, the upside and downside of this rise of the Yuppie, Dylan?


00:08:15 Dylan Gottlieb: It's a complicated double movement that I think you alluded to really well there. So on the one hand, there is a democratization and a diversification of America's elite. Just simply put demographically, like, if you're a Jewish kid, you can make it into the very highest ranks of a law firm. If you're a black woman, you may at least get into the entry level of an elite investment bank. That is new in American life, and it shouldn't be underestimated how important that is. But at the same time, as we see the small, halting, incomplete diversification of America's elite, we do see that top, say, 10% of earners pulling away in terms of their material fortunes from the rest of America that they're quite actively plundering through those jobs. So it is a sort of double movement here. Right? Democratization and diversification of an increasingly remote elite that is pulling away from the rest of America that's suffering as a result of finance's rapacious attitude towards, say, the companies they're chopping up or merging or taking over. So democratization and distinction are sort of always happening in tension in this period.


00:09:21 Andrew Keen: So you seem to suggest a strong degree of agency in this new Yuppie class. You say they're quite actively plundering. These are the new crusaders, are they? They know exactly what they're doing. They're stealing from the poor working class. Is that your argument?


00:09:38 Dylan Gottlieb: It's not that explicit. And let's remember, there are sort of offstage in my narrative, the plutocrats, the true 1% who are, let's say, the generals directing the armies of financialization. I'm not writing about them. We sort of know that the we wanna call it the Epstein class today. We understand their motivations, the way they profit from this story. What I wanna write about and actually be sympathetic to are these grunt workers, the shock troops on the front lines who are being thrown over the top on the remaking of the American economy. By those, sure, directing the action, it takes ordinary people to do the daily work of financialization, to draft the memos, to proofread the motions, to imagine the trades or the deals. It really is labor, and my book is in part of labor history in that sense. And in that way, I wanna be sympathetic to the choices of these yuppies in this moment who are making tough decisions about what industries to enter under conditions that have transformed since, say, the nineteen sixties when there were two jobs for every college graduate. If you graduate in 1979, 1981 in the midst of a recession, and you're competing against a much larger group of college educated graduates, maybe the path of least resistance but also most security is to go to a career services meeting where a bank recruiter is there and you say, yep. Sign me up. This is a path towards middle class respectability and security. This is a prestigious option. I'm a good student who made it here in strength of my credentials, and I wanna continue to do that. So I'm sympathetic to the choices they're making within a larger political economy that I'm less sympathetic to.


00:11:12 Andrew Keen: And you talk about, as I said, this sweatshop of the meritocracy. It's a lovely phrase, Dylan, but, you know, for people who have actually worked in a sweatshop or even know anything about a sweatshop and people stuffed into unpleasant buildings, in South Asia. Describing a law firm or a or bank in New York as a sweatshop seems a little bit of a stretch, isn't it?


00:11:36 Dylan Gottlieb: Oh, it's a little bit hyperbolic, and I appreciate that. But it's meant to be provocative. And I will say it's not my term. It's actually the term that young law associates apply to their very own firms. And while it might be over the top, it is perceptive about the new forms of labor organization and control that they're experiencing on the front lines of financialization. You know, in the nineteen fifties, if you became an associate at, let's say, Cravath, the ultimate white shoe law firm, it was one associate to every partner You were apprenticing for, hopefully, not all of them, but hopefully a long tenure at the firm. You yourself were probably out of that WASP elite, out of the top three Ivy League law schools. It was a clubby, if exclusionary world, and you worked a lot less than you would later. But after finance and its sort of transaction-driven attitude came to the law firm and transformed it, the working conditions for those young associates do become much more exploitative and extractive. Sure. It's not literally sweated labor, but in terms of the profit margins extracted from those associates, it really does look like conditions of disposability that are familiar from the factory floor. And they're working under new conditions of almost Taylorism that are rolled out as law firms and banks bring in MBAs to regularize and surveil their employment systems. So they get computerized billing sheets. They can track how many minutes an associate's been in the bathroom or how many breaks they've taken, how much they've reached or approached a 100% utilization rate, they call it, for the fictional associate who took no breaks, had no personal conversations, didn't eat lunch. And so as associates are increasingly tracked, surveilled, asked to work sixty, seventy, even seventy-five-hour weeks, month after month after month, they realize this is unsustainable. It's exhausting. And many of them quit, but that's by design. They're disposable. Now it's many associates for every partner by the mid eighties, and there's always a new class of increasingly indebted law students waiting to replace them. So in terms of this, you might say, surplus army of labor, in terms of the, you might say, proletarianization of white-collar workers and immiseration, it's not quite a sweatshop. They're sweating more often at the gym than in the law firm, but there are similar conditions of exploitation that we shouldn't forget.


00:13:51 Andrew Keen: No wonder Jeff Bezos, who was an early Yuppie, I think after he graduated from your university, Princeton, I don't know what he studied there. I think he studied computer science or math. He went to a bank and then, found it probably a little too exploitive, so he came out west to start Amazon, maybe opened another chapter in the exploitation surveillance economy. You mentioned the cultural aspects, the subtitle of your book. They're not just bankers and lawyers. They're also joggers and gourmands who conquered New York. The picture on the cover looks like something out of when Harry Met Sally. Is the cultural element important, Dylan, or is it just fun to make fun of these young professionals who, when they weren't working, worked even harder jogging around Central Park or eating at these expensive restaurants.


00:15:00 Dylan Gottlieb: I'm trying to make sense of their entire worldview experiences and work, but also leisure, which I do think is fundamental to the class transformation and class formation story that I'm telling here. Because yuppies don't understand themselves just as meritocrats, upwardly mobile in the workplace, but as fully fleshed individuals as we all are. And so to understand them using all the tools of social history, I wanted to go out of the workplace, beyond the workplace, and into their leisure time. So let's take something like running, which is so iconic when we think about nineteen eighties New York. And indeed, it's actually a way the city markets itself to attract even more yuppies is to take images of a race like the New York City Marathon, which is designed expressly to attract white-collar professionals and beams it to millions of viewers around the world. This is a new vision for a city that quite recently had been in fiscal crisis. Right? Jogging professionals moving through New York's five boroughs. But why do your yuppies actually take to running, and what's new about it? Well, in the seventies, late sixties, early seventies, running was jogging. Right? That was the term we used, jogging. And for many, it's a countercultural practice. It's about getting in touch with your body, loosening up, being out in nature, maybe even barefoot. It's not competitive. But by the nineteen eighties, the regimes of fitness change and align with the newly competitive world and the brinksmanship of the white-collar workplace. And this to yuppies is just catnip. Right? In my many interviews I did with folks who were members of track clubs in New York, they can still remember their finishing times in five k's from thirty, forty years ago. And that competitiveness, that sort of profit and loss mentality, the objectivity of finishers times, the competitiveness of practicing 100-mile weeks for the marathon really fits with this idea that leisure has become a new form of work, a new venue to demonstrate your fitness at the very top of the hierarchy. Sitting atop New York is a way to explore the city, but also a way to form social ties. Many describe their running clubs as something akin to the suburban golf club for the mid century professional, except now you're doing it out in Central Park Reservoir, you know, making deals, meeting a potential spouse, doing the class formation activities that help you understand yourself as part of a new cohort in the city with something in common.


00:17:22 Andrew Keen: Yeah. Class formation. Maybe we can come back to that. I'm a bit skeptical about that, but, you know, you should talk — I'm not sure if you ever have — to him. You should talk to Nick Thompson, who's the CEO of The Atlantic. He just wrote a book on running, and he was or is the fastest man over 50 in the world, and he sort of seems to epitomize your jogger or runner who conquered New York, not just New York, but the world. What about the food side? I just saw a headline in The Nation, which is a review of Jay McInerney and his Lost New York. There will always be the Odeon, which is very nice — I've been there. I would certainly not turn down a meal there. Why was food or why is food alongside running so important?


00:18:21 Dylan Gottlieb: Well, you know, in the popular imagination, food and certain food signifiers are the first thing people think of when they hear yuppie. Right? Oh, brie. It's a yuppie food or bottled water, specifically. Yeah. Pellegrino. Right? Oh, of course, there's a yuppie food. And it's a joke. It's kind of risible, and I get that. But there's actually a real story going on here that speaks to the cultural manifestation of the new inequality that's opening up in the consumer market in the nineteen eighties. So in this period, we see yuppies, particularly dual income couples or single income professionals with no kids. They're the only cohort that has an increasing level of disposable income. Everyone else, people with kids, non-college-educated Americans, they're all seeing downward disposable income levels when accounting for inflation, accounting for job loss, and deindustrialization. So on this material basis, forges a whole new culture of upscale consumption. Retailers understand that they can either chase the downwardly mobile consumer and race to the bottom on price or rebrand and chase the upwardly mobile, those who are enjoying the fruits of an unequal economy. And that's what many do, particularly in a city like New York where Dean and DeLuca, the Silver Palate, Zabar's, Odeon, McNally's restaurants, all of them understand that if you rebrand for the new population that's enjoying the spoils of the financial economy, you can have a value-add market that's ripe for the taking. Now for yuppies, why are they interested in it? Right? Well, these are a class of people who made their name on higher education. Right? It's not inherited wealth. It's about demonstrating your savoir-faire and cosmopolitanism, talking about your trips to Europe that you took during college and demonstrating it through wise consumption choices, broadcasting it for an audience of fellow yuppies and to gain the most sort of social esteem by consuming omnivorously across the city that's being designed for you and your tastes.


00:20:22 Andrew Keen: And speaking of McInerney, he was very popular in the nineteen eighties. Do the yuppies have a scribe or a filmmaker? What about the role of — McInerney, of course, is famously associated with the club scene and drugs, designer drugs. Do they have a scribe? And what's the role of sex and drugs and rock and roll in all this?


00:20:48 Dylan Gottlieb: That's a great question. I think that Bret Easton Ellis has become probably the leading satirist of these people because I think he perhaps was one and grasped them deeply, the moral emptiness at the center of these pursuits, he satirizes really beautifully in American Psycho. Well, not beautifully — but no one captured the type better than that book or film.


00:21:09 Andrew Keen: [unclear — possibly Bonfire of the Vanities] is like him in some ways as well.


00:21:13 Dylan Gottlieb: Absolutely. So there is this quality of the hedonistic excess. Cocaine is the ultimate boost to one's ego. You know, forget LSD, which was all about communing and sort of leveling and dissolving the ego. Cocaine is a drug.


00:21:28 Andrew Keen: As you're saying.


00:21:29 Dylan Gottlieb: Exactly. But cocaine is a drug of the eighties to boost the ego for the competitive nightlife that follows an exhausting day at the office. So there is some resonance with the drugs that are being taken that align with the material shifts in work, in leisure. In terms of other forms of culture, there's some interesting stories. I think, actually, of Min Jin Lee here. Her first book, Free Food for Millionaires, is actually the story of, you know, an Asian American woman who finds herself in a law firm. So there's a sort of different non-white-male account of this era as one of breaking into the provinces that were not formerly open to different sorts of workers and finding them strange and alienating, but also alluring. And so that's a vein of literature that maybe we don't associate with yuppiedom, but I think maybe we should.


00:22:18 Andrew Keen: How much is I mean, yuppies are obviously very much a feature of the eighties, but a lot of the ways you're describing this new class and this new economy bring to mind, Gatsby and the twenties in America. What are the comparisons? I mean, of course, Thorstein Veblen's theory of the leisure class, I'm sure you know that book off by heart, speaks of the old leisure class, which is replaced in some ways by Gatsby and the new class of the twenties. Is history in a way or was history in a way repeating itself in the eighties?


00:22:57 Dylan Gottlieb: That's a great question. And it's funny because, actually, some of the iconic styles of the nineteen eighties rehash maybe the deco styles of the nineteen twenties. There's a self-consciousness about reviving that cultural moment. And that's maybe not a fully self-aware realization that they're in the midst of a bull market that resembles the frothy nineteen twenties in a similar way. But Gatsby, you kind of hit the nail on the head. I use a Gatsby quote to open my book to sort of call back to that early era of acquisitiveness and also to that striving quality that Gatsby comes from the provinces and finds his way into the very heart of American capitalism. That is a recurrent theme in American life that is resurrected in the nineteen eighties. But what I think is different is it's a post-'65 America. It's a post women's movement America, and it's a different group of people who are now going to storm the citadel of American capitalism, not just the foreign-born from the West who makes good at Yale and then finds his way to Wall Street, but now a whole range of people who are coming to corporate life maybe as a realization of their feminist leanings from the seventies. This is one way to actualize those dreams, however skeptical we might be of that now. It could be seen as one totem of liberation: to storm the ranks of partners at Skadden Arps. You were the first woman to do it. It's a different type of person than the Gatsbys of the nineteen twenties, even if the financial machinations are quite familiar.


00:24:27 Andrew Keen: Yeah. Storming the ramparts. The way you talk, I'm not sure if it's Marxist language, but you imply in some ways — and maybe you disagree — that there is an element of criminality about all this. Maybe not in terms of the law, but maybe in the moral universe. Of course, Gatsby himself was very much, at least according to Fitzgerald, bound up with criminals of one kind or another. It's one of the more interesting sides of his story. In your view, is there a criminal quality to the yuppie class, either in grand historical terms or literally in terms of the way in which they're stealing from other people?


00:25:12 Dylan Gottlieb: That's a great question that I haven't really thought about before. I mean, behind every great fortune is a great crime. Who said that? Is that Tolstoy? I don't remember.


00:25:30 Andrew Keen: Was it Churchill?


00:25:32 Dylan Gottlieb: There you go. I mean, so in a larger sense, is inequality a social sin? I think we can probably say so at some point. But I don't think it's fully criminal in the sense that I am sympathetic to my individual actors' choices given the set of incentives and political economy they are confronted with in this moment. And I wanna be sympathetic to the choices we all make when we leave college desperate for a job, looking to make our way in the world. And we don't choose the circumstances in which we enter that job market.


00:25:56 Andrew Keen: We, to quote somebody else, make our own history, but not quite in the way we think we do.


00:26:04 Dylan Gottlieb: There you go. Carl. Our old friend Carl. But he's not wrong there. Right? But at the same time, we critique the systems, and maybe they are embodied in this class of people that arises. I do wanna be sympathetic to them as workers. Right? As people who are making choices, making history to the extent that they can within, let's say, a mode of production they haven't determined. So sympathy and not condemnation. Because, you know, so much of the literature in the eighties is about greed, capital g. We hear Gordon Gekko. We think of all of the people who are prosecuted, Ivan Boesky, on and on, at the end of the eighties as a sort of moral recompense for what's gone on. And I'm just not that interested in pointing fingers and calling it a den of thieves as so many journalists were in the eighties. I'm more interested in how is this a new sort of political economy, and how do people make choices within it, not, are there criminals like Michael Milken that we need to point a finger at and lay all the sins of the decade at his feet, but rather understand how we all let this happen and how our politicians encourage this mode of accumulation to run amok.


00:27:10 Andrew Keen: Yeah. You've introduced the p word, politicians, politics. We haven't talked much. You mentioned Gary Hart earlier. We did a show a couple of days ago with a historian at Yale. I'm sure you know him, Ian, Shapiro, who basically makes the argument it's the politicians who have screwed up since the eighties — on his account, we can blame them for our current situation. And, of course, in American terms, at least, the politician he begins his finger-pointing at is Bill Clinton. In yuppie terms, Dylan — you begin in the eighties — but was the climax of yuppie politics the nineties — the nineties of Clinton?


00:27:57 Dylan Gottlieb: That's a great question. In some ways, I'm telling a prehistory of the Clintonian Democrats. When you put the final nail in the coffin of new deal era financial regulation, it's not Reagan, privately, who passes most of the things that deregulate the banks that lead to both enormous profits and enormous risk. It's actually Clinton, but it begins earlier. It does begin, actually, in Carter's administration, but accelerates in the Reagan years. But those bills are not passed by Republicans by and large, but by Democrats. People like Chuck Schumer, who are making very quickly more money from Wall Street than even the more senior members of the senate banking committee, are thinking about a new sort of growth engine for both the city's economy in New York and the nation's by pivoting to finance, which will, by the mid eighties, outpace manufacturing and services as the very engine of our economy. You know, politicians like a Schumer and later a Clinton will see this as a way to compete on the world stage and have a competitive advantage for The US who will not be the manufacturing powerhouse of the world anymore. They see the writing on the wall, and they're looking to hasten that transition to move towards a technology heavy, technocratic governance that puts yuppies at the vanguard, whether they're on Wall Street or later Silicon Valley. So, yes, all the changes that are brought about by Clinton are inaugurated, I think, in the seventies, accelerate in the eighties and climax in the nineties.


00:29:22 Andrew Keen: Do you think that this worked in a sense? I mean, I use that word carefully, work, because as you acknowledge, there were all sorts of problems and all sorts of ironies and paradoxes, including the fact that a lot of the yuppies were rather miserable in having to work so hard in their so-called sweatshops — that this could work in a Cold War environment. Shapiro, of course, begins his story with the fall of the wall, and Fukuyama's famous end of history, which was only really the beginning of history. But sure, you could have the rise of a yuppie class in the eighties when you had the existence of the Soviet Union and its empire. And suddenly, when that disappeared, everything looked a bit different even in New York, which is a long way from Moscow.


00:30:10 Dylan Gottlieb: Yeah. It's funny. I haven't really thought about it so much as a Cold War story, but, actually, it's one of the first chapters of financial globalization, where certain cities like New York are actually, even as early as the nineteen seventies, thinking about themselves competing not just with or sitting atop an American domestic market, say, in corporate headquarters, but thinking about competing with Singapore, competing with London, competing with all the other nodes of finance capital in the world. And as early as the nineteen seventies in the midst of the fiscal crisis, New York banks are saying, hey. We need more deregulation locally. What if we turn Manhattan into a free trade banking zone off the coast of The United States? And indeed they do to absolve themselves of some of the Federal Reserve requirements, to make it sort of a special economic zone in the mode that Quinn Slobodian has written about, to turn New York in a sense into Singapore. And so in that sense, I think the seventies, as others have written, of course, is actually one of the first salvos in financial globalization, as well as in the rise of the class who does that work. So this is a familiar story if you were in London after the Big Bang and you looked at Canary Wharf and its transformation. But I've heard from people around the world who say, well, this Yuppie story, it's actually very resonant with my time in Mexico City or in Hong Kong, that wherever this financialized economy appears, and as you're right, in an accelerating fashion after the end of the Cold War, it produces this class of workers to do the work of financialization, to be the brokers, to be the lawyers, to be the white-collar management consultants who will remake the economy in a pattern set by New York, I would say, first in the eighties.


00:31:46 Andrew Keen: Yeah. I don't know if you've seen the new book by, Patrick Radden Keefe, London Falling, which is a book about the sort of last gasp of what you would call financialization in London, where everything becomes internationalized. And, the city is, at least in his language and his vision, is sort of invaded by Russian oligarchs. That didn't — and, I mean, before that, of course, it was money from The Middle East, Arab money, oil money. That didn't happen as much in New York. Although, when you walk around New York now and you see these huge buildings, which are mostly empty, full of apartments worth millions, sometimes billions of dollars, At what point was your sweatshop, your sort of domestic sweatshop economy in New York, replaced by a more globalized international one?


00:32:45 Dylan Gottlieb: That's a great question. I think that already by the nineteen seventies, the petrodollars that are coming out of, say, OPEC states are already flowing through New York. So you might not have Saudi bankers in New York, but the dollars are already flowing through the commercial banks that are located there that, you know, investment banks are underwriting new securities to redevelop what was still being called the Third World at the time. I do think that New York is actually a central node in the remaking of the global economy in this period. You're right, though, that we don't have sheikhs walking down the street quite yet, but in an accelerating way after — or during — the bull market of the nineteen nineties, we begin to see capital flow to New York as a hedge against international instability, And especially in Bloomberg's New York, which he, of course, terms the luxury city, where the express policy is to attract the world's best and brightest, whether they're the professionals on the front lines or the investment class, the real estate oligarchs who will sit or more likely not sit in those apartments atop the super tall towers. The vast rezoning of New York to their ends happens in accelerated fashion in the 2000s under Bloomberg. But now, interestingly, we have Mamdani who is proposing, in a very contested proposal to tax those extra homes located there as a strike back, maybe symbolic, maybe actually real to extract some value back for the local economy they sit atop of, or that they've profited off but don't really pay into.


00:34:14 Andrew Keen: I wanna come to Mamdani in a minute. Right? We can't talk about all this without mentioning, the current American president who doesn't need a name. We know who he is. You write about him in your New York Times piece suggesting that the tribune of the white working class, the reactionary working class from Queens, is, of course, Donald Trump. You literally use that word, tribune. So hard hats begin, and we've done shows on the hard hats, Nixon, blah blah blah. How important is Trump in developing a critique of yuppie culture and yuck — not yucky, yuppie economics. And, you know, the obvious irony is of all the people to be making the critique of the yuppies, it's Donald Trump.


00:35:09 Dylan Gottlieb: This is the irony. I think that many commentators misplace him or mislabel him as a yuppie. They think eighties. They think New York. They think rich. They call him a yuppie. But I think that's profoundly wrong. He's an outer borough striver who, on the strength not really of his educational credentials or his own intellectual sophistication, but really his father's funds, plays at being a real-estate developer. And there's this wonderful picture. It's a cover, I believe, of New York Magazine I saw in my research from 1988, and it's a picture of all the big New York families in real estate. The Rudins are there, and Trump is in the back, like, trying to peer out over their shoulders. Like, hey. I'm here too, as sort of an imposter.


00:35:52 Andrew Keen: You've seen the movie The Apprentice, which did a very good job with it.


00:35:56 Dylan Gottlieb: Exactly. Right? So he wants to gain the esteem of these real estate investors. He wants to gain the respect of the yuppies he's meeting at the clubs, but he just doesn't have the manners, and he doesn't have the juice, really. Right? They don't respect him. They think he should go back to Queens and be a slumlord like his father. And that resentment over his rejections, you know, he skulks off to New Jersey to try and make his way in Atlantic City. And that rejection foments all sorts of resentments that, of course, have racial connotations as well. Don't forget, in 1989, he takes out a full page ad calling for the death penalty for the incorrectly accused so-called perpetrators of the Central Park Five assault, but also a profound resentment at the new elite that's in the city. And so if you're a Staten Island hard hat, you're someone listening to talk radio in New York in the outer boroughs or suburbs, his resentments rhyme with yours. There's a sense that who are these new people moving into my neighborhood, my city, changing its orientation? Who — you know — I'm having a tougher time making ends meet as real estate prices begin to climb in my neighborhood in Brooklyn. Who are these new arrivals? And Trump later would ventriloquize those resentments at a national level where a similar resentment at a cosmopolitan urban elite would be a hallmark of the Trump coalition. And, you know, we mistake this sometimes as working-class animus, but no. If you're quite well off but living in the hinterland, maybe a less educated owner of a construction company or an RV salesman who's done quite well for himself financially, but still resents that cosmopolitan elite who refuses you entry, who makes fun of you because you don't know which fork to use.


00:37:37 Andrew Keen: It's not hard to make fun of an RV salesman, is it, Dylan?


00:37:40 Dylan Gottlieb: There you go. But, you know, maybe they deserve our ire. But, you know, Trump can ventriloquize those resentments and give them a sense of power and pleasure by poking fun at that supercilious elite who've rejected them in turn. So in that sense, I feel like Trump is very much a New York character, but New York is the whole universe, isn't it? Queens is the hinterland of the city, and there's a core-periphery dynamic.


00:38:02 Andrew Keen: And then you've got Cambridge up the road and San Francisco to the West. You contributed, I think, to a collection, the limits of professional class liberalism. Of course, all liberals were horrified with Trump's remarks about Central Park Five or seven, however many there were, and the implicit, sometimes explicit racism. What's your take on the liberalism of this professional class? Is it genuine? Is it self interested? Is it absurd? Does it all end with Bill and Hillary and their ugliness in one way or the other?


00:38:41 Dylan Gottlieb: I think it's a foreshortened version of liberalism that it does have some real promise to it, just like going back to the democratization of the elite. Right? It is remarkable that women make up 40% of law students by the end of the eighties. That is a seismic change in American life that shouldn't be discounted. But at the same time, liberals need to reconcile those gains of the rights movements of the sixties with the increasingly unequal political economy that they're inaugurating, say, with financialization or the rise of Silicon Valley. How do you make sense of those two things together? And that's difficult. It's hard to square that circle, and sometimes it produces some very perverse outcomes. The idea that we've moved past the problem of race once Obama is elected, for example, sure. He was the editor of the Harvard Law Review. That's wonderful and remarkable and something that could never have occurred in my life.


00:39:29 Andrew Keen: A bit of a yuppie himself in his own way. He technically ran, but he carried his coffee around with him.


00:39:35 Dylan Gottlieb: Deeply — oh, deeply yuppie. I mean, he meets his wife while interning at Sidley Austin, a Chicago law firm. He's through and through an embodiment of this contradiction. Right? A Black face in a high place, which we should applaud. Right? We should note as a sign of progress. But if that's the limit of our horizon of transformative change in a country that's actually getting more unequal all the time, where the racial wealth gap is the same or worse as it had been fifty years earlier, it's a very limited vision for what liberalism can do and should do. Just in a series of technocratic nudges and fixes is not gonna get us very far, and that seemed to be how, say, Obama governed. You know, famously, he used the term smart 900 times while he was in office. Smart is the watchword for yuppies. Right? They want smart policy. They want technocratic fixes. They want abundance. They want something they can read in a policy packet or an Atlantic article.


00:40:29 Andrew Keen: Oh, I'm guessing you're not a big fan of Pete Buttigieg.


00:40:33 Dylan Gottlieb: Oh, you know. I think he's every boomer's idea of a good successful young man, and, you know, he's very smart, but perhaps too smart for his own good. And I think lacks the sort of small d democratic impulse to lift up all the people that are needed to build a large coalition, not just those who feel that their savvy is being satisfied by yet another smart policy.


00:40:57 Andrew Keen: Were there any people who really began to understand this? I mean, there are a lot of people. I'm not saying what you're saying isn't original. It is. It's true. And you certainly wrap it in an original way, Dylan. But more and more people are coming to understand what's happened over the last forty years. You should have a look at the Shapiro book. I think you'd find it interesting. But I think of somebody like Robert Reich who fought the good fight within the Clinton administration and lost, or, others on the left within the Clinton administration who left or were sidelined or quit. Does anyone come to mind for you who warned us about what was actually happening in the eighties and nineties?


00:41:46 Dylan Gottlieb: That's a great question.


00:41:47 Andrew Keen: In a progressive sense.


00:41:49 Dylan Gottlieb: Yeah. I think the figure I was gonna raise was Reich because he, in the first Clinton term, wages this battle from a left-liberal perspective, a real critique of post-industrial transition. And he's fighting at all moments with, Rubin, who's gonna be the secretary of the treasury, comes out of investment banking and represents more of the yuppie impulse in financializing the economy. And they go back and forth on economic policy. Who's gonna win? Are we gonna listen to the bond markets and their discipline, or are we gonna seriously think about what we do with all these blue-collar workers who are being left behind by the transition, the wrenching transition to a post-industrial economy. And, you know, we know the answer that Rubin wins. But there is and we shouldn't discount conflicting visions within the Clinton administration and even in the Biden administration. Right? We see multiple strands of liberalism coexisting. The question is which wins, which feels commonsensical, which feels possible. And in that sense, the that foreshortened vision of professional class liberalism, it does win. It says, well, we gotta run this by the CBO. We can't deficit spend. We can't be pie in the sky. We need sound fiscal discipline. The bond markets do ultimately rule things, and our donors on Wall Street have our ear. And it's very difficult to make transformative industrial policy or real climate action when you need JPMorgan Chase, or you see them at the fundraising dinner that you'll be attending that evening.


00:43:17 Andrew Keen: Yeah. A few weeks ago, I was in Washington DC, and I went to interview Peter Edelman, who quit in disgust from the Clinton administration. He's an old man now, but a longtime fighter on inequality and poverty. Couple more questions. You've been very generous with your time. Dylan, this new class, and no longer a new class, the old class by the twenty-teens or even the beginning of the twenty-first century, these bankers, lawyers, joggers, and gourmands who conquered New York. It didn't, of course, conquer the West Coast. And with the rise of the Internet and a bro culture or a bro economy That's the right word to describe it. The digital revolution. Do these yuppies in New York, are they increasingly marginalized themselves?


00:44:16 Dylan Gottlieb: It's an interesting question. I think one thing that persists is the recruiting pipeline that's constructed in the nineteen eighties is actually a replicable structure that's picked up by other industries. In the nineteen nineties, it's management consulting that goes to America's campuses and siphons off a whole generation to work there. In the 2000s, as you intimate, it's Silicon Valley that does a similar thing with America's best and brightest. So in that sense, the structures that shape young meritocrats' decisions about where to work, they're actually quite persistent. Are they being left behind now? Well, there's a larger question about a white-collar job apocalypse that many of us are thinking through and arguing about.


00:44:57 Andrew Keen: And that's the Scheiber mutiny argument.


00:45:00 Dylan Gottlieb: So there are two things going on there. One, there is it already for a long time, a downwardly mobile tranche of yuppies that already were identified by Barbara Ehrenreich decades ago. The journalists, the academics, those whose work and conditions, whose wages were already falling relative to those


00:45:17 Andrew Keen: Like you and I do.


00:45:19 Dylan Gottlieb: The downwardly mobile — it's very apt. But, you know, those are perhaps people who voted for Mamdani and want to align themselves or see themselves as increasingly precarious in this new economy. And then there are those investment bankers who thought they made all the right decisions. They thought they positioned themselves for a lifetime of high earnings, even if those industries are precarious and will dispense them as soon as the markets go bust. But now we're facing a technological replacement, which I think is not yet fully arrived, and I think is actually just a bludgeon that employers are using to cut bloated workforces. I talked to a HR representative for an investment bank recently. I won't name her or the bank, but she said, we're moving from a pyramid structure to a cylinder structure for employment. What does that mean? Our base of entry level workers is just gonna be much smaller than it was before. We're gonna select just the best and brightest and promote them. And that really does portend a new era. I'm writing about the era of the large pyramid, the exploited many at the bottom who hope to make it to the top of this white-collar world. But what happens if our elite shrinks? Does it go extinct? Does it replicate itself? Does it get more exclusive and white and male as it did in mid century? No one knows, but it's certainly interesting to watch that space.


00:46:36 Andrew Keen: Well, let's end with Mamdani. I don't suppose you read the free press very often, but there was an interesting piece in it last year about how your Yuppies — or how the Yuppies, but they're Dylan Gottlieb's yuppies, you own the term now, Dylan, became socialists. Is there some truth to this that the yuppies because, I mean, partly this mutiny of the college educated ex middle class, meritocratic class increasingly becoming the working class. Is socialism or Mamdani style socialism, is it the new preserve of the Yuppie, especially in New York? Sure.


00:47:18 Dylan Gottlieb: Right. I was gonna say there's a geographical story here as well. When we all live — when all the journalists live in Brooklyn, the stories they seem to tell us about their friends. So let's discuss that.


00:47:28 Andrew Keen: I would say 50% of my guests are from Brooklyn. It's astonishing.


00:47:32 Dylan Gottlieb: Tells us something. Maybe that's book two for me. But I do think there's some truth, and it's a longer running trend than, say, just COVID, that the pressures of the sweatshop of the meritocracy have embittered and immiserated many members of this professional class. You know, if you're an academic, their working conditions are demonstrably worse than they were 40 years ago, when 70% of academics were tenure-track. If you're a doctor, you're graded on a scale that has striking resemblance to those of a factory worker or an Amazon employee. Right? I know doctors, and they're immiserated as well. You're competing in a very expensive—


00:48:09 Andrew Keen: Well, everyone's miserable these days.


00:48:11 Dylan Gottlieb: Sure. But you're competing in a very expensive housing market. The cost of the education to replicate your social standing for your children has skyrocketed. All sorts of these yuppie inputs are going up in cost. And at the same time, the pathway to economic security through professions that were once respectable and well paying — journalism, academia, medicine — they're narrowing. It hasn't hit the investment bankers quite yet, but with the rise of AI, I do think that you'll see more and more workers who we might have called yuppies understand that their plight actually has more to do with the Amazon employee, has more to do with the DoorDash delivery person, maybe. The problem is there's this whole edifice of professional ideology, of myth making. Right? Meritocratic thinking is very pervasive and very deep. You've been told you're a very special boy since you were little, since you were accepted into Yale, and it's gonna be hard to break that sense of profession.


00:49:09 Andrew Keen: Everybody goes to Yale. I mean, maybe in your world, Dylan. So it's a precariat-of-the-world-unite. You have nothing to lose but what? Your sense of specialness?


00:49:19 Dylan Gottlieb: No. Everything to lose but your running shoes. I don't know if the lawyers will truly see themselves as embattled workers or say, nope. I'm different. I'm smarter. That's gonna be a real political question in the coming decades.


00:49:31 Andrew Keen: Well, it's all very relevant. The book is out this week. Yuppies: The Bankers, Lawyers, Joggers, and Gourmands Who Conquered New York. I mean, you can tell from Dylan Gottlieb's incredibly articulate and entertaining presentation that this is not a boring academic book. It's not a boring academic subject. Maybe, Dylan, you should have called it the theory of the unleisured class.


00:49:59 Dylan Gottlieb: Oh, that's a great idea for the paperback.


00:50:01 Andrew Keen: Well, congratulations on the book. It's out this week. Lovely to see you on the show, Dylan. Thank you again. Thanks so much.