“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.