Illustration: Melanie Lambrick

The Heartland Billionaire Destroying the Working Class

Joe Ricketts’ memoir tells of making it on his own—while crushing unions, scamming customers, and undermining local media

InIn a recent episode of HBO’s Succession, Kendall Roy, heir to a vast media fortune, personally lays off the entire staff of the fictional website Vaulter: a digital media mashup of BuzzFeed, Gawker, Vox, and Vice. With Kendall’s brief announcement, a few hundred millennial journalists are suddenly without work, all so that Waystar Royco, Vaulter’s parent company, can both trim a bit of fat and smother a potential union.

If you happened to be on Twitter while the episode aired, you probably heard about this scene, because it was painfully familiar to nearly every journalist on the platform. In the past several years, all of us have seen friends lose jobs as sites shutter, restructure, or “pivot to video,” often in retaliation for a union drive. Again and again, sites that provide unquantifiable value to real audiences are being cannibalized and resold by billionaires or private equity groups who don’t understand what journalism is, hold journalists in contempt, and eagerly ruin journalistic careers out of sheer petty malice. The only thing about Vaulter’s demise that felt even slightly unrealistic is that the executive had the guts to lay off his employees face to face.

On November 2, 2017, many journalists witnessed an especially egregious version of the same scene, when Joe Ricketts, the billionaire founder of TD Ameritrade and the owner of the Chicago Cubs, abruptly laid off the entire staff of Gothamist and DNAinfo, two networks of local news websites he had recently merged. He also shuttered both networks, replacing tens of thousands of articles with a letter justifying his decision. “DNAinfo is, at the end of the day, a business, and businesses need to be economically successful if they are to endure,” he wrote. “And while we made important progress toward building DNAinfo into a successful business, in the end, that progress hasn’t been sufficient to support the tremendous effort and expense needed to produce the type of journalism on which the company was founded.”

This was, to be blunt, bullshit. Ricketts had purchased Gothamist, which employed young reporters in five cities, a mere eight months prior. At the time, the site was modestly profitable and operated with low overhead. Its founders, Jake Dobkin and Jen Chung, had spent 14 years building up Gothamist, expanding from New York into cities like Washington and San Francisco, before deciding to cash in. While the site and its founders had always had a left-wing sensibility, in the end, they sold to Ricketts, an avowed conservative who the previous year had donated at least $1 million to Donald Trump’s presidential campaign, and who already owned a rival local news network, DNAinfo. Following the acquisition, the newly combined editorial teams in New York rushed to form a union, which Dobkin and Chung tried to discourage. The staff’s all but unanimous vote in favor of unionizing came just a week before, and almost certainly provoked, Ricketts’ decision to terminate the site.

Ricketts is representative of a less chronicled American elite — plutocrats who are culturally conservative, who don’t live on the coasts, whose businesses aren’t hip, but who form the real base for Trump.

Over the next several months, most people following the story knew a few big things about Ricketts: We knew he hated unions because he wrote a whole blog post about it (“I believe unions promote a corrosive us-against-them dynamic that destroys the esprit de corps businesses need to succeed”), we knew he backed Trump after initially sponsoring an anti-Trump Republican super PAC, and we knew his family fortune grew by $700 million between November 2016 and January 2017, when the newly inaugurated Trump nominated Joe’s son, Todd Ricketts, as Deputy Secretary of Commerce. (Todd now serves as finance chair of the Republican National Committee; his brother, Pete Ricketts, has been the Republican governor of Nebraska since 2015, and at one point employed a white nationalist as his statewide field director). Those of us with long memories might also have recalled that TD Ameritrade, the financial services giant Ricketts founded, was fined nearly half a billion dollars in the wake of the 2008 financial crisis for unethical conduct (the company settled another securities fraud class-action suit just last year), a year after it was successfully sued for a massive data breach affecting six million customers. And in February 2019, we learned that Joe Ricketts also marinates in racist online conspiracy theories — he believes “Muslims are naturally my (our) enemy” and also that Barack Obama is one — due to a cache of emails obtained by Splinter, a left-wing news website shuttered by venture capitalists last month. (Just last week, the entire staff of Splinter’s beloved and profitable sister site, Deadspin, resigned in protest of the arbitrary and abusive management of those same venture capitalists).

But now we have the opportunity to understand Ricketts in his own words, thanks to his new book, infuriatingly titled The Harder You Work, the Luckier You Get: An Entrepreneur’s Memoir. The figure who emerges is as uninteresting as one might expect, but there’s still value in engaging with his tepid prose. For several years now, we’ve endured a genre of mainstream political reporting in which the supposedly authentic, white working-class of states like West Virginia or Michigan is counterposed against the libertine coastal elite, whether that refers to Mark Zuckerberg or Beyoncé or Kendall Roy.

Ricketts is representative of a different, and far less chronicled, American elite — plutocrats who are culturally conservative, who don’t live on the coasts (having spent most of his life in Nebraska, he now lives in Jackson Hole, Wyoming, about as far from the major cities his news sites covered as one can get), who don’t embrace fame or glamour, whose businesses aren’t particularly hip, but who form the real base for Trump and other Republicans. Subjecting ourselves to Ricketts’ own self-conception can help us understand what the media industry, and democracy itself, are up against.

TThe first thing Joe Ricketts would like you to know about himself is that he is a product of that fabled white working class in the heartland. Born in Nebraska in 1941, the world of his childhood that he evokes is one of farms and factories, hamburger stands and drugstores, Jesus and Elvis. Most crucially, it’s a world in which he worked very hard all the time. “I always had a job,” he writes, “First a paper route, then a position as a clerk at the grocery store. I was a carryout boy and stocked shelves and swept floors, and I enjoyed it. If a skill is something you have to learn and a talent is a gift you are given, then working, liking to work, was part of my talent.” Other kids cared about grades or sports, but Ricketts is frank that from an early age he cared mostly about earning money. He once told a friend that he would like to be a millionaire, and when they asked him why, he said: “It would be an achievement,” which, he adds ruefully, didn’t seem to mean anything to the friend.

He paid his way through Creighton University, a Jesuit-run college in Omaha, by working at a bread factory where he claims he once pulled a 24-hour shift. “The unionized employees wouldn’t work three shifts in a row, but to me, it was an opportunity,” writes Ricketts, already a budding young scab. There was nothing to eat but vending machine candy bars and the bread itself. Ricketts relates the delightful story of how a worker lost a finger in one of the machines and it ended up in a loaf of bread on someone’s kitchen counter. “To this day, the smell of a factory bread reminds me of working those long hours with an upset stomach. It makes me feel sick,” Ricketts (who personally bears an uncanny resemblance to a loaf of factory bread) adds, without ever stopping to consider whether there’s any role the union he eagerly undermined might have played in alleviating these dehumanizing conditions.

Ricketts once told a friend that he would like to be a millionaire. When they asked him why, he said: “It would be an achievement,” which, he adds ruefully, didn’t seem to mean anything to the friend.

In the 1960s, Ricketts enrolled in a training program as a stockbroker and relocated with his wife Marlene — his high school sweetheart, naturally — to San Francisco, setting up some amusing fish out of water moments. This was, he writes, the first time his young kids ever “experienced people with different skin colors, different languages, different smells, and different clothes.” In Golden Gate Park, his kids “met other children, many of them from hippie families, but Marlene found the hippies strange — dirty and sickly, she said. Back at the apartment, the smell from the hallway that she thought at first was incense turned out to be marijuana. She had never lived near drug users before, and I suppose that added to her feeling of living in a slum. Even when we drove through Haight-Ashbury, the now legendary center of the counterculture, she said it gave her no feeling except a vague impression of sadness.” Soon enough the family was back in Nebraska.

Here Ricketts is telling us that while he came of age in the proverbial ‘60s, he never partook. Once a literal Boy Scout, he would remain a figurative one for decades to come. In San Francisco, his preferred vice was to go out with his fellow trainees, all men, “to drink and joke and flirt harmlessly with the waitresses.” More than a decade later, describing the Reagan-era bull market, he writes, “When I heard about those brokers in New York with their Quaaludes and their prostitutes, I thought they were lost.” Movies like The Wolf of Wall Street, he adds, “showed stockbrokers destroying their lives with dope, alcohol, and sex, which was just another kind of drug.” Of his own recreation in those years, which he spent in Omaha overseeing Ameritrade’s growth, he recalls:

Our substance of choice was beer. Beer, whatever its drawbacks, is not dope. Marlene generally did not come out for drinks on Friday at the Rookery. She went home and got supper ready for the children. Often, I did not get home in time to eat with them. I might have had twelve beers on a Friday evening. I might have had more. I’m sure there were a few nights that it was only by the grace of God that I didn’t have a car accident. But it was only beer and it helped me get rid of all my pent-up stress. I got myself home, and our family and our business could press on together.

New York and San Francisco are thus both rendered as stereotypical dens of iniquity in Ricketts’ telling, whereas regular Americans in flyover country prefer wholesome activities such as driving while extremely shitfaced.

Being from the heartland is a major chip on Ricketts’ shoulder; at one point, he recounts how Marlene would tease Wall Streeters on the company phone by playing the hayseed. “A lot of the traders were from New York and New Jersey, and they thought that all of us in Nebraska must be hicks from the sticks,” he writes. “Sorry I couldn’t get back to you sooner,” Marlene would tell them. “Nebraska’s a corn state, so we were having a Mazola party…You know, everyone takes off their clothes and pours on the corn oil, and then we all just sort of squish together.”

At multiple points, Ricketts acknowledges that women of his generation never got to be traders or executives, and instead, like Marlene, worked as administrative assistants and raised families. But this doesn’t complicate his own bootstraps narrative, and the struggle against the racist apartheid that was legally sanctioned until his mid-20s doesn’t enter the narrative at all. Politics, in general, don’t seem to interest Ricketts much, despite his real-life commitments. The names “Trump” and “Obama” are nowhere to be found. He mentions that his daughter Laura is a lesbian and a board member of the LGBTQ advocacy group Lambda Legal, while his sons, Pete, Tom, and Todd, are respectively a Republican governor, the manager of a baseball team, and a Republican operative committed to “saving Western civilization.” Ricketts seems equally proud of all of them. He does, however, offer this ideological parting shot in his epilogue:

Many Americans, I’m afraid, no longer respect free enterprise. The term has come to seem the property of conservatives, while liberals appear drawn instead to socialism. Many Americans, especially young people, apparently do not understand what economists have clearly shown, that for this country to provide jobs for our graduates and our immigrants, we need to increase gross national product by at least 3 percent per year. Free enterprise is what creates jobs and makes the economy expand. I don’t see how we can be America without it. And while I’m not going to get on my soapbox here, I do have to point out that in a socialist country there would have been no Ameritrade.

So what would that horrifying socialist dystopia without Ameritrade actually look like? It’s worth dwelling on this, because the company Ricketts founded, which in the most recent fiscal year boasted $5.4 billion in revenue and more than 9,000 employees, is the real protagonist of the memoir. Ricketts sees himself as a pioneer — at one point he compares himself to Daniel Boone, braving bears, cougars, and “hostile Native Americans” in the wilderness. His innovation was to take advantage of an SEC rule change in 1975 to deregulate stockbroking, offering discount services to traders to compete with more established Wall Street brokers. Beginning in the early 1980s, Ricketts notes that “the increasing deregulation of global banking systems brought a flood of investment capital into the United States, which helped bankroll the activities of a new breed of corporate raiders” who “represented potential new customers” for Ameritrade. In the 1990s, the company cornered the market on electronic trading, and in 2006 it merged with Toronto-Dominion to become TD Ameritrade, a deal which made Ricketts a billionaire, but also necessitated his retirement from the chairmanship.

Politics, in general, don’t seem to interest Ricketts much, despite his real-life commitments. The names “Trump” and “Obama” are nowhere to be found in his book.

Conveniently, the book’s timeline ends there, aside from a coda about acquiring the Cubs and ending their World Series curse. As such, it entirely skips over TD Ameritrade’s aforementioned data breach in 2007 and its major ethics scandal in the wake of the 2008 financial crisis. The millions of victims of the data theft whose names, phone numbers, email accounts, and home addresses were exposed to hackers received two dollars apiece, while their lawyer earned $1.8 million. As for the ethics scandal, in which Ameritrade misrepresented auction-rate securities as liquid, short-term investments, leading to steep losses for their investors, it was just one high-profile example of the dangers of an under-regulated financial services industry. Companies like Ameritrade have a profit incentive to lie to customers about where their money is being invested, and they know they will never face serious consequences. In a socialist country, presumably, none of this would have happened. But on the other hand, in a socialist country, the Ricketts family wouldn’t be worth an estimated $2.2 billion.

To hear Ricketts tell it, extreme wealth is less satisfying than being the boss:

Wealth gave me the freedom to do as I pleased. I bought a ranch in Wyoming near Yellowstone National Park on beautiful land that was, in many ways, unchanged from frontier days. Marlene and I began to travel the world. In England, we enjoyed the chance to meet former prime minister Margaret Thatcher and her husband, Sir Denis Thatcher. We also met former chancellor Helmut Kohl, who gallantly kissed Marlene’s hand and became her smoking buddy. We discovered we had the opportunity to meet almost anybody if we put the introduction the right way. We also found, though, that the thrill wears off fast. At some point, you want to go home and get back to the rest of your life. The rest of my life, though, had been my work, and now my work was gone.

Ricketts dealt with this restlessness by purchasing the Chicago Cubs, starting a niche bison meat business, and — though he neglects to mention it anywhere in the book — investing in digital media. A New York Times article last month explored why rich people feel the need to keep working when they could simply enjoy lives of leisure, and suggested a variety of possible reasons: addiction to making money, status anxiety, an unwillingness to confront the nature of existence, fear of another financial crash or of a spate of new regulations, and so on. But at the very end of his memoir, Ricketts offers a different answer. “When I go to work, it’s not because I need more money,” he writes. “I’m working at my businesses because that kind of work brings not just prosperity but joy. To see people make good wages, do well, and send their kids to college — that’s what gives me joy today.”

In point of fact, at least some of Ricketts’ former employees, the mostly millennial journalists in the DNAinfo/Gothamist empire, were making barely adequate wages, and certainly not on the scale necessary to send any hypothetical kids to college in the near future, or even to pay back the student loans many of them likely took out before launching their journalism careers. Working for Ricketts brought them neither prosperity nor joy, and when they tried to assert the most basic leverage over their working conditions, he retaliated by exposing them to far greater financial insecurity and toyed with destroying all of the fruits of their labor just to show he could.

Ricketts had been willing to fire 115 media workers across the country, most of whom hadn’t even had an opportunity to vote, to punish the brave handful in New York who had lawfully organized for basic bargaining rights. He also removed their entire archive from the internet, damaging both their ability to find future work and the public’s access to a decade of local news reporting — and while this turned out to be temporary, no one initially knew whether their work would be restored. (Four months later, Gothamist, but not DNAinfo, was sold to the public radio station WNYC, and revived under the editorial leadership of Dobkin and Chung.)

When Ricketts’ employees tried to assert the most basic leverage over their working conditions, he toyed with destroying all of the fruits of their labor just to show he could.

Unlike the fictional Kendall Roy, Ricketts didn’t have the decency to show up in person to tell his staff they were fired. One Gothamist editor, Rebecca Fishbein, recounts in her new book that she was at LaGuardia Airport departing for a vacation when she checked her email and “discovered a maniacal billionaire was shutting down the beloved local blog where I worked.”

“To make matters worse,” she adds, “he’d replaced the entire website with a stupid letter alerting readers to the site’s closure, temporarily rendering the archives inaccessible. My job was gone. Six years of my work was, to my knowledge, erased.”

That labor, meanwhile, had a value that can’t be measured on the Nasdaq: Every day, Ricketts’ employees were working to keep readers informed, to make sure important stories were reported and not forgotten, to hold public officials accountable, and to foster a sense of community, without which urban life can be alienating. It’s far easier to explain the social value of local media than it is to explain the social value of TD Ameritrade, a company that grew in tandem with the financialization of the U.S. economy, preyed on consumers until the 2008 crisis exposed its business model, and then went right back to profiting off an uncertain and deeply inequitable system. In the two months after Trump’s election, TD Ameritrade’s stock jumped 34% on hopes for deregulation, and it rose to even greater heights over the course of Trump’s first year in office, which culminated in sweeping tax cuts for corporations and the wealthiest Americans.

The story Ricketts tells about himself is just the latest riff on a familiar American fable, in which an unremarkable person — ideally, a white guy from Nebraska or thereabouts — achieves wealth and success by working hard, never complaining, and seizing opportunities. Even assuming this story is true as far as Ricketts is concerned, it ignores the millions of people who tried to follow the same path and failed, and by extension, the absurd randomness that dictates that a guy like Ricketts should be able to sabotage dozens of careers on a mean-spirited whim. To whatever limited extent Ricketts is representative of his upwardly mobile generation, the source of his prosperity — the deregulation of capital since the 1970s — has almost completely destroyed the prospect of upward mobility for the generations that follow. Of course, none of the Ricketts kids will have to worry about that.

David Klion is News Editor for Jewish Currents and a writer for the Nation, the New Republic, and other publications.

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