Is Scott Galloway the Howard Stern of the Business World?

Scott Galloway sat in his home studio in Delray Beach, Fla., staring off into space, trying to think of a joke to kick off the 164th episode of his podcast, “The Prof G Show.” His team of producers waited patiently. After a minute of silence, Mr. Galloway, an N.Y.U. marketing professor and business guru, started a riff about people (like him) born in 1964, including Sandra Bullock. He likened her career to Covid — it continues but no one seems to care. (Mr. Galloway used saltier language.)

Crickets. “I need positive reaffirmation,” Mr. Galloway told his team. “Were those good?”

Claire Miller, one of this producers, said, “I think you can do better.” He tried out a joke about Mary Poppins performing fellatio. “Not a fan,” said Caroline Schagrin, another producer. Mr. Galloway attempted one more, about accidentally giving a diabetic friend a spoonful of sugar. After a pause, Ms. Schagrin weighed in: “We can go with that.”

Then, in a high-speed nasal baritone by way of Venice Beach, Mr. Galloway, 57, went into the meat of his show: a discussion of international money laundering, layoffs at fast-growing companies, and the legal intricacies of Elon Musk’s Twitter deal (which at that point seemed more likely to happen).

In any given episode, Mr. Galloway serves a heady cocktail of data-driven analysis, bold-to-brash bets, center-left politics, dirty jokes and sudden emotional vulnerability that appeals to his core audience of men, and helps him stand out in a world of bland talking heads. He’s a little like Howard Stern for aspiring M.B.A.s and restless middle managers, offering listeners permission to have feelings and assert mildly politically incorrect opinions. (Fast Companycalled him a “progressive Jordan Peterson.”)

His hobbyhorses include the worship of tech founders (we should stop), antitrust regulation (we need more), higher education (costs too much), “failing young men” (they need role models), physical fitness (he does CrossFit) and the importance of building personal relationships. He is also apt to take off his shirt, as he did in a promo for a doomed Bloomberg TV show, or put on a wig, as he did at a tech conference while lip-syncing to Adele.

“He’s one of those rare people who cut through,” said Jeff Zucker, the former president of CNN, who hired Mr. Galloway to host a show on CNN+ before the streaming network shut down in April. “I don’t know if everything he says is right, but he says it in a damn interesting way.”

Mr. Galloway aspires to be “the most influential thought leader in the history of business,” he said. Sometimes it seems as if by “most influential” he means “most frequent”: In addition to the main podcast, his company, Prof G Media, produces a weekly newsletter, four podcast episodes a week, YouTube videos, a column for New York magazine and a book every 18 months or so. (The latest, Adrift: America in 100 Charts, will be published in September.)

Plus, he makes regular prime-time TV appearances and teaches brand strategy one semester a year at N.Y.U., along with online courses for his education start-up, Section4. Mr. Galloway, who was already wealthy from selling two companies and taking a third public, also makes more than $5 million a year from speaking gigs, he said, largely from corporations and industry groups that pay him $50,000 (for virtual events) to $250,000 (for international events). “I should be broken up,” he joked.

‘A Huge White Space for Heterosexual Men to Talk About Their Emotions’

Mr. Galloway got his most meaningful break as a pundit in 2017 when, during an appearance on Kara Swisher’s podcast, he predicted that Amazon would acquire Whole Foods. Four days after the episode aired, Amazon announced plans to do just that, and Ms. Swisher, a tech journalist who is a former columnist for The New York Times, soon invited him to host a new podcast with her, “Pivot.”

“Literally nobody knew who he was,” Ms. Swisher said. When she first saw him speak, she thought he was a jerk, she said. “Then he said something super-friggin’ insightful.” Each episode now gets a quarter-million downloads, according to Mr. Galloway, putting it on the cusp of Apple’s top 100 podcasts, in a league with “The Glenn Beck Program” and the NPR show “Wait Wait … Don’t Tell Me!” He said his newsletter reaches an audience of about 250,000, and “The Prof G Show” about half that.

His celebrity has grown along with his audience. In 2019, Mr. Galloway wrote a scathing indictment of WeWork, calling its $47 billion valuation “seriously loco,” which set the stage for the collapse of its I.P.O. In the Apple TV+ series “WeCrashed,” the actor Kelly AuCoin channels Mr. Galloway — shiny dome, glasses and all — as he interrogates Adam Neumann, the WeWork founder (played by Jared Leto), during an event at J.P. Morgan, all of which really happened. “It was chilling how exact the dialogue was,” Mr. Galloway said on a podcast.

Mr. Galloway tends to seek out confrontation. At a recent conference for the digital advertising industry, he told the audience that “most advertising sucks.” “The reason I brought him here is to be a provocateur,” the host Anthony Katsur told me afterward, adding that it’s helpful to have Mr. Galloway “call us out.”

In various forums, he has lately offered blistering opinions on the executives behind the stock trading app Robinhood (“mendacious”), Mark Zuckerberg (“the most dangerous person in the world”), Sheryl Sandberg (she made a fortune by exploiting “personal loss” and “this important conversation around gender balance”), Tesla stock (“My prediction: pain”) and chasing one’s dreams (instead, “make Benjamins”).

But Mr. Galloway also has a willingness — compulsion, even — to get personal. He weaves in anecdotes about family, failure and grief. One of his most popular newsletters reflected on the death of his dog. Ms. Swisher described him as an “open wound.” Mr. Galloway said his vulnerability amounts to a competitive advantage: “You fight the enemy with the weapons they can’t use.”

“I can’t out-CNBC them,” he added, “but I can talk about my kids or my up-and-down relationship with my dad.”

His work often verges on self-help, particular for struggling young men. With a “Prof G Show” audience that’s three-quarters male, according to Mr. Galloway, he said his imagined listener is a young father who’s “in the thick of it, stressed out, and what I call at the bottom of the smile curve,” or the U-shaped chart that maps happiness against age. He offers these men “an emotional outlet,” he said. (The business talk perhaps gives them cover.)

Mr. Galloway, who cites Muhammad Ali and Richard Simmons as heroes, also models a certain type of masculinity: nerdy but fit, aggressively liberal but not dogmatic, a bro who nonetheless likes a good cry. He believes this kind of man is underrepresented in media: “I think there’s a huge white space for heterosexual men to talk about their emotions,” he said.

When I asked one listener, Connor Queen, 28, a former sales executive in Idaho, how Mr. Galloway had influenced him, Mr. Queen said he recently started telling his brother that he loves him.

Not everyone enjoys the schtick. The entrepreneur and investor Jason Calacanis, an early backer of Uber and Robinhood, has made Mr. Galloway a regular target of derision on Twitter. Mr. Calacanis chides “Professor Cold Takes” for making predictions without having “skin in the game.” (“I have a lot of skin in the game,” said Mr. Galloway, who has investments in Airbnb, Amazon and Apple, among other companies.)

Keith Rabois, another prominent investor, mocked Mr. Galloway on Twitter in 2019 for suggesting that the microblogging company replace Jack Dorsey: Mr. Dorsey and Elon Musk “can do more in their sleep than Prof Galloway can do 24/7,” he wrote. Mr. Dorsey resigned as C.E.O. of Twitter in 2021 and left the board of directors this year.

Mr. Rabois described Mr. Galloway in an email to me as “a buffoon who likes attention.” (Mr. Galloway said many of his haters are just mad that he has criticized their companies.)

Critics also point out that his predictions often miss, sometimes wildly. In 2015, he speculated that Macy’s would beat out Amazon. Macy’s has since shed three-quarters of its value, while Amazon’s stock has sextupled.

In 2019, Mr. Galloway said that Tesla stock would tank by 80 percent; it has since exploded upward. His forecasts inspired Julie Young, an investor and analyst, to propose an index that invests by betting against Mr. Galloway’s predictions. The imaginary “Anti-Galloway Index,” albeit based on one set of prognostications and fluctuating wildly in recent months, currently has a return of about 200 percent.

‘I Worry My Narcissism Is Getting the Better of Me’

“I am financially much more secure than I ever thought I would be,” Mr. Galloway said. “I still have massive anxiety and fear around it.” We were sitting on matching leather armchairs in his 3,300-square-foot SoHo apartment with floor-to-ceiling windows overlooking the cobblestones of what he said is “supposedly the most Instagrammed street in the United States.”

Despite the bustle outside, the room was nearly silent with the windows closed, as if to complement its clean minimalism — everything gray scale except for an orange, scroll-like print by the gender-playful British artist Grayson Perry hanging above the dining table.

Mr. Galloway’s 11-year-old son lounged on the L-shaped couch, watching European soccer on mute. Mr. Galloway and I sipped protein shakes after a circuit workout at the Equinox around the corner. (Mr. Galloway got his first job out of college, at Morgan Stanley, in part because he was a personal trainer for someone at the firm. Also because, he says, he lied about his grades.) His wife, Beata, 43, a property developer from Germany whom Mr. Galloway first met at a hotel pool, soon arrived to take their son to their seaside mansion in Florida.

Mr. Galloway grew up in Los Angeles to immigrant parents. His father, a charming sales executive raised in Depression-era Scotland, had a “terrible relationship with money,” he said. His parents divorced when he was 9, and he lived with his mother, who worked as a secretary.

“It was an enormous source of stress that we didn’t have money,” he said. “It was also very emasculating.” Mr. Galloway became obsessed with money, and bought his first stock (Columbia Pictures) as an eighth grader. He wasn’t popular. “I looked like Ichabod Crane with bad skin,” he said. In high school, he ran for class president three years in a row, and lost each time. He also developed body dysmorphia, he said.

He went to college at U.C.L.A. and described his time there, in a not-entirely-convincing tone of regret, as a “missed opportunity to be responsible.” He joined a fraternity, rowed crew and gained 20 pounds of muscle. “Quite frankly, my life changed,” he said. “All of a sudden women were very interested in me.”

During business school at the University of California, Berkeley, he and a classmate started a firm called Prophet Brand Strategy, advising companies on how to build their brands. This being the early 1990s, their advice often amounted to: Use the internet. They attracted big clients, including Williams-Sonoma, Levi Strauss and Apple. In the dot-com boom, they started a series of companies, including an e-commerce site called RedEnvelope, where people could buy and send last-minute gifts.

RedEnvelope got an influx of cash from venture capital firms, including Sequoia Capital, but Mr. Galloway thought the new financiers were steering the company in a terrible direction. His battle to replace the board failed, but did attract the attention of hedge funds. “They said, ‘We like the cut of your crazy jib,’” he said.

He entered a new phase as an activist investor and started looking for companies to flip, like Gateway and Sharper Image. “It fit my personality,” Mr. Galloway said, describing himself with a profane synonym for jerk. In 2008, Mr. Galloway and a partner targeted The New York Times Company, buying nearly 20 percent of the company and securing two seats on its board. (It was a tense relationship, and he stepped down in 2010; Arthur Sulzberger Jr., then the publisher of The Times, declined an interview request made through a spokeswoman for the company.)

His profile began to rise. During the very public Timessaga, a reporter from the gossip site Radar Online turned up at a showing of Mr. Galloway’s house in the Hamptons and spotted some of his old college photos on the wall. A series of pictures showed Mr. Galloway partying with his frat brothers, with captions that included “The Vagilantes” and more crude nicknames.

After that, any time Gawker or the Intelligencer blog (at New York magazine) reported on Mr. Galloway and his dealings with The Times, they used one of those nicknames.

Cable networks starting inviting him on to share his takes. In 2014, to promote his new luxury brand intelligence firm L2, Mr. Galloway started a YouTube series called “Winners and Losers,” in which he highlighted companies that did especially well or poorly. The videos were shot in black and white, with Mr. Galloway appearing from the waist up against a white background, wearing what he calls his “uniform”: Brunello Cucinelli shirt, John Varvatos jacket and chunky Warby Parker glasses.

Mr. Galloway hit his stride when he started calling out big tech companies. In 2015, in a speech at the DLD conference (a tech summit in Munich), he deadpanned that “Google Glass is not a wearable, it’s a prophylactic ensuring that you will not conceive a child, as no one will get near you.” The speech, Mr. Galloway said, got him a contract for his first book, a jeremiad against big tech called “The Four: The Hidden DNA of Amazon, Apple, Facebook, and Google.”

Despite his multimedia success, episodic television has proved Galloway-resistant. In 2020, he quit his show on Vice TV after the first few episodes turned out so badly that, he said, his wife cried. (She confirmed that she’d been upset by the quality.) Then, in 2021, Bloomberg TV scrapped his new series after Mr. Galloway shot a teaser in which he appeared shirtless and cracked jokes about one-night stands and erectile dysfunction.

It was a big deal, therefore, when Mr. Zucker called Mr. Galloway last summer and offered him a show on CNN+. In April of this year, a few weeks after the network started, Mr. Galloway’s producer called with good news: His show was the service’s top weekly program. (A spokeswoman for CNN declined to comment.)

The next morning, Mr. Galloway got a text from Ms. Swisher asking if he was OK. It turned out that CNN’s new parent company, Discovery, had decided to shut down CNN+. While his show’s cancellation wasn’t his fault, this made him 0 for 3. “The universe is telling me I have a face for podcasting,” he said. Adding to the stress, his education start-up laid off a quarter of its staff around the same time.)

But within days after the shutdown, he said he was already fielding calls from TV networks. “I worry my narcissism is getting the better of me,” he said. Despite TV being “pretty much empty calories” and “by far the lowest R.O.I. of any medium I’ve engaged in,” he said, “I keep coming back for more.”

For all his obvious desire for attention, Mr. Galloway said he’s an introvert. Indeed, one on one, he can seem distant, avoiding eye contact and often reverting to a monotonous autopilot. Any question you ask, he manages to steer the answer back to one of his talking points, like a jukebox of monologues.

When I first met Mr. Galloway for lunch, at Balthazar in SoHo, he told me that one of his core tenets is atheism. “I’m one hundred percent convinced I’m going to look into my sons’ eyes at some point and know our relationship is coming to an end,” he said. “And that’s OK.”

Later, as I read through his recent newsletters, I stumbled on a familiar line: “At some point I’ll look into my sons’ eyes and know our relationship is coming to an end. And that’s OK.”

Is He Cancellation-Proof?

Last November, Mr. Galloway’s son came home from school and asked: “What’s a numbskull?” The day before, Elon Musk had called Mr. Galloway an “insufferable numbskull” on Twitter, and some of his son’s classmates had brought it up. “I told him, ‘We have a funny little back-and-forth.’”

In fact, Mr. Galloway has been one of Mr. Musk’s most vocal antagonists, criticizing him for a host of misdeeds, including manipulating Tesla’s stock price (an accusation Mr. Musk denies), calling a private citizen— a caver who helped with the rescue of Thai schoolboys — a “pedo,” and exploiting tax loopholes (Mr. Musk has denied this as well). Mr. Galloway said that bad behavior by tech executives like Mr. Musk “triggers him, in part because it reminds him of himself. “I’m disgusted with some of my past behavior,” he said.

Mr. Galloway remembered one incident that occurred soon after he started L2. He was sitting in a meeting with a couple dozen people, watching a man in his 20s go through a slide presentation. Afterward, Mr. Galloway turned to the presenter and, using harsh language, told him he wasn’t making sense and was wasting everyone’s time.

Later, Mr. Galloway went to the bathroom and stood next to the young man at the urinals. “I saw his hand shaking,” Mr. Galloway said. “And I thought, Jesus Christ, this guy actually has no control over his motor functions because of what I said to him.” The incident rattled Mr. Galloway. “I thought, what’s the point of being successful if you make people feel that way?”

Mr. Galloway gives his critics plenty of ammunition. Perhaps most notoriously, he speculated publicly that the GameStop stock frenzy of early 2021 was the result of young men not having enough sex. Julie Young, the financial analyst, called his Twitter thread on the subject “legitimately insane”: “If a female commentator were this confident and this wrong this often, she would be destroyed in the media.” Instead, Netflix approached Mr. Galloway to consult on its GameStop movie script.

Mr. Galloway said he has been criticized for his gender-normative analysis before, sometimes fairly. But he argued that he’s always hired and promoted people from underrepresented groups. “Every C.E.O. of every company I’ve ever hired except for one has either been gay or a woman,” he said.

After his keynote speech at South by Southwest in March, an audience member named Christopher Haines confronted him about his proclivity for putting on women’s clothing as comic relief, arguing that it perpetuates stereotypes that promote bullying. “I’m wondering,” Mr. Haines said, “as a father of a transgender child, if you would consider retiring your cross-dressing, transphobic presentations?”

Mr. Galloway became uncharacteristically flustered. He worked through his thoughts onstage. “Regardless of what I think I’m doing, I recognize my privilege may make me ignorant to the impact that you’ve just outlined,” he said. “So, let me cut to the chase: I believe that you are sincere. I will stop.”

Mr. Galloway seemed sincere, too, even if he knew that the moment would make for great TV. The incident closed out the first episode of his CNN+ show.

I asked Ms. Swisher if she worries about Mr. Galloway crossing a line in a way that torpedoes his career. “Every day,” she said. But Mr. Galloway seems in some ways immune to cancellation. He runs his own company, and has enough income streams that one or two or even five could dry up and he’d be fine. He’d have to alienate his own audience, who were presumably drawn in by his provocations in the first place.

And if it didn’t happen when he endorsed Dr. Mehmet Oz for U.S. Senate, or when he fat-shamed Mr. Musk, or when he applauded the decision by the world governing body for swimming to limit the participation of transgender women in international competition, or when he regularly denounces “wokistan,” it’s hard to imagine when it will.

In September, Mr. Galloway and his family are moving to London. “We want our kids to experience a different culture,” he said. He’s currently exploring a new TV project with the BBC. He’s leery after his hat trick of TV fiascos, but said he tries not to worry about failure. “What if this doesn’t work? We’re all going to be dead,” he said. “Well, it’s going to be a really public failure. Well, OK, the person you’re worried about is going to be dead, and so are you.”