It’s a Thursday evening in spring, there’s a Billy Joel concert at Madison Square Garden and Anthony Scaramucci is psyched. The 55-year-old entrepreneur is coming to the end of a grueling week, having flown from New York to Boston to San Francisco to Washington, D.C., and back to New York meeting with financial advisors at several big banks to promote his firm, SkyBridge Capital. There’s just one more stop before he can let loose with the troubadour of working class Long Island—Scaramucci’s home turf.

Scaramucci is running late and rushes into the midtown Manhattan auditorium at Barclays Investment Bank. It’s full of young hedge fund types there for a Wharton School alumni networking event. Scaramucci, the featured speaker, puts aside his two cell phones and his sunglasses (which he is carrying despite the fact that it’s raining), and immediately starts talking—no microphone, no PowerPoint slides. He doesn’t stop for 74 minutes.


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“Is this Trump 2020 campaign headquarters?” jokes Scaramucci, who wears his politics on his navy blue suit via a diamond, ruby and sapphire–encrusted flag pin. He’s already sized up the crowd of diverse young financiers—African Americans, Asian Americans and women among them—and figured that many are likely not fellow Trump supporters.

It doesn’t matter. They’ve come to see “the Mooch,” as he is both affectionately and derisively called.

Scaramucci, who founded hedge fund of funds SkyBridge Capital in 2005, is on a whirlwind comeback tour that began almost the day after he was famously fired from his job as communications director for the Trump White House after only 11 days in July 2017. Or as he puts it, “fired like an Austin Powers villain, getting ejected into the sky and dropped into the fire” for an expletive-laden conversation with New Yorker reporter Ryan Lizza.

I thought I would last longer than a carton of milk.

“I thought I would last longer than a carton of milk,” he quips to the crowd. Now, as he rags on his fellow White House denizens Reince Priebus and Steve Bannon and castigates Washington as more venal than Wall Street, he says, “I think you can tell, I really don’t give a shit.”


Such insouciance is disarming—and charming. “He’s very charismatic, incredibly engaging and a really smart guy,” says Robert Wolf, a former Obama economic advisor who runs 32Advisors and has teamed up with Scaramucci on a bipartisan think-tank venture called Strategic Worldviews. “He’s not a guy I would be shorting.”

The White House debacle wasn’t Scaramucci’s first setback—only the most publicly humiliating. As he explains, it was like the difference between “removing a splinter and open-heart surgery. It was harder by an exponential quantum.”

Among the challenges that came before, Scaramucci failed the bar exam twice after graduating from Harvard Law School (he finally passed) and got fired from Goldman Sachs (and rehired). After becoming an entrepreneur, he watched two investment firms he founded nearly go bust.

Coming back from failure has become a theme in interviews and speeches (not to mention at least two of the four books he has penned). Scaramucci goes from political musings to motivational tips to macro analyses without skipping a beat. “No whining” and “forgive yourself” are common refrains, referring to the importance of acknowledging one’s mistakes and then not beating yourself up about them.

BT—the term he gives to the time before Donald Trump—Scaramucci became well known in financial circles as a hedge fund impresario for launching the SALT, or SkyBridge Alternatives, hedge fund conference in Las Vegas in 2009, a decision made in the depths of the financial crisis when SkyBridge was on the verge of going under. A bold purchase of Citigroup’s hedge fund management group would save the firm, and the man who ran it, Ray Nolte, is now the co-managing partner who runs the money at SkyBridge. Scaramucci owns 44 percent of SkyBridge but maintains 51 percent control. 

Former president Bill Clinton keynoted SALT in 2010.

SALT was a huge hit, bringing the worlds of hedge funds and politics together in what became known as the “Davos of the Desert.” Scaramucci’s marketing savvy, in large part deployed through SALT, led the combined firm from $1 billion in assets to a peak of $13.5 billion in 2015. Although he supported Bill Clinton’s presidential bids and Barack Obama in 2008, Scaramucci is a longtime Republican in the New York mold of what he terms “social inclusiveness.” Through SALT, he got more involved in politics as a Republican fundraiser, eventually embarking on an admittedly disastrous foray with his support of Trump in 2016 after the New Yorker won the nomination.

“Anthony just wanted to be involved in politics, that’s all. There’s a million Wall Street guys like that,” says Vanity Fair special correspondent William D. Cohan, who has moderated sessions at SALT for many years. “Then I think when he finally got to the center of Trump World, he briefly got drunk with the power.

Every decision I’ve made in life where I’ve inserted my pride and ego has been a bad decision.

Scaramucci is the first to concede his flaws. “Every decision I’ve made in my life where I’ve inserted my pride and my ego has been a bad decision,” he says. “Every time you do that, your emotions go high and your intelligence goes low. It leads to a debacle.”

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Critics have called him an opportunist. But Scaramucci, who grew up in a working class household in Port Washington, N.Y, where his father worked as a laborer in the sand mines, says backing Trump and taking a job in the administration was just another of the outsize risks he had to take to get where he is in life.

“When you come from a background like mine, you have to take some risks. I’ve taken on a lot of risks,” he says. “And I’ve stumbled. One of the things I try to tell kids, when I’m teaching, is if you’re making mistakes, the first person that you have to forgive in life is yourself. I can’t walk around kicking my heel into my little heinie, saying, ‘Oh, I made a mistake at the White House and got fired. I’m miserable.’”

That might be the key to understanding Scaramucci and the wild ride he’s still on.

Trump’s surprise electoral victory put Scaramucci in line for a White House job. When he first planned to join the administration at the beginning of 2017, Scaramucci left SkyBridge and reached an agreement to sell the firm to HNA Group, the Chinese conglomerate—which would have netted him about $80 million. After more than a year of regulatory uncertainty, the two firms officially backed out of their deal on April 30, 2018, and Scaramucci rejoined SkyBridge as co-managing partner focusing on strategic planning and marketing.

Scaramucci—who still supports Trump but is often critical of his policies and actions—has said that going to Washington was the worst mistake he’s ever made. During the midst of the White House uproar, the divorce filing of his pregnant wife, Deidre, was splashed across the tabloids. The two have since reunited and have a weekly podcast, Mooch and the Mrs. (News flash from a recent episode: Scaramucci, an Italian American Catholic, gave up butter for Lent after his SkyBridge colleagues told him he had gained weight.)

I got my company back. I got my wife back.

“The good news is I got my company back. I got my wife back. There’s no complaining here. I’m sitting here, from a position of gratefulness and appreciation. It’s like the scene in It’s a Wonderful Life where he bumps his head. He’s in an alternative universe that he doesn’t want to be in. Lucky for him, he gets back to where he was,” says Scaramucci, adding his signature kicker that shows he’s just a kid from the streets of New York: “You know what I mean?”

And now, he wears his White House firing as a badge of honor. After all, Scaramucci’s hardly the only one to be ousted. And guess what else? “It made me more famous,” he says.

Being famous has never been more important to Scaramucci, as he seeks to rebuild his firm. Last year SkyBridge outperformed the markets and its peers, gaining 3.23 percent in its flagship fund while the S&P 500 fell 4.4 percent, and the Hedge Fund Research Institute fund of funds composite index was down 3.48 percent.

But SkyBridge, which now runs $9.4 billion, lost more than $4 billion, or 30 percent, of its assets in recent years. SkyBridge invests in other hedge funds, so it’s not surprising that some of that money fled due to poor performance in 2015 and 2016 when the underlying funds did poorly. The drain continued with the uncertainty of the HNA deal, then others pulled their money due to Scaramucci’s support of Trump.

“There are some people who just left and said, ‘I don’t want to have a firm affiliated with Donald Trump anywhere near managing my money, period, end of discussion,’” acknowledges Nolte, who says it was a small number. The good news, he adds, is that during the last quarter of 2018, the fund’s assets were on the upswing again, following 27 months of positive performance.

SkyBridge’s investments, for the most part, are decidedly unsexy—the perfect foil to Scaramucci’s flamboyant personality. Dan Loeb’s Third Point is perhaps the only hedge fund in SkyBridge’s portfolio that has name recognition. A number of its other funds, such as Hildene Opportunities and EJF Debt Opportunities, invest in structured credit, complicated debt investments that have come back in the past decade of low interest rates, and are what’s called “relative value”—strategies that are low risk.

Since 2003, what is now SkyBridge’s flagship fund has outdone its peers in the fund of funds space. SkyBridge has a 6.10 percent annualized return, beating the HFRI funds of funds composite index, which gained 3.39 percent annually during that time. But during the same period, the S&P 500 has been up 9.44 percent annualized—making hedge funds less enticing.

I’ve been doing this for 30 years now. The hedge fund industry sucks.

Or, as Scaramucci says, “I’ve been doing this for 30 years now—the hedge fund industry sucks.” He gives two main reasons why. First is the Federal Reserve’s “zero interest rate policy. If you jam interest rates down for a decade and every asset in civilization floats up, what do we know about financial assets?” (They go up, which hurts hedge fund strategies, like shorting.)

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The second reason why the industry “sucks,” according to Scaramucci, is “the supply of capital in our industry. Frankly, for a period of time, there was an oversupply of capital, so trades got very, very crowded. When trades get very, very crowded, the economic rent associated with those trades is narrower.”

Funds of hedge funds, which take an additional layer of fees, are in worse shape. “As bad as the hedge fund industry sucks, the fund of funds industry sucks to the 10th degree,” he says. (Scaramucci prefers to call SkyBridge an “outsourced multi strategy fund”—as opposed to a fund of funds—because it invests in a number of different strategies and has been able to keep its fees relatively low.)

In an effort to pivot away from hedge funds, SkyBridge has launched a new Opportunity Zone Fund, a product created by the 2017 Trump tax legislation that allows investors to sell investments without paying capital gains taxes on the profit for several years as long as the gains are invested in designated “opportunity zones” in inner cities. “It has an opportunity to create job growth and infrastructure rebuilding,” Scaramucci says. The fund closes September 30, and SkyBridge is targeting $1 billion by year-end. If the idea takes off, he thinks the fund can raise $3 billion.

It’s just one of the products Scaramucci has been flogging as he does his part to raise back what was lost at SkyBridge, and then some. “My goal right now is to try to double the size of this company in five years, which I think is achievable if we just get a 7 percent return, and we create a multiple-billion-dollar platform in the opportunity zone space. That’s a big challenge, and that’s a lot of fun,” he says.

After Labor Day last year, Scaramucci says, he put himself on an aggressive travel schedule. Over the past six months, he has gone to Abu Dhabi, Dubai, Kuwait, Tokyo, Seoul, London—and 30 different cities in the United States, as well as Davos, Switzerland, for the World Economic Forum.

SkyBridge has a retail platform for investors to access alternative investments, which may help explain what many view as Scaramucci’s most bizarre action in recent months—his stint earlier this year on Celebrity Big Brother, the reality TV show starring B-list celebrities like Kato Kaelin, who became famous as a witness in the O.J. Simpson trial, and Dina Lohan, the mother of actress Lindsay Lohan.

Scaramucci was on the show for only four episodes—on one day dressed in a purple suit and looking like a character out of Guys and Dolls, the next day sporting a cowboy hat and flowered shirt. He admits those outfits were uncomfortable, as he makes no effort to hide his vanity. But he says he had a blast. “I’m a guy who likes to have fun. I’m a guy that likes to explore and experiment with things.”

I’m not going to change my personality.

Most people who’ve criticized Scaramucci for doing the show—which is just about everyone except his wife—are “boring,” he says. “I’m not going to change my personality to adapt to whatever everybody thinks I should be doing.” The point he wants to make, though, is that Big Brother is a long-running show and has five to eight million viewers each night. Maybe people “are missing that they have a reality television star as their president,” he muses.

If Scaramucci is channeling Trump’s marketing savvy, there is definitely a method to what some might call his wackiness. He has long aspired to offer investments to the masses, or the “mass affluent,” as he calls them. Was going on Celebrity Big Brother another way to reach these people and democratize his brand? “It’s pretty clear-cut,” says Nolte. (Scaramucci says it also will help him reach inner city kids in his charity work.)

He’s like a male hedge fund version of the Kardashians.

To be sure, Scaramucci’s working-class roots make him more comfortable in such settings than the average Harvard-educated financier. “He’s a bit of a Zelig,” says Cohan, referring to the chameleonlike Woody Allen character. “Anthony’s the kind of guy who can go from Davos one minute to the set of Big Brother the next. [Scaramucci famously left the show’s set and flew directly to the World Economic Forum.] I give him credit for that. He’s like a male hedge fund version of the Kardashians.”

Adaptation is part of his DNA. “You’re talking to a guy that grew up a certain way and had to make major adaptations to get to where I am,” says Scaramucci, who notes he didn’t go to a boarding school, had never walked into a country club or hit a tennis ball as a youth.

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“When I showed up at my first interview at Goldman, I was wearing 100 percent polyester. I had a polyester shirt. I had a polyester tie on. I had Capezio dance shoes on from the 1970s,” he says. It was 1989. He was 25 and known as the worst-dressed person at Harvard Law School. After being told he shouldn’t go for the callback interview dressed in polyester, he recalls, “I had to go out and put on a credit card a Brooks Brothers suit and a cotton shirt.”

What’s next for the Mooch is anyone’s guess—even his own. Observers expect him to sell the firm once he builds it back up—something he says he isn’t thinking about now. “I’d like to be working until I’m at least 70, and I don’t see any reason to sell the company. I’m having a great time running it, and we’re doing well.”

Of course, Scaramucci wants to do more media. (He has a SAG card from his cameo in Oliver Stone’s 2010 sequel, Wall Street: Money Never Sleeps.) A big loss from his White House escapade was Wall Street Week, the iconic Louis Rukeyser TV show that he had revived, after buying the rights. The show was taken over by Fox when he joined the administration. Scaramucci is coy, but hints that something similar is in his future.

Maybe I’ll go on Dancing with the Stars.

And even though he can’t dance, Scaramucci says, “Maybe I’ll go on Dancing with the Stars. I don’t know. If they ask me, I probably would do it.”

Then there’s politics. Scaramucci’s current disdain for political life can’t hide his obsession with the topic. Not only is he on TV as a Trump supporter on a regular basis, Scaramucci talks politics even when it’s not expected. In his address to the Wharton alumni, the topic took up at least half of his comments.

And so, no one was surprised when, as the Wharton event neared its end, Evan Katz, managing director of Crawford Ventures, asked a question from the crowd that was on everyone’s mind: “Anthony, when are you running?”

“I’m never fucking running,” Scaramucci promised. “I’m just trying to stay married.” And then he had to leave—Billy Joel was going to be onstage in 30 minutes.

Michelle Celarier is a freelance journalist specializing in business and finance whose work has appeared in Worth, New York, Institutional Investor, Slate, the New York Post and Fortune, among others.