How to Know if Your Boss is A” Douchebag”: Lessons from the Fyre Festival

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Spoiler Alert: This post contains spoilers for the Netflix documentary Fyre: The Greatest Party That Never Happened.

Plenty of us have supervisors we hate. Some of us work for douchebags. This distinction is significant because plenty of people are inconsiderate, immature, selfish, competitive, and dishonest. But we’re not entitled to a workplace free from unethical ineffective people. We are, however, entitled to employment free from the douchey.

According to the viral blog post by my friend Professor Michael Mark Cohen, a douchebag is not only an asshole, but a subset of asshole who is primarily concerned with increasing and asserting his White wealthy male heterosexual privilege. He is a one-percenter (or more often an aspiring one-percenter) who engages in amoral and abhorrent behavior to achieve discriminatory goals. Because the douchebag prefers to rely on entitlements assigned to his Whiteness, maleness, straightness, and wealth

more than anything else to advance professionally, he is usually fatally toxic to any endeavor. The douchebag is merit’s enemy and mediocrity’s whore.

To be crystal clear for the #AllLivesMatter folks, according to Professor Cohen anyone can of course be an asshole. And all straight white wealthy men are not douchebags. The term should only be applied based on an individual’s known bigoted behavior that is concurrent with his rich straight white maleness. For example, R. Kelly is clearly an asshole. Well-known douchebags include former media mogul Harvey Weinstein, former professor Emanuele Castano, Supreme Court Justice Brett Kavanaugh, and the 45th President of the United States.

We can also add Billy McFarland, former CEO of Fyre Media, Inc. and orchestrator of the Fyre Festival fiasco to this list. I expected the Netflix documentary, Fyre: The Greatest Party That Never Happened, to make a statement about our overreliance on image in the social media era or how music festival culture has officially jumped the shark (Beyoncé can’t save all of them). In fact, this is a gripping tale about douchebaggery in the workplace, and how it makes employees and contractors who are people of color, women, LGBTQ, youth, and/or from developing countries particularly vulnerable.

Based on the Fyre Festival example, here is a quiz with three questions that can help you determine whether or not your boss is a douchebag. Don’t despair, at the end there’s also tips on how to overcome him. If your boss is just an asshole, I’m sorry. Tell me about it in the comments.

1. Does He Put Models Over Merchandise?

Bella Hadid. Courtesy Fyre Media, Inc.

I was stunned to learn from the Fyre documentary that the music festival was intended initially to be a tool for marketing the Fyre app. This app aimed to provide everyday event organizers with a reliable and efficient way to book celebrities. As a producer, activist, professor and event planner, who has faced the hurdles of hunting down talent, I think this is an excellent and useful idea. Also, public events are a tried-and-true marketing method that allows brands to build community with their consumers and demonstrate how they are problem solvers. Talent exhibition for a talent booking app? Great business thinking.

But the documentary illuminates how almost immediately McFarland shifted the focus away from promoting the app through the festival to glorifying his ability to access young women who were professionally charming and attractive. He hired a production company and crew of supermodels including Chanel Iman and Bella Hadid to shoot a commercial for the event featuring himself and his business partner Ja Rule. The commercial itself does not show the app, or confirm whether the models were booked using the Fyre app, or explain the relationship between any of the festival’s features and the app’s functionality. The takeaway from this lovely short film is that these women are beautiful, McFarland knows them, and they were all playing on the beach in the Bahamas.

America’s culture and court system are pretty forgiving when it comes to exaggeration, or “puffery,” in marketing. However, the douchebaggery is evident in McFarland’s preference to create a commercial that showcased him as a straight, White, wealthy man that dominated nature, women, and his best complicit Black friend Ja Rule. There are stomach churning scenes in the documentary in which Ja Rule, more than a decade past the peak of his cultural relevance, serves as McFarland’s oppression hype man by declaring their entitlement to bother the islands’ turtles and force women employees to swim against their will. The finished product was not a vehicle for promoting the app, which was being developed by earnest hard-workers in New York. It was a siren call to other douchebags that promised, “if you come to the Fyre Festival, you can flaunt your entitlement, too.”

McFarland’s obsession with featuring models to promote an app for event organizers is particularly telling. The model’s job is to be a vessel for a creative vision, logo, or other abstract concept. For the most part women models are charged with doing this while also conforming to the mainstream’s ideal of femininity by appearing young, thin, and fun. In contrast, organizers are leaders who transform a vision into a reality. They are usually assertive, uncompromising, and dead serious. Douchebags are only comfortable in scenarios where they can dominate and exploit, so   McFarland could never truly connect with Fyre app’s target audience of organizers. True leaders rarely fan the flames of anyone’s ego.

If your boss puts models or other avatars of straight wealthy white male dominance above the actual product your organization offers, he might be a douchebag.

2. Does He Terrorize Truth Tellers?

After the American cheese sandwich tweet seen around the world (left), McFarland and some of his inner circle attempted to blame unforeseeable circumstances for this catastrophe. “Do not lie!” an employee reportedly exclaimed as McFarland and his crew prepared a public statement at the festival site. The fact was McFarland’s faithful hardworking employees had repeatedly warned him that he “was selling a pipe dream” to ticket holders due to the logistical realities on the ground. McFarland chose to terminate or ignore the truth tellers to indulge his fantasy.

McFarland launched the Fyre Festival on a classic douchey premise: colonialism. His branding of Norman’s Cay in the Bahamas, the original site of the festival, as “Pablo Escobar’s private island” in unspoiled paradise was inaccurate. According to Frontline, between 1978 and 1982 only part of the Cay was owned by Medellin cocaine cartel’s leader Carlos Lehder. He organized the use of the island’s private airstrip as a layover point for small private planes smuggling narcotics from Columbia to the US. Eventually, the Bahamian government shut down his operation and Lehder was incarcerated. I could find no evidence Escobar ever went to Norman’s Cay or personally owned any property there.

By providing this tantalizing fictional tidbit about the festival’s locale, McFarland sought to capitalize on decrepit stereotypes about the lawlessness and exploitability of the Caribbean and Latin America. Pablo Escobar, the Latinx caricature not the actual human being, looms large in the douchebag's imagination as a symbol of the hypermasculine indulgent criminality he believes his straight White male privilege entitles him to enjoy. However, the douchebag does not expect to suffer the same consequences as Escobar—imprisonment and death—because he is not Latino or from the developing world. McFarland felt free to deploy Escobar’s legacy and the idea that Norman’s Cay was available to use with abandon. That is how douchebags have treated the region and its residents since 1492.

Unsurprisingly, McFarland’s puffery was soon poked by reality. The Bahamas is a very real wealthy majority Black country with immigration, customs, taxes and a booming tourism industry. The festival’s ticket holders were quite nonfictional people who needed food, water, and bathrooms. Norman’s Cay was owned by a multinational consortium of developers who expected to get paid in actual dollars.

Just as Christopher Columbus refused to listen to the Arawak and Taino when they informed him they were not in India and instead began burning them alive, McFarland “would not take advice” from his employees that the Fyre Festival would not be the luxury bacchanal he had sold to thousands of ticket holders. The employee that advocated for docking a cruise ship near Norman’s Cay for guests because the island lacked electricity, internet access, and plumbing was fired. Another employee who advised it was impossible to find the dozens of luxury seaside villas McFarland had promised nonpaying influencers was chastised for not being solution-oriented. Andy King, the gay employee who expressed concerns about McFarland’s inability to pay taxes for imported water, was charged with bribing a local official with fellatio.


In Fyre, McFarland’s sincere former employees expressed how they were flabbergasted by his unwillingness to respond to facts. The douchebag’s aversion to the truth should never stupefy.  He is, after all, propelled by the most enduring fiction in human history. The fantasy that whiteness, maleness, heterosexuality, and wealth entitles anyone to dominance over anyone else. If your boss is allergic to the truth, he might be a douchebag.

3. Does He Generate Actual Profits or Just Fit the Entrepreneur Profile?

Supermodel Chanel Iman and friends on a private jet hired by McFarland and paid for by investors and employees. Courtesy BravoTV.

In McFarland’s defense, according to the documentary he appeared to be taking a lot of cues from The Silicon Valley Entrepreneur’s Handbook composed by the examples of Mark Zuckerberg, Elon Musk, and Elizabeth Holmes. He did whatever he could to fit the profile of the Next Big Thing for venture capitalists. He was a lower upper class college dropout with a baby face, winning smile, and millennial white American voice that connoted youth and tech wizardry. The Maserati and private plane rides conveyed existing billionaire support. The rapper accessory in Ja Rule broadcasted cool and cultural insider-ship. Wealthy people stay wealthy through value investing—buying low and selling high. VCs wish they had a time machine to meet Jeff Bezos in 1994 or Zuckerberg in 2004. McFarland began convincing some investors the Fyre app might be their Facebook.

As employees and contractors, we also engage in this kind of professional profiling. After a lifetime of receiving images and messages from schools and the mainstream media that people with great business ideas never look like us and always look like douchebags, we believe it. MaryAnn Rolle, a Black Bahamian woman who is owner of the Exuma Point Bar and Grille, explained that she agreed to work with the Fyre Festival because they seemed to “have a lot of money” and promised the Festival would be an annual event on the island for the next five years. It is quite possible that, to Rolle and the other contractors and Fyre employees, McFarland fit their profile of a successful White foreign businessman. Hungry for opportunity and eager to demonstrate their hard work and competency—as many of us are—they did not do their homework on McFarland. As a result, they suffered grave consequences.

The problem with profiling is that in a society still very much influenced by racism, sexism, homophobia and other forms of marginalization, shorthands for success always benefit the douchebag. Fitting the shallow profile of “successful entrepreneur” has little to do with whether or not one is generating actual profits. For example, according to the Netflix documentary McFarland was running his company more like a pyramid scheme than a business. He spent millions of dollars keeping up the facade of success. Neither the app or his earlier project Magnises were generating sufficient revenue to sustain these expenses. So he solicited more and more investment, and helped himself to employees’ credit lines, to keep the charade going—without ever increasing profits.

Once the pyramid collapsed and the Festival fiasco went viral, McFarland attempted to make himself scarce. His employees and contractors were left in financial and reputational debt because of his fraud. Ms. Rolle, who helped cater the Festival, claims in the documentary while fighting back tears she lost $50,000 of her savings to wages and supplies that were supposed to be paid through her contract with McFarland’s company. Others claimed to have lost hundreds of thousands of dollars or weeks of wages. Ironically Ms. Rolle, who runs her business with her husband Elvis, provided the true sterling example of entrepreneurship by taking responsibility for her decision to work with McFarland and not passing on her losses to her workers.

In sum, if your boss puts more money into looking like a success than generating actual revenue, he might be a douchebag.


The Takeaways


MaryAnn Rolle in Her Still Successful Business Courtesy Scott McIntyre/New York Times

If you've answered yes to 2 or more out of the three above questions about a supervisor who is a straight White man, I’m sorry but your boss is a douchebag.

The good news is there are a few tips we can remember to help us overcome the toxicity of douchebaggery in the workplace.

First, know the difference between avatars and actuality. McFarland’s work as an “operational sociopath,” as one of his employees described him, shows how douchebag’s rely on our belief in avatars for success and achievement. Look past models, bottles, and Maseratis, or whatever the eqiuvalent is in your field, and evaluate your boss’s demonstrated outcomes and achievements. If there’s no there there, there probably never will be.

Second, if he lives on lies then leave. By leave, I mean actually change jobs as soon as you can. In the meantime, withdraw your emotional, financial, and time investment as much as possible. As we see with McFarland, douchebags adore exploiting the diligent and capable while making us bash our heads against a wall of frustration. Save your emotional investment for a boss who deserves it.

Third, make him show you the money. If you took this quiz, chances are you are suspicious your boss is not what he claims to be. Trust your instincts and seek proof that he can pay his bills as soon as possible. If you’re at the beginning of the relationship, try to negotiate established intervals for payments of salary or invoices. If he misses one, stop work until it is resolved and don’t be afraid to cut your losses. Although MaryAnn Rolle pointed out in a New York Times interview: “be careful of strangers,” which is good advice, a Go Fund Me campaign replenished her losses and provided a surplus she pledges to share with her community. Lost money is not your last money. But don’t put the good investment of your time and mental health where you know it will not pay off.

Remember, the era of the douchebag is clearly in decline. Billy McFarland probably never expected to endure consequences like his hero Pablo Escobar. Convicted of mail and wire fraud, McFarland is federal inmate #91186-054,


-- Robin J. Hayes, PhD