The Profile: The master of failing up & the Bitcoin bandits

Whenever a revered entrepreneur falls from grace, we collectively gasp and ask ourselves: “How could this possibly happen?” 

Logically, the answer is typically pretty straightforward: they were bleeding cash, the company’s financials didn’t make sense, or you know, they were running a complete fraud. But to get to that point, the founders had to convince a whole bunch of people to fund their vision and pay thousands of dollars to attend a music festival that never took place. 

And that part has absolutely nothing to do with logic. It has to do with charisma. And charisma is the ultimate double-edged sword. Just look at how society describes the following: Theranos’ Elizabeth Holmes was “a striking female entrepreneur with a heartfelt personal story.” Fyre Festival’s Billy McFarland was “a charming, seemingly trustworthy salesman.” WeWork’s Adam Neumann had “an inexplicably persuasive charisma and a taste for risk.”

In the Neumann profile featured below, there’s one part that stuck with me. Harrison Weber, a former WeWork editorial director, remembers how Neumann would talk about creating the first “physical social network,” referring to a place where members could talk about jobs, family, love. “It was like, wait, you mean life. What you’re talking about is just regular life,” Weber said. 

It reminded me of the time a founder sent me the following pitch: “It’s like a jacket, but for your legs.” And I thought, “Oh my god, he’s talking about pants.” They may speak in clichés, but if they’re charismatic, the clichés sound revolutionary. 

In this fascinating 1996 Fortune feature, Pattie Sellers delves into the mysterious, elusive “X factor” all leaders chase but only some possess. “Charisma is a tricky thing. Jack Kennedy oozed it—but so did Hitler and Charles Manson,” she writes. “Con artists, charlatans, and megalomaniacs can make it their instrument as effectively as the best CEOs, entertainers, and presidents. Used wisely, it’s a blessing. Indulged, it can be a curse.”

She goes on to outline five key qualities of truly charismatic leaders: they simplify and exaggerate, romanticize risk, fight convention, empathize, and goad & challenge. The people featured in the profiles below have charisma in spades, but the question is: Who’s using it wisely and who’s bound to get cursed?

THE PROFILE MEETUP: Wow, a whole lot of you signed up for The Profile’s global hangout. The fact that this newsletter has reached people from the U.S. all the way to Nairobi, Kenya blows my mind. THANK YOU. This is the last chance to fill out the survey. I’ll be emailing you about our local meetups this week, so sign up now if you want to participate. Cheers to making new friends!

Lots of excellent profiles this week:

The master of failing up [**HIGHLY RECOMMEND**]
— The Bitcoin bandits
— The leader of the #YangGang
— The secret lives of NHL dentists
The CEO battling Google
— The Texas secessionists
— The four-time New York City Marathon champion
— The college party kingpin
— The exclusive women’s club sparking controversy
— The robots exploring the depths of the ocean

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The master of failing up: WeWork’s implosion was one of epic proportions. The company’s valuation plummeted, it withdrew its initial public offering, and also underwent an executive exodus. Yet somehow, its downfall came with an astonishing exit package for its ousted founder Adam Neumann. He could receive more than $1 billion after selling his shares while simultaneously collecting a $185 million consulting fee. This story explains how Neumann managed to fail up as his company was spiraling out of control. (The New York Times)

“He’s an incredible evangelist. He’s an incredible visionary. He’s hired a lot of amazing people. He’s built an amazing brand, right?”

The Bitcoin bandits: With its cheap geothermal energy, Iceland has become one of the leading miners of digital currency. The Advania data center houses computers that are part of the largest concentration of Bitcoin mining power in the world. Advania pulls in what’s estimated to be millions of dollars a year. But wherever there is money, crime is sure to follow. Thieves broke in and stole 550 Bitcoin computers, totaling $2 million in tech gear. These days criminals aren’t robbing banks — they are stealing the presses used to print digital money. (Vanity Fair)

“Why go to all of the expense and effort to start your own Bitcoin mine when you can get a head start into the business by stealing computers from the competition?”

The leader of the #YangGang: If Andrew Yang is the presidential candidate of Silicon Valley, then why is he railing against it? His whole message is premised on the dangers of automation taking away jobs and the risks of artificial intelligence. He criticizes tech companies and makes a villain out of Amazon. But Yang’s message is catching on, and he might end up the star of one of the most compelling political stories of 2019. (Wired)

“In places where jobs disappear, society falls apart.” 

The secret lives of NHL dentists: There’s one popular spot many hockey players go the day after a game: the dentist’s office. Being a dentist in the National Hockey League means you see some really gory stuff — bloody teeth, dangling nerves, swollen gums. In a sport where losing teeth is a badge of honor, take a look at how hockey has transformed NHL dentists into the unsung heroes of the athletic world. (ESPN)

“Lesson No. 1 in hockey: Sooner or later, everyone answers to the dentist.”

The CEO battling Google: Yelp CEO Jeremy Stoppelman thinks about tech behemoth Google more than the rest of us. “In Yelp’s case, it's been the thing that I probably have been most focused on for the last decade,” said Stoppelman, “finding a way to survive knowing that one of the most powerful companies in the world didn't want us to succeed.” This profile delves deep into Stoppelman’s 15-year battle with Google, and why his persistence is finally paying off. (BuzzFeed)

“The first seven years or eight years, there was a lot of eye-rolling in Silicon Valley about Yelp being a complainer … I think the reality is now the world has caught up.”

The Texas secessionists: Daniel Miller is the president of the Texas Nationalist Movement, which is devoted to ending Texas’s 175-year membership in the United States of America. He demands a referendum on secession and calls his plan “Texit” (yes, like Brexit). Miller argues that Texas sends the U.S. government more in taxes than it receives in federal funds. Texas itself is, in some ways, its own civilization — should it be its own country, too? (The Atlantic)

“The difference is that our decisions will be made here, and we will accept the consequences of those decisions.”

The four-time New York City Marathon champion: As a young girl, Mary Keitany’s nickname was “The Lightning.” Growing up in Kenya, she ran at least 10 kilometers every day. In the last decade, Keitany has become a fierce marathon champion. In 2018, she ran the second-fastest time (2:22:48) ever by a woman at the New York City Marathon. Take a look inside the mind of a marathon runner whose record-breaking career isn’t what helps her find meaning in life. (ESPN)

“You have to teach yourself that you're not running for yourself.”

The college party kingpin: While university tours and campus promo videos give students an idea of the academic environment at a college, a digital media company called I’m Schmacked gives them a look at the parties. The CEO recruited undergraduates as content creators, promising thousands of dollars in compensation and online fame. But none of that ever came. (The New York Times)

“They see a guy with one million followers and is verified. You just never would think someone with that much power would do that.”


The exclusive women’s club sparking controversy: Ever since it first launched three years ago, The Wing has struggled to define its ideal customer. It’s inclusive (welcomes all women) yet its exclusive (they have to have $2,000 of annual disposable income). No one gets rejected yet there are 35,000 people on a waitlist. The women-only members space claims to be an accelerator for the feminist revolution. But how progressive is it really? (The Guardian)

“I really wonder what the plan is to grow while staying true to their values.”

The robots exploring the depths of the ocean: We care more about understanding the emptiness of outer space (hello, Elon) than the living seas that make up 70% of our planet. The deep ocean is the final frontier of exploration. Sooo that means it’s time to bring in the robots. Backed by billionaires and venture capitalists, a wave of entrepreneurs are developing high-tech, low-cost robots to enter the deep waters that we barely understand. Here’s how affordable tech can unlock strange, new worlds. (Outside Magazine)

“Things that used to take months, now you can do in a day.”

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