The Most Insane People of All Time: #3 Elizabeth Holmes (aka You’re Outta Control!)

Epigraph: 

“This is the dawning of the age of Aquarius…”

— Aquarius/Let the Sunshine In, The 5th Dimension

Elizabeth Holmes emerges in Silicon Valley with the full prodigy package: Stanford dropout, world-changing ambition, and a carefully constructed persona. She leans hard into the comparison with Steve Jobs — black turtlenecks, minimalist language, intense seriousness — and presents herself as the young visionary who will revolutionize medicine. The pitch behind Theranos is irresistible: hundreds of diagnostic tests from a single finger prick. Investors, politicians, and media figures line up. The board fills with heavyweight names including George Shultz, and the company’s valuation soars to roughly $9 billion. Holmes becomes, on paper, the youngest self-made female billionaire. It’s classic Silicon Valley moonshot energy — bold claims, secrecy, and belief outrunning reality.

The problem, as insiders begin to realize, is that the technology doesn’t work at all. Engineers and lab staff struggle to produce reliable results, while Holmes and her partner Ramesh Balwani continue presenting the system as revolutionary. The company begins quietly using conventional lab equipment while maintaining the illusion. Whistleblowers emerge, including Shultz’s own grandson, who raises concerns at significant personal cost. The leadership circles the wagons. Meanwhile, John Carreyrou of The Wall Street Journal begins investigating, encountering secrecy, evasive answers, and mounting contradictions. His reporting — later expanded into the book Bad Blood — becomes the turning point. The narrative collapses, regulators move in, partnerships evaporate, and the once-mythic startup implodes.

Legal consequences follow. Holmes and Balwani are charged with fraud, and after a long, high-profile trial she is convicted on multiple counts. She delays reporting to prison after becoming pregnant, later giving birth with partner Billy Evans. Eventually she begins serving her sentence in a minimum-security federal facility. Even there, the mythology lingers — supporters, critics, and observers debating whether she was a calculating fraud, a true believer, or some combination of both. The arc is striking: Stanford prodigy, Jobs imitation, $9 billion valuation, total collapse, and prison. Less chaotic than John McAfee, less creepy than Keith Raniere, but still unmistakably outta control — a billion-dollar story built on belief, performance, and a technology that never worked.

Steve Jobs represents the template Elizabeth Holmes tried to emulate. Jobs cultivated a minimalist aesthetic, black turtlenecks, product mystique, and a “reality distortion field” that persuaded investors, employees, and customers to believe in things before they fully existed. But the crucial difference is that Jobs ultimately delivered. From the original Macintosh launch in 1984 to the iPod in 2001 and the iPhone in 2007, Apple shipped real, transformative products. Jobs bent reality rhetorically, not technically; Holmes attempted to bend reality where physics and chemistry refused. The comparison highlights both the ambition and the failure — she borrowed the style, but not the substance.

Bernie Madoff represents the classic institutional fraud parallel. A former NASDAQ chairman, Madoff operated a decades-long Ponzi scheme through Bernard L. Madoff Investment Securities, promising steady returns that attracted elite clients, charities, and feeder funds. By the mid-2000s, billions were under management, including investments tied to major institutions and wealthy families. In December 2008, amid the financial crisis, Madoff confessed to his sons, was arrested, and the scheme collapsed, revealing losses estimated at roughly $65 billion in paper value. The deception persisted largely through reputation and trust — investors assumed competence because of his stature. Holmes operated similarly: prestigious board members, high-profile endorsements, and a narrative of inevitability masked a system that didn’t work. Like Madoff, she benefited from credibility cascading downward — once enough influential people believed, the illusion sustained itself.

Sam Bankman-Fried provides the modern startup-era comparison. Bankman-Fried founded the cryptocurrency exchange FTX in 2019, and within a few years it was valued at around $32 billion. He cultivated a quirky, disheveled persona and promoted “effective altruism,” pledging to donate vast sums to global causes. FTX attracted major investors including venture firms and high-profile endorsements, while its sister trading firm Alameda Research operated closely behind the scenes. In November 2022, liquidity concerns triggered a rapid collapse, revealing commingled funds and massive shortfalls. Bankman-Fried was arrested in December 2022 and later convicted in 2023 on fraud and conspiracy charges. The arc mirrors Holmes: meteoric rise, media fascination, complexity masking weakness, and sudden implosion once scrutiny arrived. Where Jobs built something real and Madoff ran a traditional financial fraud, Bankman-Fried and Holmes sit in the same modern category — startup mythology outrunning reality.

In the end, the most astonishing thing about Elizabeth Holmes is not just the scale of the deception but the audacity of it. How, exactly, did she think she was going to get away with it? Blood testing is not social media. It’s not software. It’s chemistry, biology, physics — things that eventually either work or don’t. Yet she and Ramesh Balwani kept pushing forward, covering, deflecting, and doubling down as the gap between claim and reality widened. That’s the outta-control element: the belief that charisma, secrecy, and prestige could override science indefinitely. At some point, the story had to collapse. But like many figures in this series, Holmes seems to have inhabited a gray zone between calculation and belief — part fraud, part self-hypnosis — which made the whole thing both more dangerous and more surreal.

Then there’s the broader cultural context, including the willingness of powerful people to buy in. Even Barack Obama publicly embraced the Theranos narrative early on, holding Holmes up as a symbol of innovation and entrepreneurial promise. Chump. In retrospect, it’s striking how easily the image worked: the black turtleneck, the calm intensity, the world-changing pitch. Smart people — very smart people — saw what they wanted to see. It’s a reminder that charisma plus narrative can override skepticism, especially when wrapped in Silicon Valley optimism. The episode becomes a cautionary tale: will future founders learn from this, or will the same hubris reappear in new forms? The myth of the visionary is powerful, and the temptation to believe in it hasn’t gone away.

The quiet hero of the story, meanwhile, remains the Theranos whistleblower — George Shultz’s grandson — who raised concerns when doing so meant alienating family, risking his career, and standing against a multibillion-dollar narrative. He saw that the technology didn’t work, said so, and held his ground. In a story dominated by hype, status, and belief, that kind of stubborn insistence on reality stands out. Holmes’s rise is outta control, her fall inevitable, but the ending belongs to the people who refused to play along.

Note: If you liked this piece, you may also like the other ones in out “You’re Outta Control” series.

On George Santos (aka The Fabulous Kitara)

Note: This piece uses the figure of George Santos as a kind of cultural parable. The story of Santos—his improbable congressional run on Long Island, the famous unraveling of his résumé (including the legendary and totally outta control Baruch volleyball claim), the rapid collapse of political support from fellow New York Republicans, his eventual expulsion from Congress, and his strange second act as a Cameo celebrity—forms one of the more surreal public morality plays of recent American politics.

The apartment story that frames the essay is not meant as a literal equivalence. Kitara is not Santos, and roommates are not members of Congress. The comparison operates at the level of archetype: the charismatic figure who arrives full of sunshine, quickly becomes central to a small social world, and then—through one small but revealing detail—forces everyone around them to confront the uneasy coexistence of charm and opportunism.

The name “Kitara,” Santos’ drag name from back in Brazil where he if from (Santos is gay of course) is used here in the spirit of narrative shorthand rather than biography. Anyone who has lived with roommates long enough will recognize the basic situation. Shared apartments are small republics built on trust, improvisation, and the quiet hope that everyone involved is playing roughly the same game. Most of the time that hope is justified. Occasionally it is not.

If the tone of the piece drifts toward amusement, and even affection, rather than outrage, that is deliberate. Characters like Santos—and the occasional fabulous roommate—have a peculiar ability to provoke both exasperation and reluctant admiration. The performance can be infuriating. But it can also be oddly entertaining.

Such people rarely disappear completely. They simply move on to the next stage. Sometimes that stage is Congress. Sometimes it is Cameo (get that scratch Georgie baby!). And sometimes it is just the memory of a roommate who once seemed almost too good to be true.

Epigraph

“People seldom do what they believe in.
They just do what is convenient, then repent.”

— Bob Dylan


I. The Fabulous Roommate

Every apartment has its mythology.

The quiet one who never emerges from his room except to microwave things at strange hours. The earnest one who tries to establish chore charts that everyone pretends to follow for about ten days. The one who adopts pets with a confidence that suggests the rest of the household has already agreed to care for them.

And then, once in a while, there is the fabulous roommate. Kitara was that roommate.

She arrived with the sort of personality that immediately rearranges the emotional furniture of a place. Cheerful without being cloying. Social without being exhausting. Organized without being smug about it. She seemed to understand, instinctively, the delicate social contract of shared living: when to chat, when to disappear, when to clean something quietly so no one felt guilty.

Visitors loved her. Friends who came by would inevitably say some version of the same thing: “Your roommate is amazing.”

And she was. At least at first.

She was the sort of person who made the apartment feel like a small, cheerful republic. There were occasional dinners, occasional drinks, occasional pets that appeared temporarily in the orbit of the household. Nothing dramatic. Just the easy, slightly improvised domestic life that happens when a handful of semi-adults share a roof and try to keep the machinery of living running smoothly.

There are people who move through life like that—people who bring lightness with them. People who make small environments work better simply by being present. You think, when you meet someone like this: what a lucky break.


II. The Sunshine Personality

There is another category of person, however, that resembles the fabulous roommate from a distance. These people also arrive with sunshine. They are charming. They are energetic. They seem to know how to move through rooms with effortless confidence. They shake hands warmly. They remember names. They tell stories. They radiate the sort of friendliness that makes everyone feel briefly like a co-conspirator in something cheerful.

The difference is subtle, and it often takes time to notice. These are not merely charming people.

These are the performers. And, one of the most remarkable recent examples of this type in American public life was George Santos.

Santos appeared, seemingly out of nowhere, in the political ecosystem of Long Island. His run for Congress was, at least initially, improbable in the way that many modern political stories can be. The district had long been competitive, but his rise through the local Republican apparatus was unusually smooth. There was little serious opposition within the party. The campaign itself unfolded with the sort of confident momentum that often accompanies candidates who seem, at least on paper, to possess a compelling life story.

And what a life story it was.

Santos presented himself as the son of immigrants who had risen through the financial world, a man with an impressive résumé and a philanthropic sensibility. He spoke of professional success, cultural fluency, and various achievements that painted a portrait of upward mobility and cosmopolitan competence.

The voters of Long Island sent him to Congress. And then, almost immediately, the details began to unravel.


III. The Volleyball Player

The first cracks appeared through the ordinary mechanism of local journalism. Reporters from Long Island newspapers began to do what reporters traditionally do: verify things.

The résumé turned out to be an imaginative document. The professional history did not quite match reality. The educational claims were questionable. Various details that had seemed impressive during the campaign began to dissolve under scrutiny.

One of the most memorable revelations involved an oddly specific athletic claim. Santos had described himself as a standout volleyball player during his time at Baruch College. Not merely a participant, but something close to a star—someone whose record-setting performance had been part of his biography.

There was just one problem. Baruch College had no record of him playing volleyball. None at all. Outta control. The story collapsed on that small detail. It is often the small details that do that.

A résumé can contain many large claims, and those claims can hover in a kind of vague plausibility for a surprisingly long time. But one precise, checkable fact—the volleyball team roster, the game statistics, the athletic department archives—can puncture an entire narrative.

The reporters pulled the thread and the sweater unraveled.


IV. The Grifter Archetype

Once the unraveling began, it accelerated. Claims about employment at major financial firms proved dubious. Educational credentials evaporated. Personal history mutated in various directions depending on which previous statement one examined.

Soon the story had migrated from the political pages into the broader theater of American spectacle. Late-night comedians noticed. Cable news panels convened. Social media filled with the strange, almost baroque details of the saga. Members of his own party began to distance themselves.

Several Republican members of the New York congressional delegation—figures who had initially welcomed a new colleague—publicly called for him to resign as the scope of the fabrications became clear. The situation became untenable. The House of Representatives eventually voted to expel him, a rare and historically notable step.

It was a dramatic fall.

And yet even during the collapse, Santos retained something remarkable.

Charm.

He gave interviews. He sparred with reporters. He adopted, at times, an almost mischievous tone about the entire affair. There was a faint air of theatricality to the proceedings, as though the story had become a kind of performance art about the boundaries of credibility.

The grifter archetype has a peculiar resilience. Even when the illusion collapses, the performer often remains oddly entertaining.


V. The Apartment

Watching the Santos saga unfold, I found myself thinking more about Kitara.

Because the thing about grifters is not simply that they deceive.

It is that they charm.

They charm their way into rooms, into institutions, into social networks. They radiate warmth. They build small communities of goodwill around themselves. And for quite a while, everything feels perfectly normal.

Until one day something small happens. Something missing.

In the apartment it was GM’s silver. Not a vast treasure. Not an heirloom of historic significance. Just a small, familiar object that lived in a particular drawer and had always lived there.

One morning it was gone. The initial reaction in situations like this is always practical. Maybe you moved it. Maybe it fell behind something. Maybe someone borrowed it.

The mind runs through a series of benign explanations, each one slightly less convincing than the last.

And then a thought appears.

Quietly.

Oh shit.


VI. The Knowledge You Don’t Want

Roommate life operates on a fragile form of trust.

You share space. You share kitchens. Sometimes you share pets, groceries, furniture, phone bills, music, stories. The arrangement functions because everyone tacitly agrees not to test the boundaries of that trust too aggressively.

When something disappears, the entire structure trembles.

But there is another complication.

Sometimes you realize what probably happened. And you also realize that confirming it would destroy the social equilibrium of the apartment.

So you do a strange psychological maneuver.

You know. But you decide not to know.

Life continues.

The dishes are washed. Conversations occur. The roommate remains charming. The apartment continues to function as a small republic of semi-functional adults.

But a hairline crack now runs through the arrangement.


VII. The Fall

For Santos the crack widened into a canyon.

The congressional investigation intensified. Ethical questions multiplied. Party support evaporated. Eventually the House voted to expel him, ending one of the most surreal political tenures in recent memory.

Yet even after the fall, Santos demonstrated a familiar trait of the charismatic grifter.

He adapted. He appeared on podcasts. He commented on political scandals involving others. He expressed a certain moral indignation about the ethical lapses of fellow politicians—including members of his own party—sometimes with a tone that was almost hilariously sanctimonious given the circumstances.

The performer remained on stage. And then came the truly modern twist.

Santos joined Cameo. And he’s fucking great on it!

For a fee, he would record personalized video messages: birthday greetings, congratulations, small performances of his peculiar brand of post-scandal celebrity.

The internet, as it often does, embraced the absurdity.


VIII. The Cameo

At some point I watched a few of his videos.

There he was, smiling warmly into the camera, delivering a cheerful greeting to a stranger somewhere in America. The tone was friendly, relaxed, slightly mischievous.

And I laughed.

Because the performance was genuinely funny. The charm, infuriatingly, still worked. It reminded me of the old fable about the scorpion and the frog.

The scorpion asks for a ride across the river. The frog hesitates, noting that scorpions have a reputation for stinging frogs. The scorpion assures him that such a thing would be irrational; if he stung the frog mid-crossing, both of them would drown.

The frog agrees.

Halfway across the river the scorpion stings him.

“Why?” the frog asks as they sink.

“I can’t help it,” the scorpion replies. “It’s my nature.”

The scorpion cannot help himself.

But every now and then the scorpion also sends someone a birthday message on Cameo, smiling warmly and wishing them a fantastic year ahead.

And you find yourself laughing anyway.

The truth about characters like Santos—and perhaps about certain roommates—is that their charm is not an illusion.

It’s real.

The trouble is that it coexists quite comfortably with everything else.

Dedication:

For Kitara. May you make a fucking mint on Cameo and look totally gorgeous while doing it.

Note: If you enjoyed this story, you might also enjoy these other pieces about American grifters.