The Devastating Decline of a Brilliant Young Coder

Lee Holloway programmed internet security firm Cloudflare into being. Then he became apathetic, distant, and unpredictable—for a long time, no one could make sense of it.
diptych man walking in a yard and the words What Happened to Lee
Artwork by Amy Friend; Photograph by Jack Bool

On Friday, September 13, 2019, Matthew Prince and Michelle Zatlyn, cofounders of the San Francisco internet security firm Cloudflare, stood on a slim marble balcony overlooking the floor of the New York Stock Exchange. A cluster of the company's executives stood near Prince, ready to shout out a countdown. “Louder! Loud!” Prince urged them. “Five! Four! Three! …” At 9:30 am sharp, the founders reached down to ring the exchange's famous bell, kicking off the day's trading and offering their 10-year-old company on the public market. It was a rite of passage and also their payday, a moment that unlocked many millions of dollars in newfound wealth.

More than 100 employees and investors cheered from the trading floor below, their phones held high to capture the scene. Kristin Holloway, employee number 11, looked up at the balcony and snapped photos, then popped them into a text to her husband, Lee Holloway, the company's third cofounder. He was home in California. Every so often, a familiar face pushed through the throng to say to her, “Lee should be here.”

In Cloudflare's early years, Lee Holloway had been the resident genius, the guy who could focus for hours, code pouring from his fingertips while death metal blasted in his headphones. He was the master architect whose vision had guided what began as a literal sketch on a napkin into a tech giant with some 1,200 employees and 83,000 paying customers. He laid the groundwork for a system that now handles more than 10 percent of all internet requests and blocks billions of cyberthreats per day. Much of the architecture he dreamed up is still in place.

But some years before the IPO, his behavior began to change. He lost interest in his projects and coworkers. He stopped paying attention in meetings. His colleagues noticed he was growing increasingly rigid and belligerent, resisting others' ideas, and ignoring their feedback.

Lee's rudeness perplexed his old friends. He had built his life around Cloudflare, once vowing to not cut his hair until the startup's web traffic surpassed that of Yahoo. (It took a few short months, or about 4 inches of hair.) He had always been easygoing, happy to mentor his colleagues or hang out over lunch. At a birthday party for Zatlyn, he enchanted some children, regaling them with stories about the joys of coding. The idea of Lee picking fights simply didn't compute.

He was becoming erratic in other ways too. Some of his colleagues were surprised when Lee separated from his first wife and soon after paired up with a coworker. They figured his enormous success and wealth must have gone to his head. “All of us were just thinking he made a bunch of money, married his new girl,” Prince says. “He kind of reassessed his life and had just become a jerk.”

The people close to Lee felt tossed aside. They thought he'd chosen to shed his old life. In fact, it was anything but a choice. Over the next few years, Lee's personality would warp and twist even more, until he became almost unrecognizable to the people who knew him best. Rooting out the cause took years of detective work—and forced his family to confront the trickiest questions of selfhood.

On the floor of the stock exchange that September morning, Lee's younger brother Alaric weathered the morning in a state of low-grade panic. He snapped selfies with early employees and fired them off in texts to his brother. Alaric had never worked at Cloudflare, and he knew barely anyone there. But his dark hair flopped over his forehead with the same distinctive swoop as his brother's, and his long, tapering face had the same dark eyes and olive skin. “It was surreal,” Alaric says. “People kept looking at me like they knew me.”

At home with his parents in San Jose, Lee, 38, was restless. He paced the rooms and hallways of the 1,550-square-foot house, a loop he'd been tracing since he'd moved in with them two years earlier. He didn't speak. His parents had the TV on, and they called him over whenever Prince or Zatlyn appeared onscreen.

Later, he paused at the family's Roku to search YouTube for videos of Cloudflare. Then he resumed his circuit: walking the halls, buzzing his lips, snacking on cashews.

Lee Holloway spends time with his youngest son at home on California's Central Coast.Artwork by Amy Friend; Photograph by Jack Bool

What makes you you? The question cuts to the core of who we are, the things that make us special in this universe. The converse of the question raises another kind of philosophical dilemma: If a person isn't himself, who is he?

Countless philosophers have taken a swing at this elusive piñata. In the 17th century, John Locke pinned selfhood on memory, using recollections as the thread connecting a person's past with their present. That holds some intuitive appeal: Memory, after all, is how most of us register our continued existence. But memory is unreliable. Writing in the 1970s, renowned philosopher Derek Parfit recast Locke's idea to argue that personhood emerges from a more complex view of psychological connectedness across time. He suggested that a host of mental phenomena—memories, intentions, beliefs, and so on—forge chains that bind us to our past selves. A person today has many of the same psychological states as that person a day ago. Yesterday's human enjoys similar overlap with an individual of two days prior. Each memory or belief is a chain that stretches back through time, holding a person together in the face of inevitable flux.

The gist, then, is that someone is “himself” because countless mental artifacts stay firm from one day to the next, anchoring that person's character over time. It's a less crisp definition than the old idea of a soul, offering no firm threshold where selfhood breaks down. It doesn't pinpoint, for example, how many psychological chains you can lose before you stop being yourself. Neuroscience also offers only a partial answer to the question of what makes you you.

Neural networks encode our mental artifacts, which together form the foundation of behavior. A stimulus enters the brain, and electrochemical signals swoosh through your neurons, culminating in an action: Hug a friend. Sit and brood. Tilt your head up at the sun and smile. Losing some brain cells here or there is no big deal; the networks are resilient enough to keep a person's behaviors and sense of self consistent.

But not always. Mess with the biological Jell-O in just the right ways and the structure of the self reveals its fragility.

Lee's personality had been consistent for decades—until it wasn't.

From an early age, he was a person who could visualize sprawling structures in his mind. Growing up in the 1990s in Cupertino, where his dad worked at Apple, Lee had early access to the latest computers, and he and his brother grew up bingeing on videogames. As a gamer, he was legendary among his friends for being able to read a complex situation, rapidly adjust strategies, and win match after match. And it wasn't just videogames. His childhood friend Justin Powell remembers Lee strolling into a middle school chess club tournament cold. He wasn't a member of the club, but he won the tournament anyway. Lee avoided becoming insufferable by channeling his wit into snarky commentary. “Watching a movie with him was like a version of Mystery Science Theater 3000,” Powell says. “His very presence challenged you to keep up with him.”

Lee and his friends would cart their computers to each other's houses to play games together. He became curious about the machines themselves and started learning computer science, first in high school, then at a local community college and UC Santa Cruz, where an unlikely set of circumstances connected him with Matthew Prince.

Then a young entrepreneur, Prince was pursuing an idea for an antispam software tool when he encountered Arthur Keller, a UC Santa Cruz computer science professor. Keller and his students had already worked out a very similar concept. Prince and Keller agreed to share a patent, along with Keller's students. One of those students was Lee, and Prince hired him on the spot. “I had no idea this school project would turn into something much bigger,” Lee later said in a video interview with a group called Founderly.

Prince set up the company, Unspam Technologies, in Park City, Utah, about a mile from a cluster of slopes where he could indulge his passion for skiing. Lee moved into Prince's basement, at first working for free in exchange for food and housing. But Lee and the other Unspam engineers grew restless, and they started spinning up side projects, including one called Project Honey Pot, which tracked spammers as they crawled the web. That's all it did—it collected and published data on spammers, but it didn't do anything to stop them. Still, the project quickly amassed a loyal following.

In 2007, Prince left Utah to start business school at Harvard, and Lee moved to California to live with his girlfriend, Alexandra Carey. They'd known each other as undergrads, when she was a teaching assistant in his computer architecture class. Lee had goofed off in that class, once pranking the professor by scrawling childish notes on the transparencies of an overhead projector. Alexandra had been amused, but it wasn't until after college that a relationship bloomed. Living in different cities, they fell for each other while playing and chatting within a multiplayer videogame called Savage. Now, with Prince leaving Utah, it seemed a natural time for Lee to join Alexandra. They married in 2008.

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Lee and Prince kept working at Unspam from their respective cities, but as Prince was wrapping up business school, Lee called to tell him he was considering other job offers. Prince countered with a new and rather audacious pitch: He and a classmate, Michelle Zatlyn, had hit on a startup idea they thought had potential. What if they expanded Project Honey Pot to not just recognize spammers and hackers but also fight back against them? The plan was to build out massive networks of servers around the world, convince website owners to route their traffic through those servers, and gather enough data to detect malicious requests amid the good ones. That might give them the tools they needed to stop even the world's biggest denial of service attack. But Prince needed a technical cofounder, and his about-to-defect employee was his top choice.

Prince talked for an hour straight. At the end of this spiel, Lee's side of the line was quiet. “I was like, ‘Are you still on the phone?’ ” Prince recalls. “Then he said, ‘Yeah, that'll work, let's do that.’ ” And that was it.

They whipped together a demo and in late 2009 raised a little over $2 million from two venture capital firms. It was enough to rent a converted two-bedroom apartment above a nail salon in Palo Alto, where they could start building their idea in earnest. Lee would show up every day wearing the same Calvin Klein jeans, leather jacket, and beanie on his head, and lugging a giant ThinkPad laptop nicknamed the Beast. “We had this shared vision,” Zatlyn says. “And Lee was the architect behind it. He just obsessed over it.”

The following year, Prince talked his way into TechCrunch Disrupt, an onstage competition for startups that can lead to big funding rounds. As Disrupt approached, Prince and Zatlyn grew nervous. Lee had missed a lot of days of work due to migraines. He didn't seem anywhere close to finishing a demo. When the day of the event arrived, Prince and Zatlyn walked onstage praying that the software they were presenting would actually work.

Prince started his pitch. “I'm Matthew Prince, this is Michelle Zatlyn, Lee Holloway is in the back of the room. We're the three cofounders of Cloudflare,” he boomed, stabbing the air with his finger as he spoke. In fact, Lee was backstage furiously fixing a long list of bugs. Prince held his breath when he ran the software, and, perhaps miraculously, it worked. It really worked. In the hour after he walked onstage, Cloudflare got 1,000 new customers, doubling in size.

They earned second place at Disrupt. “In the next couple of weeks, all these somewhat mythical VCs that we'd heard of and read about all called us,” Prince says. Under the onslaught of attention, Prince, Holloway, and one early hire, Sri Rao, rolled out constant fixes to hold the system together. “We launched in September, and in a month we had 10,000 websites on us,” Lee said in the Founderly interview. “If I'd known, we would have had eight data centers instead of five.”

With customers now multiplying, Ian Pye, another early engineer, hollowed out a toaster, tucked an Arduino board inside, and hooked it up to the network. Whenever a website signed up for Cloudflare services, the toaster sang a computerized tune Pye had composed. “It was horribly insecure,” Pye says. “But what were they going to do, hack our toaster?” The toaster lasted two weeks before the singing became too frequent and annoying and they unplugged it.

Cloudflare was growing fast, and Lee worked long days, often from home in Santa Cruz. He and Alexandra now had an infant son. During the first few months of the baby's life, Lee and Alexandra still made time to play videogames together. Alexandra remembers cracking up when Lee co-opted a nursing pillow to support his neck while he sat at his computer. Several of his old friends came over once a week to play the board game version of Game of Thrones or the multiplayer videogame Team Fortress 2. Alexandra focused on childcare, but she made sure the players had food. “I was doing it for him,” she says.

But around 2011 she started noticing that Lee was growing distant and forming some odd new habits. He spent a lot more time asleep, for one. After long workdays, she recalls, he'd walk in the door, take off his shoes, and immediately pass out on the floor. Their cat sometimes curled up and napped on his chest. His son, not yet 2, would clamber over him, trying and failing to rouse him to play.

When people invited them to parties, Lee refused to go. Alexandra started attending her friends' weddings by herself. It hurt her to see everyone else there as a couple, while the chair next to her sat empty. At home she'd cook dinner, and he'd look at it and say he was ordering pizza. On a weeklong family trip to France, he spent three days sleeping in the hotel room. “I'd say, ‘What's going on, we're going to these places—are you coming?’ ” Alexandra says. He'd insist he was too tired. She was finishing up a master's degree and shouldering the bulk of childcare; she, too, was tired. Alexandra begged him to go to therapy and cajoled him to play with their son, but he didn't engage. “After a while you think, well, this is the person I'm with,” she says.

In 2012, Alexandra told him she was taking an internship in Southern California, at NASA, and she was planning to take their son with her. She says his response was to calmly ask her to file for divorce before she left. “I was crushed. I said, ‘Maybe it doesn't have to be that way,’ ” she recalls. “He said, ‘No, no, it does.’ ”

When Lee told Prince and Zatlyn about his divorce, they both expressed their shock and gave their condolences, but Lee seemed to barely acknowledge the change. Prince and Zatlyn found his behavior tremendously odd. Still, they could rationalize it away. Relationships end for many reasons. Alexandra and Lee had married young, and both had worked long hours; perhaps they had grown apart. Besides, Lee was thriving at the company, so they didn't press.

Lee and his Cloudflare cofounders, Michelle Zatlyn and Matthew Prince, attend a holiday party in 2011.Artwork by Amy Friend; Photograph courtesy of Cloudflare

Some months after Alexandra moved away, Lee was sitting at a table with a couple of coworkers, including Kristin Tarr, who ran communications at Cloudflare. She'd just published a blog post describing how customers could enable two-factor authentication on their accounts. He turned to her and said, “I read your blog post. It was really good.” A friend saw the interaction and teased her: Lee's flirting with you!

Lee and Kristin started spending time together. On one of their first dates, Lee took her to see his favorite metal band, the Swedish group Opeth. He revved up her interest in basketball, and they became Golden State Warriors junkies, watching every game. Kristin brought her own interests and energy into the relationship. She convinced him to trade in his old jeans-and-leather-jacket uniform for nicer shirts from Rag & Bone. He still wore beanies and hoodies, but now they came from Lululemon, where Kristin, a running freak, had a weekend gig as a brand ambassador. Sometimes he refused to get out of bed or retreated with a migraine; Kristin responded by signing him up for 5K races and coaxing him into training for them. Their coworkers marveled that their lead engineer had become so athletic.

Within a few months they had moved in together. She whisked him off on adventures, pulling him away from his computer and his videogames. They went tubing on the Truckee River. They played endless rounds of Bang! and Settlers of Catan with board-game-loving coworkers. Both nearsighted, they pretended they were moles, snuggled up in their burrow of a home. As their fortunes grew, they upgraded their digs, moving from Mole Hole to Mole Tower to Mole Terrace. They gave their friends animal identities too; Prince was a mongoose, while another executive was a swan. In May 2014, Kristin quit Cloudflare, and the next day they left for a vacation in Italy. They got engaged in Rome.

At work, Lee was still the star engineer. At the end of the summer of 2014, he took on a project that earned Cloudflare its first bout of internet fame: The company would help websites become encrypted for free. (It was not yet standard for company websites to be encrypted.)

Lee agreed to build the necessary software by the end of September. As the date approached, Prince asked for updates, but Lee blew him off. Then, on the day before the new system was supposed to go live, he pulled his hoodie down low on his head, put on his headphones, and sat down to bang out the code.

It was a Sunday, but the office was packed with people writing up the pending announcement or delivering coffee and food. Lee's coding, though, was the main event. “And he is typing, typing, and I don't think anyone dared to interrupt,” says John Graham-Cumming, then an engineer and now Cloudflare's chief technology officer. “His hoodie is on, he's in the zone, he's doing brain surgery on this thing.”

Then, late in the night, Lee stood up. He announced that he'd finished, and he wandered away. “It was like, bzhzhzhzh, type-type-type, ‘I'm done!’” Graham-Cumming says.

The other engineers immediately started reviewing his code. By the morning, the debugging process began for real. The gambit worked, and all of their existing customers suddenly got encryption. It was a proud moment. Says Graham-Cumming: “The size of the encrypted web doubled overnight.”

Lee and his wife, Kristin Holloway, on vacation in Rome in 2014. He proposed to her hours after this photo was taken.Artwork by Amy Friend; Photograph courtesy of Kristin Holloway

As Lee and Kristin planned their wedding, he decided to address a health problem he'd long ignored. Lee had been born with a heart issue, a leaky aortic valve, and some doctors thought it might be contributing to his migraines. “If you put your head on his chest, you could hear it,” Kristin says. “We called it his squishy heart.” Doctors were split on how serious his condition was, but in January 2015 a surgeon at Stanford insisted he get surgery right away. Lee went in for the six-hour procedure. As he lay on his hospital bed, he recorded a video to his son: “I love you! I'll see you soon with a brand-new heart.” He signed off with a smile and a wave.

Kristin now sees the surgery as a grim turning point. Lee's heart came out of the procedure stronger than ever, but mentally he never seemed to recover. He slept all the time. He'd taken a leave from work to have the surgery, but he extended his leave by a month, and then another, until he finally returned to the office in the late spring.

In June they got married, in Hawaii, in front of a crowd of friends and family. Kristin noticed that he seemed subdued. It was as if someone had washed the color out of his personality. Prince noticed too but chalked it up to a slow recovery from the surgery.

Not long after, Lee and Kristin took a trip to Europe, spending a few days in France, just as Lee and Alexandra had years earlier. Kristin had never been to Paris, and she was excited to explore the city. She ended up doing that on her own, while Lee again spent days asleep in their hotel room. “This is so weird,” Kristin remembers thinking. On their trip to Italy, he'd been eager to jump out of bed and visit museums and cafés, and walk around. She was puzzled, but between his migraines and his heart issue, there was always an explanation at hand.

At the office, he was becoming impossible to work with. He would lash out at people, and then in meetings he would zone out, openly playing games on his phone. During one meeting, Prince texted him: “Are you playing a game? People are noticing.” Then: “Not a great leadership signal.”

Prince and Zatlyn confronted him about his behavior, and Lee promised to do better. But his responses seemed rote. “I was like, why is he so disengaged? Why doesn't he seem to care?” Zatlyn recalls. They figured he must be burned out. Still, it hurt; it felt as if Lee was breaking up with them. She'd paid attention to the stories of startup founders who split up, the mess of their breakups sometimes dragging their companies down with them. “So I'm thinking, well, I guess that's what that feels like.”

They put their friend on an official performance-improvement plan. Over many weekly lunches, Zatlyn and Prince tried to get through to him. Nothing seemed to stick. “For several years,” Prince says, “the thing that was causing me just incredible anxiety was that I had all this loyalty to this person, but they're becoming a jerk.”

Eventually, in 2016, they decided Lee had to leave the company. “He kind of just said, yup, that sounds about right,” Prince says. They threw him a going-away party that July. Prince thanked him in a speech with tears streaming down his cheeks. Lee stood beside him with a beer in hand, a thin smile on his face.

Lee (center) gathered with his family for Thanksgiving in 2016, including (from left) his brother Alaric; his wife, Kristin; his older son; his mother, Kathy; his younger son; and his father, Rendon.Artwork by Amy Friend; Photograph courtesy of Kristin Holloway

Now that he wasn't working, Lee napped constantly. Kristin was seven months pregnant, and they agreed that after the baby's birth, Lee would be a stay-at-home dad, at least until he figured out what to do next. In the meantime, they would live off their savings and Kristin's salary from a new job at an ad tech firm.

Lee's actions, however, only grew more bizarre. He watched Home Alone several nights a week. He wore his beanie all day, every day, pulling it lower and lower. When Kristin went into labor, he slept through most of the two-day ordeal, first slumbering at home and then resuming his nap at the hospital. When he woke up, he insisted, against Kristin's wishes, that she not get an epidural, which provoked a heated argument with one of the doctors. After their son was born, Kristin's mom says the doctor pulled her aside and commented that she'd never seen an expectant dad react that way. Kristin confronted him about his behavior later, and he promised her, “I'll do better.”

In those heady first months of parenthood, he failed. He took copious naps. Sometimes she'd cook him dinner, and he'd reject it and order a burrito. “I was like, what is happening?” Kristin says. “Everything felt so strange and out of control.”

Distraught at his lack of interest in their son, she decided to stage a moment of parenting normalcy. If she couldn't coax him into engaging with their child, she'd settle for its illusion. While Lee lay on the couch, she handed him the infant and grabbed her phone to record the scene. “You're standing, and you're so cute!” he coos as he props up the baby on his chest. “You're smiling and making a sound!” He dotes on his baby for less than a minute before handing him back to Kristin.

She kept trying to probe what was on his mind, and he kept replying, “I'll do better.” The repetitiveness of his answers struck her as robotic. It seemed of a piece with the way he now touched every tree he passed on their walks. “I think deep down I knew something was wrong,” Kristin says. She thought maybe he'd developed PTSD after the surgery or was struggling with a bout of depression. She'd been asking him to see a counselor with her. Finally, as she prepared to return to work, she threatened to leave him if he didn't. Lee agreed.

In the couples' therapy session, Kristin cried openly and talked about how her husband didn't seem to care about their new baby. “Lee was just blank,” she recalls, and she wondered why he wasn't reaching out to comfort her. Suddenly he stood up, announced he'd forgotten to return the therapist's office bathroom key, and wandered out of the room to put it back, returning a few minutes later.

When her maternity leave came to an end, Kristin hired a nanny and went back to work, but her alarm was mounting. She started booking appointments with every specialist she could think of while Lee spent his days in bed. “So I'm cajoling him out of bed, getting him into the car, making sure my son is out with his nanny, covering my own work somehow,” and then shuttling him from appointment to appointment. “It was like that for three months.”

In mid-March of 2017, Kristin and Lee went to a neurologist to get the results of an MRI. To Kristin, it seemed that the neurologist had initially been skeptical of her concerns. Lee was young, healthy, and communicative.

The MRI told a different story: There was atrophy in the brain inconsistent with the age of the patient, the neurologist reported to them. When Kristin asked her what that meant, she said Lee had a neurodegenerative disease of some kind, but they'd need to do more tests to get a specific diagnosis. One of their doctors suggested they go to the Memory and Aging Center at UC San Francisco.

That evening, Kristin started Googling. She pulled up the website of the Memory and Aging Center and started reading the descriptions of brain atrophy diseases. She knew immediately the neurologist was right. And in that moment she glimpsed the future: This was going to kill her husband.

She remembers sitting with her son that night. “Until that point, I'd held out hope. We have the resources, the best doctors, I can fly him to get him the best care,” she says. “But to be in this position where nothing can be done is just … It's so awful.” She quit her job the next day.

A few weeks later, Kristin and Lee, their parents, and Alaric all gathered in a conference room on the UCSF campus with a panel of experts. “Do you know why you're here?” the lead neurologist asked Lee. He replied, “My wife organized this.”

“Do you know that you're sick?”

“I get migraines a lot,” he said. “And I had heart surgery.”

The neurologists delivered their verdict: He appeared to have a textbook case of frontotemporal dementia—known by the shorthand FTD—specifically, the behavioral variant of that disease. It targets a network of brain regions sometimes described as underpinning one's sense of self. As the pathological process advanced, it was carving a different person out of Lee's raw substance.

The term frontotemporal dementia refers to a cluster of neurodegenerative diseases that affect a person's behavior or speech while leaving memory largely intact, at least early on. Unlike Alzheimer's disease, FTD isn't well known. It is a rare disease, affecting roughly one in 5,000 people, though many of the neurologists who study it believe it is underdiagnosed. What is known is that for people under the age of 60, it is the most common form of dementia. Still, as a man in his thirties, Lee was unusually young to be afflicted. For some patients, one of several genetic mutations turns out to be the likely cause, and a subset of patients have a family history of neurodegenerative diseases. But nothing in the neurologists' investigations turned up even a hint as to why Lee had been struck down.

Regardless of cause, the prognosis is grim. There's no treatment. Lee's doctors warned that his symptoms would grow worse, and that over time he would likely stop talking, become immobile, and struggle to swallow, until eventually an infection or injury would likely turn fatal. The best the doctors could recommend was eating a balanced diet and getting exercise.

The family sat stunned at the neurologist's words. The brain scans were undeniable. On a wall-mounted screen the doctors showed a cross-section of the four lobes of Lee's brain. In a healthy brain, the familiar, loopy folds of tissue appear white or gray and push up against the edges of the cranium, filling every available space. Lee's brain looked nothing like that.

Black voids pocked his frontal lobe, areas where brain tissue had gone dead. Seeing it, Kristin gasped. “There were huge dark spots in his brain,” Alaric says. “That's what … that made it concrete.”

Lee received his death sentence with pure calm. While his family cried beside him, he complimented a doctor for having a nice wedding ring. At that, Alaric looked at him and realized for the first time the depths of his brother's transformation.

Lee still takes part in some activities with his wife and children, including working on jigsaw puzzles.Artwork by Amy Friend; Photograph by Jack Bool

Few disorders ravage their victims' selfhood with the intensity of the behavioral variant of FTD. It takes all the things that define a person—hobbies and interests, the desire to connect with others, everyday habits—and shreds them. Over time, the disease transforms its victims into someone unrecognizable, a person with all the same memories but an alarming new set of behaviors. Then it hollows them out and shaves away their mobility, language, and recollections.

Because it is relatively unknown and can resemble Alzheimer's or a psychiatric disorder, FTD is often hard to diagnose. As in Lee's case, the early stages can be misinterpreted as signs of nothing more serious than a midlife crisis. Patients can spend years shuttling to marriage counselors, human resources departments, therapists, and psychologists. By the time patients learn the name of their disorder, they are often unable to grasp the gravity of their situation.

Depending on where in the brain the disease first strikes, the symptoms can be jarring. Some sufferers become deeply religious, undergo wild shifts in political identity, or have a sharp change in interests or style of dress. One stockbroker, for example, started wearing all-lavender clothes and developed a sudden obsession with painting. As his disease progressed, he engaged in petty theft and swam nude in public pools.

The loss of embarrassment is common among some FTD patients, leading them to act in ways that might have horrified their former selves. Urinating in public, shoplifting, running red lights, making inappropriate sexual advances, digging through trash cans for food—all can be symptoms. Patients can lose the ability to evaluate social situations too, making them hard to interact with. In one extreme case, a patient's wife nearly severed her finger while using a pair of borrowed gardening shears. She shrieked to her husband, who had FTD, that she needed to go to the hospital. He replied by saying they had to first return the shears to their neighbor.

These behaviors all arise because neurons are dying off in the frontal and temporal lobes, two large areas of the brain. Particularly vulnerable within these broad continents is a dispersed set of regions known as the salience network, which sifts through a barrage of sensations, memories, and emotions to focus a person's attention on what matters most in that moment. When this network breaks down, people may fail to grasp the emotional impact of their actions on others. “Emotions drive most choices in life, so if you don't have those systems, you're not the same person,” says Virginia Sturm, a neuropsychologist and neuroscientist at UCSF. “There are no tight anchors to your sense of self anymore, and the boundaries of self become loose.”

Eventually, many FTD patients end up as apathetic as Lee, the light of their personhood dimmed to a pale flicker. Apathy also leads to incontinence, as patients lose the desire to take even basic care of themselves.

In the months after Lee's diagnosis, Kristin spent as much time with her husband as she could. His decline had been steady so far, and she realized he would only slip further away. They spent the summer of 2017 going on long walks together. They took family trips. She found herself scrutinizing every interaction: Was that his last joke? His last laugh? His last hug? She never knew. He started leaving the apartment without saying anything, and she'd have to grab the baby and chase him down San Francisco's busy streets.

Lee was quickly becoming unmanageable. Once the baby learned to crawl, Kristin installed a gate at the top of the stairs to keep him from falling down the steps. But whenever Lee walked past the gate, he'd reach down and unlatch it. He started blasting music videos in the living room at 11 o'clock at night, despite the small child asleep in an adjacent room. Sometimes he'd stay up all night, walking around in circles. Kristin struggled to take care of her son while making sure her husband didn't duck out the door unnoticed.

She and Lee's parents grew increasingly worried he could get lost or mugged or wander into traffic. His parents, who are in their sixties, volunteered to take over Lee's care, and in the fall of 2017, Kristin agreed it was time for him to move in with them in San Jose while they figured out a long-term plan. “It's too hard to keep him safe in San Francisco,” his father, Rendon Holloway, says. “He has to have his walks.” Kristin was working full-time in San Francisco; she and their son stayed behind. Lee would visit them a few days a month.

Kristin and their son spent many of their weekends in San Jose. In the first year, his mother, Kathy Holloway, recalls, when Lee saw the two of them arrive, “he always ran to his bedroom and grabbed his suitcase.” He would say, “I want to go back to San Francisco.”

Lee often tried to leave the house. His parents eventually added an alarm that chimed loudly whenever the front door opened. They hid his shoes. He'd hunt for them, and if he found them he'd lace up and bolt out the door.

When he wasn't trying to escape, Lee settled into a rhythm of scrolling through family photos on his phone, playing Mario Kart, or watching YouTube videos, all in roughly 30-second spurts. He'd search YouTube for “Cloudflare,” “Kristin Holloway,” or his favorite bands and watch snippets of their music videos. Then he'd pace heavily around the house, loud footfalls thudding at all hours of the day. Kathy lined the floors with rubber mats to deaden the sound.

As the months passed, he spoke less and less. In one video from July 2018, Lee has his arm wrapped around his son while he reads him a bedtime book. Lee mumbles the words unevenly, without inflection, and hurries through the paperboard pages.

From behind her phone's camera lens, Kristin saw that this might be the last bedtime story he read their son. Still, she kept recording, and she ended it with a “Good job!” to them both.

Conversations soon became impossible. Lee started chattering in repetitive, unceasing loops. He would tell Kristin: “We met at Cloudflare. We got engaged in Rome. We got married in Maui, Hawaii.” He repeated it hundreds of times a day. Then the loops got shorter, more cryptic. He spoke fewer sentences, instead muttering sequences of numbers or letters.

In September 2018, Prince and Zatlyn went to visit him while he was on one of his trips to San Francisco. Seeing Lee for the first time in many months, they thought he looked like a zombie, trooping aimlessly from room to room with empty eyes. At intervals during their visit he'd sit down in the living room, turn on the TV, and flip through the channels, never watching any one thing for more than a minute. Then he'd wander off again, all the while whispering numbers: 1 2 3 4 5 6 7. 1 2 3 4 5 6 7.

He was both present and absent, a combination that kept his family on edge. When I visited his parents' house in April 2019, Kristin and Alaric were also there for the day. We were clustered in the front hallway while his mother slipped into the kitchen to make tea. Lee, dressed in a Henley shirt and sweatpants, emerged from the back of the house. He stood tall and silent, and his arms hung heavily at his sides. He looked at Kristin, expressionless, as she introduced me and explained I'd come to write a story about his life. He turned to wander into the living room and kitchen, where he leaned his elbows on the counter and reached a hand out to his mother, wordlessly requesting a snack. Then Kristin and Alaric went out with him for a walk, while I sat down with his parents.

As we sat in the family's living room, Kathy described caring for her son, even as he grew increasingly distant. She misses the warmth in their daily interactions. “He used to come give me a hug and say, ‘I love you, Mom,’ ” she says. “No more.”

Kathy is not the only one struggling to accept Lee for who he is—whoever he is. Managing his decline has strained the family, and his relatives sometimes clash over who should take care of him and how he should live. Kristin has spent many hours in therapy working through her grief and her feelings of guilt over deciding to live apart from Lee. She says she has felt alone in their relationship for years, and she's determined to give her son a relatively normal childhood. Alexandra, Lee's first wife, wonders whether her marriage fell apart because of the disease or their incompatibility. Was Lee simply someone who could sleep through European vacations and reject a homemade meal, or were those early incidents symptoms?

There's no way to know for sure. Who was he then? Who is he now? How tightly knit is any person's selfhood across time? The philosopher Derek Parfit might have approached the issue by asking how many psychological chains bind Lee today to Lee in the past. His links are more tenuous than most people's. But they persist.

In January 2019, Kristin was driving in a grocery store parking lot when her phone rang. She glimpsed the screen and froze. Lee was calling. There on the screen was his face, an old photo from when they had just started dating. She hadn't seen the photo in almost two years—it had been that long since he had called her.

She answered, and the words tumbled out of her. “Baby, I love you so much, I miss you,” she cried. “Are you OK? Do you need anything?” He didn't say anything, but she could hear his breathing on the other end.

He hung up.

In that instant she realized how desperately she missed hearing his voice. “I'd been in this process of losing him, then to have this moment of him reaching out from wherever he is,” she says. “It blew my mind.”

The Cloudflare IPO in September raised $525 million. Lee, as one of the founders, suddenly became a whole lot richer. With his financial future now secure, Kristin set in motion the plan for his long-term care. She bought a 5,000-square-foot house on an acre of California's Central Coast, a spot they chose in the hope that his father, Rendon, could walk with him along the shore. She worked with a landscape architect to tailor the outdoor space to Lee's needs. There are zigzagging paths on which Lee can roam and a fence to keep him safely inside. Nontoxic plants only. No nut or fruit trees allowed; those could be choking hazards once he develops difficulty swallowing, as his doctors anticipate he will.

Lee and his parents have moved there, and he has full-time care assistance too. Kristin shipped some of the furniture they'd bought together to make the house feel more familiar to him, and she blanketed a wall in family photos. She, Alexandra, and their sons visit occasionally.

Kristin hopes she has designed the perfect environment. Most FTD patients aren't so fortunate, if you can call it that, to wind down their lives on a personalized estate with a staff dedicated to keeping them safe and calm. Their families don't always have a choice in how involved they want to be. Still, all the money in the world can't answer the question of who, really, is living in that house.

On rare occasions, Lee still surprises his parents with an affectionate pat on the back. He calls people from time to time, even if he never speaks a word. An old colleague recently saw that he'd liked a post on LinkedIn. However diminished, a person lingers in the shattered roadways of his mind.

Some months ago, Lee sent Kristin a series of text messages. In them were photos she'd shared with him earlier: she and their son on Halloween, a trip to the park, Christmastime. At the end, he'd typed the words: “the love.”


SANDRA UPSON (@sandraupson) is a senior editor at WIRED. This is her first feature story for the magazine.

This article appears in the May issue. Subscribe now.

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