Darius: In 2014, Cloudflare decided to give free encryption to all its customers. The engineer leading it, Lee Holloway, locks himself in a room the day before launch, hoodie up, headphones on. He codes through the night, doesn't speak to anyone, and ships it. The amount of encrypted traffic on the entire internet doubles overnight because of him.
Harper: That's a legend. That's the story you tell about a founder for decades.
Darius: Right. Two years later, that same guy gets fired. His co-founders said he was playing games on his phone during meetings and just wasn't there anymore.
Harper: Wait. What? From doubling the encrypted web to playing Candy Crush in a meeting? How does that happen?
Darius: That's the question at the heart of this piece by Masaichi Urabe about Lee Holloway. He was the third co-founder of Cloudflare, the technical one. The 'resident genius.' He grew up in an Apple family in Cupertino, won a chess tournament in middle school on a whim. Just one of those guys.
Harper: The kind of person you need to build something like Cloudflare from scratch.
Darius: Exactly. He meets Matthew Prince, the CEO, in college. Prince has this idea for an anti-spam project, Lee is working on something similar. Prince basically hires him on the spot. Lee goes to live in his basement in Utah, getting room and board instead of a salary, and they build what becomes Project Honey Pot.
Harper: Which is still around, right? It tracks web fraud.
Darius: Still around. And the data from that project becomes the seed for Cloudflare. The idea was, instead of just tracking spammers, what if we could block them? Prince pitches it to Lee, who just says, 'That's interesting, let's do it.' And he builds the first prototype. He was the architect.
Harper: So when things started to go wrong, it must have looked like classic founder syndrome. Gets successful, gets rich, becomes a jerk.
Darius: That is exactly what everyone thought. The article says the changes started around 2011. He's only 30. He'd get home from work and just collapse from fatigue. He stops going to company events. He and his first wife, Alexandra, drift apart. She thinks they're just having marital problems.
Harper: Which would be a normal explanation.
Darius: Totally normal. They eventually get divorced, and his colleagues just assume, 'Okay, Lee's gotten selfish. Success and money changed him.' But it was something else entirely.
Harper: But the behavior at work... I mean, playing games on your phone? That's not just being tired.
Darius: It got much worse after 2015. He'd had a heart surgery that year for a condition he was born with. After that, his personality just seemed to... flatten. He was listless. He'd stubbornly oppose his colleagues' ideas for no reason. Matthew Prince and Michelle Zatlyn, the other co-founders, kept meeting with him, trying to get him to change, but nothing worked.
Harper: I can't imagine those conversations. These are his friends who he built the company with.
Darius: And they're watching him disappear. Prince said it was like 'losing a best friend.' They finally decide he has to leave in 2016. At the all-hands meeting where Prince is giving this tearful farewell speech, Lee is just standing there with a smirk, holding a beer. He was 36.
Harper: That's brutal. But from their perspective... if your CTO is completely checked out, what else do you do? You have a responsibility to the company.
Darius: I know, but that's the tragedy. They're treating a brain disease like a performance problem because nobody knows what it is. His second wife, Kristin, is seeing it at home too. He's watching 'Home Alone' over and over. When she's in labor, he sleeps through her contractions, then wakes up and argues with the doctor about the epidural.
Harper: That's... not just being a jerk. That's something else.
Darius: She starts dragging him to hospitals. They think it's burnout, depression, after-effects from the heart surgery. He just keeps saying 'I'll get better.' Finally, in 2017, a neurologist does an MRI.
Harper: And?
Darius: His brain showed atrophy. Significant shrinking, way beyond his age. They refer him to the UCSF Memory and Aging Center, and they get the diagnosis: behavioral variant frontotemporal dementia. bvFTD.
Harper: Dementia. At 36.
Darius: Yeah. The article explains it's not like Alzheimer's where memory goes first. With bvFTD, it's personality, behavior, empathy. The very things everyone thought were his character flaws were actually the first symptoms of his brain dying. There's no cure.
Harper: So all those years... the divorce, getting fired... he was sick.
Darius: He was sick. And I honestly don't know what the right way to handle that is. I don't know how you're supposed to tell the difference between a difficult employee and a person with a degenerative brain disease when the symptoms look the same.
Harper: You can't. That's the impossible part. You just have the behavior in front of you.
Darius: The article ends with the scene where the doctors give the diagnosis. They show the family the MRI, these black holes where his frontal lobe used to be. His wife, his parents, his brother—they're all devastated, crying. And Lee... he's just calm. He accepts it like it's happening to someone else.
Harper: ...
Darius: It's just an unbelievable tragedy. There's no other word for it. I'm Darius.
Harper: I'm Harper.