What Happened to Lee

In September, after we'd released our S-1 but before Cloudflare's IPO, I took two weeks off and went back to my home town of Park City, Utah. (It's actually where Lee and I had been roommates many years before.) That two week period before you go public is known as the quiet period, so I was generally avoiding social media or answering my phone or doing anything other than resting and getting ready for the pre-IPO road show.

We hadn't talked much publicly about Lee's disease, but Michelle and I had written a bit about it in the S-1 Founders Letter:

"Finally, there are two of us signing this letter today, but three people started Cloudflare. Lee Holloway is our third co-founder and the genius who architected our platform and recruited and led our early technical team. Tragically, Lee stepped down from Cloudflare in 2016, suffering the debilitating effects of Frontotemporal Dementia, a rare neurological disease. As we began the confidential process to go public, one of the early decisions was to pick the code name for our IPO. We chose 'Project Holloway' to honor Lee’s contribution. More importantly, on a daily basis, the technical decisions Lee made, and the engineering team he built, are fundamental to the business we have become."

One evening my phone rang and the called ID came up as "Lee Holloway." I checked the number and it was his. I didn't answer and the caller didn't leave a voicemail. My first reaction was that somehow his phone had been hacked or his number was being spoofed and someone was using it to somehow screw with me. Figured someone had read about his disease in the S-1 and was being a jerk.

I reported the call to Cloudflare's security team to investigate. I also texted Lee's wife to let her know to be on the lookout. She wrote back: "No, that's Lee. Sometimes I think when he's feeling nostalgic he reaches out to old friends. He never says anything, but I think it's his way to let you know he's thinking about you."

So I still shoot him text messages from time to time to let him know I'm thinking about him. And I hope, somewhere inside his mind, there's a part of him that still knows that.

Lee bought a few material things, but he was mostly able to live out of his backpack for years at a time, at least before he got married. He didn't have many material desires (no fancy car, clothes, or big gaming computer). He periodically lived on other people's couches (including mine) between starting university and getting married.

I remember he drove through at least a few red lights because he was in the zone deep in thought processing some coding concepts / business plans in his mind while driving. Once I noticed this, I didn't let him drive me; instead he started to code on his laptop in my passenger seat.

When we were waiting in line to rent a UHaul-type truck, he was pacing the retail waiting area thinking through some coding for a future Unspam feature. I remember it because the guy standing behind me saw him as a stranger threat and started to get anxious that Lee was pacing in a hoodie nearby. I mention it because he never concentrated much on the small daily tasks like waiting in line and mostly overloaded those tasks to optimize his long term goals (eg. startup success).

He didn't write big architecture docs (possibly the part of his work that didn't scale much), but his mental capacity to juggle lots of small facts and tasks was pretty incredible. It worked great with a small team with very low turnover. I miss those days when I just checked in with him 2-3 times a day rather than having to spend a lot of mental effort to figure out how to serialize lots of trivial stories/subtasks into Jira.

While Lee's personality changed a lot over time, he was always the guy who got more out of hanging out in a garage building something than someone touring France/Italy/etc.