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Helping To Build Cloudflare, Part 1: How I came to work here


4 min read

This is the text I prepared for a talk at Speck&Tech in Trento, Italy. I thought it might make a good blog post. Because it is 6,000 words I've split it into six separate posts.

Here's part 1:

I’ve worked at Cloudflare for more than seven years. Cloudflare itself is more than eight years old. So, I’ve been there since it was a very small company. About twenty people in fact. All of those people (except one, me) worked from an office in San Francisco. I was the lone member of the London office.

Today there are 900 people working at Cloudflare spread across offices in San Francisco, Austin, Champaign IL, New York, Washington D.C., London, Munich, Singapore and Beijing. In London, my “one-person office” (which was my spare bedroom) is now almost 200 people and in a month, we’ll move into new space opposite Big Ben.

The original Cloudflare London "office"

The numbers tell a story about enormous growth. But it’s growth that’s been very carefully managed. We could have grown much faster (in terms of people); we’ve certainly raised enough money to do so.

I ended up at Cloudflare because I gave a really good talk at a conference. Well, it’s a little more complex than that but that’s where it all started for me without me knowing it. Fifteen years ago, a guy called Paul Graham had started a conference at MIT in the US. At the time Paul Graham was known for being an expert LISP programmer and for having an idea about how to deal with email spam. It wasn’t until a year later than he started Y Combinator.

Paul invited me to give a talk at this MIT Spam Conference about an open source machine learning email filter program I had written. So, I guess the second reason I ended up at Cloudflare is that I wrote some code and open sourced it. That program is called POPFile and you can still download it today (if you’d like your email sorted intelligently).

I wrote POPFile because I had an itch to scratch. I was working at a startup in Silicon Valley and I was receiving too much email. I used Microsoft Outlook and I wanted my mail sorted into different categories and so I researched techniques for doing that and wrote my own program. The first version was in Visual Basic, the second in Perl.

So, I got to Cloudflare because of a personal itch, open source, public speaking and two languages that many people look down on and joke about. Be wary of doing that. Although languages do make a difference the skill of a programmer in their chosen language matters a lot.


If there’s a lesson in there it’s… share with others. Share through open source, through giving talks, and through how you interact with others. The more you give the more people will appreciate you and the more opportunity you will have. There’s a great book about this called Give and Take by Adam Grant. We gave everyone at Cloudflare a copy of that book.

One of the people who saw me speak at MIT was Matthew Prince, Cloudflare’s CEO. Matthew was speaking also. He saw me speak and thought I was interesting, and I saw him speak and thought the same thing.

Over a period of years Matthew and I stayed in contact and when he, Michelle and Lee started Cloudflare he asked me to join. It was the wrong time for me and, to be honest, I had a lot of doubts at the time about Cloudflare. I didn’t think many people would sign up for the service.

I’m glad I was wrong. And I am glad that Matthew was persistent in trying to get me to join. Today there are over 13 million domains registered to Cloudflare and I have ended up as CTO. But I wasn’t hired as CTO and it wasn’t my ambition. I joined Cloudflare to work with people I liked and to do cool stuff.

I’m very lucky that my background, upbringing, parents and career have enabled me to work with people I like and do cool stuff. The cool stuff changes of course. But that’s technology for you.

It's Terrible

When I was first at Cloudflare I went to quite a few meetings with Matthew. Especially meetings with investors and people would always ask him in a jovial manner “How’s it going?” and he would always answer “It’s terrible”. At first, I thought he was just being silly and was playing for a laugh to see how people would react.

In part, he was doing that but there’s also a lot of truth in the fact that startups are “terrible”. They are very, very hard. It’s very easy to get distracted by the huge successes of a small number of companies and not face the reality that building a company is hard work. And hard work isn’t enough. You might not have enough money, or the right people, or you might discover that your market is too small.

Silicon Valley lives in a schizophrenic state: everyone outwardly will tell you how they are “crushing it” and doing so well. But inside they are full of fear and doubt. Mentally that’s a very hard thing to sustain and it’s not surprising that some people suffer mental health problems because of it. We shouldn’t be ashamed of admitting that things are hard, as Matthew did.

Silicon Valley also likes to use very positive language for things that might be a little negative or tough. One such term is “pivot”. There’s nothing wrong with changing direction or responding to customer or market demands. But face it with reality that you had to change direction. That’s OK. To quote George Bernard Shaw: “Progress is impossible without change, and those who cannot change their minds cannot change anything”.

Part two is here.

Helping to Build Cloudflare

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