What's struck me is how much it's changed over the last 6 (!) years of building CloudFlare.
2009: "Student Life" / CloudFlare started as a student project. First year felt very academic. Worked irregular hours. Weren't sure what we were supposed to be doing. Lots of research. Lots of change (relocated from Boston to the Bay Area). The whole time we didn't really think we were building a company, we thought we were researching an interesting problem and seeing if we could come up with solutions for it.
Pre-October 2010: "Playing Company" / We'd raised money at the end of 2009 and hired our first employees and moved into our first office in Palo Alto in Jan 2010. I'd take the train from SF every morning answering emails on my iPad on the way down and playing Angry Birds (for a stint I was among the top ranked players in the US) on the return. We struggled to get our first 100 beta users and took the whole team to Vegas when we did. We weren't sure exactly what we were building and sometimes the uncertainty made me anxious but generally this was a fun time. The 60 days before we launched at TechCrunch Disrupt on Sept 27th were stressful but fun and incredibly productive. Everyone had a clear goal and date it needed to be done by.
Personally, I was wearing many hats (occasional coder, biz dev, and primary customer support) and nearly 100% of my time was dedicated to obsessing about CloudFlare. There was still a lot of uncertainty and throughout the course of 2010 there was increasing sense that we had a big opportunity and it was ours to take or screw up.
During this time I tried all kinds of tricks to manage my own psyche. Most effective was going to Suchadda Thai Massage near my house every weekend and getting a 90 minute really deep tissue massage that was hard enough that it took my mind off anything other than the knee or elbow being jabbed into my back. I'd been dating a woman who was an academic for the last two years but had become a pretty terrible boyfriend. Not a surprise that we broke up just after this period.
October 2010-December 2011: "Chaos" / We launched. We didn't get around to putting on any limits on who could sign up so anyone and everyone did. Thousands signed up in the first few days. Every signup increased the traffic across our network. There were only 8 of us and we were running a 24x7 network. I lost the ability to sleep for more than about 2 hours at a time. My phone would buzz with every network issue. At the same time, it was fun to see that things were generally working. Customer attention lead to investor attention and the relationship with investors shifted from us pitching them to them pitching us. I wasn't doing any more coding and spent much more of my time managing potential investors and trying to recruit. We moved the office to San Francisco within a few blocks of my house. Being closer removed the regular routine of the train and, somewhat counter-intuitively, meant I worked longer hours because the last bullet train leaving Palo Alto didn't define the end of work anymore.
With the lack of predictability came a feeling that every day held a new crisis. One afternoon in the spring of 2010 we got word some group called Lulz Security had signed up. Then the media started calling. We had no idea who Lulzsec was. I stayed in the office well past midnight reading Twitter and articles on the group and trying to figure out what to do. I only went home when I got spooked sitting in our dark office and thought I heard someone. I headed home only to be awakened by a call from my co-founder. Turned out someone had broken in and four laptops had been stolen. I raced back to the office and a bunch of us holed up on a conference room and debated (seriously) whether it was the hackers, law enforcement, or some corporate espionage agent who had broken into the office. That's how crazy life felt. Turned out the truth held fall less intrigue: it was a simple burglar who had broken into several other offices and was caught several months later.
I started dating a cancer surgeon. She lived on the other side of San Francisco and had a similarly chaotic schedule. We'd find time to get dinner a couple nights a week and exchange stories about the chaos in each others' lives. Having nothing in common almost felt like a virtue for a time as we could both provide each other an escape.
2012 - 2013: "Growing" / We built up the start of a competent team and things began to feel more stable. I started to attend more external events and spend more time outside the office. Started attending more conferences. Telling the CloudFlare story more broadly. I started writing regularly for our blog, largely telling stories about technical challenges we'd faced and how we solved them.
Being more of a public figure made me more of a target. Some of our less savory users, or the hackers trying to take down the sites we protected, decided to mess with me from time to time. I'd been pretty casual with the personal details of my life. It wasn't hard to find my cell phone number or home address. One night at 4:00am I had the SWAT team called on my home. Thankfully they rang the buzzer rather than breaking down the door. At the office, we regularly had bomb threats phoned in. We became pretty good friends with Maggie the bomb sniffing dog. Our Board suggested that I should have personal security, especially when traveling, which seemed absurd given how small a company we were. It also didn't thrill my quite private physician girlfriend. Having nothing in common started to be more of a liability and we broke up.
2014 - Today: "Real CEO" / Today I have three jobs: recruiting, external affairs, internal affairs. I spend about equal time on each. We're hiring about 3 people a week at this point and I still talk with all of them to answer their questions and try and judge whether they'll be a cultural fit. External affairs involves speaking to customers, investors, analysts, bankers, media, etc. Internal affairs involves a bit of product strategy but mostly managing people and team dynamics. Talking with CEOs of public companies that are far ahead of where we are today, my sense is this will be my role for the rest of my time leading CloudFlare.
My work day is pretty tightly scheduled but I have quite a bit of control of that schedule. I don't have a lot of downtime during the day which has made it harder to find time to do things at work I used to really enjoy, like writing technical blog posts. I find myself much more playing what Jeff Bezos, CEO of Amazon, described as "switchboard operator": taking some input of an idea and routing it to the right person on our team. It's rare that I write an email that's more than a couple sentences anymore. It surprises me every day to walk into the office and see so many people. We've passed the Dunbar Number of employees and it's hard that I don't have a personal relationship with everyone on the team. Soon I won't know everyone's name. We've tried to keep the organization very flat, in order to ensure that we're the kind of place where the best idea will win, and I am surprised whenever I hear someone hesitates to "waste my time" with something because I'm "the CEO." I try to stay approachable but see how that inherently gets more difficult over time.
I'm getting better at taking time for myself, secure in knowing there's a great team handling things better than I could myself. As a fellow founder said recently, the job of CEO is to fire yourself from every job within the company -- and replace yourself with someone more competent. I like that and think it's right.
I'm proud of the fact that the three of us that co-founded the company are all still at the company and are all still friends who respect each other. That's very rare. Our story would make for a very boring book. Other personal relationships are sometimes difficult. You lose a lot of friends along the process of starting a company -- largely because I haven't made time to keep up the relationships. At the same time, I've met a lot of great new people who I think will develop into meaningful, long-term friends. Dating presents a real puzzle -- but that's a whole other topic for another time.
Looking ahead we're likely on the path to being a public company and I'm trying to spend as much time talking with other newly public CEOs about how that changes their lifestyle. For now, I count myself fortunate that I can take a few hours on a sunny Saturday morning in San Francisco and, on a whim, sit down and write an answer to this question and not have to send it my our compliance department to ensure it doesn't contain any forward-looking statements.
Great story thanks for sharing. The parts about your personal and business security problems was surprising. I would think Cloudflare is a pretty niche product with a rational customer base. But I guess if you really piss off some developers they can think of clever ways to make life miserable.
wow amazing story, thanks for all the detail. Very enjoyable to read. Quick question, whats most influential book you read? (in terms of decisions or directions you took with CloudFlare)
2009: "Student Life" / CloudFlare started as a student project. First year felt very academic. Worked irregular hours. Weren't sure what we were supposed to be doing. Lots of research. Lots of change (relocated from Boston to the Bay Area). The whole time we didn't really think we were building a company, we thought we were researching an interesting problem and seeing if we could come up with solutions for it.
Pre-October 2010: "Playing Company" / We'd raised money at the end of 2009 and hired our first employees and moved into our first office in Palo Alto in Jan 2010. I'd take the train from SF every morning answering emails on my iPad on the way down and playing Angry Birds (for a stint I was among the top ranked players in the US) on the return. We struggled to get our first 100 beta users and took the whole team to Vegas when we did. We weren't sure exactly what we were building and sometimes the uncertainty made me anxious but generally this was a fun time. The 60 days before we launched at TechCrunch Disrupt on Sept 27th were stressful but fun and incredibly productive. Everyone had a clear goal and date it needed to be done by.
Personally, I was wearing many hats (occasional coder, biz dev, and primary customer support) and nearly 100% of my time was dedicated to obsessing about CloudFlare. There was still a lot of uncertainty and throughout the course of 2010 there was increasing sense that we had a big opportunity and it was ours to take or screw up.
During this time I tried all kinds of tricks to manage my own psyche. Most effective was going to Suchadda Thai Massage near my house every weekend and getting a 90 minute really deep tissue massage that was hard enough that it took my mind off anything other than the knee or elbow being jabbed into my back. I'd been dating a woman who was an academic for the last two years but had become a pretty terrible boyfriend. Not a surprise that we broke up just after this period.
October 2010-December 2011: "Chaos" / We launched. We didn't get around to putting on any limits on who could sign up so anyone and everyone did. Thousands signed up in the first few days. Every signup increased the traffic across our network. There were only 8 of us and we were running a 24x7 network. I lost the ability to sleep for more than about 2 hours at a time. My phone would buzz with every network issue. At the same time, it was fun to see that things were generally working. Customer attention lead to investor attention and the relationship with investors shifted from us pitching them to them pitching us. I wasn't doing any more coding and spent much more of my time managing potential investors and trying to recruit. We moved the office to San Francisco within a few blocks of my house. Being closer removed the regular routine of the train and, somewhat counter-intuitively, meant I worked longer hours because the last bullet train leaving Palo Alto didn't define the end of work anymore.
With the lack of predictability came a feeling that every day held a new crisis. One afternoon in the spring of 2010 we got word some group called Lulz Security had signed up. Then the media started calling. We had no idea who Lulzsec was. I stayed in the office well past midnight reading Twitter and articles on the group and trying to figure out what to do. I only went home when I got spooked sitting in our dark office and thought I heard someone. I headed home only to be awakened by a call from my co-founder. Turned out someone had broken in and four laptops had been stolen. I raced back to the office and a bunch of us holed up on a conference room and debated (seriously) whether it was the hackers, law enforcement, or some corporate espionage agent who had broken into the office. That's how crazy life felt. Turned out the truth held fall less intrigue: it was a simple burglar who had broken into several other offices and was caught several months later.
I started dating a cancer surgeon. She lived on the other side of San Francisco and had a similarly chaotic schedule. We'd find time to get dinner a couple nights a week and exchange stories about the chaos in each others' lives. Having nothing in common almost felt like a virtue for a time as we could both provide each other an escape.
2012 - 2013: "Growing" / We built up the start of a competent team and things began to feel more stable. I started to attend more external events and spend more time outside the office. Started attending more conferences. Telling the CloudFlare story more broadly. I started writing regularly for our blog, largely telling stories about technical challenges we'd faced and how we solved them.
Being more of a public figure made me more of a target. Some of our less savory users, or the hackers trying to take down the sites we protected, decided to mess with me from time to time. I'd been pretty casual with the personal details of my life. It wasn't hard to find my cell phone number or home address. One night at 4:00am I had the SWAT team called on my home. Thankfully they rang the buzzer rather than breaking down the door. At the office, we regularly had bomb threats phoned in. We became pretty good friends with Maggie the bomb sniffing dog. Our Board suggested that I should have personal security, especially when traveling, which seemed absurd given how small a company we were. It also didn't thrill my quite private physician girlfriend. Having nothing in common started to be more of a liability and we broke up.
2014 - Today: "Real CEO" / Today I have three jobs: recruiting, external affairs, internal affairs. I spend about equal time on each. We're hiring about 3 people a week at this point and I still talk with all of them to answer their questions and try and judge whether they'll be a cultural fit. External affairs involves speaking to customers, investors, analysts, bankers, media, etc. Internal affairs involves a bit of product strategy but mostly managing people and team dynamics. Talking with CEOs of public companies that are far ahead of where we are today, my sense is this will be my role for the rest of my time leading CloudFlare.
My work day is pretty tightly scheduled but I have quite a bit of control of that schedule. I don't have a lot of downtime during the day which has made it harder to find time to do things at work I used to really enjoy, like writing technical blog posts. I find myself much more playing what Jeff Bezos, CEO of Amazon, described as "switchboard operator": taking some input of an idea and routing it to the right person on our team. It's rare that I write an email that's more than a couple sentences anymore. It surprises me every day to walk into the office and see so many people. We've passed the Dunbar Number of employees and it's hard that I don't have a personal relationship with everyone on the team. Soon I won't know everyone's name. We've tried to keep the organization very flat, in order to ensure that we're the kind of place where the best idea will win, and I am surprised whenever I hear someone hesitates to "waste my time" with something because I'm "the CEO." I try to stay approachable but see how that inherently gets more difficult over time.
I'm getting better at taking time for myself, secure in knowing there's a great team handling things better than I could myself. As a fellow founder said recently, the job of CEO is to fire yourself from every job within the company -- and replace yourself with someone more competent. I like that and think it's right.
I'm proud of the fact that the three of us that co-founded the company are all still at the company and are all still friends who respect each other. That's very rare. Our story would make for a very boring book. Other personal relationships are sometimes difficult. You lose a lot of friends along the process of starting a company -- largely because I haven't made time to keep up the relationships. At the same time, I've met a lot of great new people who I think will develop into meaningful, long-term friends. Dating presents a real puzzle -- but that's a whole other topic for another time.
Looking ahead we're likely on the path to being a public company and I'm trying to spend as much time talking with other newly public CEOs about how that changes their lifestyle. For now, I count myself fortunate that I can take a few hours on a sunny Saturday morning in San Francisco and, on a whim, sit down and write an answer to this question and not have to send it my our compliance department to ensure it doesn't contain any forward-looking statements.