Entrepreneur, Stage 1: Bootstrapping, Burnout, and Babies

How I got here, how it went, and what happened along the way. I didn’t want to start a company. But I had no choice.

I was a SysAdmin after college, because I tried everything else and got fired from them all. I had seven jobs in two and a half years. I’m very fireable. System administration was just the chair where I happened to be sitting when the music stopped. More a safe, fun place than a source of deep passion.

By that point in my career, I was a little easier to keep around. More importantly, I had become worth the hassle. I did good work because I liked the puzzles.

I had a particular way of working. My boss would say, “You should do this thing, and you should do it this way.” He did not look at how I worked, only the result. That gave me the freedom that made the job worth it. When I told him I had finished he would say, “Great, how did you do it?” and I’d say, “Look, is that a bird?”

I automated everything I could, whether it needed it or not. Automation has a built-in reward mechanism. I would take this well-paying but stultifying job - Type this command 1,000 times - and I would reframe it: How about I tell the computer to type the command 1,000 times? It will work. I’ll watch. Bam! Now I can move on to other fun stuff.

Over time I did so much automation I kind of ran out of work. I was in Nashville at the time, while my wife was getting her PhD, so there were no interesting jobs that needed my skills. Hmm.

I could go to business school, but - sorry! - I don’t have any respect for the MBA. Everything I hear about business school is how valuable the network is. If I want that, I’ll take a cruise. I thought about going to law school, but it is so expensive you have to become a lawyer afterward. I didn’t want to be a lawyer. I just wanted to change my career.

So I was like, I’ll find someone who’s doing what I want to do-building a product to help people like me-and I’ll go and help them.

Oh my god, that was miserable. I lasted five months.

Commuting back and forth between Boston and Nashville did not help. I also had the brilliant idea of commuting seven miles each way by bike. In the winter. In Boston. I gave myself permission not to ride if it was under twenty-seven degrees. Being on the road in Boston is dangerous in a tank. On a bike, in the snow, was a cruel joke.

But mostly I just hated our software. I hated what we were building. At one team meeting, a senior developer said, “What does it matter what our customers think? They’ve already bought the product.” Reaction to that statement - nothing at all - told me I was in the wrong place.

So I left.

I got home. I said, I have a little money saved up, and I’ve tried everything else, and now that I think about it, I guess my dad was kind of an entrepreneur. I mean, he did run his own business for thirty years. Technically. I suppose.

Maybe I should start a company?

I know everyone in the world who is building automation tools for sysadmins, and none of them are going to build a business. “I built this, so, obviously, it’s the best.” But they’re only interested in publishing papers and getting academic tenure. Their software was already perfect, so they saw no reason to listen to anyone’s reasons for not using it.

I thought, what if I build something? And then listen to the people who are using it? (And maybe those who aren’t?) Hmm. Could work.

I quit my job. Well, I quit my job first and said, “Eh, I should probably find a way to eat.” So after trying everything else, I started a company.

We lived on my wife’s generous graduate student stipend of $23,000 a year - the job I quit paid $110,000 a year - and, like I said, I thought I had some money saved up. At some point the IRS sent me a letter that said, “We disagree,” and it turns out when the IRS disagrees with you, well, you know how that goes. And even if you’re right, by the time you prove you’re right, “Ok, I had ten grand, and I spent ten grand on a lawyer proving I have ten grand, and…” Just send them the check.

So I was broke when I started my company.

As a sysadmin, you’re not a developer. People will tell you: In DevOps, everyone’s a developer. Those people are lying to you. Or selling something. Which, you know. So I had to become a developer. I had written some code before Puppet, maybe 5,000 lines total. But by the time I handed it over, it was 130,000 lines of code.

The people I handed it to regretted my learning experience.

I adored it.

I learned a lot. It was, to be frank, super fun. One of the densest learning periods of my life. Programming is the best puzzle. I find it harder to step away from it than anything else I’ve ever done. It’s been two days since I ate, I think my wife has been trying to get my attention for the past twelve hours, I should probably … and then I try to move, my legs don’t work. I’m lightheaded from hunger and my feet are tingly.

Good times.

After about ten months I got my first paying customer.

I often advise other entrepreneurs. Much of what I tell them is to avoid what I did. I only had a vague idea for how to make money. I figured, “I’m confident I can make something valuable. I kind of have a plan, but I know my plan is stupid. If I bring my plan to people and listen to them, that could help make my plan less stupid.”

This is not that bad of a strategy! But it’s not exactly specific.

I didn’t really ask myself: What is my overall business going to look like? How will I get there? I started with services, because I’d been consulting for a while, and I was confident I could make enough money to eat. I know investors are down on services businesses, or anything that doesn’t look like a founder throwing themselves off a cliff with what they hope is a parachute. But you gotta eat. And services are a fantastic way to make money while you’re figuring things out.

I had a lot to figure out.

At the time - 2005 - there were a lot of open source companies out there. When I say a lot, there were four. I thought, “They’re doing well, I will copy one of them at some point later on.” That was not that great of a plan. Two years later Red Hat was the only one left. They’re a software powerhouse today, but they went public during the bubble as a T-shirt and mug company. There’s no copying that.

I did start making money, though. We consulted for three-and-a-half years. “We.” I was the only employee. About three years into the company, I discovered one day that I was incredibly burned out. This was the first of three major burnouts for me at Puppet.

Burnout Strikes

I distinctly remember realizing I was burned out. I was standing next to my wife, at the doctor’s office, looking at an ultrasound. We just learned we’re going to have twins, and I get a sudden flash of insight: My life is unsustainable.

I personally can’t recommend, when you’re in a bootstrapped startup, planning to have a baby. I would work especially hard to avoid having more than one at a time. But that’s what we did.

(Speaking of which: All you people who had your babies serially, you’re lazy and you don’t know what you’re doing. You think you had it hard. We were tested. Y’all are amateurs.)

The technician said, “Oh, you are going to get scanned a lot.” Um. You’re going to have to explain that one. She told us we were having two. We laughed. She must be incompetent. Just because you have twins (she did) doesn’t mean you can recognize them in someone else. While using an ultrasound wand. Which is your job. Scan… scan… BING! The two fetuses clearly popped into view. My wife would have fallen over if she weren’t already lying down. My knees shook. I thought, I can’t do this anymore.

I had been working every hour I could. I counted once: It was about 72 hours in my busiest week. There are people who say, I work 100 hours a week. You might stand there 100 hours a week. I’m skeptical you’re working. Based on what I know about productivity, I hope you’re not.

I couldn’t do it anymore. Since February 2008 or so, coincidentally the same day I found out we were having twins, I haven’t worked more than 40 or 50 hours a week. No evenings and weekends. I might dabble sometimes, but I won’t let it become a pattern.

Don’t worry. I managed to burn myself out two more times without those extra hours. It can still be just as bad. Pack that intensity into fewer hours, and you’re all good.

So. I need help. How?

Getting Help

I had tried to hire people in the past. Both of them were misses.

The first hire was the most notable. In the three months it took to figure out he wouldn’t work out, the best person I could possibly have hired became available and then unavailable. This guy’s biggest impact was ensuring I couldn’t hire the person who would have been most helpful.

There’s one more crazy story about him. In the middle of his interview at my house there was a drive-by shooting next door. He had taken a bathroom break when the shooting happened. They weren’t trying to hurt anybody, just shooting up a car to send a message. One of the bullets ricocheted off the car, then my porch, and broke my front window. He came out of my bathroom, and I said, “Are you ok?” “Yeah, why?” “No reason.”

I needed him to work in my house.

(Yes, I did actually tell him. Eventually.)

When he didn’t pan out, I concluded, I guess I just can’t hire. I’ll do it all myself.

Pro tip: Don’t do that.

Puppet worked in spite of these decisions, not because of them.

Things had changed, quite suddenly. I needed help, and now.

I hired the only people I could think of who might do me a favor: my college roommate and my best friend. Two separate people. Again: Don’t do this. I paid them full salaries.

Years later, I realized, “Wait a minute, if I was paying them full salary, they weren’t really doing me a favor, were they?”

Burned-out people make low-quality decisions. Your brain is gone, and you’re stupid. You work too many hours, you get burned out. You hurt your business doing this kind of thing. Get sleep, eat well, get exercise, step away from work. It’s good for you.

We were making a few hundred grand a year. And by “we” I mean “me.” I’m the only person consulting. I’m getting a little help with the code and stuff.

But now I’m going to hand all the consulting off to my best friend. “Ahh. I can see the light.” And by light, I mean impending twins.

The transition is bright in my memory. He was shadowing me. Μy last gig, his first one. “Hey, funny story, tomorrow this is your job.” We were in San Francisco, my only development gig fueled by Red Bull. I had made a promise to Stanford University, in exchange for some money. If I did not keep that promise by - I think it was - August 31, the Sunday after my gig ended, I had to give the money back. Of course I didn’t have the money anymore. I had to give them the code instead.

I’m at my client’s office during the day, and back in my hotel room at night pounding energy drinks and my keyboard. My kids are due any day, it’s my last flight, my last trip before they are born.

I finish it. I ship it at 1:00 a.m., send Stanford a note with all the details, and go to sleep.

My wife calls me two hours later and says, I don’t think it’s a drill, my water broke.

Well. I’m in San Francisco, and she’s in Nashville. You cannot get from San Francisco to Nashville fast enough to catch a baby. Everyone told me, “Now don’t worry, it’ll take 24 hours.” The kids had other plans.

Seven hours.

I was a father before I landed in Dallas. Cell phone pictures in 2008 were terrible, but they were enough to make me cry in the aisle.

Once again, things not to do, but it mostly worked out. My kids didn’t even notice.

My mother-in-law is actually thankful. She got to be in the delivery room instead. She would have been staring through the window if I had been there. It was great for her, and a great bonding experience for them. It was just, you know, complicated for me. If I’m going to flail at fatherhood, I could at least be present for it. Absent bad father is just a step too far.

That was summer of 2008. We were a little over three-and-a-half years in at Puppet. Lots of change all at once. We added two people and two babies. The business was picking up. I was spending more of my time at events and out in the community than writing code. Mostly this meant that the code wasn’t getting written, rather than that I had delegated it.

Again, my wife was getting her PhD. Nashville is kinda my hometown, and so as a result I, you know, hate it. I always told her I wouldn’t be at her graduation, I would be in the U-Haul honking the horn.

But she was pregnant with twins when she graduated. I was running a bootstrapped startup. We couldn’t afford to go anywhere.

What it all means

The birth of our kids was more than a turning point for our family. It transformed Puppet. It forced me to acknowledge I could not do it alone. I brought in help before they were born, and by the time they turned one I’d raised a funding round and moved to Portland.

In the four-and-a-half years of bootstrapping, we went from zero to around $250k a year in revenue, and from one to three people. In the seven years after funding, we grew to five hundred people and more than seventy million dollars in revenue. More importantly, we had an impact on thousands of people and thousands of companies.

I think founder stories are important. They’re usually educational, and often inspiring.

But they’re myth. They are a specific version of what really happened, refined and presented. Often, the myth so obscures what really happened that the lessons are dangerous rather than helpful.

This is a key story in my founder myth. For better or worse, I’m not afraid of you making catastrophic mistakes by trying to emulate me.

They say you can either be a good example or a horrible warning.

I think this story proves you can be both.