I’m Often Asked

Since these are questions I’m often asked, I thought you might be interested in their answers.

How did you get from a hippie commune to starting a software company?

I was born on a hippie commune in Wisconsin, then moved to a related one in Tennessee when I was 4 (this was “The Farm”, best known for having produced Spiritual Midwifery, a book that was a major contributor to reviving midwifing in the US). When I was 8, I cut a foot of hair off my head and began attending public school in Nashville, Tennessee as a vegetarian who’d never heard of capital-G God.

Suffice it to say, it did not go well.

Much later, as I worked my way through college, I realized that my coping mechanism for dealing with the stark conflict between those two cultures was to literally forget everything I knew. It was then I realized I only retained a few memories of my childhood on the Farm. Given contradictory but unverifiable information — and Nashville and the Farm were definitely both — the only reasonable response is to discard it all. That explains why I didn’t trust the kids in 4th grade who told me I was going to burn in hell for 10,000 years because I wasn’t baptized, and it also explains why I do not resemble someone raised on a hippie commune.

I graduated from high school a year early, mostly to escape my incredibly violent 3,000 person high school run by jocks. I didn’t exactly have role models to show the real possibilities of what going to school can do — nearly every adult I knew went to college, but I knew I didn’t want to use my degree to build shoddy houses and dig outhouse holes in the woods. When it came to picking colleges, I eliminated all schools that had fraternities, sororities, or organized sports (because I wanted my school run by the geeks, the nerds, the brainiacs), and then I picked the best school I could find the furthest from my home town.

I looked at schools in Alaska, but the one I found that fit the criteria was too small at 400 people. It never occurred to me to consider overseas schools. Then my home room teacher pointed out Reed College, in Portland, Oregon. I’m sure their whole book was useful, but the only bit I remember was how their Guerrilla Theater of the Absurd ingested red, white, and blue mashed potatoes in preparation for a visit by then-vice president Dan Quayle, and then threw them up at his speech. I was in. That was a whole different kind of patriotism than they practiced in Nashville.

I was too poor to visit any schools, so I showed up at Reed having never been on the west coast, or within a thousand miles of Portland. The black and white photos in the school book didn’t quite capture the place. Seeing the campus for the first time is unquestionably the first time I remember honestly crying for joy.

One of the first things I did there was buy a computer, and one of the last was decide not to be a scientist.

How did you get from a chemistry degree to starting a software company?

I had seven jobs in two and a half years at the end of college, so I tried a lot of things. I got fired a lot. Until my last year, I was planning to be an academic scientist, but Reed did a great job of training me on exactly what that job entailed, and the result was that I didn’t want it. For all that science is all about trial and error, they don’t actually allow much failure in your career — you better pick the right boss, the right school, the right project. Anything else means you can’t get the grants, because there’s just too much competition for too little money.

Once science was out, there weren’t a lot of other great options. I am not one of those who grew up with a computer; I didn’t get one until my sophomore year in college, and taking a loan out for it is one of the first things I did in school. I had spent a lot of time playing with my computer, and I found I was particularly adept at breaking it. When are you most likely to break it? When you’re procrastinating. And when are you most likely to procrastinate? When you really, really need your computer to work because there’s something big due the next day.

This meant that I also got pretty good at fixing it quickly. Or maybe, setting it up in such a way that it was always easily fixable.

When it came time to look for work, this is pretty much what I had to go with: A science degree, and facility at breaking computers. That led to a QA job, a couple of mac admin jobs, and finally a support job, which soon turned into a Unix administration job. Most of those jobs I was fired from (who gets fired from the Plaid Pantry?), but the last one was a great fit for me, and I only left because I was moving to Nashville.

Once I got there, I continued my investment in scripting and automation, which two jobs later resulted in my being a consultant, having worked myself out of a job. I quickly concluded I could make good money at consulting but hated the job. I thought about an MBA, because the badge is useful, but I didn’t think the schooling would be. I almost went to law school, but then I realized it’s so expensive you have to become a lawyer afterward, which I didn’t want. So, I did the only thing left: I started a software company. I figured I’d learn more failing to start a software company than I would succeeding at getting an MBA.

Puppet wasn’t my only idea — I’m still pretty enamored of a software product I wanted to build for scientists — but in the end I concluded it was the one I was most likely to succeed at, based on my own knowledge and on the market. In the end, I started Puppet to get out of system administration, not because I loved it.

Did you ever think Puppet would get this big?

I always knew it was a possibility, but I never let myself get hung up on whether it would happen or not. Any given situation has many possible futures, and it’s generally unwise to be too attached to any one of them. With Puppet, I was always committed to some of the constraints, but generally not so much to the specific outcome, and certainly, I didn’t spend much energy trying to predict it. With the right constraints, I hoped we would end up in a good place, which was the most I could hope for.

In terms of those constraints, they were things like maintaining a high quality business, where deals were good deals and customers generated real revenue, where we focused on the user and not the buyer, and where we maintained our authentic voice even in marketing.

That being said, I did think that Puppet could succeed, and in a big way. I knew the market was measured in the billions of dollars a year, and I knew it was composed primarily of bad software sold by dying companies. Someone was going to come in and take business away from those companies, take users away from them, and I saw no reason why it wouldn’t be me.

“Someone has to do something, and it’s just incredibly pathetic that it has to be us.” — Jerry Garcia

Did I hope for something like this outcome? Heck, I hoped for more, faster. This is one of the better possible futures Puppet had when I started, but there were far better futures available, and it’s tough not to see those and ask, “What if?”

In the end, though, I am incredibly proud, pleased, and surprised by what we were able to accomplish. I know how lucky I am, how rare this outcome is, but I also know that it wasn’t entirely accidental, that I started at the right time with a good idea, a good market, and a pretty decent plan, and I worked intensely while passing up many opportunities to make mortal mistakes.

Why That Startup Advice is Useless

Starting companies is a high-risk enterprise, especially so for high-growth, venture-backed companies, which fail more than 90% of the time. Yet people generally talk about successful companies as though their achievements are somehow inevitable and reproducible. We look at Google, Netflix, and Amazon thinking that if we can just copy their practices and decisions, we can also achieve their outcomes. After all, their actions are clear-cut (in most cases), as is their success; what’s missing?

Yet, no amount of studying these companies has significantly increased the win percentage. Part of that, of course, is that every startup is studying the same playbook. I think the bigger part, though, is that we don’t talk about high-growth companies in a way that really reflects the experience. In years of researching growth companies and talking to leaders of thriving and failed enterprises, I’ve found that even the best companies went through what seemed to be life-threatening experiences, and in general, you couldn’t tell from within the company that it would achieve the success that it eventually did. The steps to prosperity are obvious in retrospect, but their rightness is nearly always concealed when looking forward. What follows is a metaphor that helps to explain why it is so hard to think about this clearly.

When we look at a successful company, we can clearly see the path it followed to get where it is. You can look at the key decisions or hires they made, the practices and habits they adopted, the market forces that affected them (or didn’t), and how they worked with and around key players. I call this the ridge they walked. We can look back and say, Wow, that one decision, or person, or market change, really made the difference. What if Google hadn’t gotten ad selling just right just then? It doesn’t matter, because they did. What if Amazon hadn’t invented S3 when they did, giving them the freedom to create all of AWS? It doesn’t matter, because they did. What if Netflix hadn’t been brave enough to switch from DVD distribution to online video? It doesn’t matter, because even though they made some missteps, they made it through.

Looking backward, that ridge is clear.

However, in all of these cases, and countless other equally critical events for these same companies (and for every other growth company), they couldn’t see then what we see now. What they saw then is what everyone leading a growth company sees: an infinite expanse of uncertainty, akin to a field of ice that you have to pick a path across. As the leader of a growth company, you have to believe that there is a path across that ice that leads you to (at least temporary) success. Your job is to find that path. As the company progresses, the ice alongside you falls away. If you are lucky, you are standing on solid ground and it’s only the ice on either side that falls away, leaving a clear ridge behind and below you. If you are unlucky, you picked wrong; you step off the ridge and the ice cracks. If you are really unlucky, there wasn’t any solid ground anywhere, and you’ve led your company to an ignominious end where everyone suddenly realizes the whole company is built on thin ice. Everyone laments the massive mistake that is now suddenly evident. But crucially, until you took that step, the difference between your path and one that was successful was invisible.

I don’t mean to imply that leaders have no visibility into the likely success of their work, nor that the only way to manage risk is to plow forward and hope it works out. This analogy does, however, help to explain why seeing someone else’s clear path to success isn’t nearly so useful as we’d like in helping us navigate the infinite expanse of ice in front of us. It might be that working in small increments and building a lean organization will make the difference between small, correctable errors and catastrophic mistakes, but it might not. Building a great advisor network of people who have done it before might be exactly what you need to navigate the ice fields of entrepreneurship, but no one gets to navigate the exact same ice field twice, so they might just as easily confidently lead you to a crevasse that didn’t exist when they ran this race.

Note that no matter who you are, and how well you’re doing, at some point you will hit a growth wall. All marriages end in death or divorce, and all great companies end up getting bought or going flat in growth, because infinite growth just isn’t possible. At this point, everyone will suddenly say they could see it coming all along. Well sure, you did too. It was one of the possible futures.

When you look to understand a growth company, either because you are hoping their lessons will increase your chance of success, or because you want to share the key lessons with others who are striving, you get limited utility from studying the ridge of non-deadly decisions behind someone. Equally useless is studying the infinite expanse of deadly but featureless ice in front of an organization.

Instead, to get the most out of studying a company’s success, you must live their experience at that seam between the proud success behind them and the scary uncertainty in front of them. It’s not useful to simply understand that Intel pulled off a massive strategic shift in switching their focus to microprocessors. The real value comes from examining what state were they in at the time that enabled them to make that decision. Oh, it turns out that they were having their clocks cleaned by competitors in memory, and microprocessors were already generating a lot of their revenue, so it was less about switching focus and more about shifting identity than business. If anything, Intel failed in making fast enough a decision that observers and many insiders knew was right. When you frame the decision that way, it seems more manifest and relatable. The important lessons are about emotionally wrenching identity changes and making correct decisions with urgency, not some sort of prescience about how the market was moving.

We so often ascribe some kind of mystical foresight to great entrepreneurs, when in fact, they suffered just as any of us do, but for whatever reason, had a different result. The founders of Google had no pretensions to organizing the world’s information, and instead desired to sell their algorithm. They started the company only because no one took the algorithm seriously. Mark Zuckerberg had no particular interest in building a social graph; he was just rating girls on the Internet. He built a company after it became clear he had lucked into something great.

And perhaps most notably, Steve Jobs is considered the exemplar of tech industry triumph, as evidenced by the early success of the Apple I and II, the truly innovative Mac computer, and the wild popularity of Apple products in his second stint with the company. However, to focus our attention solely on these successes overlooks many key aspects that limited or propelled his achievements. For example, the Mac shipped so late and was so expensive that it was functionally irrelevant for a long time, and the rest of the industry caught up. Would a wiser Steve Jobs (or you, having internalized his lessons) have shipped earlier before the competition claimed the market? Would he have made compromises to bring down cost and make the Mac less of a specialist device? Would he team up earlier with someone with operations chops, freeing him to exercise his product design prowess? Can we learn these lessons without spending the decade in the wilderness that Jobs did? Only if we examine his steps and choices in their actual ice-field context rather than with the 20/20 hindsight we tend to use when canonizing our heroes.

In retrospect, the right answers to these questions are often easy and obvious, but the full context that was necessary to see those answers wasn’t available to anyone at the time. We build myths about why people did things, or how evident greatness was at the time. Those myths are not just wrong, they’re pernicious. The simple truisms they provide keep us from examining the real motives and conditions that were in play, and obscure the truly useful frameworks that we can apply to our own situations. They also dramatically underplay the role of luck in success.

Building greatness is a miserable journey, largely because you’re trekking over an infinite expanse of ice with unknown thickness. So much of greatness is being willing to continue pushing forward, even in the face of fear and uncertainty. We do a disservice to people who did important things if we act like fundamentally tough decisions were obvious at the time, or that great entrepreneurs had a single good idea that led them to greatness. In truth, the successful entrepreneur grows their knowledge and experience in ways that no one else can replicate.

I hope that in the future, people will look back and say I built a great company. I hope they laud my good decisions and lambaste my stupid ones. But I also hope that people are honest about the fact that I started the company with small goals, and only through success was I able to build larger goals. I hope that my decisions are studied within the context of hope, fear, and experience that I made them in, rather than their historical obviousness.

Developing My Future

Those who know who I am are likely aware that in September I stepped down as CEO of Puppet, the company I founded, and whose first product I built. The question everyone asks these days is, “What’s next?”

However, I am committed to not committing to anything until at least the fall of 2017, which means I couldn’t answer that question even if I wanted to.

As a result, you have an opportunity to watch and participate with me as I take this journey. Along the way, I’ll be trying to share what I have learned and what I believe, and to the extent I can, my thought process as I figure out what’s next. If you follow along, I expect you’ll be informed, sometimes entertained, and at least periodically offended.

Taking Time

Part of my reason for delaying a commitment is that I want to spend the summer traveling with my family (a summer where both parents are unemployed and have some cash is a privilege and luxury I’ve never had and don’t expect again). Primarily, though, it’s about giving myself enough time to think deeply about what I want to do next, and why. By the time my last day at Puppet rolls around in March, I will have been working on Puppet for 12 years, full time.

Most people seem to think I started Puppet (or, more insultingly, I decided to turn it into a “real company”) when we first got investment in 2009, but in fact it had been my full time job since March 2005, and we were ramen-profitable by the end of the first year. Even before that, I had been doing sysadmin work full time since 1997, which means 20 years in one industry. Talk about a monogamous relationship! It’s impossible to spend that much time in one area, and then immediately pick a new direction that isn’t encumbered with biases resulting from such focus.

I am truly thrilled not to know what I’m doing next, to have the opportunity to explore ideas without a strong gravitational pull or a narrow time window in which to work, and just to be in a state of high uncertainty where I can pursue curiosity without worrying about how it relates to commitments I’ve already made. I am quite confident, though, that I will not be starting another company in the infrastructure space.

There are multiple areas where I think I would be excited to start another software company (most of them somewhere in the productivity space; if you squint, even Puppet qualifies as a productivity tool). But I’m also interested in helping to create many companies, not just one, which makes investing, advising, and board membership interesting. Diversity, especially in the tech world, is a huge priority for me, so it would be great to find some way to contribute meaningfully there. And whether I want to or not, I expect to spend some chunk of my time learning how to be productively involved in our civil and political discussions. Heck, some part of me feels guilty for not investing all of my energy there.

About the only thing I can promise is that whatever time I put into companies will almost all be focused — whether investing, advising, or operating — on helping individual people spend more time on the things they care about and add value to them, and less time on the menial work that gets in the way. That could take the form of productivity tools, automation, or management tools, for example. I’m generally more comfortable with B2B models, because I understand better how to build a business there, but I’d love to help build great tools companies for consumers that aren’t ad-driven.

If you’re interested in following along at home, I’ll be writing in this space as I pursue this decision, and hopefully after. My goal is to write often, and on any topic that strikes me, but you should expect to see articles on technology, finance, people, and the industry, with a periodic dose of just me being a person. I have many hypotheses right now, and not a lot of data, so I will be quite surprised if this space looks in a year like I’m thinking of it today.

My hope is that my writing is more about what I learn and conclude, rather than sharing my personal journey, but don’t be surprised if some of the articles are more about me than the industry.

For those who do decide to follow along, I hope you get some value, some interest, even some excitement from some of what I write. I also hope you’ll share with me anything you think is related, intriguing, or just confusing in topical areas. The best place to find me at this point is on twitter.

Thanks,

Luke