Framing the Risk in Your Business

Growth requires risk. But don’t overdo it.

Originally published on NewCo shift

I was asked by a CEO recently, “How do I know if my product is ready to scale?” He thought he was ready to raise money and start growing the company, but he didn’t really know how to be sure.

Venture capital exists to invest in enterprises that have a huge opportunity but are also a big risk. Yet VC firms tend to actually be pretty conservative, relying on pattern recognition and social networks to make their decisions. This turns investor pitches into bizarre encounters where you have to help them see the huge risks in your business and how this risks can generate massive returns, but you also must convince them that you have all of that risk managed, so there’s no reason to be afraid. I’ve been turned down so many times by investors “until we’d taken the risk out of the business,” and every time, I’d sit in the car outside their office park thinking, “But don’t you exist specifically to make big bets?”

I can’t tell you how to raise money, because no matter what it’s hard, and there’s no special trick to it. Well, there’s one trick: Sell a company for a billion dollars. Do that, and you’ll never have trouble raising money.

This article is only for those who are not quite so lucky.

What I can help with is framing your company so that you can more coldly see and explain where the risk is, and with that hopefully you can help others get excited about the vision in your head, the beautiful thing you’re trying to build.

Step one is understanding your market risk. If you’re raising money, you have to convince your prospective investors (if you’re talking to typical valley VCs, anyway) that you can build a company that can do $100m in revenue at some point. So, convince me your market can support a company that can hit that scale and still grow. That means the market needs to be hundreds of millions, and probably billions. With Puppet, we knew the overall management market was between $6B and $25B a year, depending on your definition, which made this part pretty easy for us, but lots of companies are creating a market, so they have to spend a lot of time on this topic.

The next big question is why you, particularly, will win. Sometimes this is called technology risk, but companies win for many reasons other than technology, especially these days. Puppet didn’t necessarily have the best tech in the world, but we had a focus on the user that no major player in our space had. Everyone else was worried about the buyer, and we focused on helping the individual users succeed. Other companies have a cultural edge, or even just a mindset that others can’t copy. Whatever it is, though, there needs to be some reason why you’re going to take this big, awesome market.

I call this strategy risk. You’re planning to take the market in a particular way, and you think it will work but you don’t really know until you play.

A high-growth company usually trades off strategy and market risks. If everyone else agrees this is a great market, then you’ll have lots of competition so you need a unique strategy that sets you apart. If it’s a mature market with clear revenues and margins, you need a great strategy to fight against big incumbents, who won’t go quietly. If, on the other hand, no one else agrees this is a good market, and you get it all to yourself, then the strategy doesn’t need to be differentiated, so you can run the least risky strategy you can think of.

You can’t walk into a VC’s office and say there’s neither market nor strategy risk, because that business is just too obvious. It’s either so obvious it’s actually stupid, or so obvious that you’re one of a hundred players running the same game — both of these are bad bets. You’re not getting that funding round.

The last piece is execution risk. You’ve got a good market, you’ve got a solid strategy. Now convince me that you, particularly, can build a team and make this happen, within the window you have available. This is 99% about the team. Can you hire people? A lot of them? Get them working together? Do you know how to ship software, sell software, market it, etc? Some of this you can do through force of will, some you can do by just being smarter or faster, and some requires that you really nail a couple of pieces, but most of it is about building and scaling a company that can execute your strategy. This is the grit, the work, the hard part. The best strategy in the best market is worthless if you can’t do the work.

There’s one more critical point about risk. It should be obvious, but somehow it’s not.

You want to minimize the risks you take. There’s something about what you’re doing that’s unlikely, probably scary, and quite possibly stupid. That thing has to exist, because it’s what makes your business valuable. Without that huge risk, you can’t possibly achieve the massive payoff you’re looking for. Take that risk, put it on a pedestal, love it.

And then do everything you can to not let other types of risk into the rest of your business. If you know your major risk is strategy, why introduce a massive execution risk at the same time? No. Your work is scary enough that you should be conservative everywhere possible. Pick something you know works when you have that luxury, because you won’t get it very often.

This frame should at least get you the first three slides of your presentation. There’s plenty more to know before you can convince someone you can go out there and win, but being able to clearly talk through the risks in your business and how you’re managing should at least help you get a seat at the table.

Productivity Is Not About People

How best to combine “software” with “management”?

First published on NewCo Shift

You’re doing productivity wrong. Actually, it’s worse than that. You have no idea what it is. And no, this isn’t some sort of technical, jargon-y sense where I’m arguing over whether to measure it in terms of lines of code, hours spent typing code, or something else. Your core understanding of productivity is entirely wrong, and it’s making your company worse at everything it does.

Productivity in the software world is discussed in terms of the individual, and usually phrased as getting more of a person’s time on the thing they were hired for. “Hey, I didn’t hire you to talk to users or attend training! I hired you to write code!” Even the developers join in: “Every minute I spend in meetings instead of writing code is wasting company money.”

This is stupid and wrong.

I had a conversation with a CFO recently who asked me why his company should use Puppet. I asked him in turn, what does it cost you to ship software right now, and what’s the value of lowering that cost? He said, not surprisingly, that he could not answer that. This isn’t to pick on him — most software CFOs would say the same things, since their job rarely delves into software operations.

Can you imagine having the equivalent job description with a manufacturing company? Picture the CFO of GM saying their job doesn’t require they understand the financial aspects of building cars. They’d be shipped out in disgrace. Yet somehow the software world tolerates ignorance of the financial implications of their core work product, software.

Sure, you might say, our finance teams can’t help us build more, better software for less money, but we don’t need their help because we intuitively know that more time spent writing code equals more productive development teams. Right?

No, you don’t. Again, you’re wrong. This is exactly, specifically how you’re wrong.

Toyota showed decades ago ensuring everyone is busy all the team is a great way to lower productivity. Yeah, you read that right. Lower. If you can’t shut the factory down (thus making everyone idle), you can’t fix problems at their source, which means every car you make is broken in the same way.

As another example, teams can almost never be perfectly balanced in output. Maybe you make doors much faster than you make engines, so if your door team is always busy, you end up with too many doors. Just like in development: The interface team might work a bit faster than the backend team, so they build an interface on a myth and then you can’t ship their work because there isn’t coverage on the backend. Oops. But hey, at least that interface developer didn’t spend any time in training, testing their prototypes with users, or bringing fancy coffee to the backend team.

The stupid thing is modern industry figured this out with its very first business consultant, Frederick Taylor, who developed a thing he called ‘Scientific Management.’ His ideas sounded good: I’ll hold a stopwatch and find ways to encourage people to get more done in a given amount of time. Seems reasonable, right? Probably more advanced than how most software companies do it today. In fact, he was really successful: He spawned our nation’s first management consultants, and they’ve continued to make tons of money on the fraud that he perpetrated more than a century ago.

Because that’s exactly what he was: A fraud. He was fired from his first gig because it ruined actual productivity, yet managed to convince corporate America that it was such a good idea they should ignore the little problem of it not working. Here we are a century later and the Harvard Business Review is still giving advice using Taylor’s own language.

But, you ask, what do I focus on if I’m not allowed to just track what the developer works on?

Now, Grasshopper, you set foot on the path to wisdom.

These are examples of waste in the form of rework (fixing quality problems later) and inventory (the built but unshipped interface work), but there are many other kinds that pervade modern software development. Lean Manufacturing is our most complete and coherent philosophy of productivity, and its name isn’t just decorative. It reframes the problem of optimizing productivity into the practice of reducing seven (or sometimes eight) kinds of wastes, including those above.

The funny thing, though, is that none of these wastes are visible if you just look at the individuals involved, so measuring what the people do isn’t just worthless, it’s actively counter-productive. See what I mean about all the wrongness?

Transport is a great example. You might have a person at your company specifically tasked with this (the most famous example from this is certainly from Office Space, but there are rational reasons for such roles in modern software teams). Intuitively you’d want this person to be 100% busy, yet optimizing the system to need more transport hurts the system even while it makes your individual stats look better.

Our world of software is fundamentally confused because it can’t move past thinking about the people to seeing the system. The first page of results on software productivity pretty much exclusively focus on the people, and even developers will say they should be spending more time writing code and less time doing other stuff (like in meetings with product managers or customers).

This is the challenge of our industry over the next few decades. It took around two centuries to get from the first industrial mills in the 1700s to the development of lean in the late 1900s. There are times where I think we can do better, learn faster, but then I realize how much more complicated our problem domain is, and I start to wonder. At least in factories you can physically measure inputs and outputs, and you’re consuming and producing discrete, easily measurable work. With software — especially SaaS built on the public cloud — discreteness is impossible, and even measuring the cost of inputs often approaches impossibility. It’s much harder to optimize systems that extend far beyond our own data-centers (if we even have them).

Nonetheless, this is our challenge. The first step is to move away from this focus on people, from this view that the developer’s precious time at keyboard is our main concern. Only then can we start to truly get better at building better software, faster, and for less money.

Leadership Is Direction Plus Constraints

How I went from a capricious boss to a powerful partner.

Originally published on NewCo Shift

Early in my tenure at Puppet, I had one of my employees, José, make laptop stickers. He said we already had some, and I said, yeah, but they suck. So he designed something different. I said nope, still not right. Finally, in frustration, he said, “You clearly know what you want, can you just tell me what it is?”

I expect many of you will recognize this problem. It is sometimes called “Bring Me a Rock”, which pretty well captures its absurdity. Becoming a better leader required I find a way past it.

To my chagrin, I am often described as having “vision.” I hate this. It implies I know what I want, that I have some kind of clarity. I don’t. If anything, I pride myself on my uncertainty. I am a deep believer in open-minded, unsentimental experimentation and I think one of my true skills is knowing where to focus that research, rather than knowing what the research will find. This is pretty much the exact opposite of having a vision. So why did so many people think I had one? Why did everyone around me look to me for answers, instead of doing their own exploration?

I was tempted, but Kanies’s Razor kept me from believing it was just because I was so smart. Finally, someone partnered fantastically with me and helped me see that these are the same problem, solvable through better communication on my part.

In 2014, Puppet moved into a large, new office in Portland, OR, and we had the opportunity to strip the building down to its bones and build out the space we wanted. We were lucky enough to work with Corey Martin of Hacker. He and his team were great at really listening to me, and pulling out what I truly cared about, never getting frustrated or giving up when I was equal parts opinionated and incoherent.

I don’t always know what I’m talking about, but I’m pretty much always sure that I’m right. — Mojo Nixon

Corey quickly realized that I didn’t know what I wanted, but there was something worth extracting from all of the beliefs I was expressing. And, of course, I was paying him, so he did kind of have to actually listen to me. We spent the first term of our partnership working out the direction: What do you want the space to feel like overall? What impression do you want to leave? There are a few different ways to arrange this kind of office, which one appeals more and why?

Once we had that theme, now we could create an actual design. This is where we started pulling little ideas off the shelf — some mine, many theirs — but a design needs rules, some rubric to tell the good ideas from bad. For instance, one of the awesome things about our space is all the great windows and the views they provide. It was important to me that every person be able to get natural light (which is in short supply in Portland) and to have part of that view. This is one area I wouldn’t compromise, but there were many other hard constraints, for reasons of style, cost, or good old Newtonian physics. We captured all of these, and used them to quickly reject ideas that didn’t fit, no matter how great they might have seemed.

We still didn’t have a design, but we had a direction, and a bunch of constraints. Crucially, the whole team had them, they weren’t just some black box between my ears.

It turned out that this was enough of a platform that the team could quickly generate, tune, and reject new designs, so their creativity was opened wide, and my feedback on their ideas made sense. Once the framework was explicit, it became easily extensible. Suddenly discover a constraint you care about but haven’t shared? Add it to the list. Reevaluate your design with the new rules. Done.

They built a beautiful office. Yes, there are some details I lay claim to, and there are a couple of areas where I put my foot down on high-level design components, like open stairways between the floors, but this is their design, their awesome work space.

As I reflected back on how successful this partnership was, I knew it was a teaching experience. You learn far more from successes than from failures, and most of my attempts at this kind of partnership had failed.

Obviously, a big part of it was just how well we were able to partner. You can’t force this. Corey and his team trusted me and knew they had to deliver something I loved, and I trusted them, knowing that they were great at both the creative and implementation aspects of their jobs.

The framework that grew from this partnership enabled the team to do great work, work that I loved. I think I’m most proud of just realizing how special the experience was, ensuring I took the time to understand why. That investment provided a tool I’ve been able to use in almost all of my subsequent work as a leader.

My single most important role as a leader is to describe the direction I want to head, and if at all possible, I need to explain why. A lot of leaders can’t or won’t cover that, and frankly, lots of people have done great work without ever knowing why they were doing it. I agree with Simon Sinek, you’re a better leader if you Start With Why, but you don’t meet the basic qualifications of a leader if you can’t at least point the team in a direction.

That’s not enough, though. The gap was why I often found myself saying the equivalent of, “No, a different rock.” Working with Corey and his team taught me the importance of expressing the constraints, not just the direction. These allowed the team to take ownership of the design, which was absolutely critical to unleash their best work.

This framework of communicating direction and constraints provided necessary separation. I could step away, stop being in people’s faces and checking their work, and they could go off to their lab benches and iterate in peace, knowing both that they could quickly see if they were close, and also that if we had some sort of problem, we had something we could tune and evolve.

In the other big projects I’ve had since then, such as rebranding Puppet, designing new products, and hiring executives, this framework has helped immensely. With it, I am a better leader, and a more pleasant leader, and the teams I worked with do better work, faster. And we all enjoy the process much more.

When It Comes to Culture, You Can Be Right, or You Can Be Successful

Apply the lessons of product design to your company culture

Originally published on NewCo Shift

Every founder understands the importance of culture in the long-term success of their company. Yet rather than valuing and supporting all employees, organizations like Uber still manage to build a toxic, poisonous one. How does this happen, and what can you as a founder do to prevent it?

We’re still in the early days of understanding how to build great culture. However, the barriers to doing so are surprisingly similar to another area where we’ve come leaps and bounds in the last decade: Creating great products. The similarities in their problems mean the tactics for solving them should be portable, too. In both cases, the barrier is essentially:

You’re creating for someone else, and they get to decide whether you succeeded.

Your opinion matters, but only as part of the feedback loop between your work and the outside world. Eric Reis and Steve Blank have done a great job of teaching us that facts live outside the building, and the real test is to go find them. You can’t rely on your own perspective, because you’re not the ones deciding whether to buy.

A product solves a specific problem for a specific customer, whose perfect solution might fail the very same problem on another person. When it comes to testing your product, the only experience that matters is that of your target customer. Failing them is failing full stop.

Your culture has the same need to dial into your audience. As the founder, it doesn’t matter what you think of the company’s culture. It’s not for you. But for better or worse, you do get to decide who your culture is for. A lot of these failures of culture are actually the CEO making bad decisions about who the culture is for.

For example, we all know stories of toxic employees driving other people out of the company. The excuse we hear is that this person is “too important to fire.” It’s presented as a choice between firing this person or making some people uncomfortable, in which case it’s easy to keep this high performer around. But that’s not actually the choice you’re making.

When you choose not to fire someone who harasses women, what you’re really saying is, “This person is more important to my company than women are.”

You’d rather your organization and leadership discriminate against women, have them leave your company, and have your people and teams suffer all the psychological damage that results from choosing to protect one person over a whole class of people.

It’s the same for an employee who discriminates against minorities, veterans, disabled people, or any other group. You can keep that one person, or keep the ability to hire from that entire labor pool.

Of course, that toxic person won’t actually prevent you from hiring from a whole group. That would actually be better in the long run. Instead, you’ll hire a few, but they’ll only stick around long enough to be almost valuable to you. People who stick around for one to two years are incredibly expensive — but your toxic employee will cause them to leave. You get to pay to recruit and replace them, to train them up, to watch teams form, and then to watch them fall apart again. And again. All because you couldn’t make a hard call on one person.

Conveniently, you’ll then be able to look back after a couple of years and say that these people who left just didn’t fit in, as though it’s somehow their fault that you’ve designed an organization that excludes them as target users.

I think there’s a strong moral case to made for inclusion, but you don’t need it. All you need is basic economics. Great people are scarce, and every group you exclude reduces that pool even further. Your investors want you to have the biggest possible user base to increase your addressable market; don’t you also want the largest possible employee base? Women are 51% of the population, and in the US, whites make up 72% of the population. If you only hire white men, with maybe trifling exceptions, then your target market is only 36% of the country. Reduce to just the working age population, and you’re at 22% of the pool. And that’s before you slice for experience, location, etc., much less silly requirements like a degree from an elite school and experience working at Google or Facebook. Every demographic you exclude reduces your possible employee base, and with it your chance for building a great business.

Let’s say I’ve convinced you. You have to design your organization to include other groups. Now what do you do to ensure it’s working for them?

Again, the facts live outside the building. Even worse, as the founder you don’t get the truth. Most people do not speak truth to power because they either feel unsafe, or actually are. Even worse, most powerful people don’t want to hear it. This attitude helps explain why a lot of cultures are so broken. You have to fight your instincts, your comfort, and often, your happiness to get the truth from those who own it.

In the fall of 2014, I had dinner with eight women who worked at my company. This was my most difficult experience as CEO. They were pissed off. Their experience was very different from what I thought was happening, and hearing it directly from them hurt.

I realized in hindsight that I’d made the tactical mistake of collecting the most upset women in the company — getting together with everyone who was having the worst experience— but that didn’t make their experiences any less valid or their feedback any less important.

Thankfully, I was aware of some aspects of what they were struggling with, and I was able to point to three separate projects I was working on, all with defined goals, owners, and deadlines, that would target what I thought were the biggest issues. But I had not realized how bad it was for them, and I was far from achieving my own goals in this area.

My behavior as a result of that dinner would make an explicit statement about who my company was for. I could have taken that deep pain, that searing discomfort, and run from it. I mean, I didn’t experience any of that, and all I had was these whiny women who had this problem. Right?

Would you accept that with your product? Would you dismiss the feedback of eight customers who were on the verge of dumping your product? Would you look at their feedback and say, well, it’s just eight whiny users, I can ignore them?

Many founders choose this path in culture. They keep around the bad managers, the toxic star player, or the oppressive HR policy. But like with your modern software, you have the opportunity — and I say the obligation — to do better.

So go, build your best culture, set high standards for your team. But be very clear about whose feedback you rely on to test whether you’re meeting those standards. If your goal is inclusion and diversity, which it absolutely should be, then you need to listen, really listen to diverse voices, and to those who are systematically excluded from most organizations.

If you can do this, you can emulate the Dodgers hiring Jackie Robinson and the Sorbonne University promoting Marie Curie as the first woman professor of general physics. If not, you will find yourself competing with them instead.

The High Cost of Fitting In

They say authenticity is the key to success, and once you can fake that, you’ve got it made. My experience says it’s not quite so simple.

Originally published on NewCo Shift

When I was 23, I was hired as a system administrator for the first time. I joined BlueStar Communications, which was a young but well-funded company stupid enough to take on the incumbent telecom carriers. Their CEO was a maverick, especially in staid telecom in Nashville, Tennessee. He was bringing always-on internet to small businesses in the southeast (yes, there was a time when this innovative), and blended in about as well as a hockey player in a three piece suit. I was excited to work with someone who I could identify with, and learn from.

He was fired the week I started.

Like the founder of BlueStar, I’d had my own struggles with long tenures. I was fired from a cabinet company after only a week. I lasted a full three month contract at Adidas before having it ended the day I left to visit family. I also lasted only three months in QA and Mac administration jobs.

For all of these firings — except maybe the cabinet shop, which bored me to tears — I wasn’t bad at the work, I just didn’t fit in. You could say I wasn’t really housebroken, that I didn’t know the rules of how people acted in American corporate environments.

All of my prior work experience was remodeling houses with my family, after growing up on a commune. I had no idea what made people normal, I just knew I was missing it.

These failures inspired me to work harder at being worth keeping around, but in parallel I started learning to look like I knew what the rules were and was at least trying to follow them. For someone who only a few years earlier walked around campus with knee-high boots, a spiked leather jacket and a mohawk, this was no mean feat.

This experience with firings was a huge influence when I started Puppet in 2005, six years after I met the CEO of BlueStar. I bootstrapped the company for more than four years, partially because I failed to find an investor I trusted to keep me in the CEO role. The first term sheet I ever received was on the condition that I accept a friend of the investor’s as CEO. (I declined.)

As I grew the team, things got more difficult. One of the first people I hired immediately declared his greater fitness for the CEO role, with zero relevant experience, and tried to convince others to oust me from the company I’d built and they’d just joined.

Yes, I was paranoid, but they really were out to get me.

From my first hire through raising $87m in funding and growing to nearly 500 employees, I could never get comfortable. Everyone I worked with reminded me — unintentionally — that I didn’t fit in, that I didn’t behave as they expected. As I grew into my role, I excelled in areas, but continued stepping in holes that everyone else could see.

The suspicion that I wasn’t faking things well enough was confirmed as I was raising a later round of funding.

Before a pitch meeting, an investor said to me “Now try to be more like a Valley guy, not so much a Portland guy.”

Infuriatingly, I knew what he meant, but also that I’d never be able to pinpoint what I was doing wrong. I worked every day on my “Valley guy” pantomime, from the clothes to the books to the words. This pointed statement told me in stark terms that my efforts were obvious failures to even the casual observer.

Knowing the world saw me as an imposter caused me to hold back. I don’t mean I had imposter syndrome; I suffered from it like most high performers do, but that’s not what this was. The world around me constantly pushed back against what made me “me”, making me worse at just about everything.

I had put myself in a box. I wasn’t even willing to consider ideas that I didn’t think the people around me would accept. I was brave, within that window. I was daring, but not too much. I could do anything I wanted, as long I still kind of looked the part. This box excluded many great options, and notably, excluded a lot of what I most wanted. My weirdness isn’t skin-deep, and a lot of what I wanted just didn’t fit, so I tried to do something that did. Thankfully a lot of it worked out, but I think it could have better, and I know it would have been more pleasant, if I had been more brave, more willing to own my lack of belonging.

It’s worth noting, this was all as someone who did theoretically look the part. I’m a medium-sized white male with a degree from a great school.

I can’t imagine how much worse it would have gone for someone who literally looked different — wrong skin color, wrong gender, wrong accent, disabled, too short, etc. Maybe that was my real problem — people let me in the door thinking I was like everyone else, and only once they started talking to me did they realize how weird I was.

Finally, after almost ten years of running Puppet, I found a way to escape this box I had put myself in. I would quit.

It’s not fair to say this was the only driver for my decision, or even that I was thinking of it this way at the time. What can’t be denied, though, is how much it changed me. I lost my fear of being fired for not fitting in, because I was working to leave anyway.

I couldn’t see the box when I was in it, but when freed, unavailable actions suddenly became doable. I could trust myself for the first time since that first hire, so my cost of decision-making plummeted. I didn’t need to look to society as some sort of arbiter of what’s reasonable.

I had been preventing myself from using my now-highly trained instincts, which reduced me to tackling easy problems or making slow, bad decisions. Or sitting there and doing nothing, which is generally an even worse decision.

Outside the box, my inductive reasoning center could operate without all the second-guessing. I was able to hire a product leader based on instinctive conviction that we were aligned on how to work. I made an incredibly tough call on hiring for Business Development, by following my thread of fear that maybe I was being pulled toward too easy of an answer elsewhere. Most importantly to me, though, I was able to develop and begin rolling out what I think is a truly great product strategy.

I did some of the best work of my life.

This experience has an interestingly conflicting lesson.

On the one hand, the cost of trying to fit in is often too high. No matter how much you want it, you might have to choose between failing at what you want and succeeding at what you can authentically do. If you’re building a team, the choice may come down to those who are great at the job and those you can work with.

On the other hand, I somehow fooled people into thinking I was normal (well, normal enough) for long enough to become a successful CEO in a field where I seemed like an alien to everyone involved. That pantomime was critical in developing the instincts I was able to apply so well as my tenure wound down, and now I have opportunities I never could have dreamed of.

I think the duality of this lesson is important in the conversation around diversity. Puppet couldn’t have existed without some tolerance for my weirdness, but it was also much harder because of it.

I’ll never know if getting out of that box earlier would have caused me to do even better as CEO, gotten me fired ignominiously years earlier, or even maybe caused the company to fail early on. What I do know is that I was deeply hurt by not facing and acknowledging my fear of being fired.

Fear is healthy and reasonable. But you have to pursue it, nail it. Understand it. Not run from it.

I am privileged to have no idea what is in store for me, and no fear at the prospect. I feel no need to fit in anymore, both because I have nothing to prove and because the cost of not fitting in is now one I can afford to pay. If anything, I’m now considered more valuable because I don’t fit the mold.

The lack of pressure to conform brings incredible freedom. Freedom that everyone deserves.

How Can I Help?

I am not a technologist. This surprises many, including a CEO I was on the phone with recently. I explained that I had no pet software projects I was working on at home, and thus couldn’t demo her software. She paused for a second, like, “Uh, why are we on the phone, then?”

It’s true that I have worked on tech since graduating from college, and that I wrote Puppet essentially alone while I bootstrapped the company for years by myself. I enjoyed the work, but those were all a means to an end, not the goal. This became more and more clear to me as I hired large teams who really were technologists. I was able to do the work, but they loved it. I naturally fell into different, complementary areas.

So no, I can’t really help your company in sorting out its software stack. Or rather, I could, but you really shouldn’t want my help there. There are better people. Far better. People have found my advice really helpful in the past, but not in this area.

Strategy is where I’ve had the biggest effect as an advisor. You are already deeply committed to your goals — you don’t need my help figuring out what to do. You are just as committed to how you’re going to achieve them, but probably haven’t spent as much energy thinking about it and expressing it. This ‘how’ is your strategy, and key aspects are decided early on, whether you mean to or not.

Do you want a big field sales force, or a self-service model? Either way, why? How does that choice affect your product price point and service attach rate? There isn’t necessarily a right or wrong answer, but a choice will be made, and it has massive consequences on the life of your company. My great ability is pestering you with questions until you’re forced to put your opinions on the table and really examine them. As a leader, your job isn’t just to be opinionated — it’s to be able to usefully express that opinion to your team.

Product is the second major area I will push you. Again, this isn’t about the tech, or the code. I don’t care how it’s built. The first step is being clear about what problem you want users to hire you for. I bet you have a decent grasp of this, but you have to go down a layer into which users you’re going to start with, how you’re going to parlay them into a larger group, and how all of that relates to adoption within a single organization and across a market. The path of a product’s adoption is as critical to plan out as the features you build.

All of that ties into how you price. How does it drive user behavior? What do you want to incentivize through low or free pricing, and what must you charge for to make your business work? How does charging per seat vs consumption vs features change their behavior and affect your business?

All of this must come together into a coherent system that pushes you, your team, your customers, and the market to focus on the right problems at the right time. You should seek my help in seeing the whole system, and especially the gaps in it. I hate software, but oh boy, do I love systems. My brain is so optimized for managing, storing, and assessing systems that I lose nouns constantly. It’s worth it, for me and for you.

I can also help you.

You’re not a coincidence. You have to understand, it’s not an accident that you’re here. Even if the only thing that makes you special is that you were the first one to raise your hand… it’s been a few years now. Because of that one little action, you’re different than everyone else. It’s up to you to demonstrate whether that difference is good, or useful, but it’s definitely there.

I don’t mean to say that you’re better, or that only certain people can be entrepreneurs. History shows the exact opposite, and I’m a huge believer in empowering ever more. What I mean is, the mere act of taking the step permanently changed you. One of the hardest acts for most founders, especially those from underrepresented groups, is believing that they belong, that they deserve to be out front. I can help you see how just sitting in the seat has led you to be a different person than you were before, led you to special insight and special opportunity.

It’s up to you, now, to make the most of the opportunity, to believe in it and to deliver on it. You have to learn how to extract that difference, to bottle it, to share it. And when to dump it down the sink.

Founders are so full of dreams that they have a hard time letting go. “It’s true we can’t do this today, but I’m going to keep talking about it in hopes we can do it tomorrow.” Your business is on death’s door and the wrong success gets you all fired, but sure, go ahead and distract your team with something you know you can’t and shouldn’t build, and that your customers would never buy.

Everyone knows founders have to make hard decisions, but most don’t seem to realize the hardest ones are about their own dreams. To build something great, you have to give up on other dreams. You can’t build it all at once. You can still hold it, treasure it. But you don’t get to talk about it. You can’t distract people with it.

You haven’t earned it yet. When your company is a massive success, and throwing off more cash than you know what to do with, that’s when you pull out your other great ideas and turn your success into a platform for experimentation. Until then, you have to focus. Let go.

Beyond all that, I enjoy working through demos and user experiences, helping people see your work through new but educated eyes, asking a thousand questions that you might not have answers to. This teaches us both a lot about you, your product, and your company. The differences between the easy and hard answers teach you a lot, too.

What I don’t like to do is tell people what to do. At most, I will share frameworks I’ve used for decision-making in the past and recommend some of them for you, but preferably, I will focus on pulling from you what you really believe, and then make you really confront it. It’s not about me. I can’t live your life. I don’t know your customers. I can’t run your company.

But maybe, with the right prompting, I can help you look at it in a new light, help you make the right decisions faster, and help you avoid some of the worst parts of this insane decision you’ve made.

It Shouldn’t Get Easier

Anderson’s knife can cut anything, taking a chunk from everything in the land.

Master Terrence’s strokes remove less with each cut.

Greg LeMond once said, “It never gets easier, you just go faster.” This quote has been a rosary for me, a source of contemplation and meditation over the years. I think of it every time a new problem reveals itself as an echo of something I thought I already solved.

When I started Puppet, everyone I worked with stressed the need for me to recognize my position as founder and CEO, to bring people with me. The summer before I stepped down, more than a decade into practicing this skill, it still showed up in every coaching session. Not because I haven’t improved — but because it is a life skill that I can improve at every year and still die with more work in front of me than behind.

I found it incredibly hard to hire those first few people. I second-guessed myself, was slow, looked like a fool, felt an even bigger one, and finally made bets based on too little information. When I rebuilt the executive team in my last year, I second guessed myself, went too slowly, made what looked like basic mistakes, and felt incompetent the whole time.

This isn’t a coincidence. It’s not a sign of my incompetence. It’s the exact opposite: It shows that I never let things get easier, instead I kept my intensity up and always focused on going faster.

LeMond knew how to win. You train, you work, you focus, and all that effort delivers leverage. What you did yesterday when giving 100%, you can do today giving only 97%. What do you do with that 3%?

If you want to win, you reinvest it. In what? Counter-intuitively, exactly what got you that leverage in the first place.

For each and every one of us, there are two kinds of skills: Those it’s worth devoting our lives to, and those it’s not. A given pursuit can be less important because it doesn’t matter to you, because you’ll never be good enough at it, or because you just don’t like it. Those that matter, though, are a perfect intersection of your love, your abilities, and your values. They will reward any amount of investment by making you better at what you care most about, and are best at.

You have to love it because you really can’t devote the time and energy needed to dominate unless you like the work. You need at least some ability. You don’t need to start with a natural talent, but you are most likely to be rewarded for investing in areas that come easier than when you’re starting at the bottom. And your investments have to match your values. Some people care most about skills that earn them money, others about having an impact on people’s lives, and yet others want to build. You have to believe that what you’re investing in will help you spiritually, not just materially. It’s the only way you can convince yourself to work as hard as you need to.

Yes, there absolutely are things you will never be good at that you have to invest in. When I started Puppet, I was an outright liability in some areas, such as business operations. I had to get better at those. But I was never confused into thinking I would be great at them. That’s what team building is for.

Given two skills, one where you’re 8/10 and the other where you’re 3/10, where do you invest? Some might recommend the skill you suck at.

Not me. If that skill mattered, you would never have gotten hired in the first place. The reason you have a job is because of your 8/10 skill. Get 10% better at your weakness, and wow, you’re at 3.3/10. Big whoop. Get 10% better at your strength? You’re at 8.8/10. That’s a huge difference.

But getting 10% better in your area of expertise is fantastically difficult. It’s your life’s work.

I am suspicious of people who say the hard things are easy. What I hear is not that it’s easy, but that they’re not trying very hard. Or they’re too embarrassed to be honest.

Greg LeMond was the fastest cyclist in the world, but never stopped trying to ride faster.

Miyamoto Musashi won more than 200 individual duels with a sword, but never stopped trying to cut faster.

Excellence requires perpetual intensity. You should be confident enough in your strengths to admit that it’s hard. It should be hard. It’s the only way to get better.

Learning to Write

Reese’s keyboard produces truth of complexity and beauty, admired from a distance by all.

With a violent strike of Master Aaliyah’s pen, Jorge is enlightened.

I set out in January to study the realms of finance, software, and my own desire, but found myself adrift with no laboratory for experimentation. Programming was my testing ground for the hypotheses that led to Puppet, but my new questions cannot be answered in silicon. Clumsy studies provided two conclusions: Writing itself can and should be how I express and test my beliefs, but only if I get much better at it.

I started Puppet with core hypotheses, considered stupid by the experts around me. There was no point in talking about them; anyone can talk, and listeners similarly get to pick their conclusions. Only those I could prove had merit.

Proof is complicated. Few of us live in the world of math, where there’s enough overlap between objective reality and our language for discussing it that we can be truly sure. Computer science is itself lacking the unsentimental judge that the natural world provides to actual science. In truth, I should not discuss proofs, but rather disproofs. My real challenge with Puppet was to get rid of my false beliefs and let the remainders shine through, and there, programming was the perfect foil.

The best product idea in the world is worthless if it can’t be expressed in software in a sufficient timeframe. Merely building Puppet forced me to discard many convictions, and early rejects often became critical axioms undergirding the whole system. Of course, in the world of software, the compiler is only the first test. The real arbiter is your user, your customer. Once you’ve expressed your belief in a form someone can use, do they? I remember arguing for hours with a customer against a feature he requested, but the cold hard reality of his problem had me spending that night in my hotel room fixing it.

I am often asked if I miss programming. I do not.

What I miss is the laboratory it provided me, and the complete world that enveloped me, pressing in on me with its constraints, requirements, and complexities. I miss the hours I spent focused on one problem, and the complex systems needed to turn my ideas into a form usable by others.

I am thrilled and relieved to see that writing can be a new and even better laboratory for me. When I was programming full time, problems would haunt me, refusing to leave. I wore holes in my shoes walking back and forth between my keyboard and the local coffee shop, trying to line things up so they made sense. I’d scrunch up my face while drinking the coffee, drawing enqueries as to my wellbeing.

Writing is harder than that. The problems are bigger, and yet deeper inside, and harder to extract. I was never afraid of programming, but every idea I fail to write frightens me at least a little. On the far side, successfully expressing something is cathartic, a release, and it washes everything out with it.

It’s a better laboratory, because I have far more opinions about the real world than about the software world. Like those hypotheses that led to Puppet, I don’t know if they’re good. But I do know they’re different. I’ve bounced off reality enough times, asking for help from the crowd of onlookers and then getting back up, that I have a good sense of which of my beliefs are widely shared, and which are rare. For better or worse, little of what I believe, of what I think is important, is widely shared.

I’m excited by disagreement. Alignment is critical to execution, but diversity is needed for learning.

More than anything, I look forward to sharing my ideas, and as I did with Puppet, either finding them useful to other people, or having them cut to shreds to reveal new constraints, insights, opportunities. To do that successfully, though, writing is not enough: People must be able to read it.

Writing is no easier than coding, and in both, it’s ten times harder to write for others as for oneself.

One of my earliest optimizations in building Puppet was to prioritize my own productivity wherever possible. I explicitly chose to program in Ruby because I was faster there, even if it was slow and unpopular (Puppet was started before Rails was released). It took years for my programming style to reveal itself as an implicit personal optimization, highly effective for me but inscrutable to others.

My writing turns out to have a similarly mixed legacy.

All of the great shifts I initiated at Puppet began life as an essay, some extruded in a single sitting but more often sculpted over months and years. Once a hypothesis could defend itself, I then spent months and (more often) years translating it, turning it into something people could execute.

I’m proud of that work — how can I not be, when it helped build Puppet into what it is today?

But it’s fair to define good writing as something that doesn’t need a translator into its own tongue. By that measure, I’d failed.

Like a young programmer, I used to see people’s confusion as a sign of my genius and the value of my work. Now I look back with my designer’s eye and see it as a missed opportunity. We could have been there years faster if my beliefs had come with a better user experience. Kanies’s Razor is as applicable in prose as it is in code: Never attribute to genius that which can be adequately explained by incompetence.

I sit at the keyboard today as thrilled and scared as I was at the shiny benches of my science classes in college. Today I smell tea instead of banana oil and denatured ethanol, and I have no lab tech to stonewall me when I ask for easy answers, but the feeling of hope, of optimism, of a world to be discovered, understood, and fought through lifts me up just the same. I believe I can enjoy writing as much as I ever enjoyed programming, I can develop and test a wider range of hypotheses with a greater impact on those around me, and I can even learn get those ideas across to other people.

This, to me, is joy.

The Job of the Filesystem

It should do more so you can do less

Originally published at Hacker Noon

Apple just released iOS 10.3, which for the first time puts one of their production platforms on their new filesystem, APFS. I’m pretty happy that they are finally replacing such an aging, obsolete piece of core technology, but I’m nowhere near as excited about it as John Siracusa is. All APFS seems to do is finally meet the basic needs of a modern operating system, and not even all of those. It doesn’t come anywhere near doing what I care about most in the filesystem, which is owning metadata so applications don’t.

As anyone following the discussion of federal surveillance knows, metadata has become at least as important to our lives as our data. It’s not just the phone calls, it’s who you called, when, and for how long. It’s not just the phone, it’s which ones are your favorites and how they relate to each other. This metadata is as important to us personally as it is to the NSA, because it’s what brings simplicity, usefulness, and most importantly accessibility to the reams of information we create and rely on.

The reason I’m disappointed in APFS is that it missed the opportunity to promote metadata into something as important as the data, and as a result I’ve largely lost hope that computers will ever be as useful and open as they can be.

I’ve been trying for months to convert from Apple’s Photos to Adobe’s Lightroom for photo management, and the biggest barriers to doing so are metadata. It’s easy to get all of the photos — just drag the Masters folder into Lightroom. Oh, you organized your photos into albums? Yeah, that’s all gone. You had thousands of photos categorized as favorites so you could easily find the best? Oops, we ignore that.

Google Photos has the exact same problem. I can’t imagine how anyone who cares even a snit about photos could migrate to it, because there’s literally no way to do so that preserves any metadata at all. You get to keep the photos, but not how you organized them, and your only option is to rely on what they think matters to you.

Can you imagine switching email providers but losing all of the information about who the email is from or when it was sent? That’s as idiotic as what’s happening here.

If my filesystem owned this metadata, on the other hand, no conversion would be necessary. Any application could be written to read and write it directly, or I could trivially use any scripting language I wanted to do so. In fact, I could easily switch back and forth between different apps for different purposes, because they would not be able to lock me into their proprietary databases.

This shift is hard to understand, as we’re so used to thinking of applications and their metadata as somehow intertwined. For those in the programming world, there’s a clean analogy that helps to explain the horror of the modern filesystem:

For most of the history of software, applications have been written to directly access databases. They needed to understand the structure of tables and rows, and they had to write and manage their own queries for interacting with that data. Because of the complexity of duplicating this ability, applications tended to own their data entirely, and no other apps could get access.

We’ve recently instead seen a trend towards building very simple data services on top of databases, so that no app directly accesses them. This data service provides an API that understands how all of the data works, and also provides all of the key operations that can be performed on the data. This way, any application can access the data — for both reading and writing — without worrying that its use of the data is somehow incompatible with another consumer. You get the added benefit that any optimizations in the data service help every consumer, not just the one or two apps you remember to change.

Those data services are exactly what have enabled modern applications to scale to the level they do. The application developer can focus on their goals for the data, relying on the data service to provide consistency, portable operations, and everything else.

In the land of the operating system, though, we have no such luck. Everyone who talks to the filesystem gets about the thinnest interface imaginable: Get me a blob of data. Yes, there’s basic metadata (who owns it, when it was created, etc.), but none of it is or can be custom to the application, which makes it useless. Can you imagine how unpleasant it would be if we had to shoehorn both the subject of an email and the subject of a photo into the same keyword?

As a result, everyone turns that blob that the filesystem is trusted with into a database, and that’s where they put all of the metadata. Some even put the data there, even if it means huge database files and entirely non-portable systems. Really great app developers then go to the effort of building a full read and write API on top of this database that allows you to manage and port everything in the database. That’s enough work that most people skip it, though.

I would never have seen this missed opportunity in the filesystem if I hadn’t used BeOS. I went to Reed College, where Steve Jobs famously attended briefly (I made the unfortunate mistake of graduating, unlike him). This meant I was a Mac user all through school, which were the bad days of Quadras and MacOS 8 and 9. shudder I switched to BeOS because, well, I could, and it’s what really turned me into an OS junkie. There were many awesome things about it (many of which are now in OS X), but my favorite became how much responsibility the OS took for metadata. Applications became smaller, simpler, and in many cases, you realized your whole concept of an application was a way of organizing metadata, which meant you could rely on the OS entirely, and needed to write no code.

The greatest irony is that the author of Be’s awesome filesystem, Dominic Giampaolo, is now a lead engineer on APFS. Through the work of him and the rest of the team at Be, I came away with a clear idea of the value of my metadata, and especially the benefit of the operating system putting it on center stage.

So while I’m happy that my phone is no longer running the oldest, crappiest filesystem around, and I’m looking forward to the days when my computers aren’t either, I’m not excited. Until it was released, I could always dream that Apple saw the same future I did.

Now that the new filesystem is here, that hope is lost.

The Wrong Successes Kill Companies

Just because it’s working doesn’t make it right

Startups are in a constant life and death struggle, where a short succession of failures can destroy them completely, or a sudden string of successes can lead to growth and stardom. Exactly because of this constant risk of death, startups grasp at every flash of success, and their eventual failure can often be traced back to those successes they bet on, rather the roadblocks they hit.

This means what you decide to double down on is as important as the fires you decide to fight. This is true in any company — a specific form of this is covered in depth by Clayton Christensen in “Innovator’s Dilemma”, where successful companies over-solve their customers’ problems rather than finding additional customers. It’s especially true for startups, though, which are so risky that every potential customer, employee, investor, or partner can be the difference between making payroll and going bankrupt.

Steve Blank and Eric Reis have done a great job of teaching the world about the importance of quick learning and iterating until you get wins, but reality is more complicated. Say you’re in the middle of rapid product iteration and you get a rash of customers who sign up but are completely different from those you have been trying to attract. Is this awesome or horrifying?

How could new customers be such bad news, you ask? Easy: They could be the wrong customers. “Wrong” could mean many things. They could be from a very small market, such that success with them isn’t enough to build a scalable business; they could be unprofitable, in that they’ll be very high-cost to acquire and support, so every added customer loses you money over time rather than making it; and most commonly, they’re just not the customer your company strategy set out to find.

Eric Reis might say finding this kind of customer is the sign you need to pivot. That might be true. But it’s not automatically so. You were right enough to get this far, why give up so quickly on your definition of the perfect customer?

Because once you change your direction from focusing on the customer you want to customer you have — that is, once you start focusing on whatever seems to be working rather than your goals — you will quickly find yourself running a different company than you had planned.

This is one of the hardest problems for entrepreneurs: How do you decide when good news is leading to a better place, or a fatal compromise to your dream?

This came up constantly for me while running Puppet, in almost every part of my job. For instance, we did all of our high-growth hiring from Portland. Because of the small market and especially small tech sector, you have to be pragmatic about who you hire. You look up in 2 years, and you’ve got complete teams built off that first compromise hire. That first developer hire was a success, but changed your team’s direction. Now that that person has hired a team, or at least provided the template for the team, are you where you wanted to be, or completely off track?

You can argue that this isn’t a problem we would have had in the Bay Area, but not compromising when hiring is as pernicious a myth as true love. Even if you think someone is perfect, they’re still a real person, with opinions, behaviors, and habits that affect the destiny of your company, in good and bad ways. Again, the point here isn’t that you failed when you hired this person — the point is that the success you experienced changes your destiny in ways you can’t undo or predict.

That first customer started making feature requests and filing bugs, and two years later you’ve built something that can attract a lot more customers like them. Yay, or boo? There’s no right answer. I know one company that was almost destroyed by its biggest customer, and easily lost two years of roadmap progress focusing on them, but I know another company who built an amazing business by initially focusing on a couple of heavyweight customers.

When no decisions have been made, all life in front of you is opportunity. Choosing one opportunity inherently closes off others, and great decision makers know and accept this. If anything, sometimes a decision is great because of the opportunities it rejects, rather than those it selects. Running a startup is an accumulation of these bets, these selections and rejections. It’s hard to predict the consequences of even one of these big decisions, and it’s impossible to know what their legacy will be in a few years. You might end up exactly where you want… but you might be sowing the seeds of your downfall. That’s what makes the job hard.

The only tool I ever developed for managing this over the long term was to hold clearly to a specific set of goals, and to a specific strategy. When successes came along that didn’t fit our goals or strategy, we could decide to change them. But if we chose not to, then we essentially ignored it. It was a false positive. On the other hand, if you look up and a series of false positives starts to look like a trend you want to refocus on, then you must first rethink your goals and strategy, and only then switch your execution.

Or at least, that’s what I did. In truth, though, I don’t think I held the line enough. I think I was too willing to listen to people who were tactically great but didn’t buy into our strategy, and I was too willing to believe someone else’s expertise should take priority over my opinions. That doesn’t mean these were all mistakes, but it does make my time at Puppet easy to see through the lens of compromise and regret rather than the great success it really is.

In the end, when I look at how Puppet evolved, my sharpest pains come from compromises in strategy, and my brightest joys shine from a flawed execution in service of a pure vision.