I decided to finally give vibe coding a try. I’ve barely written any code since I hired developers at Puppet in like 2009. And I’ve been a staunch AI/LLM skeptic. But I figured I should at least be an educated skeptic.

After a false start, and a couple of months of periodic usage, I’ve come to some conclusions about it. The first one is the most important:

You should treat AI like an untrustworthy consultant.

Think of this scenario: You need help with your company’s core product. You have to bring in an outside expert, either just as another body, or more likely, because they have knowledge your team doesn’t. What do you do?

Give them commit access and let them work unsupervised? Of course not.

At the least, you have someone sit by their side, checking every line.

More likely, you don’t even let them touch the keyboard. After all, you want more than the help – you want your team trained up so they don’t need that help next time. The only way you’ll get that is if your team does the work, even if someone else is telling them what to do.

That’s how I consulted at Puppet: I show up, I walk you through all the work, and when I leave you have more than a functioning system; you actually know how to use it. Sure, it was faster and easier to do all the work myself. But no one ever learned anything then.

All the coding I’ve done with AI help is in Swift, using SwiftUI, to build iOS apps. I’ve never worked with anything like any of that – I’ve not used any of the specific tech (other than an iPhone as a user). I’ve never used a UI framework. I’ve never worked in statically typed languages. And I’ve barely ever worked in compiled languages. So, it seemed like a solid use case for getting some fast help.

My first try used Cursor, and let it edit everything.

After a few iterations, I had a bare-bones application. But… I felt like I was pushing around a bag full of bolts. There was definitely stuff in there. But I didn’t even know how to think about the changes I needed, because I didn’t understand enough.

So on the second iteration, I decided I would do all the typing: The AI does not get to touch the keyboard. When I started it was all gibberish, because I didn’t understand anything. But after only a session or two, I have a pretty good sense of how both the language and framework work. That’s about when I realized the second big thing:

AIs are crappy architects.

It kept giving me stupid advice. For instance, every time it encountered an error, it would just catch it and print some logs. Uhhh… that’s bad. It would encounter a small problem, and design a big stupid solution instead of doing a small rearchitecture. Because it can’t think, it couldn’t realize when it hit a design wall that needed rethinking.

After a while, I concluded that it wasn’t very good at the back end code – I have a lot of experience with modeling and data flow, and I kept finding dumb things it did. But I never found those dumb things in the area I have no experience: the UI.

But… then I thought for a bit. And I realized, duh, that’s probably just because I’m not good enough yet to recognize the dumb stuff it’s doing.

Coincidentally, I am now hitting a repetitive wall with Swift’s type checking. I keep having to break a view into smaller and smaller files so that it can compile fast enough. Turns out that’s the AI’s only trick for fixing this problem. But a small amount of research shows there are other options. In particular, I can instrument the compile and see what’s actually taking all the time, and focus on just rewriting that code to be more compiler-friendly. This is the kind of stuff an experienced programmer does without thinking, but a crappy consultant whose entire experience is based on trawling Stack Overflow probably never figures it out.

I did find one area where LLMs absolutely excel, and I’d never want to be without them:

AIs can find your syntax error 100x faster than you can.

They’ve been a useful tool in multiple areas, to my surprise. But this is the one space where they’ve been an honestly huge help: I know I’ve made a mistake somewhere and I just can’t track it down. I can spend ten minutes staring at my files and pulling my hair out, or get an answer back in thirty seconds.

There are whole categories of coding problems that look like this, and LLMs are damn good at nearly all of them. Where did I fail to log correctly? Where am I not handling an error appropriately? If I am updating this method name, which files do I have to change?

I’ve had about five to ten sessions of using Claude – just on the command line, no fancy tools, and no editing allowed. I have about enough experience with Swift and SwiftUI that the terms of the relationship have changed. I feel more like the senior engineer, and it is the junior developer I have working on a short term contract. I can pass it the stupid grunt work (rename this method through the whole system, fill out this boilerplate for a new view, figure out how this new library works).

But I absolutely can’t trust it to make any big decisions. And I have to check all of its work. (Even better, it won’t be offended when I do.)

After a few more sessions, I’ll probably start letting it edit files directly. But only for that kind of large scale, small change work. Once I build the error management framework, it can probably push it through the system (especially since I’ve sprinkled my code with comments when the error management was missing). But I’ll still walk through all the changes to ensure it actually makes sense.

Of course not. But the fact that people think I do says a lot.

Photo courtesy of Andre Hunter.

Seeking a round of funding is about the most miserable thing I’ve ever done. Truly. Fundraising was less pleasant and more demeaning than anything else I did at Puppet. But Clickety’s final (abandoned) round was uncomfortable in a new way.

Two different investors asked me the same question:

Why are you fundraising if you hate investors?

The question caught me flat-footed. Mostly because it’s such a stupid one.

I don’t love working with real estate agents. I feel like I’m being scammed. Even if I like my own agent, I usually don’t like the other one. I’m uncomfortable the whole time.

But in the US, it’s way harder to buy or sell a house if you don’t use an agent. And even if I went without, the other side of the party probably would hire one. So, I use a real estate agent. And I work with the agent on the other side at the same time. You want the house, you use the system.

And when I buy that house? I ask my banker for a loan. It’s not because I love bankers. It’s because I need help buying the house, and he’s in the business of helping people buy houses. Seems pretty straightforward. It has nothing to do with whether I like bankers, banks, or the mortgage financing system.

The legal system is similar. I actually do like a lot of lawyers. But… god, not all. And the way lawyers often work is stupid. I don’t actually think lawyers designed modern legal documents as a form of job security, but it sure looks like it sometimes.

But when I need to work with complex contracts, I hire a lawyer. It doesn’t matter whether I like lawyers or the US contract system; I have a job that demands legal help, so I go get it.

There’s a huge difference between all of them and venture capitalists, though: Bankers, real estate agents, and lawyers don’t demand that I act like I like and respect their industry. But VCs don’t just want me to start a great company. They want me to like and respect them for trying to make money off the work of me and my team.

Why was I fundraising from VCs?

To paraphrase Willie Sutton (maybe?), because they’re the ones with the money. If I want funding for my company, I need venture capitalists. What does it matter how I feel about the venture industry?

If you’re an entrepreneur today, there is no other source of capital. You can either bootstrap, or raise money from VCs. There are a few firms experimenting at the edges, like Calm, but they have a minuscule amount of money compared to the venture capital industry.

Yes, I could bootstrap. I’ve done it before. But it took four and a half years. I’m not as patient today as I was when I was 29. I also thought it made sense to start this company as a CEO and product manager first, rather than as a programmer. (In retrospect that was a mistake.) That made it impossible to bootstrap. I needed a team.

This question is just offensive, though. Its implication is “you should not raise money from investors unless you are willing to show respect and appreciation for the money they give you”.

Why? The world famously hates bankers and lawyers, yet continues to work with them. Why does this field get to demand our respect, when others don’t? Finance, especially, is just here for the money, and everyone – them included! – knows it. We just have to convince them we’ll help.

VCs are gatekeepers

Investors display their power by demanding your respect. They don’t invest in people who don’t show fealty to their image of themselves.

It’s how banking used to work: Some people got money, and some people didn’t. Fundamentals had nothing to do with it. You had to be in the right network, have the right skin color, the right class. Eventually bankers realized they made less money when they only loaned it to their friends. (And the US government forced them to back off their discrimination a bit.)

Most investors today will tell you to just “play the game”. This is what they mean: Participate in our discriminatory process, and show us proper respect. This is why you usually need a warm introduction to even be allowed to pitch them.

It’s a broken system that leaves broken people in its wake.

But I raised money within it, many times, because that’s where the money is.

Hate the Game, not the Player

No, I don’t hate investors.

But I do hate the world of venture capital. It is fundamentally flawed. It incentivizes behavior I can’t stand, and quashes behavior I find respectable and moral.

For what it’s worth, I also hate the larger finance industry. It’s not like venture is some rare target for my ire. There’s a reason I’ve never considered working in finance. (Well. There are several.)

Venture is an amazing engine for creation and invention. But it mostly invents stuff I wish didn’t exist. And it does not seem to be able to solve the problems that matter most to me or the larger world.

People appear to hear my dislike for their industry and think I hate them, personally. I can’t do much about that. I respect and like some investors. I dislike some others. But I generally have no particular feelings about a given individual.

That being said…

I don’t tend to respect investors.

Being a venture capitalist doesn’t automatically disqualify you from garnering respect. But it also does not automatically deserve it.

In the 1980s, finance was at its peak. People made ungodly amounts of money ruining the lives of thousands and thousands of people. And they were held up as heroes of business. We’ve largely learned that stripping financial assets is maybe not something we should be proud of. These people still get rich, but we have learned not to lionize them.

Is the modern venture investor as heartless and shameless as a PE investor from 40 years ago? Generally, no. (Although there are definitely exceptions.) But like those 80s wolves of Wall Street, VCs have found a money-making edge, and they’re ruthlessly exploiting it.

I’m just not that impressed.

I can see why someone would read that disregard and disrespect as hate. Especially given the power dynamic: I’m asking them for money, yet I’m not showing “proper respect”.

My banker didn’t demand I “play the game” when I applied for a mortgage. He just needed evidence that I could afford the house I was buying, and that it was worth what I was paying.

Being autistic means I’ll never be able to “play the game”. It’s literally constructed so only the in-crowd can join. I can mask for a while. But it takes hundreds of meetings to raise a round. Most people in the meetings look the same, dress the same, went to the same schools, and ask the same questions, yet think they’re special geniuses. And most of them give the same answer (“no”). It becomes hard to hold a facade.

It’s not a choice, or a lack of skill. It’s a hardwired neurological limitation. You might as well ask me to be taller, or have a lower voice.

For better or worse, I’m not sure it matters now. My personal limitations are likely to prevent me from trying to raise money again. But I hit those walls in large part because of how harrowing fundraising is.

Will I do it again?

My experience at Clickety tells me I’m unlikely to run another venture backed startup.

It looks like I’m already a bit of a pariah, which might explain part of why it was so hard to raise. (Not that I don’t deserve some of that reputation.) It’s not about to become easier for me. The older I get, the less I can handle gatekeepers. And I was already crap at tolerating them when I was younger.

My health — both physical and mental — would need to significantly improve. Running a company is stressful enough. Raising money was too much.

I won’t rule it out. I know my future is going to look different from my past. I have a lot of healing to do.

But I still believe in the power of software to make people’s lives better. And venture capital is a fantastic source of acceleration. I hope to continue to work with founders, and intrinsically that means working with investors, too, sometimes.

I also love solving problems. I hope to help others do it. But I won’t rule out trying to solve some problems on my own.

And maybe one of those solutions will be so good they can’t ignore me.

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.

Automation is not to blame for all the job destruction and wage stagnation. But you can still do great harm if you build it for the wrong reasons.

We’re told that automation is destroying jobs, that technology is replacing people, making them dumber, less capable. These are lies, with just enough truth to confuse us. You can have my robot washing machines when you pry them from my cold, wet hands.

I’m not some Pollyanna, thinking tech is only ever positive. Its potential for abuse and hurt is visible across the centuries, and especially so today. But I’m more optimistic about the upside than I am pessimistic about the down, and I’m uninterested in scaremongering screeds against it.

And yet. Technology and automation are not forces of nature. They’re made by people. By you. And the choices you make help to determine just how much good or bad they do. Even with the best of intentions, you might be doing great harm. And if you don’t have good intentions at all, or you don’t think ethics are part of your job, then you are probably downright dangerous.

I’m here to convince you that you have a role in deciding the future impact of the technology you build, and to provide you - especially you founders, tool builders, automators - some tactical advice on how to have the best impact, and avoid the dark timeline.

As I was building Puppet, explaining that I was developing automation for operations teams, execs and sales people would think they got it: “Oh, right, so you can fire SysAdmins!”

Ah. No.

When prospective customers asked for this, I offered them a choice: You can keep the same service quality and cut costs, or you can keep the same cost, and increase service quality. For sysadmins, that meant shipping better software, more often.

Their response? “Wait, that’s an option?!” They only knew how to think about their jobs in terms of cost. I had to teach them to think about quality. This is what the whole DevOps movement is about, and the years of DevOps reports Puppet has published: Helping people understand what quality means, so they can stop focusing on cost.

And those few people who said they still wanted to reduce cost, not increase quality? I didn’t sell to them.

Not because they were wrong. There were real pressures on them to reduce costs, but I was only interested in helping people who wanted to make things better, not cheaper. My mission was completely at odds with their needs, so I was unwilling to build a product to help them fire their people.

This might have been stupid. There are good reasons why a CEO might naturally build what these people want. The hardest thing in the world to find for a new product is a motivated prospective customer who has spending authority, and here they are, asking for help. The signal is really clear:

You do a bunch of user interviews, they all tell the same story of needing to reduce cost, and in every case, budgets are shrinking and the major cost is labor. Great, I’ll build some automation, and it will increase productivity by X%, thus enabling a downsizing. The customer is happy, I get rich, and, ah, well, if you get fired you probably deserved it for not investing enough in your career. (I heard this last bit from a founder recently. Yay.)

This reasoning is common, but that does not make it right. (Or ethical.) And you’ll probably fail because of your bad decisions.

Let’s start with the fact that you have not done any user interviews. None.

The only users in this story are the ones you’re trying to fire. Executives aren’t users. Managers aren’t users. It seems like you should listen to them, because they have a lot of opinions, and they’re the ones writing checks, but nope.

This has a couple of consequences. First, you don’t understand the problem if you only talk to buyers, because they only see it at a distance. You have to talk to people on the ground who are doing the work. Be careful when talking to them, though, because you might start to empathize with them, which makes it harder to help fire them.

Even if you do manage to understand the problem, your product will still likely fail. As much as buyers center themselves in the story of adopting new technology, they’re largely irrelevant. Only the people at the front line really matter. I mean, it’s in the word: Users use the software. Someone, somewhere, has to say: Yes, I will use this thing you’ve built, every day, to do my job.

If you’ve only talked to buyers, you have built a buyer-centric product, rather than a user-centric one. Sure, maybe you got lucky and were able to build something pretty good while only talking to managers and disrespecting the workers so much that you think they’re worthless. But I doubt it. You’ll experience the classic enterprise problem of closing a deal but getting no adoption, and thus not getting that crucial renewal. Given that you usually don’t actually make money from a customer until the second or third year of the relationship… not so great.

Users aren’t stupid. Yes, I know we like to act like they are. But they aren’t. If your value promise is, “Adopt my software and 10% of your team is going to get fired,” people know. And they won’t use it, unless they really don’t have a choice. Some of that is selfish - no one wants to help team members get fired, and even if they’re safe today, they know they’re on the block for the next round of cuts. But it’s just as likely to be pragmatic. You’re so focused on downsizing the team that you never stopped to ask what they need. Why would someone adopt something that didn’t solve their problems?

What’s that you say? You ignored their problems because you were focused on the boss’s needs? This is why no one uses your software. Your disrespect resulted in a crappy product.

Call me a communist, but I think most people are skilled at their jobs. I am confident that I can find a learned skill in even the “low skill” labor. I absolutely know I can in most areas people are building software.

I was talking to a friend in a data science group in a software company recently, and he was noting how hard it was to sell their software. He said every prospective buyer had two experts in the basement who they could never seem to get past. So I asked him, are you trying to help those experts, or replace them?

He said, well, our software is so great, they aren’t really necessary any more.

There’s your problem. You’re promising to fire the only two people in the whole company who understand what you do. So I challenged him: What would your product, your company look like if you saw your job as making them do better work faster, rather than eliminating the need for them?

It’s a big shift. But it’s an important one. In his case, I think it’s necessary to reduce the friction in his sales process, and even more importantly, to keep those experts in house and making their employers smarter, rather than moving them on and losing years of experience and knowledge.

The stakes can get much bigger than downsizing. In his new book, Ruined By Design, Mike Monteiro has made it clear that designers and developers make ethical choices every day. Just because Uber’s and Instacart’s business model requires that they mistreat and underpay workers doesn’t mean you need to help them. While I don’t think technology is at fault for most job losses, there absolutely are people out there who see the opportunity to make money by destroying industries.

This is not fundamentally different than the strip mining that happened to corporations in the 1980s, except back then they were making money by removing profit margin in companies and now they’re making money by removing “profit” margin in people’s lives. Jeff Bezos of Amazon has famously said your margin is his opportunity, and his warehouse workers’ experiences makes clear that he thinks that’s as true of his employees as it is of his suppliers and competitors.

Just because they’re going to get rich ruining people’s lives doesn’t mean you have to help.

I think your job matters. I think software can and should have a hugely positive impact on the world; not that one project can by itself make the world better, but that every person could have their life improved by the right product or service.

But that will only happen if we truthfully, honestly try to help our users.

When, instead, we focus too much on margin, on disruption, on buyers, on business problems…. we become the problem.

To really win, you have to seem strange to your true peers, not just the world at large.

Photo by Elias Castillo

Look, I have to say it: You’re weird. Even if I don’t know you, I’m confident: Somewhere, maybe lurking deep inside, something about you is just not right. I don’t know what, specifically. For all I know, you might be one of those weirdos whose particular strangeness is just how authentically normal you are. shudder.

This might be insulting to you, calling you weird. It happens a lot: I think I’m complimenting someone and they get all huffy. Conversely, people are often afraid I’ll be hurt when they shyly let me know that I, ah, don’t really fit. Don’t worry; you’d need to know me a lot better to successfully offend me.

Society is not a huge fan of weirdness - I mean, the definition is pretty much, “does not fit into society” - and it trains you away from it. We’re social animals, so you probably do what you can to conceal, or at least downplay, anything different. It makes sense. It’s a basic survival mechanism.

I know I do it. I can’t hide everything - some stuff just can’t be covered up - but I can usually skate through a conversation or two before people back up a step and give me that funny, sometimes frightened, look. Being on the west coast helps; I’m a little less weird here than I was in the south. It probably also helps that I cut my mohawk, and the spiked leather jacket and knee high boots stay in the closet now.

I’ve written a bit about my struggles to balance authenticity and fitting in. I think it’s important to call out it out, because those who experience this struggle rarely have the luxury of admitting it. I’m lucky enough in multiple ways that I can be up front about it now. But resolving this conflict matters for more than psychological reasons. Our own goals usually require that we learn to embrace our weird. Not just grab on to it, actually, but really live in it. Inhabit it.

That weirdness is how we win.

This is easiest to show in investing. We have a natural tendency to do what is proven to work, but that is only assured of getting “market” - in other words, mediocre - returns. If you study the best investors, they’re all doing something that seems weird. Or at least, it did when they started. The first people who paid to string fiber from NYC to Chicago to make trades a couple milliseconds faster were considered pretty weird, but they knew the truth: Normal behavior gets normal returns, anything more requires true weirdness. (Well, or fraud. There’s always that if you’re afraid to stand out.)

It’s the same way in life. You can’t say you want something different, you want to be special, but then follow the same path as everyone else. “I’ll embrace what makes me special just as soon as I get financial security via a well-trodden path to success.” Oh yeah. We definitely believe that.

There’s a nice sleight of hand you can do, where you can say you’re doing something different, but really you’re a rare form of normal. The first few doctors and nurses were really weird. Those who recommended you wash hands before surgery were literally laughed at, considered dangerous crackpots1. But now? Most people become a doctor in pretty much the same way. Being a doctor is normal now, even if it’s not common. That’s probably good.

But what if your job is innovation? What if you’re whole story revolves around being different? Can you still follow a common path?

Because that’s what too many entrepreneurs today are doing: Trying to succeed at something different, by doing what everyone else is doing.

I mean. Not literally everyone else. But close enough.

It starts out innocently enough. There aren’t many people starting tech companies at first, and boy howdy are they weird. Someone makes a ton of money, all their weirdness gets written up - “hah hah, see how he has no sense of humanity but is somehow still a billionaire?” - and now we’ve got something to compare to. Hmm. Well. We can’t consistently duplicate Jobs, Gates, Packard. But if we tell enough stories enough times, we find some kind of average path through them. Ah! Enlightenment!

Now that we know what “most” people do, we can try it too. I mean, we have no idea if the stories about those people have anything to do with why they succeeded, but why let that get in our way? Conveniently, every time it works we’ll loudly claim success, but silently skip publishing any failures. Just ask Jim Collins: He got rich by cherry-picking data in Good to Great to “prove” there was a common path to business success. It turned out to have as much predictive value as an astrological reading, and is just business garbage dressed up in intellectual rigor, but that doesn’t seem to have hurt him.

The business world keeps buying his books. They need to believe there’s a common path that anyone can travel to victory. Otherwise, what would they sell? What would they buy?

Obviously this doesn’t work. There is no standard playbook to winning an arms race. Once there’s even a sniff of one, people copy it until it doesn’t work any more. This is pretty much the definition of the efficient market hypothesis: There’s no standard way to get above-average results. Once Warren Buffet got sufficiently rich as a value investor, so many people adopted the strategy that, well, it’s hard to make money that way. Not impossible, but nowhere near as easy as it was fifty years ago.

Of course, you can go too far in being weird. There has to be something in your business, in your strategy, that makes you different enough that you just might win. But adding a lot of other strangeness for no good reason worsens already long odds. The fact that Steve Jobs did so well even though he was a raging asshole, even to his best friends, made his success just that much less likely. Most people are a bit more like Gates and Bezos: Utterly ruthless in business, and caring not a whit for the downsides of their success, but perfectly capable of coming off as a decent person whenever required.

I’m rarely accused of being a world-class jerk, but I don’t pass the smell test as normal for very long. Jim Collins might say maybe if I were more pathological I would have succeeded more. With Jobs and Musk as examples, it seems reasonable, right? In truth, it’s just as reasonable that I would have done better by dropping out of Reed College, like Jobs did, rather than foolishly graduating from it. Think it’s too late to retroactively quit early?

Yes, you have to learn to love your weird, but it shouldn’t be arbitrary. You can’t realistically say that you’re going to rock it in business because you’re addicted to collecting gum wrappers from the 50s. I agree that that’s weird, but is it usefully so? Being a jerk is weird, and bad, but it’s not helpfully so. And really, dropping out of college isn’t that weird for someone in Jobs’s financial position at the time. It’s only if you have a bunch of money that it seems so.

I recommend you take the time, think deeply on what opinions you hold that no one else seems to, what beliefs you have that constantly surprise you by their lack in others. What do you find easy that others find impossible? What’s natural to you, but somewhere between confounding and an abomination to those who notice you doing it?

Those things aren’t all good. And in many cases, you’ll need to spend your entire professional life managing their downsides, like I have. But somewhere in that list is what sets you apart, what gives you the opportunity to truly stand out. They’re the ground you need to build your future on.

Unless you just want to be normal. In that case, I don’t think I can help you.

1. This is an amazing example of sexism. The doctor’s wards had three times the fatality rates of the midwife wards, but of course, they were doing nothing wrong at all. ↩