There is a new movement around tools for managing your calendar. My favorite is Reclaim, but there are many others. They provide help running meetings, rearranging them, and avoiding them.
It’s great that these tools exist. The calendar is the least improved area in the average office worker’s life in the last few decades. My particular bugaboo is that calendar apps don’t know that you exist as a physical person, so they are perfectly willing to let you schedule two in-person events five minutes and 3000 miles apart. Any other kind of application would see that as a catastrophically brain-dead bug, but somehow the tools we use to arrange our lives don’t.
But… Something always struck me as off about these new tools. I didn’t want to use any of them. I’m a tool junkie, so this is pretty weird. Even Reclaim took me a while to understand and fit into my life. It was obvious these tools weren’t for me, but why not? Who were they for?
They’re for front-line workers: Developers, accountants, SREs. I used to be one of those. I’ve certainly been yelled at enough by them for putting meetings on their calendars.
But I’m not one today. I haven’t been in at least a decade.
My employees at Puppet used to say they hated meetings (I’m sure they still do, they just don’t work for me any more). I would tell them: Replace “meeting” with “collaborating with my team-mates” and say that again, eh?
So yeah, I have a different perspective on meetings.
Not that I think they’re all awesome. But for me — and most other leaders and managers — meetings are how we do our job. The life of a manager is built around communication. Much of it can be unscheduled, and ideally asynchronous. But a lot of it needs to be direct, synchronous, interactive.
That interactive time is much less efficient than, say, email, which means managers have to schedule their time carefully to ensure they get everything done. And of course, employees hate it when a manager shows up at their desk unannounced and asks for time. They want that meeting scheduled, too.
So a manager’s day is built around meetings, and there is a new crop of tools to help with them. What’s not to love?
Well. The tools are built by and for people who hate meetings, and often who aren’t very good at them. Instead, I want tools for people whose job is built around meetings, and who know they must be excellent at them.
Managers do need help. Not nearly enough of them are actually good at the mechanical parts of their jobs, including managing meetings. But these tools are mostly about avoiding or constraining them. They’re for the people asked to join, not for the ones calling them or running them.
I hope these tools do well. I want there to be a mature market of great tools in this space.
But even more so, I hope to see a parallel mature market for tools to help make better meetings. The average employee suffers from all the meetings they have. If managers were better, there would be fewer meetings, and the ones remaining would be better.
Why and how my team built board reports instead of PowerPoint decks. Fifty pages, less work than slides, and more valuable.Image courtesy of Drew Beamer.
Board meetings are a critical time of communication and reflection for a company. You have to share enough information that the people in the room can make existential decisions about the business. Yet most CEOs I know share only slides (the “board deck”) with their board.
This is a huge mistake.
People who worked for me at Puppet claimed I hate PowerPoint or Keynote. Nope. I use them myself when presenting on stage in front of a large crowd. But they are a horrible choice for communicating without a talk track, and are incapable of conveying large amounts of information, or anything of detail.
Don’t trust me? Ok, how about Edward Tufte , The Godfather of information design, who partially blamed them for the Columbia space shuttle explosion:
These [NASA] review boards examined what is probably the best evidence available on PP for technical work: hundreds of PP decks from a high-IQ government agency thoroughly practiced in PP. Both review boards concluded that (1) PowerPoint is an inappropriate tool for engineering reports, presentations, documentation and (2) the technical report is superior to PP. Matched up against alternative tools, PowerPoint loses.
What’s that you say? Running your business is easier than shooting rockets into space, so you are fine dumbing down your communication? You’re not in great company.
Bezos revealed that “narrative structure” is more effective than PowerPoint. According to Bezos, new executives are in for a culture shock in their first Amazon meetings. Instead of reading bullet points on a PowerPoint slide, everyone sits silently for about 30 minutes to read a “six-page memo that’s narratively structured with real sentences, topic sentences, verbs, and nouns.”
There’s a much better option right in front of you.
For most of my time running Puppet, we prepared a board memo: A text document written in normal English, with supporting images and charts. It averaged between 35 and 55 pages in length.
It worked great.
It took less time to prepare, and conveyed the state of our company more effectively. I recently shared my last board report, from 2016, with a friend, and he protested, “This is an SEC filing, not a board report!”
I’m not sure if our process is a fit for you, but hopefully it will at least inspire you to find a better solution than slides.
I used to be like you. Well. I never walked through slides in the meeting. I always drove a short (3ish items) agenda. My goal was discussion, not presentation. But I did start out using a deck.
I still cringe a little at the thought. But one of my startup principles is “Innovate only when necessary.” Your business requires a certain amount of breaking new ground. But don’t add risk by doing something unnecessarily new. If I avoided everything I thought was dumb I’d never get anything done.
Everyone else did board decks. My team was used to them. 🤷♂️ Sure, we’ll give them a try.
I hated it.
We spent too much time, on the wrong work, and did a poor job in the end.
Wow. The team spent so much time on fonts. And arranging images. What, exactly, is this adding to the board meeting? I understand: An ugly deck makes us look bad. But it seemed like we were spending a third of our time prettifying something instead of actually communicating.
There’s a good reason it was so hard to make them attractive: We had a ton of information to convey. We had to include detailed information about sales, marketing, engineering, and operations. The reader needed to quickly gain a sense of what was working, what was not, and what the vectors were around the company. No amount of picking fonts and rearranging images could deliver that understanding with PowerPoint.
So one quarter we ran an experiment. It was early on, only a year or two after our first round.
I gave each member of my team a choice: You can produce slides, or prose (i.e., plain text, using full sentences and paragraphs). Unsurprisingly, sales and marketing picked slides, and engineering and services picked prose.
What a stark difference.
The prose was done faster, communicated more, and just felt so much better.
Experiment over, prose won, we switched.
But how?
I don’t remember exactly how the process evolved. I do remember where we ended up, six years into using producing what we called board reports.
We did all the writing in Google Docs. We could all work at once and not step on each other’s toes.
I would build a skeleton of the report: Write out each section heading (“Summary”, “OKRs”, “Product”, “Marketing”, “Sales”). Then I’d use a comment to assign each section to the relevant executive. They’d either produce the text themselves, or do so in partnership with their team. Sales, marketing, and finance would include a lot of charts and graphs; product tended to stick to prose with a couple of diagrams or screen shots.
As people filled out the document, I played a few roles.
I spent most of my time assessing when someone was done. I’d read through people’s work and mark something that was insufficient, unclear, or missing with a comment in Google Docs. These are easy to spot even when scrolling through a fifty page document. As people worked, they marked their progress as done or ready to review. A completed section was easy to recognize: All comments and suggestions were resolved.
In this way, I could scan a large document and instantly see where work remained to be done.
My second job was overcoming a shortcoming in Google Docs. Or maybe a lack of training of office workers. Docs has built-in headings, and if you use them, your document is visually consistent, and auto-generates a table of contents. However, most people who worked for me never used the headings. They’d make a headline bold and increase the font size. So I had to go through the entire document and correct the markup. This was probably a quarter of my time.
By the end, I delegated this to a senior copy-editor who we trusted to see the entire document in process.
My last major role, and the only one that resembled the work of a CEO instead of an editor, was to ensure we were telling a single, coherent story. I’d write the summary to set the key messages. Then as I assessed everyone’s work, I pointed out inconsistencies or gaps. Most of this simple editing: Ensure all of the text used the same voice (first person plural, usually). It involved plenty of strategic work, though: tying company goals to team performance, ensuring the whole story was told, and asking everyone to cover the ‘why’, not just what happened.
You can guess this process triggered a few tense side conversations as I dragged information to light.
That, in the end, is the real point of the board report: Make sure we all understand the true state of the business. The writing was more important than the reading. It was on me to ensure we did the real work, rather than just packing it with information without saying anything.
I usually spent about four hours on it. Again, on a fifty five page report. My team each spent 1-3 hours. I did have the odd executive here or there or spend more like four or five hours on their part. We also never invested enough in automated reporting, so I’m confident some parts of the org had to work harder than I’d like to admit to generate their charts.
We targeted completion at least a couple of days before the board meeting. I’d share it with the board as a PDF. A couple of times I tried sharing it as a Google Doc (copied, so they can’t see the edit history), in hopes they would ask questions that could drive the agenda. It never got much engagement so I stopped.
Without a board deck, what did we actually talk about? I mean, without slides driving every minute, don’t you lose track?
No way. I ran a tight ship. But we measured time in half hours and big topics, not individual clicks.
My board meetings were usually three hours long. I’d spend an hour with just the board discussing high level status of the business and team. Then we’d take an hour and a half to cover our agenda, usually with portions of my team in the room. Then we’d spend half an hour at the end again just with the board, discussing what we learned and what we expected to do about it. This is when we also assessed individual executive performance. By the end of my tenure we also had a few minutes set aside for just the board, with me absent.
This process created space for deep conversation in the meetings. Everyone who read the report (which was, well, nearly everyone) was caught up on the business. They were fully prepared to discuss the three topics. And we had no structured flipping of slides to get in the way of discussion.
After the meeting, I edited the report as needed then sent it to the whole company.
Usually this involved removing just a line or two. Sometimes it was larger surgery, and others no changes at all. Mostly I cut out discussion of personnel changes, or removed sentences that required more sensitive, political phrasing than I practiced in these reports.
The end of this cycle ensured everyone involved in the company was up to date on, well, everything. Goals, status, progress, weaknesses, strengths.
I don’t know if everyone should use this process. I know many people were raised by American business to think slides are the best form of communicating. That’s a hard habit to break. I won’t even judge you if you use slides during the meeting to display the agenda and schedule, and maybe key images.
Slides are perfect if you want to tightly control the message, and not leave much room for hard questions.
But if your goal is to do real work in board meetings, skip the deck and write a report.
A single drink perfectly captures the weirdness of raising money for the first time.Photo courtesy of Dylan de Jonge
I found myself at a hotel with some friends. I was visiting Portland for a conference. Puppet’s first investment round – and mine! – was closing. The money was being deposited.
Have you seen a David Mamet movie, like The Spanish Prisoner? They’re fantastic. But eerie. Disquieting. They build up a story, brick by brick. Then they yank a few bricks away, exposing the whole story as a lie. Only a hollow truth remains, unrelated to your built up belief. It makes you question everything.
I’m waiting for the closing in this hotel, and I order a Macallan 18 to celebrate. This was back when it was only expensive, not egregious. I lift the glass, and I think:
The money is being deposited into my bank.
I think it’s a real bank.
I mean, they had, like, a website. And websites are pretty hard to… wait a minute.
Who introduced me to the bank?
The investors introduced me. They specifically wanted me to work with this bank. They’re the ones giving me the money. They wouldn’t say they’re giving me the money then give it to someone else. That’s a silly kind of fraud. I just have to trust them.
I sit there. Sipping my whiskey.
I think it’s a real bank.
I think I’m getting $2.25 million.
I had never seen a bank account with that many zeroes - and I still may not at that point! I have no idea what to do.
So I sit there. Savoring that delicious, delicious whiskey.
I didn’t mean to raise money. I was just focused on running the company. We had bootstrapped for almost four and a half years. I figured we were going it alone.
I had talked to people in the past about raising money. It was like Groucho Marx’s joke about clubs: I wouldn’t take money from the investors willing to give it to me. “Wow, I would love them as an investor,” you get nothing. Or, “I would happily give you money and ruin your life.” Hmm. Not really the deal I’m looking for.
One day at an event, an investor tracked me down. He said, I’d like to invest in your company. I said, That doesn’t sound right. A lot of investors say, We should talk. He said: We should talk on Monday. That specificity made all the difference.
He made a very confusing offer: We would like to write a $1.75 million check into a $2 million round. I said, how can you be that bad at math and work in finance. He said, Go find other, rich people that you know to give you the rest of the money. I said, you are, literally, the only rich person I know. He said, I just joined this firm. I am not rich. Then we’re stuck, I said.
I lived in Nashville at the time. There are a bunch of rich people there. But they’re all musicians. They don’t do technology. We most emphatically did not hang out. We weren’t going to fill this round through my network.
Eventually, by connecting me to their network of rich people, I was able to raise $2.25 million. Mostly through luck not skill. I didn’t build a deck. I didn’t run a formal process. I didn’t pitch multiple investors to get competitive term sheets. I pretty much did the exact opposite of the play book. The investor who filled out the round turned me down at first, but I heard his wife persuaded him. I don’t know if she liked me or was cursing him.
Once all of the investors are in place, you wait.
The things you learn in your first round.
Closing takes about thirty days. Five rounds later, I have no idea why. It takes thirty days, and it costs $30,000. One of the terms in the term sheet you get from your investors states that you pay for closing. “We’re going to give you this money, and then you’re going to give some of it to the lawyers.” Investors cap the fees, and the lawyers coincidentally hit that exact number every time.
I honestly don’t know what the lawyers do at closing. The documents are massively long, but they’re pretty much the same. At a late-stage company, I can understand: There is diligence to do (although not by the lawyers), financial data to look through (done by analysts, not lawyers), customers to talk to (by the investors, not the lawyers). At an early stage, though, there just isn’t much information. I don’t know what they do.
But it takes thirty days. And costs thirty grand. Says so on the term sheet.
So you wait.
But when that waiting stopped, boy howdy did things move.
The money did get deposited. It was a real bank after all.
Within a month I’d moved from Nashville to Portland. Within two months, I had my next three employees. And within six months I had a team of ten.
Raising money set us off like a rocket. Bootstrapping for more than four years provided a fantastic foundation for quick growth.
Looking back, I’m glad we raised money. I only wish we had done it earlier.
You can either be a good example or a horrible warning. When it comes to enterprise sales, I had two horrible warnings before I started Puppet.
In 2000, I worked at Bluestar, a business DSL startup in Nashville. Pretty much everything that can go wrong with a startup did with this one: Founder was pushed out the week I started (I swear it wasn’t my fault), they raised too much money ($450m) and then spent it badly (e.g., on hardware that didn’t work and on salespeople that didn’t sell), they brought in a big business CEO who had no idea how to run a growth company, and then the regulatory framework shifted to highly advantage monopolies again so they all went broke. But in the meantime, I got to learn a lot, both about the problems that eventually resulted in my starting Puppet, and also about what does and doesn’t work in business.
At one point, the company decided to buy a new product. I honestly can’t remember what it was for. Something related to asset tracking? Or maybe some kind of operational monitoring software?
I don’t know. I just know I shifted from being a sysadmin to responsible for making it work. I wasn’t part of the team that decided whether to buy something, and if so, which one to buy, I was just designated to put their decisions into action. In the months I worked on it, I don’t think we ever even got it installed anywhere except on a test server, and at some point we just, ah, decided we didn’t need it any more. The project went away, so I returned to my old job. The executive who had made this horrible decision had the gall to say my moving back to my old role was a strike against me, and it would reflect on my tenure at the company. No worries, he was gone the next month.
This wasn’t just a software problem. While the company was slowly dying, they had an argument with EMC over a storage array they never should have purchased. A million dollars of hardware sat in a receiving warehouse for almost a year, because we would not accept it, and EMC would not take it back.
The second warning was during my brief stint at Bladelogic. I worked there for less than six months, but I learned a lot. Again, mostly what not to do. I was ostensibly a product manager, but in practice they just wanted me to maintain their lab and maybe write some justifications for how their product worked. Certainly they did not want to listen to me. My most memorable experience is being in an all-dev-team meeting when the most senior engineer said something like, “What does it matter what the customer thinks? They already bought the product.” Astoundingly, the CTO did not fire him on the spot, and instead just moved on, ignoring the comment entirely.
It was clear Bladelogic’s business model enabled them to just not care what their customers thought. Only_prospects_ mattered. Once the deal was closed, meh, they got paid, no biggie. You literally could not upgrade their software without losing all of your data - you know, the stuff you’re using to build and deploy your whole infrastructure - and doing any real work with the system required that you do everything twice, once to deploy and the second time to update. But you’d never discover that unless you actually used the software, which would be long after their salespeople left, so who cares? Not them.
You can maybe see why I lasted less than six months. It didn’t help that I was commuting between Boston and Nashville, and I’d managed to rent an apartment at the center of a cold vortex in Boston where my roommate collected Grateful Dead grape juice.
So when I started Puppet, I didn’t know much, but I at least had some anti-patterns. I knew we had to care more about our customers successfully using the product than we did about closing the initial deal, and that selling to people who would not use the software was a bad idea.
It turns out, that’s not quite sufficient to develop an effective sales strategy. Who knew?
I was lucky enough to hire the best sales leader in Oregon, who was not only incredibly skilled and experienced, he was also used to entrepreneurs and found me relatively sane compared to bosses he’d had in the past. Where a bunch of our engineers complained every time I opened my mouth, this guy quietly soldiered on. That made our years-long argument much easier to manage.
Early on, I didn’t know enough to break down what I wanted and what I didn’t, or how to talk about the individual behaviors, so I just wrapped up everything I hated and called it “enterprise sales”. We weren’t doing that. Ironically, our sales leader agreed with most of my concerns, so it wasn’t a real fight in the normal sense, but there were multiple areas he was convinced we needed to change, and it’s hard to do that when your ignorant CEO just puts up a ward against the evil eye and changes the subject.
Within a couple of years, he wouldn’t even say the word ’enterprise’, because I would jump down his throat, proverbially speaking.
In the first few years of building Puppet, I tended to focus on preventing sales from skewing our product plans. I wanted to be sure we built products to be used, not sold, and I didn’t trust myself or the team to be able to tell the difference. I think this was basically right, but today, I would know that you should treat ideas from sales like you treat those from customers:
Always listen to what customers tell you, but never do what they say.
The sales team has a limited lens into the product world. They are smart and highly educated about your customer, but that doesn’t automatically translate into good solutions.
This is a general risk at any company with sales teams, but you have an even more pernicious variant with enterprise sales teams: Being confused on who your customer is.
Are you building the product for the person who buys it, or the one who uses it?
Remember back to that product I tried to set up at Bluestar. It was purchased to solve a business problem, and the person who decided to buy it did so based on discussions with sales and, probably, looking very closely at a grid of check marks comparing it to its competitors.1 Actually using it was someone else’s problem.
In fact, I was not going to be the user either - I was supposed to be its administrator. Some other team (support or installation, probably) was going to actually use it. So they were even further from the buying decision.
If you’re selling to the enterprise, getting a deal done requires that you convince the buyer that your product is a winner. That makes them the most important person at the customer. Now, a quality company would also involve users, administrators, and many others in a buying decision, but in the end, buyer decides. Two or three decades ago, these decisions were mostly made on the golf course, so schmoozing was the most important feature. Today, it’s a lot less corrupt, but not a whole lot more functional.
This brings us to the other problem in this separation between user and buyer: Enterprise sales is a team sale, not selling to one user. Suddenly you succeed based on your ability to manage the interpersonal relationships of warring sub-teams at your customer, instead of the strengths of your product. I distinctly remember a dinner with tens of customer employees, and there was almost a flashing DMZ between two teams, who had differing opinions on whether our solutions was the right one. Salesperson quality and experience begin to matter more than anything else, because you’re basically managing internal politics to get a deal done.
Where did the focus on our product go? How do we stay focused on building something our users love?
We don’t, really. It’s hard to sustain an effective a feedback loop that includes sales if they’re focused more on people and politics than products. Not impossible. But hard.
At a big company, you can begin to navigate this kind of cognitive dissonance - listen to your sales team, but don’t build the products they demand. But in the early days of Puppet, I knew I couldn’t handle it. I am not good at dissonance in general - I’m a bit too fond of the idea that there’s just one truth - but I especially knew my organization could not handle it. We needed to be 100% aligned, and that meant sales needed to be working on the same problems as our product teams. Thus, no enterprise sales.
As we got bigger, the other big problem with enterprise sales starts to show up: Wow is it expensive. Lew Cirne of New Relic told me the primary reason he sold Wily when he did is because he needed to $150m just to build out the sales team and it wasn’t worth it.
If you’re doing inside sales, you’ve probably got someone who can talk through most of the product, they can talk to ten or more customers a day, and only once in a while will they pull someone in to help get a deal done. Once you go enterprise, you have field reps who might be covering thousands of square miles of territory, so if you’re lucky they’ll do three meetings a day on average, and they need a sales engineer on almost every visit. They pull in an expensive executive for meetings as often as an inside rep would pull in a cheap sales engineer.
Yes, you can get much bigger deals done this way, but think about the disruption to your organization: Essentially everyone on your leadership team is taking time away from running the business, not to learn from customers but just to make them feel loved enough to write a big check. Your deals start taking nine months to close instead of six weeks, and getting a check signed begins to look more like a challenge level in a video game than a partnership to solve customer problems. And the boss fight of that game is the worst part of enterprise sales: Procurement.
I’m not in the habit of disrespecting roles or teams, and I think procurement is often staffed with experts who play a vital role in their company. But they are generally paid based on how much money they “save” the company. All that discounting that you have to do for enterprise clients? It’s because procurement’s bonus is based on how much of a discount they force you to give. Absolutely everyone knows this is how it works, and that everyone knows this, so it’s just a game. I offer my product for a huge price, you try to force a discount, and then at the end we all compare notes to see how we did relative to market. Neither of us really wants to be too far out of spec; I want to keep my average prices the same, and you just want to be sure you aren’t paying too much.
But because companies compensate procurement based on saving money rather than making good decisions about what to buy, we can sell crappy products at a steep discount but not good products at list price.
It’s a helluva boss fight.
There’s often a miniboss, too: Legal. They just want their pound of flesh, and often this seems more like a puzzle level than a direct fight. I recently saw a deal that had been in legal for a year. That’s too much puzzle for me. (Incidentally, I worked on that same customer more than 4 years ago. Talk about long sales cycles.)
So now you begin to see why I fought against enterprise sales: It encourages you to build the wrong product for the wrong person and then sell it the wrong way at the wrong price.
Why, then, is it so popular? Or rather, why is it so hard to avoid that despite my best efforts we ended up in an enterprise sales motion, which I then ran away from?
Well, first and foremost, if it works it’s incredibly lucrative. For all that Lew Cirne built New Relic in response to his experience at Wily, and pointedly avoided enterprise sales for years, once they went public they went through a dramatic transformation and added it in, because the money was just too appealing. The biggest companies buy the most software, and, well, the biggest companies want to be sold a specific way.
In many cases, you just can’t avoid it. That’s a lot of what happened at Puppet: Our products were built to solve problems that big companies have. Heterogeneous environments, every operating system and application known to man, complex networks, and heavy compliance needs. Turns out it’s rare that a company has all these problems but buys large software products like you buy toilet paper.
Our first deals at companies did tend to look very consumer-like. But once they wanted to expand to other teams, and especially if they wanted to cover the whole company, the relationship naturally switched to a team sale, where we’re having to work with legal, procurement, executives, and then reps from three or four other teams. Ideally someone inside the org is an advocate for our product, so it’s more facilitation than direct selling, but the problem still stands: This is a clear enterprise sale.
But when it works… wow. You start closing $100k deals, then $300k, then $1m, then $10m. This starts to add up.
And for all that I’ve said this is hard… it’s actually the easiest way to sell.
What’s actually hard is having the best product, and only ever winning based on merit. Enterprise sales is the default motion, and in many cases it’s chosen to paper over weaknesses in the product. After all, only the user would actually notice those; in a meeting with the CIO, procurement, legal, and project management, no one’s going to install the product and give it a runout.
We’re still super early as an industry in our understanding of how to build a product that doesn’t rely on enterprise sales. For all that Atlassian relies more on sales than it has said, there’s no question that they managed to avoid an enterprise selling motion. I’m hoping the next generations of software companies will learn from them instead of Workday.
In the meantime, hopefully this story of how I fought enterprise sales, and why, will help you make better decisions about how to build your own teams. At the least, maybe I can just be a horrible warning.
These feature check lists are bad ideas. Don’t trust them as a user, don’t make them as a product marketer. ↩
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.
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. ↩
I’m a tech founder and recovering SysAdmin. I helped found DevOps and grew up in open source. These days I am convalescing from a decade of physical and mental neglect while running Puppet.
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