“I came to see, in my time at IBM, that culture isn’t just one aspect of the game. It is the game.” Lou Gerstner
The best culture I ever built ran out of an old firehouse with a bank vault in the basement and jail cells we used as storage closets. Make of that what you will about my management style.
That was SmarterChaos, the company I ran from 2010 to 2020, and She Is Media right beside it. We got to reminiscing about the place on a team call this week. Ring toss in the hallway. White elephant parties that went sideways. The ten minutes of nothing-talk before anyone got to the agenda. The kind of bonds you only build sharing a weird old building with people for years.
Then somebody said the quiet part. We do not have that anymore. I am building again, we are remote now, spread across time zones, and the culture that used to run on its own just does not.
Here is what took me too long to admit. That culture was never a strategy. It was a byproduct. It happened for free because a group of people who liked each other were trapped in one building all day. The room did the work. Take the room away and the free ride ends. Nobody kills the culture. You just wander off from the thing that was quietly making it and assume it will follow you home like a stray. It does not.
So here is the lesson I wish one of the gray hairs had handed me twenty years ago, because gray hairs are experienced people, and this one cost me. Culture does not scale by accident. It only scales on purpose. When you lose the room, you have to become the room. Here is how.
What You’ll Get in This Issue
Why the culture that made you special when you were small is really a side effect of being small, and why it quietly dies the day you scale or go remote unless someone rebuilds it on purpose. The three moves that turn culture from a happy accident into something you engineer: over-communicate the vision until you bore yourself, make room for people to be human and never kill it with a lazy phrase like “take it offline,” and close the distance yourself before silence fills it with the wrong story. And why none of this is soft stuff, because what culture actually buys you is speed.
Part One: The Room Was Doing the Work
Here is the trap almost every founder walks into, and I strolled in whistling. You build something special when you are small. A tight team, a shared mission, inside jokes, a way of doing things that feels like magic. And you fall in love with it, so you assume it just comes along for the ride as you grow, like it is stitched into the company DNA.
It is not. Most of what you were calling culture was proximity. Fifteen people in one building, overhearing each other’s calls, solving a problem at somebody’s desk in ninety seconds because you could just walk over. The trust, the shorthand, the shared direction, all of it was getting manufactured for free by the simple fact that you were stuck together all day. The room did the work. The building picked up the tab. You never noticed, because you never got the bill.
Then you scale. Add people, add cities, go remote, and one day the magic is thinner. Not because anyone failed. Because the machine that made it, all those bodies in one place, is gone. In the office I could say the vision once, loudly, and it reached everyone by lunch. Now I say it and it reaches the three people on the call, and I get to say it again tomorrow to a different three. The message used to travel on its own. Now I carry it, or it sits.
Which reframes the whole thing. Culture is not a perk and it is not a vibe. It is infrastructure, and infrastructure either gets built and maintained on purpose or it rots. When you were small, the building was your infrastructure. Scale, and you have to become it. Three moves.
Part Two: The Playbook
Three moves that turn culture from free to deliberate. None of them are complicated. All of them take intention, which is exactly why most companies skip them and then hold a meeting about where the magic went.
Move 1: Say It Until You Are Sick of It. Then Say It Again.
Small, you say the mission once and the room carries it. Scaled, you are the only one carrying it, and one telling is a rounding error.
I made this mistake for years. I would explain the vision, clearly, once, and then assume telepathy would handle distribution. It did not. It reached whoever sat in that one meeting and evaporated for everyone else. In a building, that single telling got a hundred more chances to spread, over lunch, in the hallway, at somebody’s desk. Remote, there are no hallways. There is just the thing you said once, to the people who happened to be looking.
So the job changes. Repetition is not nagging, and it is not proof you explained it badly the first time. It is the work. The leaders who hold culture together as they grow are the ones willing to say the same true thing until they are sick of the sound of their own voice, because the moment you are bored of the vision is roughly the moment your team is hearing it for the first time.
At XPFlow I built the repetition into the calendar so I could not weasel out of it. Every Monday the leadership team runs an executive stand up and lines up on the week. Every week the whole company gets an all hands where I say the same handful of things about where we are headed, one more time, whether or not I think everyone already has it. It is not the most thrilling thing on my schedule. It is one of the most important, because for a remote company it is the closest I get to walking the floor and saying it out loud.
→ When you scale, you are the room now. Say the vision until you cannot stand the sound of it, then say it again, because the day you are sick of repeating it is the day it finally sticks.
Move 2: Make Room to Be Human, and Never Shut It Down.
The best parts of the old culture were never on an agenda. The small talk before the call, the tangent that had nothing to do with work, two people shooting the breeze at the coffee pot who walked away trusting each other a little more. That is not wasted time. That is culture forming in real time. In a building it happened for free. Remote, it happens never, unless you protect it on purpose.
That is what most of our rituals are for. A Friday virtual cocktail hour with no agenda except being people for an hour. A kudos channel in Slack where anyone can put someone else’s win in front of the whole team, so praise does not only ever travel up the org chart. A real reward and a shirt when the product team ships on time or ahead, because a milestone you can wear beats one that scrolls past in a feed. And a few days in one room together a couple of times a year, because nothing on a screen replaces it. None of it is soft. It is the deliberate version of the hallway.
Now the fastest way to torch all of it, which I learned on the receiving end. The worst company I ever worked for was the one I joined after selling SmarterChaos. Call after call, an exec would hear two people warm up with thirty seconds of small talk and cut in: take that offline, this is an expensive call. He thought he was saving money. Nothing on that call ever cost as much as that one sentence did, the little piece of motivation it quietly killed in everyone who heard it. So never say it. Not take it offline. Not circle back. Not couldn’t this have just been an email. Not this is an expensive call. Every one of those tells a human being to be quiet and get back in the box. Your people already do not bump into each other in a hallway. Do not use your breath to silence them the one moment they try to connect anyway.
→ Make room for people to be human, small talk and tangents included, because that is culture forming in real time. And never tell a remote team to take it offline or keep it to an email. You are not saving money on the call. You are training your best people to go quiet.
Move 3: Close the Distance Before Silence Does.
Remote does not just remove the hallway. It removes the thousand tiny signals that used to tell you everything was fine and hands you silence instead. And silence is the most expensive thing in a scaling company, because nobody prices it and everybody fills it in with the worst story they can imagine.
Watch it happen. One team goes quiet. Another decides that means they dropped the ball or stopped caring, when really they were heads down and forgot to say so. In an office you would have walked past their desks and known the truth in two seconds. Remote, you get nothing, so you assume, and the assumption is always darker than the truth. That gap, between the silence and the story people invent about it, is where culture quietly rots. Not in blowups. In a hundred small resentments nobody says out loud.
So go first. A real slice of my week as President is exactly this, dragging two teams into the same conversation before a small misread hardens into a real one, and making it clear that a quick call across departments is the win, not the interruption. Seeing across the whole company turns out to be the job, not a nice thing I get to when there is time. Silence is not information. Go get the truth before you invent it.
→ Remote turns silence into assumption, and assumption into resentment. Reach out first, ask instead of assume, and pick up the phone before you build the case in your head. Connection will not happen unless someone goes first, so let it be you.
Part Three: What Culture Actually Buys You
If this still sounds like soft stuff, like team building for its own sake, you will drop it the second things get busy. That is the mistake.
Culture is not the reward you get once the business works. It is what makes the business work fast. A team that trusts each other skips the politics and the second-guessing and just moves. A team that shares a real mission makes a thousand small calls right without asking, because they already know what the company would want. All the speed you are chasing, moving quick at scale without every decision becoming a meeting, runs on trust and shared purpose. That is culture. It is not decoration on the machine. It is what keeps the machine from shaking itself apart at full speed.
And it compounds. Every bit of trust you bank makes the next hard conversation easier. Every shared win makes the next crunch survivable. A team that likes each other and believes the same thing runs through walls. A team of talented strangers who happen to share a Slack scatters the first time it gets hard. Same resumes, opposite outcomes. What decides which one you get is the culture holding them together, and that is either something you built on purpose or something you are about to lose by accident.
→ Culture is not the soft stuff you get to after the real work. It is the trust and shared purpose that let a team move fast without friction, and it compounds, which is exactly why you engineer it on purpose instead of eulogizing it later.
Your Weekly Chaos Challenge
Look at your team and find the one piece of culture you have been assuming will take care of itself. The mission everyone supposedly knows. The connection you figure is still there. The alignment you have not checked in months.
Then do one deliberate thing this week. Say the vision out loud again, in writing, to everyone, even if you are sure they have heard it. Put one no-agenda gathering on the calendar. Or take the one team you have been quietly assuming the worst about, call them, and ask what is actually going on. One act of building culture on purpose instead of hoping. Culture responds fast to intention. Yours has just been waiting for some.
→ Pick the one piece of your culture you have been assuming will survive on its own, and do one deliberate thing to rebuild it this week.
Final Thought
For years I thought culture was something you either had or you did not. A lucky accident of the right people at the right time, magic you caught in a bottle and then tried not to spill. That belief cost me, because when the magic faded as we grew, I treated it like weather, something happening to me that I had to wait out, instead of something I was on the hook to make.
The truth is harder and a lot more hopeful. Culture is not weather. It is architecture. It felt automatic when you were small because the building was doing the work, forcing the contact, generating the trust for free. Scale removes the building. It does not remove your ability to build. It just moves the job to you and hands you a bill you never used to pay. Most companies never pay it. They watch the thing that made them special thin out, blame remote work or the market, and never admit the culture did not leave. They just stopped building it the second it stopped building itself.
So if the magic is fading as you scale, that is not a death sentence and it is not your team going soft. It is a signal. The free ride is over, and the deliberate part is beginning. Say the vision until it sticks. Make room for people to be human, and guard that room instead of shutting it down. Close the distance before silence fills it with the wrong story. None of it is complicated. All of it takes intention. And intention, unlike proximity, does not disappear when you grow. It is the one part of culture you fully control, which makes it the part that matters most.
That is the culture we are building at Chief of Chaos and XPFlow right now. Not the old firehouse magic reborn, because you cannot rebuild a room you no longer stand in. Something sturdier, put together on purpose, one Monday stand up, one kudos, one Friday hour, one launch shipped and actually celebrated at a time. It is deliberate, and that is exactly why it will outlast anything we ever got for free.
That is also the thinking behind Alfie, the product we built at XPFlow. The hardest thing to keep when a team grows or someone walks out the door is the judgment and the relationships that only ever lived in one person’s head, the stuff the room used to hold. So we built a tool that carries it, a hundred years of hard won partnership instinct baked in, so the knowledge that used to leave with people instead stays, and compounds, no matter how big or how spread out the team gets.
If your culture used to run on a room that does not exist anymore, hit reply and tell me the one ritual you refuse to let die. I read every one.
Until next week.
Run toward the chaos.
Matt Frary
Chief of Chaos // President & COO, XPFlow
#Leadership #Culture #RemoteWork #FoundersJourney #ChaosToGrow
