GarthBox

At one of the SaaS companies I worked for, two vendors spent the better part of a year courting us. Demos, check-ins, the occasional webinar invite dressed up as a favor. Then our VP went on maternity leave, and the deal went quiet the way a bar goes quiet at three on a Tuesday. Which is not the same as closed.

The vendors didn’t know that. They read the silence as rejection, and their follow-ups turned hungry. Hungry turned annoying. I got annoyed. Eventually they marked us closed lost, tidied their pipelines, and moved on.

Weeks later we hired a new VP. Fresh eyes, fresh budget, an appetite for exactly what those vendors were selling. Neither one ever came back. They paid for a year of our attention and walked out of the theater right before the scene they’d bought the ticket for.

Different company, same lesson in a different coat…. That one was owned by a private equity firm, which meant the org chart reshuffled itself every other year like a deck in the hands of a nervous dealer. Vendors would find their one champion and pour everything into that single relationship.

Then the restructure rolled through, the champion’s box vanished from the chart, and the whole account went with it.

Neither set of vendors was lazy. They were just far away.

Trends come in layers. The top layer is industry trends, the ones everyone in your category can recite in their sleep. In beer it’s the ber months, October, November, December, when the world suddenly remembers it loves a festbier and a stout. Under that sits seasonality, which gets overlooked far more than it should: school calendars, government budget cycles, tax and audit season, harvest checks landing in ag country, the holidays themselves.

Both of those layers are downloadable. Your brain, no matter how sharp you believe it to be, is a bad almanac. Do not trust it to remember that your buyer’s fiscal year ends in June or that audit season swallows their Q1 whole. Set up a sequence of Claude runs against your planning material and let the machine cycle through what your memory was never going to hold. That isn’t cheating. That’s clearing bandwidth.

Because the third layer is where the bandwidth belongs. The mat leave. The restructure clock. The champion whose tenure has a countdown nobody says out loud. No report prints this layer. No prompt returns it. The first two layers are free at the door. The third one has a cover charge, and the person working that door does not take cash. She takes hours. Visits. Enough time in your customer’s building to notice which meetings get rescheduled and which ones never do.

I’ll say the uncomfortable version plainly: if your trend knowledge stops at layer two, you are interchangeable with a prompt. The market is figuring that out faster than the org charts are.

I get my own dose of the third layer at the bar. Right now the city is tearing up a major artery from the south side of Madison, and the construction is pinching our revenue. There is no beer-industry report titled Orange Barrels, South Side, Q3. There’s just me, on a stool, listening to regulars describe the detour like a war story, and realizing my job this season is to make the trip worth the slalom. I only know it’s a trend because I’m present for it.

Same goes for your team: if you want your people fluent in the third layer, you have to pay their cover too. Presence is a line item, and it’s the best one on the budget.

Somewhere right now, a vendor is marking a quiet account closed lost, three weeks before the new VP walks in with money to spend. The trend was right there. It just wasn’t in a report. It was in the building. You know, the one they never actually stepped in. Shame.

Stay Positive & Drive Through The Construction Yourself

My neighborhood is having a landscaping summer. Every third house has a fresh bed: black weed fabric, decorative rock the color of oatmeal, mulch still sweating its cedar smell. And every one of them is ringed by the same polite little border, maybe four inches of edging, sitting there like it believes in the honor system.

I can tell you how this ends because it always ends the same way. By September the rocks will be in the grass and the clippings will be in the rocks. The mower will find a stone and spit it like a bad opinion. The mulch will migrate with the patience of a glacier and the manners of a toddler. And nobody on the street will dig up the border and set it higher. They’ll just live with the mixing. (Guilty of doing this myself…)

It isn’t ignorance, which is the part that gets me. Every one of these homeowners has watched every other yard on the block fail in exactly this way. (Again, mine included in this…) The border still comes up short because the border feels like trim. The plants get the love. The stone gets the budget. The edge gets whatever’s left in the truck.

I’ve done the same thing with messaging.

I’ve worked on core positioning, the real stuff, the words a company uses to explain itself. We launched it, and over the months that followed I noticed something that rearranged my priorities. What earned respect wasn’t the messaging. It was the defense of it. Alongside “what this is for and who this is for,” we had written, with equal seriousness, “what this isn’t and who this isn’t for.” That second list is the border. It’s a stack of no’s, stood on edge and buried deep enough to hold.

And it held in both directions, which I hadn’t appreciated until I watched it work. A low border fails two ways at once. Their clippings blow into your rocks: the adjacent request, the one-off deck, the “can we also just say” that lands in the bed and starts growing. And your rocks scatter into their grass: your language borrowed for audiences it was never built for, until customers squint at the lawn and can’t tell where your thing stops.

There’s a wrong height in the other direction too. A border nobody can step over isn’t an edge, it’s a wall, and nothing useful gets planted behind a wall. The goal was never sealed. The goal is used but not abused. High enough that nothing migrates by accident. Low enough that a person can still step in on purpose, with a reason, through the gate you built for exactly that.

But the coldest fact in the whole yard is this one: after install, nobody re-digs. The ground settles. The edging becomes archaeology. Redoing a border after launch means digging up a line everyone has already accepted, and almost no team has the stomach for that. So border height gets decided exactly once, in the week you ship, often in the last tired hour, by whoever happens to be holding the shovel.

Which is why the border deserves what we lavish on the garden: intention, budget, argument, care. Not because the no’s are the point. Because the no’s are what let the yes stay a yes.

The bed you enjoy in year three is the border you argued for in year one.

Stay Positive & Plant Accordingly

The most effective marketing loop I know has three moves. Connection, story, connection. Somebody you know pulls you in. A story worth carrying gets handed to you. And the story is good enough that you grab somebody else by the sleeve. No ad spend anywhere in the loop. No funnel diagram survives contact with it.

I watched the whole thing run, start to finish, in about ninety seconds at Great Taste of the Midwest.

Great Taste is the kind of festival where choice becomes a weather condition. Hundreds of breweries, thousands of pours, and a park full of people slowly discovering that four-ounce samples still add up. Nobody walks that grass with a strategy. You drift. Which is why the first move matters so much: I didn’t drift to the Titletown tent. I walked there on purpose, because a guy I know was pouring. Not just a guy I know. He taught me when I was studying for my Cicerone. He knows what I know about beer, because a chunk of what I know about beer used to be his.

He handed me their West Coast IPA. Then he handed me the part that made it heavy: he’d been at the brewery three years, and this was the first recipe that was his. Three years of other people’s beers. Three years of showing up, cleaning what needed cleaning, pouring what needed pouring. Then the brewery said yes, and the yes was sitting in my cup, cold and bitter the way a West Coast is bitter, which is to say on purpose.

I did not stand there evaluating hop character. I turned around, found the friend I’d brought, and made him try it. Not “this is a good IPA.” That sentence has never moved a human being one inch across a festival ground. What came out of me was closer to: you have to taste this, the guy who taught me beer works here now, and this is the first one they let him make. Three years he waited.

Loop closed. Connection, story, connection.

Notice what the story wasn’t. It wasn’t the brewery’s founding legend. It wasn’t tasting notes or the hop bill or anything a brand team could laminate. The story that traveled was about a person, and more precisely about a company trusting a person. Titletown’s best marketing at the biggest beer festival in the Midwest was a decision made in some production meeting months ago that had nothing to do with marketing: let him brew his.

That’s the piece I keep reveling in as I think about all I learned from another year of Great Taste. You cannot write that story. There is no agency you can hire to produce “our guy finally got his shot.” You can only make it true, then let the person it happened to carry it out into the world. Which means the loop most companies try to buy at the connection end, with referral programs and ambassador kits and incentivized reviews, Titletown got at the team end, for the price of one tank of beer and three years of trust.

Invest in your people and they walk around holding stories only they can tell. Those stories reach your customers in a voice no campaign has ever had. And your customers, if the story is true enough, will grab somebody by the sleeve to share it with.

The beer was very good, for the record. But the beer was the second best thing in that tent.

Stay Positive & I Hope You Get To Pour Yours

Growth has a curriculum, and the whole thing costs about four dollars at the local store.

First you underfill. The balloon comes off the faucet looking like a sad grape, and you learn that timid doesn’t splash. Nobody ever got soaked by caution.

Then you overcorrect. You hold it on the faucet one proud second too long and it bursts all over your shoes, and you learn that more is not a strategy. More is just more, delivered faster, to your socks. Ask me sometime about the year I tried to launch coffee inside a beer bar.

Then comes the right amount, and you know it by feel before you know it by logic. A well-filled balloon has a wobble to it, a kind of confidence. Heavy enough to matter, loose enough to survive the trip across the yard. The bar taught me this one. One location, filled properly, beats three filled to bursting, which is why I’ve never bought a second faucet.

Then multiple at once. This is the stage where you find out the amounts don’t transfer. Right now I’m filling a bar, a marketing job, a blog, a novel, and a daughter’s construction projects, and every one of them takes a different pressure. Calibration isn’t a skill you earn once. It’s a skill you earn per balloon.

And then the last stage, the one nobody grades you on: you learn to have fun with it. Which turns out to be the entire point, because nobody in the history of summer has ever filled a water balloon to keep it. A balloon filled right is meant to leave your hand.

Stay Positive & Here, Catch

The week before Great Taste of the Midwest, Madison fills up with people who plan their vacations around beer. Every taproom in town does something with that week. You barely have to decide to. The week has its own gravity, and a party will assemble itself out of it the way iron filings snap into place around a magnet, whether or not anyone is steering.

I was planning ours. Somewhere between the taplist and the logistics, I asked myself a question I try to keep loaded: what’s the intent?

The first answer was thin. Because it’s that week. Because everybody does something. Because a party shaped hole opens in the calendar and a bar is biologically incapable of leaving a hole unfilled.

That’s the moment the question earns its keep. Not when it confirms you’re on track. When it catches you rolling and asks who put the car in neutral.

Intent evaporates quietly. That’s the trouble with it. Activity keeps its shape long after the aim has left it, the way a garden hose holds its coil for years after it comes off the reel. The newsletter goes out weekly because it went out weekly. The party gets thrown because the week demands one. Nothing looks wrong. Everything hums. And none of it is pointed at anything.

Which is why the question can’t be a gate you pass through once at kickoff while everyone nods into their coffee. It’s maintenance. You ask it the way you check the oil, on a schedule, and especially on the machines that seem to be running fine. The machines that seem fine are exactly the ones that drift.

When I made myself answer it for the party, I didn’t feel caught. I felt lit. Deciding who a night is for, what it should do for them, what we want to be true on Sunday that wasn’t true on Friday, that isn’t homework. That’s the fun part. The obligation stayed the same size. The work got bigger on the inside.

Four words, and they run three audits at once. Whether the thing is being done with care or just being done. Whether it will actually land on anyone. Whether you’d choose it again next year, on purpose, in writing. A lot of what a business does was never asked any of the three.

The only time the question stings is when it catches you without an answer and you have to make one on the spot. But that isn’t the question being cruel. That’s it doing the one job you keep it around for. A smoke detector isn’t annoying because it’s loud. It’s annoying because something’s burning.

The party almost threw itself. It would have been fine. Fine is what happens when nobody asks.

Stay Positive & Ask It Again Tomorrow

Some of your work gets assigned to you. Some of it nobody asked for. You need both to grow, and you mostly need them at the exact moments they frustrate you.

I learned this at Blackhawk Farms, where a few times a summer I pay good money to ride my motorcycle in circles and, occasionally (okay…frequently…), to be annoyed.

Last time out I spent a string of laps behind a rider who kept botching Turn 5. He turned in too early, every lap, pinching himself tight against the inside of the corner like a man hugging a doorframe during an earthquake. My pace dropped to his pace. My first reaction was combustion.

But a track day is not a race, and you can’t pass everywhere, so I did the only useful thing available. I studied him. If early and tight was wrong, then late and wide might be right. Next lap I pushed my entry out, stayed patient, went wide, and held the throttle harder and longer than I ever had through that corner. It opened up like a door I’d been shouldering for a year.

Then the traffic cleared. With nobody’s taillight in front of me, I could run Turn 5 at the edge of what I’d just learned, lap after lap, pushing the line and my throttle a little further each time.

That’s the whole system. The rider in front of you teaches you the corner. The empty track is where you find out whether you learned it. Remove either one and the learning stops. All traffic and you never test your limit. All open track and you’re just repeating your own habits at higher speed.

The bar taught me this before the track did. When I jump behind the bar with my teammates at Garth’s Brew Bar, I’m in traffic, and it’s wonderful. Feedback comes at me from every direction, how they pour, what they say, what they notice that I miss. But when I get the bar to myself, I push. I try to surprise a guest past what they walked in expecting. I ask them, right there while the foam is still settling, what would have made the visit better. In the moment, as often as I can. That’s my open track.

Same at work. Assigned marketing tasks are traffic. The deliverables, the foundational voice of customer grind, the things you just need to do and ship. So be it. That work runs slower than your ego wants, and it teaches you the corners of the company. My unasked work right now is a readout nobody requested: what’s working, what needs improvement, and how we might prioritize efforts that span departments. It only exists because of what I noticed while grinding through the assigned laps. Traffic wrote the notes. The open track is where I get to ride them.

So here’s an audit, one friend to another: find the tension in your week.

If you’re stuck behind something slow and it’s making you a little crazy, good. Study the line while you’re back there. If you’re building something nobody asked for and your throttle hand is a little nervous, also good. That’s the stretch. But if nothing frustrated you and nothing scared you even slightly, you’re not in traffic and you’re not on the open track. You’re in the paddock. And the paddock teaches you nothing except how to stand around.

Stay Positive & It’s Not Just The Blend That’s Important; It’s The Tension Of Both

“Really like where this is headed. Can we make it feel a little more polished? A little more positive?”

If you make things for a living, you’ve gotten this note. It shows up friendly, wearing a lanyard, asking for ten minutes. And by the third or fourth time you’ve run the translation, you know exactly what it means. Take out the parts where I can hear you breathing or where the tension lives.

I want to say something about that note, friend to friend, because I’ve watched what it does to people I care about, and I’ve felt what it does to me.

The note is rarely about your work. Somewhere above the person giving it sits another person, and above them another, and every one of them reads your draft the same way. Not “will this move the room.” More like “what does this make me look like.” A director imagines the VP’s face. The VP imagines the CMO’s. The CMO imagines the board. By then your document isn’t a message to the market anymore. It’s a mirror in a hallway of mirrors, and everyone stops to check their own reflection in it.

Optimizing for that has a name in the art world. It’s the brief for hotel art. Pleasant. Coordinated with the carpet. Selected by someone whose only instruction was that no guest, from any country, in any mood, at any hour, could possibly object to it. And it works. Nobody objects. Nobody looks at it either. In the entire history of hospitality, no one has loved a mauve abstract enough to smuggle it out in a duffel bag.

That’s what a hallway of mirrors does to work. Edit by edit, your carnival poster becomes hotel art. It hangs everywhere. It lives nowhere.

Years ago I did marketing for a company that helped parents manage their kids’ screen time. For the press push we mailed journalists a kit with an egg of Silly Putty inside and a note that said, roughly, this is what it feels like when you put the iPad down. Squishy, tactile, a little ridiculous. If that idea had crawled through four layers of review, someone would have asked whether putty was on brand. Someone would have suggested we lead with the data. And we would have shipped a very professional one-pager on the benefits of reduced screen time, a genre of document no journalist has ever covered. The putty was the whole argument. The putty is what they remembered.

Alas… the advice.

Sort the notes. There are notes that make the work clearer and notes that make a reviewer safer, and they are not the same species. A clarity note points at the reader. I got lost here. This runs long. I don’t believe this claim. Take those greedily, and say thank you like you mean it, because your personality was never living in the typos. A comfort note points up the chain. Is this too casual. Will this land okay with leadership. That note isn’t editing the work. It’s editing the reflection.

Be honest about which parts of you are voice and which are tics. Not every quirk deserves a hill. Some of what feels like personality is habit wearing a costume. The stuff worth defending is the stuff doing work. The line that makes a reader feel seen. The image that makes the idea stick. Defend that. Let the rest go without a funeral.

Trade generously and defend narrowly. Hand over the structure edits like party favors. Then pick the one line that carries your fingerprint and say, out loud, this one stays, because it’s the reason anyone will remember the rest. People argue less with someone calmly defending one thing than with someone bitterly defending everything.

And keep a cut file. Nothing sanded off you actually dies unless you let it. Every line an approval chain has shaved off me in fifteen years has landed somewhere I own, including right here, which is one long act of putting the fingerprints back on.

If you’re the one holding the red pen, one thought before you go…

Every time you edit someone’s work to protect your own reflection, you teach them to pre-sand the next draft before you ever see it. Do that for a year and you’ll manage a team of beige. You didn’t hire beige. You hired people, and the market can smell the difference, because the market has never once objected to inoffensive work, and has never once remembered it either.

Invest in a person’s bravery and it comes back to you through every customer who reads their work and feels something. That’s the direction the current is supposed to run.

The goal was never winning every edit. The goal is staying recognizable. Somewhere down the line, somebody reads a thing before the name loads and thinks, I know whose this is. That’s positioning. For a company, sure. But first, for a person.

Stay Positive & I’d Like To Recognize Your Work Anywhere… Even At A Hotel