The Prompt I Didn’t Type

I had it half-written in my head. Storyboard a short film a five and three-year-old could shoot. Six scenes. Teach framing and motion along the way. Twenty seconds of typing and I’d have had a clean little plan to hand my daughters, complete with shot angles and a suggested color palette.

My hand was already drifting toward the keyboard. Then it stopped, the way you stop at the top of the stairs when you’ve forgotten why you climbed them.

So I ripped the back cover off a coloring book (because we didn’t have any scrap paper). Markers that had mostly given up. A ruler none of us had patience to find, so the frames came out crooked. By the time we finished the first scene, one of six, I felt a strange low hum of guilt that I had even considered the other version.

I want to be precise about the guilt, because it surprised me. And quite frankly, this is therapeutic.

It wasn’t that I’d almost robbed them of something. They’d have been fine either way. It was that I’d almost robbed myself of something I didn’t know I needed until it was already happening. The arguing about what object Emree should have in her frame. The bad ideas that made us all laugh. The slow, inefficient, irreplaceable feeling of a few people making a thing that did not exist before they sat down.

Now here’s where I’ll defend the machine, because I’m not a purist and I’ve seen it earn its keep.

I ran win/loss software that leaned on AI to generate interview questions and talk to prospects and customers. And it worked. It pulled data we could actually act on, at a volume and consistency I could never have hit by hand. That was the right call. That was the boring, necessary, high-volume eighty percent of the work, and handing it to a system was not a betrayal of anything. It was good judgment.

But the line I carried into every meeting after that did not come from the software.

It came from an IT director sitting across the virtual table from me, talking about a tool his company had finally adopted. He said, “It was finally something that didn’t make me want to vomit.”

I have quoted that man in many-a-meeting. It resonates so thoroughly every time.

No survey produced it. No model would ever generate it. Ask an AI to write customer praise and you get “intuitive,” “seamless,” “a game-changer.”

You get the center of the bell curve, sanded smooth. You do not get nausea reframed as a compliment.

That sentence was too specific, too a little bit gross, and too true to have been predicted by anything optimizing toward the average.

That’s the whole thing, and it’s a marketing point as much as a parenting one. A model’s job is to find the mean and return it to you, fast and clean. But the mean has never sold anything memorable.

The line that closes the deal, the detail that makes someone trust you, the moment that sticks, those all live in the outliers. The weird specific real ones. And outliers are not something you retrieve. They’re something you make, usually by hand, usually inefficiently, usually in the part of the work you were most tempted to skip. (It makes me think of a sales leader I heard the other day say “You don’t want your prospect-facing reps prompting, you want them selling!” Which, what I heard is you want them being the human outlier in the sales process.)

The messy parts and the important parts keep turning out to be the same parts.

Some people will tell you the mess is the whole reason any of it is worth doing. I’m starting to think they’re right.

Stay Positive & Crooked Boxes Might Just Contain The Best Ideas

Your Fear Has A Bad Watch

A motorcycle track coach taught me the most useful thing I know about business, and he did it by making me afraid on purpose.

Going into a corner at speed, there is a moment where your whole body screams brake. Not a thought. A flood. The coach watched me obey it for a few laps, then handed me a strange instruction. When the fear hits, notice it. Name it. Count to three. Then turn in.

The first time he said it, I thought he wanted me to be braver. He didn’t. He wanted me to learn that the fear was early. It always was. It arrived a full three seconds before the corner actually needed anything from me. My fear was not lying about the danger. It was lying about the time.

Last week I was sitting with the founder of a SaaS company, talking positioning, and I felt the old flood come back. That nervous spike that says you are about to not be impressive, so soften it, hedge it, give him the tidy version he probably came in expecting. Brake now.

I counted. Then I said the thing I actually believed, which was that I wouldn’t touch his positioning for where the company sits today. Positioning is a hockey instinct. You don’t pass the puck to where the player is standing. You pass it to where the player is going to be. He went quiet, then leaned in. It paid off.

Now the honest part, because the clean version of this story is a lie. I did not find my braking point by being wise. I found it by running off the track.

Same corner, a few laps in a row, holding the pause a beat too long, sailing wide into the grass with the throttle full of regret. Three is not a magic number. Three is a search. You overshoot, you clip the apex late, you adjust, you try again. The seconds were never the lesson. The braking point was.

And once I had it on one corner, I could carry the same motion into the next one.

Fear is a now signal. The alarm is real. Its sense of timing is garbage.

Stay Positive & Count…Then Turn In

The Agent Was Always An Agent

We had a sour on tap last spring that nobody ordered. Good beer. A Berliner Weisse, listed on the board as exactly that, “Berliner Weisse, 3.8%,” sitting there honest and ignored while it slowly went flat in the line. Two weeks of almost nothing. Then I rewrote it as “Overfruited Sour” Same keg. Same liquid. Same brewer, same recipe, same hands that made it.

You know this is coming…It sold out that weekend.

I didn’t improve the beer. I stopped describing it like a spreadsheet.

I keep running into the software version of this. There’s a whole category of products out there quietly doing extraordinary work under a name that makes them sound like a checkbox. Think about a piece of software that watches a job site all day. It notices when someone arrives. It clocks them in without being asked. It tracks where they go, trims the time card when they leave, sorts the cost back to the right project, and fixes the small human errors nobody had the patience to catch. It does this every day, in the background, for thousands of people, and it does it well.

For years a thing like that gets sold as “GPS time tracking.” A feature. A line item with a little tick next to it, shelved next to a dozen cheaper tools that do a worse version of the same chore. Buyers compare the tick marks, shrug, and pick on, who knows, probably price. The product was years ahead of its category and the category had it filed under office supplies.

Then a new word shows up in everyone’s mouth. Agent. And suddenly the exact same software, not one line of code different, is the future. The thing was already monitoring, already deciding, already acting on its own. It was an agent the whole time. It just never had permission to say so, because the word didn’t exist yet in a way a buyer would pay for.

That’s the part worth sitting with. AI didn’t upgrade the product for a lot of SaaS out there. AI upgraded the vocabulary. The capability was real for years. What changed is that the market finally had a shelf to put it on, and a shelf is the only thing a market can actually pay for. People don’t buy value. They buy value they can classify.

If they can’t file it, they can’t fund it, no matter how good it is.

This is the quiet tax almost nobody accounts for. Not a bad product. A great product wearing a cheap noun. You can be objectively the best thing in the room and still lose to a worse thing that picked a better word, because the word is what the buyer holds in their head on the drive home.

And it isn’t only products. I’ve watched the same thing happen to people. The smartest operator on a small crew is usually doing some essential job that has no name, the one everyone calls “the stuff nobody wants to deal with.” It’s invisible until somebody finally calls it a role, gives it a title, says this is yours and it matters. (Have you wondered why GTM Engineer has gotten so popular?! We’ve been here doing the work. Now there’s a title for it.) The work didn’t change. The person didn’t change. But you handed them a noun they could grow into, and they grew.

Naming isn’t decoration. It’s permission. You can do that for a beer, for a feature, and for the person sitting three thousand miles away who’s been carrying something heavy under a label that made it sound light.

The beer was always that good. I just stopped underselling.

Stay Positive & …Until The Next Cycle

The Second Five Minutes

I texted a buddy of mine last week and we agreed to read a parenting book together. Our kids are drifting into a new stage, the one where the old chapters stop applying, and neither of us wanted to wing it.

What struck me when I hit send was a memory from the last round of parenting books, years ago, when my girls were tiny. The books helped before I applied a single technique from them. The reading itself did the work. Twenty minutes with someone else’s hard-won patience and I was a more patient dad by dinner. I hadn’t practiced anything. I had just been marinating.

That’s the whole trick, and it costs almost nothing, doesn’t it?

Your brain takes posture cues from whatever you feed it. This isn’t manifesting. Nothing in the universe rearranges itself because you listened to a podcast.

It’s closer to stretching before a run.

The input warms up the part of you that’s about to be needed.

I used to work with an agency that served the director of marketing for Wisconsin tourism, a man who read a new book roughly every month and then wanted to test what he learned, immediately, with us. The agency learned to brace every thirty days. Some people complained. I admired the hell out of it. He had built a machine where intake became experiment on a fixed schedule, and his curiosity set the weather for every team that touched his account.

Real talk…I’d have appreciated a heads-up about the forecast, but the system itself was beautiful.

I’ll admit the counterexample, because I know him personally: a marketing friend of mine who reads nothing about marketing, business, or entrepreneurship at all, and who is very good at his job. So this is not a law of physics. Some people get their inputs from somewhere I can’t see. But for most of us, the lever is sitting right there.

Which brings me to Denzel Washington. I watched an interview where he advocated for five minutes of nothing after you wake up. Just lie there. No phone, no inbox, no charging into the day. You with you. I am not going to argue with Denzel, and I’m not going to improve on the first five minutes.

I want to talk about the second five.

After the stillness, before the day grabs you, you get one clean window where nothing has claimed your attention yet. Spend it consuming something aimed at who you’re trying to become. Five minutes of a book on the thing you want to build. Five minutes of someone who already lives where you’re headed. Library app, YouTube, a single page, an AI summary of a chapter you’ll never otherwise reach. The format doesn’t matter. The aim (that warm up stretch?) does.

Marketers already know this works because we do it to other people for a living.

Nobody buys a trail running shoe the moment they see the ad. They buy it after weeks of accidentally consuming trail running, until one day the identity fits and the purchase is just paperwork. Brands don’t sell products to strangers. They feed people inputs until the people aren’t strangers to the idea anymore.

The second five minutes is simply running that play on yourself, and choosing the brand manager. (Cough cough That’s you…)

The same goes if you lead a team, by the way. Your people are marinating in something every day, and the strongest flavor in the pot is you. (Okay, getting a little weird. Lost your appetite, but you got the point.)

My buddy and I start the book next week. I already know the first chapter will work before I finish it. Not because the advice is good, though it probably is.

Because for five minutes, I’ll be a guy who reads about being a better dad, and that guy walks into the kitchen differently.

Stay Positive & Might Be The Best 10 Minutes Of Every Day

{{First_Name}}, You Were So Close

A stranger emailed me twice this week offering to build my website. Same pitch both times. Local guy, building sites for local businesses, keeping the price low, quick call sometime? The first copy had his signature filled in. The second copy still had the template showing, brackets and all, the place where his name was supposed to go sitting there empty like a costume sent with the hanger still in it.

I’ll admit something: I sometimes respond to these emails.

Part of it is curiosity about whether there’s actual value buried in there. The cost is one minute of my life, and let’s be honest, I waste minutes in far worse ways. Part of it is something closer to coaching instinct. I read these pitches the way a chef reads a bad menu, half annoyed, half rooting for the kitchen.

Because this one was close. Achingly close. One line in his prompt would have changed everything. Something like: “before you write the email, actually look at the website and shape a POV.”

Then the opener stops being “I build affordable websites” and becomes “your website is already killer, and I think I can make a few improvements you haven’t thought of yet.” That version gets a reply from me the same morning. Not because it flatters me, but because it’s accurate, and accuracy is the cheapest available form of respect.

My old CMO once joked he should just put me in charge of the company site after seeing what I’d done with mine. The guy in my inbox could have known that too. The evidence was one click away. He had a research assistant that works for free and he didn’t ask it to look.

You know the old line about outrunning a bear. You don’t need to be the fastest runner alive, just faster than the guy next to you. Differentiation works like that more often than anyone selling differentiation will admit.

The inbox is not a footrace against the whole category. It’s a footrace against the other four cold emails that landed that same Tuesday, every one of them wearing the same template.

We pour ourselves into becoming the fastest. New positioning, new brand, new everything, chasing some imagined gap of fifty miles per hour. Then you put real pressure on the problem and find out the gap was never fifty. You weren’t thirty-seven layers away from a yes. You were one. Maybe two.

He’ll never know how close he was. That’s the part that stays with me.

(Or, maybe, if he’s smart enough, he’ll read this post and try again. One layer smarter.)

Stay Positive & Fill In Your Signature
– GarthBox

Load-Bearing Assumptions

Assumptions have earned their bad reputation. Most of them are shortcuts your brain takes to avoid the inconvenience of finding out. They cost you deals, friendships, and at least one Thanksgiving per decade.

But a few assumptions are load-bearing.

Pull them out and the whole structure of getting anything done starts to sag. The difference is the math.

A bad assumption saves you a little effort now and bills you later. A good assumption is a bet where being wrong costs pocket change and being right pays out for years.

Over the years, I’ve written down many that make a difference. Here are six.

1. Assume positive intent.

The email that reads as a slap was probably typed with one thumb in a parking lot. If you’re wrong, you lose a little pride. If you’re right, you keep a colleague, a customer, a friend. That trade is so lopsided it should be illegal.

2. Assume the work will find its people.

This one feels naive and isn’t. Distribution has never been better at matching strange things with the people who love strange things. Which means the job is no longer reaching everyone. The job is being unmistakable to someone. Make the thing sharper, weirder, more specifically yours, and trust that the sorting machinery will do what it was built to do. Watered-down work is the only thing the algorithm can’t help.

3. Assume half the time and half the budget.

Not as pessimism. As design constraint. The version of the project that survives a 50 percent cut is usually the version that should have shipped anyway. Scarcity is a brutal editor, and brutal editors are the only ones worth paying.

4. Assume the newest person in the room sees something you can’t.

You’ve gone blind to your own wallpaper. They haven’t. The week-two employee asking “why do we do it this way?” is holding a flashlight, not a complaint. Teams that assume their people know something leadership doesn’t end up with people who act like it.

5. Assume the customer is right about the pain and wrong about the cure.

When someone says “you should add this feature,” believe the ache completely and the prescription not at all. They are the world’s leading expert on how it feels and an amateur at what to build. Your job is to be the difference between those two things.

6. Assume you’ll be quoted without the context.

Every sentence you write at work will eventually travel alone: screenshotted, forwarded, pasted into a channel you didn’t know existed. Write the sentence so it survives the trip. This sounds like paranoia and is actually just positioning. Clarity is what your message wears when you’re not there to introduce it.

That’s the list. But there’s one assumption that never makes the cut, no matter how generously I squint: the assumption that anyone owes you their attention. Nobody does. Not your customers, not your audience, not your team sitting through your all-hands. Every good assumption above works because it spends your own optimism. That one spends other people’s time, and they will quietly stop lending it.

Assume the best of people. Assume nothing of their attention.

Stay Positive & Am I Calling You Out In This Post? Or Is There Positive Intent?

Substance, Straights, And The Clock

(It’s track season, so you can expect a sprinkle more motorcycle-inspired marketing posts.)

I bought a Yamaha R7 knowing it would lose.

Not lose everything. Lose the straight. Put it next to a liter bike and the second the road opens up, the liter bike becomes a dot. I knew that at the dealership. The R7 looks like it was carved by someone who loved you, it handles corners like it’s reading your mind, and it was priced like a bike a normal person could actually own. So I bought the corners and the feel and the way it looks parked outside the bar. I did not buy the straightaway. The straightaway was never on the table.

That was an honest trade. I knew which game I was playing.

The trouble starts when you forget.

A lot of us spend our best hours on the part of the work that photographs well. The deck. The dashboard. The workflow diagram with the nice rounded corners. The visual system that makes you feel like a serious person.

…And almost no hours on the thing that actually feeds all of it: the data underneath, the structure, the unglamorous layer that decides whether any of the pretty stuff is even true.

I did this to myself a few weeks ago.

I built a gorgeous display for the beer offerings at the bar. Clean, alive, the kind of thing you want glowing above the taps. I loved it. Then I went to actually wire it up and found out I couldn’t get the API connection I had designed the whole thing around. The data stream I assumed would be waiting for me simply wasn’t there. The beautiful surface was sitting on nothing.

So I went down into the basement to lay the plumbing by hand.

And the strange part, the part I didn’t see coming: the basement turned out to be the most interesting room in this metaphorical house. Building the workarounds meant putting my hands directly into the raw material, and once they were in there, I found room I never would have found from upstairs. Places to add my own flare. Small decisions about how a pour gets described, what gets emphasized, where a little personality could live inside the system instead of just sitting on top of it. I automated what deserved to be automated. But I built character into the layer nobody sees, and that character now leaks upward into the part everybody does.

The surface has a ceiling. You can only polish a thing so far. The basement is where the surprises were hiding the whole time.

Alas. There’s something more powerful here… It’s that surface and substance are not good and evil.

They are two clocks running at two speeds.

The surface runs on the showroom clock. It wins the glance, the first impression, the screenshot, the “oh, that’s nice.” That clock is real. I am a marketer. Story is not decoration to me, it is the product. People buy the R7 because of how it looks, and there is nothing shameful in that.

But the substance runs on the season clock. It wins the long race, the second visit, the thing that is still standing in March. You cannot fake the season clock with showroom work. No amount of fairing closes the gap on the straight. Displacement does that. What is actually under the tank does that.

The mistake is not loving the surface. The mistake is losing track of which clock is keeping score this quarter, and spending all your hours on the one that isn’t.

The show is a game that never ends. The structure underneath is how you finally win one.

Stay Positive & See You In The Substance