The Squash You Didn’t Plant

This is not a gardening blog. Give me one paragraph and it will feel like one, and then it won’t.

I don’t garden. I have killed a basil plant that came with instructions. But I know the word, because a friend who does garden taught it to me, and it has been rattling around my marketing brain ever since. The word is volunteer. It is what gardeners call a plant nobody planted. A seed that survived the trash, found its own light, and grew without permission. The squash sprawling out of the compost pile, fruit the size of a forearm, fed by nothing but rot and indifference, while the peppers somebody actually labeled and watered sulk in their tidy row.

Businesses grow volunteers too. We just don’t notice them, because we are busy staring at the beds we planned.

I was talking recently about a slice of a business that had no team, no owner, no quota, no goal anyone was accountable for. By every org-chart logic it should have been a rounding error. Instead it was quietly outperforming. Customers in that category kept showing up, kept fitting, kept staying, and nobody had told them to.

The lesson for anyone doing positioning: demand you did not manufacture is the most honest signal you will ever get. A campaign tells you what happens when you push. A volunteer tells you what happens when you don’t. One measures your budget. The other measures your fit.

When a segment converts without a single ad aimed at it, when customers invent a use case you never built a deck for, when a vertical keeps closing with no rep assigned, that is not a curiosity to file away. That is the market voting before you asked the question, and the vote is cleaner than anything your funnel will hand you, because nobody coached it.

The danger comes in two flavors.

The first is neglect. The volunteer has no sponsor, so it gets no water, and one quarter you look up and the thing that was growing on its own has finally given up on you. Plants you ignore long enough learn their lesson.

The second is stranger, and it is the one I watch smart teams walk straight into. We find the volunteer, get excited, and immediately try to civilize it.

We hand it an owner, a target, a roadmap, a set of OKRs, a name with a color. We move it out of the compost and into a raised bed. Sometimes that move is right. Sometimes it kills the exact wildness that let the thing grow. Structure is not free. Attention has a metabolism. Every hour you spend dressing up the volunteer is an hour stolen from somewhere else, and the volunteer was, by definition, the one thing that did not need the hours.

The skill is neither neglect nor conquest. It is noticing.

Stay Positive & Some Of The Best Things You Will Ever Ship Are Already Growing

The Solo Moved, The Song Didn’t

Pull up a sales call from a year ago. Then pull up one from last week. Same kind of buyer, maybe the literal same person, same job title printed on the same badge. Listen for where they lean in.

It’s a different spot.

A year ago the thing that made them sit up was one set of words. Now it’s another set entirely, and nobody sent a memo about the swap. The buyer didn’t announce they’d changed. They’d swear they hadn’t. And in the way that matters most, they’re right.

What moved was the ground, not the person. A year ago the market wasn’t doing whatever AI is doing to it right now, and that churn quietly rewrote the conditions every buyer is standing in. New fears, new shortcuts, new ways to look smart in front of a boss. So the things they need a product to prove have shuffled. The value props that landed last spring sound a half-step flat today.

But ask them why they bought into your company, the worldview, the bet you’re making about where the world is going, and you’ll get close to the same answer they gave you a year ago. That part held.

Two layers. Two different speeds.

Think of a band. The rhythm section is your company. Bass and kick drum, holding the song’s identity steady, show after show, room after room. That steadiness is what people mean when they say they trust you. The solo is your product. Improvised for the night, bent to the crowd in front of you, different every time the room changes.

And the room has changed.

It’s full of strangers now, every one of them holding tools that didn’t exist to this degree last year.

A good band reads that room and changes the solo. The bass line stays put.

The trouble starts when a company gets spooked by the new room and decides the whole song is wrong. Everyone starts soloing at once. They drag the AI energy all the way down into the company story, repaint the thing that was supposed to stay still, and what comes out isn’t bold. It’s noise.

In a way they sawed through their own bass line chasing a sound they heard in somebody else’s set.

There’s a quieter way to get it wrong, and it’s worse because it feels responsible.

You go re-interview your customers, careful operator that you are. They tell you they still love the company. You exhale. You file the notes. And you miss that the product reasons rotted while you were being reassured. The affirmation was real and the affirmation was a trap. (It kinda, sorta, always is if you give it too much weight…) A customer saying the song still sounds like you is not the same as the solo still working.

So the question I keep circling is how you tell those two apart in the moment. When the ground shifts, is it a tremor in the solo, change the value props and move on, or is it the kind of quake that means the song itself has to change, your category moved and the company story has to follow it down?

I don’t think that question has a clean universal answer. I think it has an owner. Somebody whose actual job is standing at the seam between the slow story and the fast one and making the call, quarter after quarter. Not a document in a shared drive that gets updated when someone remembers it exists. A person. The drummer, not the soloist everybody’s watching. The one who decides when the whole song shifts tempo and when it’s just this one solo running long.

Most places don’t have that person. They have a deck. The deck doesn’t know what room you’re in tonight.

And if you want that call made well, you invest in the one who makes it before you need them to make it. That’s the part companies are realizing they’ve skipped pre-AI wave. They spent a fortune chasing the customer’s new mood after new mood and almost nothing on the one teammate built to hear it coming.

So, if you’re looking for an action step here…pull the two recordings. Sit with the gap. Notice that your buyer is loyal to the song and restless about the solo, both at once, and that the restlessness is the honest part. Then ask who in the building actually owns the difference for your brand.

If the answer is nobody, that isn’t a messaging problem.

Stay Positive & Just In Case It’s Not Obvious… That Person’s Title Often Has “Marketing” In It

Pocket Can’t Read The Room

My voice was shot.

I had just spent three and a half hours training someone on how to do a thing I have done a thousand times. It is the kind of work where you can feel the moment a person stops nodding politely and actually understands. That moment is what you came for. That moment is why your throat hurts.

A year and a half ago, mostly joking, I said out loud that I wanted to wear a constant recorder to conferences so some future AI could mine my day for the good bits. People winced. “What about privacy.” “What about consent.” Fair enough.

This morning, an ad found me for Pocket. A small device that always listens. Clips to your phone for calls. Joins your meetings. A second set of ears that never asks if you are tired. The future I joked about is now a Tuesday checkout.

Here is where I am supposed to talk about how powerful this is. How I could feed today’s training to a model and spit out a personalized onboarding doc that explains every step again in the trainee’s exact learning style. I could. I might. It would probably even be useful.

The obvious post writes itself. I want the other one…

The thing the always-on microphone makes obvious by its absence is this: the moment had to be worth recording in the first place.

Pocket would have captured every word of the training. It would not have captured the fact that I shipped my own package to the bar instead of my house, and that the package arrived right as the bartender showed up to open the place, and that the two of us stood by the back door talking about how he reroofed his garage last summer. That detour was not on the agenda. It became the agenda. The trainee saw me as a person who makes goofy logistical mistakes and bonds with strangers about manual labor, and that changed how he heard the next two hours.

Pocket would have transcribed my words during the lesson. It would not have read his face when he hit the part he kept getting wrong. There is a specific small flinch a person does when they are pretending to follow you. You only catch it if you are watching. You only know to go off-script if you catch it.

So the real gift of the always-on microphone, for me, is not what it captures. It is what it forces me to ask. If a robot will be the cheap, comprehensive version of the meeting, what am I doing in the meeting that the robot cannot do?

The package at the bar. The flinch in the lesson. The voice that ends up shot because you cared enough to say it a third way.

Differentiation used to be a luxury good. Now it is the whole job. Anything generic about how you serve someone is about to be done better, faster, and cheaper by a model that will not get tired and will not get the address wrong. The only moves that survive are the ones a transcript cannot hold.

Stay Positive & Your Move…

Slack Tide

There’s a moment in a bar, somewhere between six-thirty and seven, when the after-work crowd has paid their tabs and the dinner/post-dinner crowd hasn’t shown. The room hums but the room isn’t moving. You wipe down the same spot on the bar twice. You swivel glasses logo facing out that don’t need straightening. The music feels louder because nothing else is talking. If you’ve never bartended, you can still picture it. Every business has that hour.

Sailors call this slack tide. It’s the small window between flood and ebb, when the current goes quiet and the boat barely drifts. The ocean hasn’t given up on you. It is reorganizing itself. The next push is coming. Right now, the water is just deciding which way to send it. It doesn’t feel great, though.

We don’t have a good word for this in business. We say the dip, the lull, the trough, and most of those terms come pre-loaded with someone else’s framework. So I’m going to borrow from the sailors. The flat patch in your launch, your sales cycle, your team’s energy, your novel’s middle chapters, your kid’s reading progress, your therapy, your career, your second marriage. That isn’t failure. That’s slack tide.

The interesting question is what you do while the water is still…isn’t it?

Three moves. Just ideas to get us moving when the current isn’t.

Shrink the ask, not the ambition.

When the work feels heavy, the instinct is to set a smaller goal. That’s the wrong end of the stick. What needs to shrink is the daily commitment, not the destination. Habit researchers keep finding the same odd thing: people who promise themselves five minutes of practice keep the streak longer than people who promise themselves a full hour. The brain doesn’t audit duration the way it audits identity. Five minutes still counts. Zero does not. During slack tide, you protect the streak. You keep your hand on the rail.

A friend of mine who runs a small agency calls these “tiny touch days.” On the worst days she doesn’t write a deck. She writes one slide. She doesn’t pitch a client. She sends one email. The work doesn’t move much. But the writer in her, the seller in her, the leader in her, stays on the boat.

Change the inputs before you change the outputs.

The instinct in a lull is to try harder at the same thing. Reread your own deck. Open the same dashboards. Sit in the same chair. Eat the same lunch. The brain is a sensory animal. Bees fed only one kind of flower lose immune function. We aren’t bees, but we get duller when our diet of inputs goes flat.

So change the inputs first. New walk. New album. A book outside your field. Lunch with someone who doesn’t work in your industry. Sit in a different chair. Or better yet, stand up desk and unplug it so you can’t lower it. The output will follow, not because the inputs were magic, but because your nervous system needed to feel something new.

I’ve seen entire product teams come out of a creative slump because the founder rearranged the desks. Call that superficial if you want. The team had better ideas the next week.

Find the person three months ahead of you, not three years.

The mentor who’s a year past your problem has already forgotten the texture of it. They’ll tell you it gets better, which is true and useless. The mentor who’s a week ahead is still in it with you, and you’ll trauma-bond instead of getting unstuck. The person you want is ninety days past where you are. Close enough to remember the specifics. Far enough to have proof.

There’s a quiet finding in peer-support research: in recovery programs, the most effective mentors are the ones with six to eighteen months of clean time, not the ones with twenty years. Proximity matters more than altitude. Ask the question. Find that person. Buy them coffee.

These three moves don’t push you through slack tide. They keep you on the boat until the current turns.

Now the part that has to be said for anyone leading a team through this.

When you are in slack tide, your team is too. They feel it earlier than you do, the way lichens know a forest is in trouble before the trees do. The leadership move is not to perform momentum. It’s to ask them what’s heavy. Carry the part you can carry. Name the part that’s yours to carry. Companies break in the dip because the leader bunkers in and the team stops trusting the silence. The silence isn’t strength. It’s slack tide getting confused for a stall.

Invest in your team during the flat water. They’ll invest in your customers when the current turns. The customers will invest back. That’s the order… That’s always the order.

Stay Positive & Don’t Compare Your Captain’s Log # 5 To Someone’s # 25 (but #7 or #8 will do…)

When The Fire Stops Being Yours

I used to be the person who got the call on Friday afternoons.

The thing was broken, the customer was upset, the team was stuck, and I had a track record of walking in, asking the right two questions, and putting it back together by Monday. It was satisfying work. It also paid in adrenaline, which is the worst currency a career can run on. Best I save that for my motorcycle track days.

There was a stretch where I started noticing the same shapes inside different fires. Not the exact same fire. The exact same wiring underneath. Same misalignment between what marketing thought sales needed and what sales actually used. Same gap between what customers were saying on calls and what product was hearing two layers later. Same five percent of the work carrying ninety percent of the weight.

That is when you stop being a firefighter and start being an electrician who fixes the wiring.

This is the move most career writing skips over. The shift from solving problems to designing problems out of existence. Heroes solve. Systems builders quietly remove the conditions that made the hero necessary. Both are real work. They actually need another. Just the other night I was telling my Garth’s Brew Bar team how appreciative I was for them doing so much around the bar so I can focus my attention on systems work.

Here’s the thing that hurts me every time I talk to my team…

The system, once it is running, makes your contribution almost invisible. Nobody throws a parade for the customer escalation that did not happen. Nobody writes a thank-you note for the rep who did not get the question because the answer was already in the deck. Reorgs come and erase your fingerprints. New hires inherit the system and assume it grew there like a tree. You watch your best work disappear into the air, which is exactly what good systems are supposed to do.

That is the bargain. The bow goes to someone else. Sometimes nobody. Often the company itself. You get the quiet pride of knowing the gears are still turning.

A real one for me. The clearest piece of system work I have ever done was building a closed loop across the company with AI in the middle of it. The SRDC document feeds the collateral. The collateral arms the reps. The conversations the reps are having flow back as signal. That signal becomes the next product enhancement, the next page of the deck, the next sentence on the website. Information stops dying in one team’s inbox and starts irrigating the whole organization. No single piece of it would have been impressive on its own. The point was that none of it had to be impressive, because it kept working when nobody was watching. And it worked without me touching it.

That is what scaled product marketing actually is, when it is good. Not better launches. A better nervous system.

A caveat the loud people skip. Not everybody needs to be a systems builder. A team without people who can work inside the system is a team with a beautiful useless machine and no operators. You do not earn the right to redesign the system until you have spent enough time inside one to know exactly where it pinches the hands of the people using it. The leaders I trust the most have done the small work for long enough that their proposed systems carry the shape of real hands. Shit, I’d argue that in the current state of the tech industry, especially, a leader has to do a bit of the work. (Ask to see Todd Olson’s GitHub pull requests calendar from 2014 to today. His present engagement is symbolic of the industry at large. Hands must be on and in. At least in enough to make better systems decisions.)

If you are early in a career, work inside the systems. Notice where they pinch you. Make a list. That list is the seed of the work that will eventually carry your name without carrying your name. And, come on, you certainly remember a teacher or boss you couldn’t stand and you vow’d to “never be like them.” Do that with the work systems, not just the people. It’s a win-win because your work gets better, and you do, too.

If you are further along, the test is simpler. The next time you feel the urge to grab the fire extinguisher, sit on your hands for two breaths and ask whether you would rather be the person who put out this fire or the person who built the floor that did not catch.

Systems work is mostly an act of respect. Respect for the people inside the system, who deserve a workday that does not require heroics. Respect for the customer, who deserves consistency more than they deserve charm. Respect for the team you will leave behind, who should not have to rebuild the gears from memory.

That is the reward. You become part of something that is bigger than you and quieter than you and slightly more patient than you. The fire stops being yours. The floor underneath everybody is yours.

Stay Positive & Build For The Ones Who’ll Inherit It

Two Verbs Aren’t Enough Anymore

A wing joint outside Cleveland answers its phone with a voice agent now.

Not a chain. Not a franchise. A two-location family place that’s been there since the Browns last gave anyone hope.

The owner’s son built it on a Tuesday.

He didn’t hire a developer. He didn’t buy a SaaS subscription. He prompted an AI model, glued it to a phone number, and shipped a thing that takes orders, knows the specials, and bumps the weird calls over to mom.

Fourteen dollars to stand up.

Pennies a call to run.

(I’ve stood behind enough bars on a Friday night to know exactly what “the phone is ringing again” does to a service team trying to keep the line moving. This is the kind of move that quietly buys a kitchen its sanity back. It’s also why we don’t have a phone at Garth’s Brew Bar, but thanks to AI, I might change that.)

Somewhere, a SaaS seller pitching restaurant phone automation is sweating.

And somewhere else, a buyer who has sat through seventeen build vs buy meetings is starting to wonder why the framework feels like an antique.

Both of them are right.

Build vs buy was a question for a world where building meant hiring five engineers for a year.

That world is gone.

Build now means a weekend. A kid. A credit card. A Saturday morning before the lunch rush.

The math changed. The framework didn’t.

The deck is from the whiteboard era and the meeting is still being held.

The real menu has four verbs.

There’s build, which still exists. But the word now means two completely different things stuffed inside one syllable. The hobbyist version is somebody’s brother-in-law on a weekend. The enterprise version is a team and a year. Lumping them together hides the decision instead of helping you make it.

There’s buy, which today almost always means rent. You aren’t acquiring software. You’re paying monthly for access to a product that can change, get acquired, raise prices, or quietly pivot off your use case six months from now.

Calling it buying makes it feel more permanent than it is.

There’s partner, the missing verb. You don’t buy a relationship with a local AI shop or a consultancy that already knows your industry. You partner with them.

Different transaction. Different risk profile. Different upside.

Most build vs buy conversations skip this verb entirely because it doesn’t fit on a 2×2.

And there’s ignore, the most underrated verb in business. Not every problem is your problem this quarter. Sometimes the right call is to wait twelve months and see whether the thing is even real. (Take a meaningful look at how many cowork sessions you’ve started but never finished… I’m guilty, too.)

A lot of bad builds and worse buys come from companies that should have done nothing and called it a strategy.

Now consider the repair shop owner who wants to auto-text her customers when their truck is fixed.

She isn’t picking between build and buy.

She’s picking between renting a thirty-nine-dollar-a-month tool, owning a small thing her brother-in-law built that lives on her own systems, partnering with a guy in town who already does this for ten other shops, or ignoring it for now and just answering the phone herself.

Four real choices.

Four risk profiles.

Four very different stories about what kind of business she’s running.

If you’re the SaaS seller in this story, your old deck is broken.

Telling her “building is risky” used to mean something when building required a CTO. Now it means asking her brother-in-law to spend a Saturday.

The risk argument moved. Your pitch needs to move with it.

Stop selling against build.

Sell against abandon. Sell what happens when the brother-in-law moves to Phoenix. Sell why renting from you is actually the most flexible call, not the most permanent.

Sell partnership, not procurement.

If you’re the buyer in this story, stop asking your team build versus buy.

Ask which verb fits the moment.

Build a tiny piece. Rent the boring middle. Partner on the hard part. Ignore the parts you don’t need yet.

One more little riff…The build vs buy debate persists because it lets people avoid harder questions.

Do I trust my team to do this well?

Am I willing to be responsible for this when it breaks at two in the morning?

What business am I actually in?

Those are the questions under the questions.

Build vs buy is the costume they wear when they don’t want to be seen.

Stay Positive & Pick Your Verb

The Question Got Smart Before We Did

A guy three stools down asked the bartender what was good. He listened to the whole rundown. House lager, a stout the brewer was proud of, a sour they only had for two more weeks. He nodded the whole time, looked engaged, then ordered a Coors Banquet.

The question got smart. The order didn’t.

That’s been the year, hasn’t it. Everyone I work with has developed a new reflex. They open a draft and ask “could this be better?” They look at a deck and ask “is this the strongest version?” They forward an email to a friend or to a model and ask “what am I missing?” The reflex is real, and on its face it is an improvement. We used to ship the first thing that wasn’t embarrassing. Now we run it through one more loop.

The trouble is the loop.

Asking is cheap. Answering is expensive. The tools we’re using will happily expand, condense, polish, restructure, tighten, soften, sharpen, anything you want, in any direction, on demand.

Every one of those moves feels like progress because it cost effort. None of them are actually better. They’re just different.

The deck gets longer or shorter. The email gets warmer or cooler. The post gets more clever or more sincere. And then we ship it, and the work we produced this year looks almost exactly like the work we produced last year, except we feel more thoughtful while making it.

The question moved. The output didn’t.

There’s a marketing version of this, and it should bother you. When the reflex “could this be better?” gets applied to a campaign, what usually shows up is twelve variants of the same hollow premise. A subject line test on an offer no one wants. A landing page rewrite for a category that’s dying. A new tagline for positioning that was wrong before the model touched it. It appears that the tool will not, ever, tell you the foundation is rotten. It will help you decorate that foundation in seventeen different finishes and let you pick your favorite.

A smarter question deserves a harder answer. The harder answer is almost always “this needs to be rethought, not rewritten.” But rethinking is slow and lonely and looks, from across the room, like not working.

Rewriting is fast and feels like motion and produces a fresh artifact you can show a colleague by 4pm.

So we rewrite. Over and over. And we tell ourselves the inflection point has happened because we changed how we ask, even though we have not yet changed how we work.

I have done this. I did it twice this month. I asked the model to help me sharpen a positioning doc that needed to be scrapped and started over. I knew, by the second pass, that I was decorating a wall that should have been demolished. I kept going because the decoration was easier than the demolition. By the end I had a beautifully worded version of an idea that was never going to land. That isn’t the model’s failure. That’s mine. The model gave me exactly what I asked for. I asked a smart question and accepted a polished answer instead of a real one.

The reflex to ask “could this be better?” is a gift. Right now we need to stop wasting it.

The Coors Banquet isn’t the problem. Ordering it after the bartender’s whole speech is.

Stay Positive & Demolish The Thing You’ve Been Decorating