The Anticipation Ladder
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Three Videos, Five Years, One Scheduling Screen
The third time I hit record on the same tutorial, I paused before I said anything. Same scheduling screen. Same software. Same five steps. I had now...
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Ten Years of Dragon, Two Years of Wispr Flow
For about ten years I talked to software and then fixed what it got wrong. That was the deal with Dragon NaturallySpeaking. You read to it for hours so it...
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The Dunkin' Drive-Thru Fumble
March, you nailed a new workflow. May, it was obsolete. July, you bought a course on the thing that replaced it. Now it's August and there's already...
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Dale the HVAC Guy: The Twelve-Month Ladder
The newsletter came in on a Thursday. Another AI announcement. Something had changed, something was going to change everything, here were the five tools...
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Claude Greeted Him by Name
He opened the tab like he had a hundred times before. A new AI tool, a free trial, the usual blank cursor. Except this time a line came back before he...
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The $97 Copywriting Tool That the Eight-Dollar Model Ate
I was paying $97 a month for a specialized AI copywriting tool. Good one, too. Built by the guy who invented the Video Sales Letter. It earned its keep...
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The Lunch Interview: Son's Website in One Afternoon
On a Friday in January, I sat down to lunch with my son. He needed a website. So I interviewed him for about an hour, asked about his goals, the sites he...
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The Best Buy Aisle Barcode Scan
He walked into Best Buy to look at TVs. Found the one he liked. Pulled out his phone, opened the Amazon app, and scanned the barcode to check the price...
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The Meta / Manus Un-Sale
It was a January voice memo, the kind you record in your car because the thought won't wait. I said the big AI players were going to start buying up the...
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The Pre-Sold Tool That Never Sold: Damon's Expensive Tuition
The launch went fine. The pre-sales came in. The tool was real, it was built, and it had everything we knew how to put into it. Then the market just...
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Facebook Groups: Janitorial Work on Rented Land
He kept showing up. Every morning, same thirty minutes. Delete the spam. Boot the bots. Referee whatever argument had broken out overnight between...
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Running Friday Trainings Through NotebookLM
It was a Saturday morning. Dog on the leash, earbuds in, coffee still too hot to drink. And the thing playing in my ears was a two-host AI podcast...
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The Family-Practice AI Catching the Town's Pattern
Picture a family doctor. She sees thirty patients a day, fifteen minutes each. She is good, she is present, and she is working with a slice of information...
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The Journals Written Alone: The Unfakeable Reservoir
He keeps a plain notepad on his desk. Nothing special about it. He talks into a dictation tool, no keyboard, no AI in the room, and whatever comes out...
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The Dunkin Drive-Thru Fumble
Every week, same Dunkin. Same two orders. Same plan: pull up the app in line, QR code ready before the scanner guy leans out. It never works. The app is...
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Teaching Claude His Writing Voice
It was a Tuesday. He had a paragraph of rough notes, a Claude window open, and about twenty minutes before a client call. He pasted his notes in, asked...
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How This Book Was Actually Made
Here is how it usually goes. You spend a Saturday morning reading about a new AI workflow. You get good at it. You feel, briefly, like you are ahead. Then...
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One Recording, One Week of Content: The Weekly Pipeline
Monday you record a training call. Tuesday you need a newsletter. Wednesday a client wants a summary. Thursday you owe someone a short clip for their...
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Running Facebook Groups: Thirty Minutes of Janitorial Work
Every morning for years, same routine. Log into the group, scan for spam, bounce the obvious bots, referee whatever argument had started overnight, and...
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The January Voice Memo and the Six-Month Check
You learned the workflow in March. It was obsolete by May. That's not a learning problem. That's a map problem.
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The Amazon App in the Best Buy Aisle
You're standing in a Best Buy. A TV on the wall looks right. Price seems fair. You pick up your phone, scan the barcode, and check Amazon before the...
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Claude Says 'Hey Damon'
About two years ago, Damon opened a new AI tool for the first time. It said: 'Hey Damon, what can we start with today?'
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The Pre-Sold Tool That Never Sold
You know that feeling in March when you finally got a workflow dialed in, and then by May the tool it ran on was already a footnote? That's not bad luck...
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Ten Years Training Dragon, Two Years of Wispr Flow
For about ten years, I started every morning the same way. Sit down, open Dragon NaturallySpeaking, read a few sentences out loud to warm it up, and pray...
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The Dunkin Drive-Thru Fumble
Every week, same Dunkin. Same two orders. Same plan: pull up the app in line, QR code ready before the scanner guy leans out. It never works. The app is...
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Teaching the Machine His Voice
He'd fed it hours of webinar transcripts. His Friday-call stories. His Texas drawl in paragraph form. And when he asked the AI to define his writing...
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The $97 Tool That Quietly Died
It didn't send a farewell email. There was no announcement, no changelog entry, no moment you could point at. One ordinary week, the specialized tool he'd...
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The Dog Walk That Built SalesPageRescue
It was a Saturday morning dog walk. Nothing scheduled, nothing urgent. Damon had spent the previous day running a training session, and on a whim he'd fed...
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The Lunch Interview That Built a Website
It was a Friday in January. Damon sat down with his son over lunch, asked him about his goals, the sites he liked, who his competitors were. Standard...
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