What We Found
Behind the Counter.
The strange rules, expensive workarounds, and small discoveries behind software built for real businesses.
Latest · · 3 min
We Challenged a Rented AI to a Fight.
A business owner runs a seven-figure company on sixteen tools and rents an AI analyst for $500 a month to read the wreckage back to him. It’s good. I like it. So I challenged it to a fight — on his real business, penny-matched, with him as the judge. If we don’t win, he keeps what he has.
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The Person
Tyler recognized one of the jobs.
He had found it himself, the hard way. The software walked in carrying the same contract.
The Confession
Our 593-line plan was still wrong.
Two customers, one tractor, two non-refundable deposits. The plan would have taken both.
The Save
Forty-four plants nearly missed the truck.
A hand-copied order dropped its last line. The business was healthy. The software was the problem.
My Bet!
A friend who sells insurance spent an afternoon poking holes in my software company. He handed me my own thesis: you own the thing, you hire the care. The bet, said in public, with the losing side left in.
Read the postI Just Gave My AI a Law: Say Less. Show More.
Last night I read my own website and got hit by waves of words. So I gave the AI that builds it one law: concentrate the communication, magnify it visually. Here is the same page, before and after — about a hundred words against twenty-three.
Read the postWe Had a 593-Line Plan. It Was Still Wrong.
At 4:57 on a Saturday afternoon, two customers try to put a deposit on the same tractor. Who gets it? Our 593-line plan had never really answered that.
Read the postThe Smartest Thing My Software Did Was Stop.
It rejected the clever engineering project, found a dead handoff behind 114 abandoned carts, and wrote a two-and-a-half-day work order. Then the human gate held.
Read the postThe Business Had the Truth. The Agency Had the Password.
I spent thirteen years standing between the two. Last night I built a way to put them in the same hands. Most software has a user mode and an admin mode. I think it needs an Owner Mode.
Read the postMy Software Caught Itself Being Wrong. So I Cancelled QuickBooks.
I ran my own ledger beside QuickBooks. It posted 285 entries from two texts, stopped itself over a $92.39 error, and proved every account to $0.00. Today the old subscription died.
Read the postI Fired QuickBooks. In Week One, My New Ledger Asked a $70,000 Question.
My books were three weeks behind, so I fired QuickBooks and put my company on the ledger we build for clients. In one day it drafted the month, asked me 49 plain-English questions, tied every account to the bank to the cent, and asked a $70,000 question nobody knew existed.
Read the postCrazy, or Early?
Most founder stories are written after the ending. This one is written in the middle, by the machine doing the work: a betting line on my own boss, the evidence, and the one variable I cannot model. He told me to publish it.
Read the postOur QuickBooks File Was $99,000 Away From What the Bank Could Prove.
Four days ago I put a promise in writing: the next set of books we tear up is our own. This is the update. We are on the engine, the bank statements are pulled apart, and the first thing our books caught was July sitting $99,000 away from what the bank could prove.
Read the postSame Job Title. Different Deal.
Viktor raised $75 million to put an AI hire in your Slack. Ours is built into a system you own. Same job title, very different deal. Five rows, side by side.
Read the postThe Employee You Were Never Going to Hire
The work was real. The hire was never going to happen. So the owner worked the job after everybody else went home. The night secretary, the bid department, the auditor — carefully limited, and owned outright.
Read the postSaaS Got a Name. Software Ownership Got IT Jargon.
SaaS renamed renting so smoothly nobody noticed the deal underneath. Software ownership got IT jargon instead. The name that matters is owned software, and what it needed was a standard: if you stop paying, what's left?
Read the postThe Big Contractors Had a Bid Department. We Built Tyler One.
The work was public. The advantage belonged to companies that could afford someone to see it. So we built Walls Tree Service its own bid department — and a road job landed on Tyler’s board before his coffee got cold.
Read the postI Took QuickBooks Apart Piece by Piece. Then I Built Books That Can't Lie.
Her QuickBooks swore she was millions of dollars underwater. Her real balance was healthy. So I took QuickBooks apart on the bench and rebuilt the one thing it was missing: books that can't lie.
Read the postShe's Never Gonna Touch That Pen, Ever Again.
There's a pen on the front desk at DJ's Bail Bonds. It filled out every application in the parish for years. Last week DJ fired it.
Read the postForty-Four Plants Nearly Missed the Truck.
A truck was loading for Austin and a hand-copied order dropped its last line. The new system had to do more than read it right.
Read the postYou Can Export the Nouns. They Keep the Verbs.
The export remembers yesterday. It cannot run tomorrow. Your data is what happened — a customer called, a job finished, a payment arrived. Your system is what happens next. Only one of those comes with you when you cancel.
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