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Practical writing for owners and operators who have to make technology decisions without a degree in it. No buzzwords. No sales pitch dressed up as advice.

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How to use AI in your small business, beyond writing

Most people use AI to write, and that is the least interesting thing it can do. Six other jobs to hand it: paper to spreadsheet, equipment photos, your own numbers, contract checks, SOP interviews and tiny tools, with a prompt for each. With the video and full transcript.

Tim Wenger · October 2026
AIVideoSmall Business

Why context matters when you use AI

The same ChatGPT request, run with and without context, gives one answer I would never post and one that sounds a lot more like me. What context is, why every assumption the AI makes is a potential error, and a context brief you can copy. With the video and full transcript.

Tim Wenger · October 2026
AIVideoPrompting

Custom software vs off-the-shelf: how to choose

What to rent, what to own, and when to just fix what you have. What AI changed about the cost of building, why buying an ERP rarely skips the build, six questions to ask before you build anything, and when custom is overkill. With the video and full transcript.

Tim Wenger · Updated October 2026
Custom SoftwareVideoBuy vs Build

Hiring a freelance developer? Check the code before you take it over

A business owner's freelance-built web app shipped with code hidden in a configuration file that let an outside party run commands on any machine that opened it. What we found, what nobody knows about how it got there, and seven ways to protect yourself when you hire a freelancer.

Tim Wenger · October 2026
SecurityFreelancersTakeovers

The AI executive assistant that lives in Slack

We built a client a way to stop carrying every promise in his head: he types them into Slack like a text, AI tracks them, and a summary shows up every morning. Why it lives where he already works, and why to build the system before you hire an assistant. With the video and full transcript.

Tim Wenger · September 2026
AIVideoAutomation

Why AI gives you generic answers, and the fix

Every gap you leave in a prompt, the AI fills with a guess, and the guess is what makes the answer generic. The ice cream test, why this is a communication skill rather than an AI skill, and three questions that show you what it assumed. With the video and full transcript.

Tim Wenger · September 2026
AIVideoPrompting

How much should business owners trust AI?

I gave ChatGPT, Claude and Gemini the same software quote request twice each and got six prices from $42,000 to $128,000. The cheapest one included more than the $98,000 quote. Here's what that means for trusting AI with real decisions, with the video and the actual chats.

Tim Wenger · September 2026
AIVideoCustom Software

The software you shouldn't have to think about

Most business owners spend more attention on their software than they should have to. Here's what it actually takes to stop thinking about it, and what usually goes wrong instead.

Tim Wenger · September 2026
Long-Term SupportCustom SoftwareHow We Work

Should you hire a developer or hire a firm?

Most advice answers this with a cost comparison. That's the wrong question. Here's the one that actually decides it, plus the third option almost nobody writes about.

Tim Wenger · September 2026
HiringIn-House vs AgencyTeam Extension

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