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Latest

Aug 12, 2026

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3 min read

The Fields You Don't Need

Customers rarely leave over one bad experience, they leave over a slow accumulation of small impositions nobody bothered to remove. The businesses that remove that friction keep the customers everyone else quietly loses.

Aug 5, 2026

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3 min read

The $15,000 Lesson On Risk

A rock bottom price and none of your own money on the line look like genius right up until the market turns. After that, that’s usually the reason you can't walk away.

Jul 29, 2026

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2 min read

The $50,000 Slide Deck You Don't Need

Leaders treating faster meeting notes and slicker decks as real AI strategy doesn't provide the edge they think it does. It's that thinking that's costing them the exact edge AI was supposed to give them in the first place.

Jul 22, 2026

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3 min read

The People You Almost Automated Away

AI transformation succeeds or fails on one decision most leaders never make deliberately: what happens to your people once you take the busy work off their plate?

Jul 15, 2026

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3 min read

When the Exit Isn't a Choice

Most business owners spend years building value and almost no time deciding who should get it once they leave. Matt Middendorp has watched that question get answered badly more times than he can count, usually because it never got asked at all.

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