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We Sent Our Clients a Bad AI Email. It Built Our Best Sales Framework.

b2b sales copywriting marketing sales

David Deutsch and I do a segment every week called "2 Takes From The Field." No script.. just what we're both seeing right now. This week we went looking for the opposite of a hot take. We went looking for marketing mistakes that got turned into wins.

Here's mine. One of my client teams had an AI tool draft a client email. Nobody checked it closely enough. It went out to real clients, and it read like slop.. generic, hollow, the kind of email that makes 25 years of relationship-building look careless in one send.

That's a crisis. It's also, if you catch it in time, an opening.

The Five Rounds

Instead of apologizing and moving on, we sat down and asked a different question: what actually makes an email good? Not "sounds nice." Good enough that a client reads it and can't stop.

We took their existing process apart and rebuilt it as five rounds of improvement. Round one, two, three.. each one tightens the copy against a specific test. By round four, we're checking something most people never check at all: does this email hit enough of the emotions that actually drive a "yes"?

The Nine Emotions

Communication is emotional first, logical second. People decide on a gut level, then build the rational case to justify it to themselves afterward. So round four runs every piece of copy against nine emotional levers: vanity, greed, lust, fear, relief, addiction, nostalgia, novelty, and envy.

Write an email, check it against that list, and if it only hits two of the nine.. it's weak. Rewrite until it hits seven or eight. That's the difference between an email someone deletes and one they can't stop reading.

We turned those five rounds into a skill the team can run inside Claude Code. Write the email, run it through five iterations, go grab a coffee. Ten minutes later, you have a version worth sending. What was a crisis became a repeatable system, and the team decided, on their own, that they wanted to get good at this.

Two Older Examples, Same Idea

This isn't new. Avis was the number-two rental car company in the 1960s and turned that into the entire pitch: "We're only No. 2. We try harder." Volkswagen's Beetle was small in a market that worshipped big American cars, so they said it plainly: "Think small." Low gas cost. Easy to park. Easy to drive. The disadvantage became the argument.

Levi's did the same thing with a modern twist this year. Stadium sponsors at the World Cup had to cover their branding, so Levi's took the exact shape their logo left behind, printed it on t-shirts, and let it become an inside joke.. you know what it means, or you don't. That's status. That's belonging. That's a far better use of a restriction than complaining about it.

The Actual Lesson

A mistake, a restriction, a disadvantage.. none of it is automatically bad news. It's raw material. The question is never "how do we hide this." It's "what does this teach us, and who gets to be an insider once we've fixed it."

If you're sitting on a marketing lemon right now, that's usually the moment worth paying the most attention to, not the least.

Watch the full conversation with David Deutsch here: https://www.youtube.com/watch?v=B6xc-tR9v9I

Happy hunting.

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