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Why Your AI Emails Don't Sound Like You — & the Fix Nobody's Talking About (with Andy O'Bryan)

A real talk live stream with a copywriting and AI genius I call friend.

Thank you to everyone who tuned into my live video! Join me for my next live video in the app.

Why Your AI Emails Don’t Sound Like You (And the Fix Nobody’s Talking About)

If you have used AI to draft your emails, you have probably hit the same wall most coaches and consultants are hitting right now. The copy comes out polished. It reads smoothly. It even looks “professional.”

But then you send it and something feels off. Or you notice your emails all start sounding like everyone else’s. The personality flattens. The edge disappears. Your voice gets smoothed over until it could be written by anybody.

That is not a prompting problem. It is a creative control problem.

The real issue: AI produces “generic usable,” not your lived experience

Andy O’Bryan, copywriter and AI strategist, points out that AI can take strong source material and turn it into something clean and generic. The result is what people have started calling “AI slop.”

What gets lost?

  • Your personality and unique nuance

  • Your specific scars and history (the things that made people pay attention in the first place)

  • Your natural way of arguing, your rhythms, your phrasing habits

The scary part is that it can underperform even if it “looks good.” People may not be able to articulate why, but their engagement drops because the writing no longer carries the signal of a real human thinking, choosing, and feeling.

Prompting will not fix “flattened” writing

It is tempting to treat AI like a writing genie. You ask for better, you tweak the prompt, you request more emotion, you tell it to sound like you.

But if the starting point is missing your real input, the output will only rearrange generic patterns into a cleaner package.

That is why “better prompting” often fails. The problem is deeper: you are letting AI take the role of author too early, too completely, and too confidently.

The fix: start with your real content, then let AI shape it

The strategy is simple but non-negotiable:

  • Before AI: write a rough draft using your own brain

  • After AI: rewrite, humanize, and keep the last word

In other words, AI should be an assist, not the person driving.

The “Humanize” mindset: don’t let AI have the last word

One of Andy’s core ideas is that “humanizing” is not something you do by running AI output through another AI tool. That approach is still AI polishing AI.

Instead, you humanize by editing with your own authorship present.

Here is the practical rule many people adopt:

  • Use a minimum “you” quota. Start by humanizing at least 25% of the AI output (subject line, opener, call to action, key sentence, or the emotional core).

  • Make sure you keep the last word. Do not paste AI’s final draft into your sending workflow.

You are not trying to make it perfect. You are trying to make it recognizably yours.

Humanizer tactics you can use immediately

1) Check for “AI speak” and clichés

AI often drifts into recognizable patterns: cringy structure, overbuilt contrasts, and phrasing that feels like it came from a template. You may notice lines that feel like “it’s not this, it’s that,” short staccato sentences, and overused AI words.

A quick workflow that works:

  • Read your draft once for meaning

  • Read it again for voice

  • If a sentence does not sound like you, rewrite it or delete it

2) Do not ask AI to manufacture emotion

This is especially important for email nurture sequences. AI can “season” emotion, but it will rarely produce real feeling. When you manufacture emotion, readers can feel it.

Andy’s guidance for nurture emails:

  • Start with something real you experienced: a hard week, a frustrating moment, a surprising client comment, a small win, a moment your thinking shifted.

  • Then use AI to organize it into a clean, readable structure.

The emotion has to originate with you. AI can help frame it, but you cannot outsource the lived moment.

3) Write the raw input first: “what happened, what I think, why they care”

This is Andy’s most practical golden nugget.

Before you open AI, write three rough sentences:

  1. What happened? (The factual trigger for the email or idea.)

  2. What do I actually think or feel? (Your real stance, your honest emotion.)

  3. Why might my reader care? (The payoff for them, in their world.)

Then prompt AI like an editor, not like a replacement author:

“Help me shape this into a clear email without making it sound generic.”

This one shift changes everything because AI finally has something true to work with.

A simple framework for “AI without sounding like everyone else”

If your emails are starting to sound identical across your market, use this framework.

  1. Author first (you write rough). Your voice enters at the beginning.

  2. Delegate structure (AI organizes and tightens). Let AI improve clarity and flow.

  3. Humanize key parts (you rewrite the core). Subject line, opener, one pivotal sentence, and the call to action.

  4. Keep the last word (final edits are yours). Never send an untouched AI draft.

Balancing AI you can love with AI you should resist

Andy is not anti-AI. He uses tools like ChatGPT and has experimented with others such as Claude. But he treats AI like a negotiation.

Key idea: AI’s output is its first bid. You counteroffer. You do not accept the first draft as agreement.

He also described this as an ongoing existential tension: you can appreciate AI’s speed and capabilities while still worrying about creative atrophy. The danger is that efficiency can become a villain. You might save time, but you trade away your sharpest advantage: your human judgment.

AI subject lines: a great use, with guardrails

Subject lines are one of the most legitimate places to use AI. They are measurable and tied to open rates. If you struggle here, ask AI for options.

A workable method:

  • Ask AI for 20 subject lines

  • Choose the ones that feel most like you

  • Generate 20 more based on the top performers

Use AI for selection and iteration. Use your voice for final choice.

What about AI and copyright? (A cautious, practical view)

AI-created text sits in a gray area that keeps shifting as laws and court decisions catch up. Data sources can be unclear, and the risk increases when writing becomes too derivative of sources rather than genuinely authored by you.

Until the rules become clearer, a safer guiding principle is:

  • Write as much of the creation as you can.

  • Use AI to enhance, not to replace.

  • Do your due diligence. Especially for commercial and brand-critical work.

In other words, “humanize” is not just about sounding like you. It is also about increasing the chance that the work is truly yours.

One action to take today

Before drafting your next email, do this:

  • Write three rough sentences: what happened, what you think or feel, why they care

  • Then ask AI to shape it into a clear email

  • Rewrite at least 25% so the voice is unmistakably yours

If you do that, your emails will stop sounding like generic “better prompting” output and start sounding like lived expertise again.

Your voice is still the edge

AI can help you organize ideas and improve readability. It can shorten drafts. It can give you options.

But the parts your audience responds to are the parts AI struggles to truly replicate: vulnerability, specific history, real emotion, and authorial judgment.

Keep the last word. That is where your originality becomes your competitive advantage.

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