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Start here (before you write another email)

Emails That Don't Suck (with AI): Lesson 1

May 14, 2025 • Estimated Reading Time: 8 minutes

If you grabbed the 3‑Prompt PDF yesterday, this is the one I want you to start with.

It’s not flashy.

It won’t magically double your list overnight.

But it will make everything that comes next faster, easier, and more consistent.

Step 1: Choose your email style

Before you worry about welcome sequences, lead magnets, or offer stacks…

You need to decide how you want to show up in people’s inboxes.

You’ve basically got two options:

  • Personal-style:

    Casual. Conversational. Feels like a note from a friend.

    Great if you’re building a personal brand and selling coaching, consulting, or info-products. It’s flexible, human, and powerful for storytelling and trust.

  • Newsletter-brand:

    Structured. Skimmable. Feels more like a publication or media brand.

    Think logos, recurring sections, and curated links. If your goal is to become the go-to newsletter for a topic—like "TLDR AI" or "The Hustle"—this makes it easier to scale, attract sponsors, and build systems around content.

Neither is better. But one probably fits you better—right now.

And here’s the thing I want you to remember:

You’re not locking yourself into this forever. You’re just picking a starting point.

When I first started experimenting with an AI-focused newsletter, I tried a few different formats:

  • First, I did a short, daily, curated newsletter—Monday through Friday. Quick links. A couple lines of commentary.

    It was fine, but it didn’t feel like I was saying much.

  • Then I tried a “how-to” format: once a week, in-depth walkthroughs of tools or prompts.

    But it took forever, and again—I didn’t love the output.

  • Eventually, I landed on How I AI, and even that evolved:

    • Started with a structured weekly newsletter (sections, links, a quiz, etc.)

    • Now I’m writing more freely—sharing use cases, strategies, even experiments like this one you’re reading.

I still love both formats.

I subscribe to both styles.

But for me, right now, I want something more personal. More story. More substance.

And I gave myself permission to adapt.

You should too.

So let’s get your starting point:

👉 Paste this into ChatGPT (or your AI of choice):

Act as an email marketing coach and strategist and help me determine what email format fits me best. Ask me a few relevant questions about my audience, my business/offer, and how I naturally communicate and create content. Then recommend whether I should send personal-style email marketing or build a branded newsletter and give me a simple structure I can follow. Keep your recommendations simple, actionable, and aligned with my available time and content style.

⚡ Pro tip:

Use a fresh chat window and answer the questions it gives you.

Treat it like a real coach. The more honest and detailed you are, the better the advice gets.

Here’s what ChatGPT asked me:

Questions for You:

What’s your main goal with email marketing right now?

(e.g., selling more services, staying top of mind, nurturing leads, building authority, etc.)

What type of business are you running and what do you sell/offer?

(Physical product, service, coaching, local business, etc.)

Who is your target audience?

(Demographics, mindset, pain points — the clearer you are, the better we can tailor the tone.)

How do you naturally like to communicate or create content?

(Do you like writing casually like you’re texting a friend? Or do you prefer more polished, visual, or professional content?)

How much time can you realistically give to writing an email each week?

(Be honest — if it’s 15 minutes, great. If it’s an hour once a month, that’s helpful to know too.)

And here were my real answers:

1 - ultimate goal is to build a profitable email list - i want to be able monetize through ads/sponsorships, affiliate offers, and selling my own info products and coaching.

2 - I offer coaching/consulting services around using AI to grow a profitable email list. I want to create digital products around this as well.

3- target audience is online entrepreneurs (primarily solopreneurs / solo founders / coaches / consultants) who know they need to send more emails to make more sales but don't have time and/or have some fear or uncertainty holding them back.

4- I like to write but I'm still learning to write quickly and concisely. I also like doing live coaching sessions. I can do pre-recorded video as well but I get in my head about it.

5- I want to set aside at least 30 minutes a day to write an email.

And here’s what ChatGPT recommended:

Thanks! Based on your goals, audience, and content style, here’s the email format and approach I recommend:

✅ You Should Use a Personal-Style Email Format This approach:

Builds trust and connection (key for coaches and info products)

Feels human and low-pressure, perfect for your audience who already feel overwhelmed

Makes it easier to write consistently without needing fancy design or visuals

Sets you up well for monetizing through affiliate links, coaching, and digital offers

Your audience wants permission and inspiration to take action, and they resonate with real, relatable, and actionable content. A personal email builds that bridge.

It even gave me a simple format with examples to get me started.

(When I ran the prompt with different inputs, it recommended a hybrid format—which may be where I’m headed too.)

Run the prompt. Answer the questions.

Then hit reply and tell me what it said for you: personal or newsletter? Something in-between?

Tomorrow, we’ll tackle prompt #2: how to use AI to generate 10 (or more) email ideas in one go—so you’re never staring at a blinking cursor again.

You in?

Thanks for reading,

Nathan

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When you’re ready, here’s how I can help

I build personalized AI Email Engines that turn your own words and stories into ready‑to‑send drafts in seconds so you can hit Send on time and on brand.

I take only a few clients at a time. Even if we’re not a match, you’ll leave the call with some quick wins you can use immediately.

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