How Creative Entrepreneurs Can Use ChatGPT to Automate Personalized Email Sequences

When we launched our new quiz on our website, we wanted to provide personalized value to each person that took the quiz. But the amount of work it would take became immediately overwhelming if we were going to write every email ourselves. If there’s 6 unique results and each would get a 7 email sequence, that’s a whopping 42 emails. And if each email is a short 300 words, that still works out to 12,000+ words of copy to write…Oh, and each one needs to have actionable tips to help the reader.

This is where using chatGPT like an intern becomes really handy. We don’t expect it to be smart, or even provide any of the advice; we use it to repurpose things we’ve personally said to coaching clients in the past and fit those insights into short, impactful emails.

Here’s the exact process and prompts we used to write out all six of our sequence:

Step 1: Anchor it on conversations we've had with our clients

For each of our coaching calls, we take notes that we share with our clients. This is a GOLD MINE of advice that we've given our coaching clients within the context of a specific problem. Since each one of these call notes is linked in a Google Docs file, with multiple sessions in a folder, this easily represents 20+ hours of conversations that we can anchor chatGPT on. A couple of helpful hints before we move forward:

  • Give chatGPT a "role": you can see I asked it to be a "professional web developer who specializes in copywriting that converts". This helps it to calibrate the type of answer you want.
  • At the first level, ask it to structure the data you gave it - in our case, it gave us 6 common problem types that most of our coaching conversations fall into

Step 2: Refining the answer into what you're specifically wanting it to do

Oftentimes the first answer you get back isn't the best. So you have to shift the question, or even give chatGPT more context for it to give you a better result. The 6 pain points, that turned into our 6 sequences are:

  1. Unclear Offers & Messaging
  2. Pricing & Money Mindset Blocks
  3. Inconsistent Lead Generation
  4. Struggle with Sales & Conversion
  5. Overworking & Under-Earning
  6. Fear of Visibility & Showing Up Online

Then I had chatGPT plan out the quiz (read the blog post about building the quiz here)... but eventually came back to emails

Step 3: Ask it to train itself on best practices

In step 1, I anchored the model on our business specifically. This step is about asking chatGPT to "do homework" on how a good email for this specific use case would be written and what it would look like. Much like how you would ask an intern if they knew what they were doing before you gave them a task, it works the same way with chatGPT.

Step 4: Make the first outline

Keeping the intern analogy going, you can't ask it to write all the outlines at once because it'll get overwhelmed and the quality will drop. You have to be specific about what you want to be included in the outline and remind it that it has to use real examples rather than just making things up (it still will sometimes...).

Oh, and much like an intern you ALWAYS need to check it's work, add notes, and ask it re-do it until it gets to a “good enough” stage where you can make minor changes to get it across the finish line.

Step 5: Write the emails (one at a time)

For the first email in the series, taking the time to give chatGPT all the "rules" you want for your emails saves a TON of time. But for every email after that, I didn't have to repeat the rules; I simply gave it the next outline and iterated (aka: asked for revisions) on each email until I was happy.

Step 6: The result

This is an email going into our Overworking & Under-Earning sequence. Once we took it out of chatGPT we then did minor revisions of specific words and language used to make sure it still sounded like us:

Ever feel like every client request turns into a custom project? What should be a simple service suddenly becomes a one-off, highly personalized offer that eats up time, energy, and—let’s be honest—profits.

We see this all the time. In fact, one of our coaching clients was drowning in custom work until they made one key shift: Standardizing their services.

Because here’s the truth:

🔄 Custom everything = inconsistent results & burnout.

​✅ Clear, streamlined packages = less work & more profit.

The best way out?

Create clearly defined, repeatable packages.

​Clients don’t need more options—they need clarity. When your offers are simple, specific, and structured, people trust them more (and buy faster!).

Your quick-win challenge:

1️⃣ Identify your most popular or frequently requested service.

2️⃣ Ask: How can I simplify this into ONE streamlined package?

​3️⃣ Define exactly what’s included (and what’s not).

For example, instead of offering “custom branding,” you might create:

🚀 The Signature Brand Package – A clear, three-step process with a defined price and deliverables.

The result?

✔️ You spend less time customizing and more time scaling.

✔️ Clients feel confident knowing exactly what they’re getting.

✔️ You create predictable income (instead of reinventing the wheel every time).

Now, it’s your turn! Reply and tell us your new simplified offer idea—we’d love to celebrate with you!

And if you need help refining your offers so you can work less while earning more, book a free discovery call with us , and let’s build a business model that works for you.

A few things to note:

  • We used the GPT-4.5 model for making the outlines, and GPT-4o for writing the emails one and a time. These are both paid models as of today, but for us and the time it saved us it was some of the best $20 we've spent on our business in a while.
  • And yes, even on the paid version, we still almost ran out of GPT-4.5 prompts.
  • This wasn't all done in the same chat, so I had to repeat some of these steps when I started a new chat to "re-train" chatGPT since each chat is a new "context window," and most information doesn't get transferred between chats.
  • We don't recommend sending your audience anything directly out of chatGPT. I spent almost a full workday chatting with chatGPT before I settled on this method of getting anything close to good enough to use.
  • I re-wrote over half of the emails because, after a night of sleep, I couldn't bring myself to actually send the first versions to our audience.

Can chatGPT completely replace all our writing tasks? Nope. I still wrote this blog post. I still write my own weekly emails. But it does make a really good sounding board, creative assistance, and research partner. In other words, it's just a really good tool that’s consistently getting better.

Have thoughts to add to the discussion or questions about using chatGPT in your business? Comment below or send us a DM on Instagram @joandlyndon. I’d love to hear your thoughts.

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This article was written by Lyndon Bradfield, the left brain of Jo & Lyndon. When he’s not experimenting with chatGPT, he’s probably reading articles on business related topics, has his head in a book, is training for Mt. Kilimanjaro, or is supporting our incredible coaching clients. Curious about our coaching? You can find more info on our coaching offers and schedule a free 15-30 minute intro call here.

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