Look, I never thought I’d be sending out a newsletter. Newsletters felt like something Silicon Valley people did, or maybe those hyper-organized types who’ve had their lives figured out since 1997. But here’s the thing-I realized I had something worth sharing, and my friends kept asking me how I was using AI to actually make money. So I built a newsletter, and honestly, it took me about two hours and a cup of coffee. No writing degree required.

Why This Matters for People Like Us

We’re at this weird intersection where we’re not quite digital natives, but we’re also not dinosaurs. We remember life before the internet, which actually gives us credibility with people our age who are tired of crypto bros and 25-year-old influencers telling them how to live. A newsletter is basically a direct line to people who actually care what you think, and it doesn’t require you to be some polished writer or content machine.

The money part matters too. I know guys who’ve built their entire side income around newsletters-sponsorships, affiliate links, even their own products. But you don’t start there. You start by building a list of real people who want to hear from you, and AI takes the friction out of actually writing the thing.

What I Actually Found

I tried three different approaches because I’m basically a professional overthinker. First, I used ChatGPT with prompts like “write me a newsletter about making money with AI” and it was fine but felt robotic-like having a very eager intern write for you. Then I tried Claude, which gave me more conversational output, closer to how I actually talk. That was better. But the real game-changer was using AI to outline my thoughts first, then letting it expand them into something readable.

Here’s what actually works: you jot down three or four bullet points about something you know, paste them into ChatGPT with “make this sound like a conversation, not a textbook,” and suddenly you’ve got 300 words that actually sounds like you. Takes maybe 15 minutes, tops. I’ve been sending mine out every two weeks and people are actually opening them, which shocked me.

The platforms are almost embarrassingly simple. I use Substack because it’s free to start, handles everything, and people expect newsletters there. Beehiiv is another solid option if you want slightly fancier analytics. Both work fine, and neither charges you until you’re making real money.

How to Get Started Today

First, decide what you actually want to write about. This is the part AI can’t do for you, and that’s kind of the point. Maybe it’s what you’re learning about AI, your side hustle, books you’re reading, whatever. Pick something you could talk about to a friend for ten minutes without planning. That’s your lane.

Next, pick your platform. Sign up for Substack, takes five minutes. Create a free account and design something simple-you don’t need a fancy logo or perfect branding right now. Call it whatever feels authentic. I started with “Rewired GenX” because I was literally figuring out how to rebuild my career using new tools, and people got it immediately.

Then write your first issue however you want. Write it in Notes on your phone, voice memo, whatever. If you’re stuck, use an AI tool to help you organize your thoughts or punch up your prose. I’ve put stuff like “expand this into a 400-word newsletter about why most people fail with AI” into ChatGPT and got something I could actually send out. Not perfect, but real and conversational.

Finally, send it to people you know and ask them to subscribe. That’s it. You’re not going to reach 100,000 people right now. You’re building something real, one reader at a time.

Look, this isn’t some get-rich-quick scheme. But I’ve met people making genuine income from newsletters they started in their spare time, and none of them are professional writers. We’ve got the advantage of actually understanding our audience because we’re our audience. If you want to see exactly how I structured mine and what’s working, I’ve got some resources over at rewiredgenx.com/links/ that might help you get the technical stuff sorted.

Start this week. You’ve got nothing to lose.

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