Newsletters are the ultimate side-hustle for Gen X.
They’re easy to start, cheap to maintain, and simple to scale. And with the right AI tools? The whole thing gets 10x easier.
But here’s what most people get wrong…
You don’t need a huge list. Or post every day. Or spend hours messing with tech (not like the old days of the web anyway).
You just need a clear, simple system—and a plan that fits around real life.
That’s why I put this guide together.
It shows you how to launch a newsletter that builds trust, grows your list, and starts bringing in job-free income… all from one post a week.
Inside this guide:
AI prompts to build faster, so you’re never staring at a blank screen
The “One Post, Two Platforms” system to write once and grow twice as fast
Lead magnet prompts that actually convert (no more guessing)
3 sneaky monetization paths that work before you hit 100 subs – How to get your first 100 subs—even if you hate promoting yourself
Ready to see how it all comes together?
The exact framework I used to build multiple income streams—starting with just one post a week—is waiting on the other side…
Table of Contents
LIVE UPDATES
Just so you know this is a living, breathing document. I am will be making updates as discover new information and get feedback from readers. Right now I’m working on fine tuning the the AI prompts. So, keep this link handy and be sure to check back from time to time. If there’s a big update, I’ll let you know via email.
Last edited: 12/9/2025
Why It Matters:
Your email platform determines how easy it is to grow and monetize your newsletter. I strongly recommend Beehiiv as the best all-in-one platform for serious newsletter creators. It is the platform you are reading this on right now!
🔥 My Top Pick: Beehiiv → Sign up for beehiiv (save 20%) ($)
Best-in-class growth features (referral programs, recommendations, SEO-friendly pages).
Easy monetization (ads, subscriptions, sponsorships).
Super clean & fast setup.
Write Once, Publish Twice → Increase chances of getting search engine traffic passively by posting blog content & newsletter at the same time.
Built-in Money-Making Tools → Affiliate tracking, paid subscriptions, sponsorship management.
Modern Features That Matter → AI writing assistance, growth tools, and professional design.
Everything I wish I had when starting → No more copying between platforms.
Other options:
Kit ($) (great for creators who want automation & courses. But not ideal if you want to start a blogletter and have your newsletter discoverable on search engines for more traffic and reach).
Substack - Great if you want simple, not so great if you want to monetize your newsletter and turn it into a business. More on that in my beehiiv vs Substack for beginners comparison.
Mailchimp (okay for beginners, but limited growth features and very outdated IMHO).
🤖AI Prompt:
Compare the top email marketing and newsletter platforms—beehiiv, Substack, Kit, and Mailchimp—for a newsletter creator at the beginner, intermediate, and advanced level.
Focus the comparison on:
- Automation (ease of setting up sequences, triggers, etc.)
- Monetization (paid subscriptions, sponsorships, affiliate integration)
- Blog Publishing (on-platform publishing, and SEO)
- Business Building (scalability, ownership, integrations, analytics)
Clearly highlight which platform offers the best room for growth and long-term scalability at each experience level. Format the output in a comparison table followed by key takeaways.These are all great platforms but if you want to use Blogletter method, and multiply your efforts, you’ll need to go with beehiiv because they are the only platform list here that does this well - or at all - IMHO.
✅Action: Sign up for beehiiv for free and start your setup ($) Use my link and use code “REDEFINE” to get 20% off your first 3 months of Beehiiv ($) - a sweet deal for RedefiningRetirement readers.
📌 Step 2: How to Find a Profitable Newsletter Niche Using AI
Why It Matters:
Your niche defines your audience, content, and monetization strategy. A well-chosen niche ensures your newsletter attracts the right subscribers who are interested in doing something specific—not just passively learning.
A simple framework to niche down:
Who do you help? – Entrepreneurs, designers, freelancers, executives, etc.
What is their problem? – Overwhelm, lack of clarity, no system, etc.
How do you solve it? – Actionable strategies, templates, guidance.
Example:
Wrong: "A newsletter about fitness."
Better: "A weekly plan to lose 10 pounds by summer—no guesswork."
🤖 AI Prompt: Swap out [WHATEVER IS IN THESE BRACKETS] with your info and see what you get.
You’re a newsletter strategist. Help me define a clear niche based on:
- My expertise: [your industry or skills]
- My passion: [your interests]
- My audience: [who you want to help]
Use this framework:
- Who do I help?
- What problem do they face?
- How do I solve it?
Give me 3–5 niche ideas with clear outcomes and room to monetize.✅ Action: Review AI’s suggestions and refine your niche and audience.
You don't need a perfect plan, you have already AI and you just need a login. Beehiiv is free to start, so you've got zero excuses left. Click here to sign up. (And hey, use code REDEFINE for 20% off if you ever upgrade. Might as well save a few bucks.)
📌 Step 3: Decide on a Type of Newsletter
Why It Matters:
Before you dive in, consider what type of newsletter format best suits your niche and expertise. Choosing the right format ensures consistency and audience alignment, making it easier to provide value and sustain long-term engagement.
The Analyst – Provides deep analysis, case studies, and data-driven insights.
The Curator – Gathers and shares the best content from around the web, saving readers time.
The Expert – Offers direct knowledge, advice, and unique perspectives from your experience.
The Reporter – Covers industry news, trends, and current events with commentary.
The Writer – Focuses on storytelling, personal essays, and engaging written content. Here’s my version of The Writer - Check out the Story To Startup Model.
🤖 AI Prompt:
You are a newsletter strategy expert. Help me decide what type of newsletter I should create based on my niche, expertise, and audience.
Here’s what to consider:
- My niche: [INSERT YOUR NICHE]
- My experience or strengths: [e.g., writing, curating, analyzing, storytelling]
- My audience: [Who they are and what they want]
- My goal: [e.g., build authority, drive traffic, generate leads, build community]
Suggest the best-fit newsletter type from the following formats:
- The Analyst – Deep dives, case studies, and insights
- The Curator – Top content from around the web
- The Expert – Advice and insights from personal experience
- The Reporter – News, trends, and industry updates
- The Writer – Stories, essays, and narrative-driven content
Explain why it’s the best match and how I can make it sustainable and engaging long-term.✅ Action: Choose your newsletter type and outline how it fits your niche and audience.
📌Step 4: Choose a Name & Positioning
Why It Matters:
Your newsletter name and positioning should be clear, action-oriented, and instantly understandable. Your readers aren’t just looking to "learn." They want a result.
Naming Framework:
CLEAR Newsletter Name: Readers instantly understand the value (e.g., "10-Minute Marketing Fix" instead of "Marketing Musings").
CLEAR Newsletter One-Liner: Explain what readers will get in a short, compelling sentence.
Example: “Every Saturday morning, you’ll get 1 actionable tip to launch, grow, and monetize your business in under 4 minutes.”
🤖AI Prompt:
You are a positioning expert. Help me name and position my newsletter so it’s instantly clear, benefit-driven, and action-oriented. My readers don’t want fluff—they want results.
Here’s what I need:
1. Newsletter Name Ideas – Clear, specific names that immediately communicate value (e.g., “10-Minute Marketing Fix” instead of “Marketing Musings”).
2. Newsletter One-Liner – A short, compelling description that explains what readers will get, how often, and the outcome they can expect.
Details to consider:
- My niche: [INSERT YOUR NICHE OR TOPIC]
- My target reader: [Describe your ideal audience]
- Tone: [e.g., casual, professional, bold, witty, etc.]
- Frequency: [e.g., daily, weekly, monthly]
- Format or style: [e.g., tips, stories, curated links, short lessons]
Example one-liner:
“Every Saturday morning, you’ll get 1 actionable tip to launch, grow, and monetize your business in under 4 minutes.”✅Action: Pick a name and tagline that resonate with your brand.
Ready to bet on yourself? Let's do this. Sign up for Beehiiv for free right here ($). Use code REDEFINE to snag 20% off your first 3 months. Let's get to work.
📌Step 5: Create Your Lead Magnet
Why It Matters:
Your lead magnet (a.k.a. your offer) gives people a low threat reason to subscribe.
Types of Lead Magnets:
Buyer's Guide
Checklists
Cheat Sheet
Templates
Mini Course
Tools/App Access
Content upgrade
Join our waitlist
Quiz/Survey/Assessment
Free consultation or assessment
🤖AI Prompt:
You are a lead generation expert. Help me create a lead magnet for my business: {INSERT YOUR BUSINESS OR NICHE}.
Format the lead magnet as a [Checklist / Guide / Template] (choose one). Make it:
- Clear and easy to follow
- Actionable and results-focused
- Useful even for beginners in my audience
- Visually simple (use headings, bullet points, or short steps)
Add anything I might have missed that would make it more valuable, engaging, and effective for generating leads.✅Action: Pick a lead magnet idea and outline its content.
📌Step 6: Build Your Signup Page
Why It Matters:
Your signup page is often the first step in turning visitors into leads. A clear, focused design with the right elements boosts conversions and builds trust fast.
Key Elements of a High-Converting Signup Page:
✅ Clear Headline – Instantly communicates the value of signing up.
✅ Compelling Subheadline – Reinforces the offer and who it’s for.
✅ Benefit-Focused Copy – Tells them what they’ll get and why it matters.
✅ Strong Call to Action (CTA) – Direct, action-oriented button text (e.g., "Get the Free Guide").
✅ Minimal Form Fields – Ask only for what you need (name and email is usually enough).
✅ Visuals or Mockups – Show what they’re getting (e.g., a PDF preview or video thumbnail).
✅ Social Proof – Testimonials, subscriber counts, or trust badges to reduce hesitation.
✅ Mobile-Friendly Design – Looks and functions well on any device.
✅ Fast Loading Speed – No one waits for a slow page to load.
✅ Privacy Reassurance – Brief note that their info is safe and won’t be shared.
🤖AI Prompt:
Write copy for a high-converting email signup page for [insert product, lead magnet, or offer here].
The goal is to get visitors to sign up with their email. Include the following elements:
- A clear, benefit-driven headline (what they’re getting and why it matters)
- A compelling subheadline that supports the headline and speaks to the target audience
- Benefit-focused supporting copy (bullet points or short paragraph)
- A strong, action-oriented CTA (e.g., ‘Get the Free Guide,’ ‘Start the Quiz,’ etc.)
- A brief privacy reassurance line (e.g., ‘We’ll never spam you’ or ‘No fluff, just value’)
Optional: 1–2 lines of social proof (e.g., number of subscribers or a short testimonial)✅Action: Use AI’s output to create your signup page.
📌Step 7: Create Your Welcome Email
Why It Matters:
Your welcome email is the first touchpoint after someone subscribes. It sets expectations, improves deliverability, and starts building engagement. A well-crafted welcome email increases the chances that subscribers stay engaged and continue opening future emails.
Please note: While a 3-5 day email welcome series is ideal for nurturing subscribers further, this guide focuses on the first, most important email.
Key Elements of a Strong Welcome Email
Set expectations – Let them know what they’ll receive and how often.
Improve deliverability – Encourage a reply to signal that your emails aren’t spam.
Get new subscribers to reply – Ask a question or offer another freebie.
Move your email to the main inbox – Ask subscribers to drag your email from the promotions folder to their primary inbox.
Deliver the lead magnet – Provide a direct link to the promised freebie.
🤖AI Prompt:
Write a warm, engaging welcome email for my newsletter, [insert name]. The email should introduce me in a relatable and friendly way, setting expectations for what subscribers will receive and how often. It should feel like a one-on-one conversation, making new subscribers feel valued.
Key objectives:
1. Set Expectations: Explain what the newsletter covers and when subscribers can expect emails.
2. Improve Deliverability: Encourage subscribers to move the email to their primary inbox and reply to signal to their email provider that these emails are wanted.
3. Encourage Engagement: Ask a question or offer another freebie to prompt replies and create a personal connection.
4. Deliver the Lead Magnet: Seamlessly provide the promised freebie while keeping the email natural and engaging.
The tone should be friendly, warm, and conversational—like writing to a new friend. Use short paragraphs, light formatting (bold or bullets if helpful), and a clear call to action.✅Action: Write and schedule your welcome email immediately after signup.
📌Step 8: Announce & Promote Your Newsletter
Why It Matters:
Your initial group of subscribers is likely to come from the connections you have already established within your existing network. These could include…
👨👩👧👦 Family & close friends
👥 Colleagues & ex-coworkers
🤝 Business partners & vendors
🛒 Existing customers or superfans
📱 Social media connections
Want a deeper dive? Ask me for my step-by-step guide to getting your first 100 subscribers.
🤖AI Prompt:
Write a social media post for [LinkedIn/Twitter/Facebook] announcing my new newsletter. Make it engaging and personal. Include:
- Why I started the newsletter
- Who it’s for and what value it provides
- What readers can expect (topics, frequency, vibe)
- A clear reason to subscribe now
- A friendly CTA to join or check it out
Keep the tone aligned with my personal style:
[casual, helpful, bold, funny, etc.]
Newsletter niche: [INSERT NICHE OR TOPIC]
Link: [INSERT SIGNUP LINK]✅Action: Post link to subscribe on social media & invite your network.
📌Step 9: Write & Send Your First Email
Why It Matters:
Now, its time to send your first newsletter.
A good newsletter format is clear, consistent, and value-packed, making it easy for readers to consume and look forward to each issue. It builds trust, keeps attention, and encourages action.
Core Traits:
Skimmable: Short paragraphs, clear headings, and bullet points.
Consistent Layout: Familiar structure readers can count on (e.g., intro → value → CTA).
Valuable: Delivers insight, entertainment, or utility in every issue.
Personal: Written in a relatable voice—like a helpful friend, not a corporate robot.
Action-Oriented: Ends with a CTA (click, reply, share, or buy).
🧱 Simple Format Framework (That Works)
Hook / Subject Line: Grab attention and spark curiosity.
Personal Greeting / Quick Intro: Brief context or story that sets up the value.
Main Value Section:
A tip, insight, story, resource, or breakdown
Keep it focused—1 core idea per email is best
Bonus (optional):
Link roundup, resource, tool, or quote
Call to Action:
Invite to click, reply, share, or check something out
Signature / PS (optional):
Add personality or tease the next issue
Not sure what to write? Use the Story To Startup Method
🤖AI Prompt:
Take this rough draft of a newsletter and edit it into a polished, clear, and engaging final version. Keep the writing style sounding exactly like me—casual, direct, and conversational, like I’m talking to a smart friend over coffee. Keep any personality, quirks, or unique phrases intact. Improve clarity, flow, formatting, and readability without making it sound generic or robotic.
Here’s what to focus on:
- Tighten up the intro and hook—make it engaging fast.
- Ensure the main value is clear and easy to skim.
- Use short paragraphs, bullet points, and subheads where helpful.
- End with a strong, natural-sounding call to action (CTA).
- Fix any typos or awkward phrasing, but don’t over-polish—keep it real.
- Suggest a strong subject line that matches the tone.
Here’s the rough draft:
[PASTE YOUR ROUGH DRAFT BELOW]✅Action: Create a rough draft using the outline above, then ask AI to help you clean it up using the prompt above. Copy, paste and send the final draft.
Stop overthinking it. You already know enough to get moving. Beehiiv is free to start, so you've got zero excuses left. Click here to sign up. (And hey, use code REDEFINE for 20% off if you ever upgrade. Might as well save a few bucks.)
📌Step 10: Grow Your List Organically
Why It Matters:
Achieving growth without relying on paid advertisements is essential for ensuring long-term, sustainable success.
There are hundreds - maybe thousands - of ways to promote your newsletter these days.
Rather than go through every one of them, lets ask AI…
If you are just starting out, I suggest you pick one strategy to start. Once your good at it, then you can explore other strategies,
🤖AI Prompt:
Give me 5 organic marketing strategies to grow my email newsletter to 500 subscribers in the next 90 days. Prioritize free or low-cost methods that don’t rely on paid ads. Focus on high-leverage tactics that drive visibility, build trust, and encourage sharing. The strategies should be practical, specific, and tailored for [INSERT YOUR NICHE OR AUDIENCE]✅Action: Implement at least two growth strategies.
📌Step 11: Keep Subscribers Engaged
Why It Matters:
Consistency builds trust. Choose a posting schedule that works for you:
Best: Weekly (Saturdays are popular)
Good: Biweekly (can work, but less top of mind)
Okay: Monthly (not ideal for relationship-building)
Or, if you really want to build fast, post daily. A lot of big newsletter and email experts swear by it.
🤖AI Prompt:
Create a [daily/weekly/bi-weekly/monthly] email newsletter schedule for my niche: [INSERT NICHE].
Suggest the best frequency, then build a 3-month content calendar with:
- Topics that solve real pain points
- Ideas people are searching for on Google/social
- High-engagement potential (clicks, shares, replies)
- A mix of formats (tips, how-tos, stories, etc.)
For each topic, include:
- A subject line
- A 1-line summary
- Type of value (tip, tool, story, etc.)
- A CTA idea (click, reply, share)✅Action: Plan your first 12 issues using AI’s response.
Frequently Asked Questions
You made it to the end (or maybe you just skipped to the bottom—I see you).
Either way, you probably have a few "Yeah, but..." questions floating around in your head right now.
That’s normal.
I had the same doubts when I started, and I let them stop me for way too long. Let’s clear the air on the stuff that usually trips people up so you can actually get moving.
Short answer: You bet.
Beehiiv has a killer free tier that lets you build your list without spending a dime until you’re actually making moves. No credit card, no nonsense. Honestly, it’s the best price in town ($0). So if "budget" was your excuse for not starting, you can go ahead and cross that one off the list. Click here to sign up free ($).
Look, I ain’t about the "hustle-until-you-drop" life. We’re too old for that.
With the 1-Post-A-Week System I use, you aren't chained to your desk. You write one solid piece, let the AI handle the heavy lifting on the repurposing and polish, and you’re done. You can build a serious asset in a few focused hours a week—not days.
Do I need technical skills to use Beehiiv?
Nope. If you can type an email and drag a mouse, you’re qualified.
I spent 17 years as a mechanical draftsman, not a computer programmer. I don't code, and I definitely don't like fighting with software. Beehiiv is built for people who just want to write and grow. If I can figure it out without pulling my hair out, trust me, you’ll be fine.
How do I make money with a newsletter?
Glad you asked. There are many ways. Keep reading…
📌Step 12: How to monetize a newsletter with AI
Why It Matters:
Your newsletter should be a business asset, not just a hobby. There are multiple ways to monetize, and choosing the right one depends on your skills, audience, and goals.