How I Built a One-Person Business at 50 with Blogs and Newsletters

Back in 2004-ish, I was stuck in my cubicle as a mechanical draftsman, watching my redesigns save the company a ton of money.

My reward? A lame $1,000-$3,000 annual raise and the classic corporate "pat on the back."

That's when it hit me. I had two choices:

1. Bitch about how unfair it was (while standing there with my hand out)

2. Figure out how to get paid what I was actually worth

I chose the second option (although I did bitch a little too).

And here’s where the fun started…

The Accidental Side Hustle That Changed Everything

I started two blogs - one about fantasy football (total geek stuff) and another about music.

I was just writing about how I was setting my lineups and finding good players. Then something pretty cool happened: Google started sending people my way.

Once I finally got smart enough to collect emails (which took me WAAAY to long to figure that out), things started snowballing. Those early readers stuck around, and traffic kept growing.

By the time everyone jumped on the social media bandwagon around 2010, I was already sharing my blog posts and getting more eyeballs on my stuff. That's when it hit me - I had built this cool little engine:

• My blogs attracted new email subscribers.

• My emails brought subscribers back to my blogs.

• Those subscribers signaled to Google that my content was valuable.

• Google rewarded me by sending even more people to my blogs.

• The cycle kept repeating and growing on its own.

From Side Hustle to Real Money

Eventually my fantasy football blog was pulling in $300-$500 a month from ads just from two posts a week during the football season. Not too shabby, huh?

Then I discovered affiliate marketing had a few $500+ days selling guitar courses through my music blog. The crazy part? I had zero music industry experience.

It wasn't quit-your-job money yet, but it showed me something huge: I didn't have to wait until I was 65 to retire to do what I wanted.

And I didn’t have to jump ship from my career to becoming some 24-year-old influencer's idea of an entrepreneur - yet anyway (I've got kids and a mortgage too)

But this side gig stuff? I could make it fit into my life.

Check out this screenshot of my fantasy football blog WAY back in 2008…

The Game-Changer

Eventually, something interesting started happening. Businesses started reaching out, wanting to get their stuff in front of my readers (for example, look under “Sponsors” in the screenshot above).

Some paid upfront, others offered commission. I even created my own digital products to sell.

Hell, I still have many of the readers (subscribers) from my music sites, from over ten years ago, who open emails and buy stuff. That blows my mind.

Ultimately, all this "playing around" with blogs and newsletters taught me marketing skills that took me from making $40K a year as a draftsman to today, where I pull in between $10K-$18K monthly as a digital marketer.

The three biggest skills turned out to be pretty future-proof:

1. Writing - Turns out people actually want to read about your experiences

2. Marketing - Getting your stuff in front of the right people

3. Love of learning - Using your natural curiosity as a superpower to stay ahead

I am still benefiting from each one of these skills today after 15-plus years since I started.

Especially the love of learning, which led to me getting curious about AI (which is about as future-proof as it gets these days).

The Tools That Made It All Click

Man, when I started, all this was a giant time suck, and the learning curve was way higher. Figuring out multiple platforms, trying to get them all to work together - it was like herding cats.

Now? It's so much simpler.

For this site I use Beehiiv - blog posts and email newsletters all in one place (2 in 1 platform I’ve heard someone call a blogletter).

And with AI tools like ChatGPT? It's like having a 24/7 assistant helping me write better and work faster.

If a former tech-college dropout can figure this out, anyone can.

Wanna start your own “Blogletter”?

When you have a one-person business, you've got something uniquely yours - you call the shots, control your destiny.

Here's the thing: If you're in your 40s or 50s with years of work experience, you're already ahead of the game. You can leverage what you know and love into a blog/newsletter business while learning new skills that keep you relevant and earning.

Here's how to get started:

Step 1: Find Your Sweet Spot

Grab a free ChatGPT account (chat.openai.com) and use my handy pathfinder prompt to discover your perfect topic - one that combines your experience with what people actually want to read about.

Copy this into ChatGPT:

"I am a [YOUR AGE] individual with [YOUR EXPERIENCE, SKILLS, KNOWLEDGE ARE and/or PASSION FOR X HOBBY]. I want to start a blog and newsletter business that aligns with my life experiences, passions, and what the world needs while being financially sustainable. Please suggest 5 in-demand topics that:

1. Leverage my unique skills, knowledge, or life experiences.
2. Address intrinsic, extrinsic, and systemic values to ensure relevance, fulfillment, and impact.
3. Fall into the monetizable categories of health, wealth, relationships, or hobbies.
4. Meet the principles of Ikigai, ensuring they align with what I love, what I’m good at, what the world needs, and what I can be paid for.
5. Appeal to a defined target audience that I can connect with easily, fostering community and engagement.
6. Allow for scalability into additional revenue streams like courses, books, or consulting.
7. Include a unique angle or differentiation to stand out in the market.
8. Suggest ways to use AI tools for content creation, audience analysis, or automation.
9. Are practical to implement considering my level of technical expertise, time, and budget.
10. Address emerging trends to ensure the topics remain relevant in the next 5–10 years.
11. Have potential for cross-platform expansion into podcasts, video content, or social media."

Additionally, for each topic, include specific monetization strategies and examples of successful blogs or newsletters in that area as inspiration.

Step 2: Start Building

Use Beehiiv to create your home base - it handles both your blog and newsletter in one place. No technical headaches, no jacking around with multiple platforms.

Step 3: Grow Your Asset

Share what you're learning about AI, your industry expertise, or that hobby you love. Each post builds your platform - think of it as your insurance policy against depending on one employer.

The best part? You can start small. I built my first successful blog and newsletter while working full-time with three kids and a mortgage. You don't need to be some 24-year-old YouTube influencer or quit your day job.

Ready to turn your experience into your advantage? 

My Personal Guarantee: Sign up through my link, and if you don't see the value within 30 days, email me. I'll personally help you get the most out of it.

Let's do this,

Corey