The Audience Analysis Strategy That Makes Your Message Stick

A few months ago, I was talking with a gal named Carolyn - a super smart fractional CMO.

We were chatting about the mission here on Redefining Retirement and she said (I’m paraphrasing):

So I asked her:

“Who is Mr. T?”

She said:

“Who?”

And I I said,

“That’s why.”

If you don’t get it, then I’d have to water down the message.

I don’t want to do that. I’m building a community of people who share the same cultural moments. Who get the references. Who share the same perspective nobody else has.

And here’s the kicker: the better I understand my people, the better I can serve them.

Why am I telling you this? Glad you asked…

What Dale Carnegie Knew Before TikTok

One of the first lessons I picked up as I moved from employee mindset to thinking like an entrepreneur came from How to Win Friends and Influence People:

Translation: if you want to grab attention — boss, customer, client, future employer — you’ve got to understand them first.

That’s what this week is about: pain points.

The Exercise

I just did an exercise inside Dustin Reichman’s 7-Figure Leap cohort.

It helped be really drill down on what the audience I’m trying to reach with my new venture need help with.

My target audience: 40 to 60 year old Gen X YouTubers with 500k subscribers

Here’s the quick version of how I did it (and how you can too):

1. Collect the Complaints
   I ran a ChatGPT prompt that scraped pain points from Reddit threads, YouTube comments, and forums. No “marketing speak” — just raw, real-world rants.

   Like: “the YouTube algorithm has essentially thrown [my work] in the garbage… something’s wrong” or “ZERO idea how to get brand deals… probably lost out on $100,000s of income… am I just being stupid?”

2. Sort the Big Stuff
   Dumped it all into a doc, had ChatGPT help me ranked them most painful to least based on the data it found. For my crowd, the top three were:

   • Unstable revenue

   • Algorithm dependence

   • No direct contact with their audience

3. Write the Before/After
   This is where it clicked. I wrote out what people have, feel, and do now… then flipped it to what they want life to look like after.

   (Side note: to keep this post shorter the following example has abbreviated versions of the actual info it spit out).

4. Boil It Down
   My “working” transformation statement became:

   “Unstable YouTube Income → Profitable Creator Brand You Own”

And this isn’t just for entrepreneurs…

Why It Matters For All Gen Xers

This little framework doesn’t just work if you’re selling something.

• If you run a business, it helps you design offers people actually want to buy.

• If you’re job-hunting, it helps you rewrite your resume so the hiring manager thinks, we need this person.

• If you’re posting on social, it helps you write stuff that makes people stop scrolling because they feel seen.

Prompt of the Week

Here’s the exact ChatGPT research prompt I used to dig up real pain points from Reddit, YouTube, and forums.

Important: Be sure to select “Deep research” mode to get more thorough information.