The most valuable exercise I've done all year...

I recently went through an exercise that I think every business owner should try.

It’s simple. It’s strategic. And it completely changed how I think about our customers at Paperboy.

Here’s a little context: We’re about to start testing some paid funnels to drive leads for Paperboy.

But before we touched a single ad… I knew we had to sharpen our customer segments.

Because running cold traffic means one thing: You have to meet people exactly where they are.

You have to speak directly to their specific mindset, pain points, and goals—otherwise you’ll get ignored.

So I sat down and tried to break down all of our potential audience variants.

I figured it’d take a few hours.

It took a week.

And the crazy part? I’ve been running this agency for two years. I’ve thought deeply about our ideal client. But even still, I was surprised at how much nuance I uncovered.

Here’s how I structured the whole thing—and how you can do it too.

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Step 1: Identify Your High-Level Segments

Start by grouping your audience into clear, top-level variants. Here’s what I came up with for Paperboy:

1. People who need to be sold on personal branding
2. People bought into personal branding—but not yet doing newsletters
3. People running a newsletter—but not taking it seriously
4. People with big email lists—but not treating it like a newsletter business
5. High-ticket operators or direct-response marketers

Each of these groups has a totally different starting point. And that means they need totally different messaging.

Step 2: Answer These Questions for Each Segment

For every segment, I answered a few core questions:

1. Where are they now?
   What’s their current behavior, channel focus, or maturity? This is just meant to give a little context about their starting point.
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2. Who are they (examples)?
   Give yourself some personas: e.g. influencers, YouTubers, solo consultants, Twitter growth guys, etc.
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3. What’s their mindset?
   |What do they already believe about your area of expertise? What do they not know yet?
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4. What are their fears?
   What keeps them up at night? What's the thing that's giving them anxiety? What keeps them from doing the thing you help with?
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5. What are their objections?
   These are the actual words you’ll hear in a sales call.
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6. How can you reframe those objections?
   This is the magic part—how do you shift their thinking?

Here’s a quick example from one of our segments:

Segment: Bought into personal branding, but not yet doing newsletters

Where they are: Active on social, building a following, posting consistently—but not sending emails.

Examples: YouTubers, Twitter/LinkedIn creators, IG influencers, ghostwriters.

Mindset: They get the game. They’re building audience. They just haven’t crossed into email yet. They need to be sold on the VALUE of a newsletter. Why is it worth the work?

Fears:

• Somehow losing access to the audience they've worked so hard to build on social
• Putting in all of the work to build an audience but not being able to monetize it.

Objections:

• “I don’t have time to write a newsletter.”
• “I’m already getting great results on Twitter.”
• “Feels like extra work for limited payoff.”
• “What would I even send every week?”

Reframes:

• “You’re already doing the hard part—capturing attention. Newsletters let you OWN that attention.”
• “You're already creating content for social, use that as a jumping off point for your newsletter. Little extra work, huge benefits."
• “Newsletters give you algorithm-proof distribution and way better conversion rates.”

Etc...

By the end of this exercise, I had a detailed document that captured our audience in a way I’d never seen before.

It’s become a cheat code for everything:

• Marketing copy
• Ad targeting
• Sales calls
• Landing page messaging
• Lead magnets

If you run a service business—or honestly any business—this exercise is worth your time.

It’ll give you absolute clarity on who you’re talking to and what they need to hear to trust you.

Highly recommend giving it a shot.

If you do, let me know how it goes.

Good luck!

— Shane