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How to be entertaining (without being someone you’re not)


Issue #190 | April 14th, 2026

Hey there,

We live in a world where information is everywhere. You can Google anything, ask ChatGPT, or find a free tutorial on YouTube in seconds. Information is no longer scarce or special. It’s a commodity.

I talk about this in Lean Learning, but here’s the truth: being the person with the most information is not enough anymore. If you want to stand out, you have to be entertaining.

But what does that actually mean?

Let’s get unstuck…

Find Your Superfans!

You don't need millions of followers to build a thriving business.

You just need Superfans.

A Superfan isn’t just someone who watches your content — it’s someone who has made you a meaningful part of their life.

These are the people who buy everything you create, defend you from trolls, and spread the word without ever being asked.

On Tuesday, April 21st, I'm going live to show you exactly how to find them using the Pyramid of Fandom, my 5-level framework for turning complete strangers into loyal Superfans.

I'll also be officially introducing the Superfans System: a new feature of the SPI Community designed to give every entrepreneur and creator a clear, personalized path forward based on their relationship with their audience.

It's free. It's live. And I'd love to see you there.

Interested in sponsoring Unstuck? Fill out a sponsorship inquiry.

Story of the Week

Entertainment Is Not About Being Loud

When most people hear “entertaining,” they think of high energy, big personalities, or being the funniest person in the room. But you do not have to be a comedian or an extrovert to be entertaining.

Being entertaining is about being relatable, telling good stories, and making people feel something. It is about connection, not just performance.

What Makes Someone Truly Entertaining?

1. Relatability

Share your real experiences, struggles, and quirks. People connect with what feels genuine. You do not have to be perfect or polished — just real.

2. Storytelling

Stories are the oldest form of entertainment. They help people see themselves in your journey. Instead of just sharing facts, wrap your information in a story. What happened? What did you learn? How did it feel?

3. Surprise and Curiosity

Keep people guessing. Ask questions, share unexpected facts, or take your audience somewhere they did not expect to go. Curiosity is a powerful hook.

4. Emotion

Make people laugh, think, or even tear up. The best content makes people feel something. Do not be afraid to show your excitement, frustration, or passion.

5. Simplicity

You do not need fancy effects or over-the-top editing. Often, the most entertaining content is simple and direct. Focus on clarity and connection.

How to Be More Entertaining (Without Faking It)

  • Start with a story. Instead of jumping into the lesson, share a quick story that sets the stage.
  • Use your natural voice. Don’t try to be someone you’re not. Your unique style is what makes you memorable.
  • Ask questions. Get your audience thinking or talking back, even if it’s just in their heads.
  • Share your “why.” Let people in on what motivates you, what scares you, and what you’re working toward.
  • Practice. The more you share, the more comfortable and entertaining you’ll become.

Your Challenge

This week, before you share your next piece of content, ask yourself:

“How can I make this more relatable, more story-driven, or more emotional?”

Try starting with a story, sharing a personal struggle, or asking a question that sparks curiosity.

Remember, in a world where information is free, the real value is in how you deliver it.

Be yourself, tell good stories, and make people feel something. That’s what makes you entertaining.

Here’s to being memorable, not just informational!

Quote of the Week

"People will forget what you said, people will forget what you did, but people will never forget how you made them feel."

—Maya Angelou

New Podcast Episode!

Going viral isn’t the goal — building something real is.

In this episode of The Smart Passive Income Podcast, I chat with two creators from my 30-Day Video Challenge who committed to showing up on video every single day.

You’ll learn how embracing imperfect content can boost confidence, attract the right audience, and create lasting momentum in your business.

If you’ve ever wondered whether you’re building a brand or just posting videos, this episode will shift your perspective and give you the push you need to keep showing up. Tune in here!

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SPI 924: Unexpected Wins Fro...
Apr 8 · The Smart Passive Income...
26:37
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Cheers,

Pat Flynn

Co-founder, SPI Media

Dad Joke of the Week

What do you call a wreath made of $100 bills?

Aretha Franklins

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