Chapter 2: The $500 Speaker Trap

Why Doing MORE Free Gigs Won’t Get You Seen by The Right People

This might be a bit of a hard pill to swallow, but it’s the truth:

If doing more free gigs actually worked, you'd be booked out right now.

Your inbox would be flooded with invites.
You’d be turning down offers instead of chasing them.

But you're not.
And it's not your fault.

You've been taught that every “yes” is a step toward “success.”
That stage time is currency.
That if you just keep saying yes—especially when there's no budget—eventually the paid opportunities will show up.

But they won’t.

Christine’s Story: From Free to Five-Figures

Let’s talk about Christine Ramsay.

For years, Christine said yes to every opportunity she could find.
And it resulted in her doing a TON of unpaid speaking gigs.

Christine dreamed of being a paid speaker.
But every time she stepped on another free stage…

She unknowingly reinforced the idea that her work didn’t carry a price tag.

That changed the moment she landed her TEDx talk.

It wasn’t paid either—
But that single TEDx Talk gave her credibility and leverage.

Soon after:

Same message.
Same voice.
Completely different positioning.

That’s the power of one strategic talk over a dozen free ones.

My Story: From TEDx to Morocco

When I gave my first TEDx talk, it wasn’t paid either.
But shortly after, I was invited to deliver a $10,000 keynote in Morocco, sharing the stage with Wim Hof.

Yes, that Wim Hof.

One unpaid talk turned into a global opportunity.

That’s not luck.
That’s leverage.

The Trap Most Speakers Fall Into

The “$500 Speaker Trap” is sneaky—because it feels like progress.

You’re:

But in reality, you’re building a brand that tells people:

“I’m free. I’m available. I’m not in demand.”

Every time you say yes to an unpaid or low-fee gig, you reinforce the idea that you’re not yet worth paying.

And the people who see you on those stages?
They’re more likely to offer you another free gig, not a five-figure one.

That’s not positioning.
That’s survival mode.

What High-Paying Organizers Actually Look For

The people who write $10K+ checks for speakers aren’t at:

They look for:

They want someone who LOOKS like a $10K speaker before they’ve ever been paid that much.

In their eyes:

Free Gigs = Amateur

And that perception is hard to undo.

Less Exposure, More Positioning

Ironically, doing fewer gigs but focusing on the right ones can move your career forward faster than scattering yourself across 50 stages that don’t align with your brand.

Visibility isn’t the most important thing.
Perception is.

One strategic talk—recorded well, packaged smartly, and aligned with a big idea—can do more than a year of hustling for scraps.

Chapter 2 Exercise

Make a “NO” List

Write down 3 types of speaking gigs you will no longer accept—
Unless they align with your positioning or offer strategic value (e.g., credibility-building footage, targeted leads, aligned audience).

This is where you start shifting from:

Speaker-for-hire → Speaker-as-brand