Most business coaches only share what worked. I'm showing you what didn't, and what I learned from it.

This is building in public: the course corrections, not just the destinations.

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TL;DR:

I launched a workshop expecting results similar to my past successes. Instead: 0.7% registration rate, 20% show-up (vs. my usual 40-50%), and price objections on $250/month.

The diagnosis? I changed my messaging from "how to build leverage" to "hit $10K months," which attracted broke beginners instead of growth-ready entrepreneurs.

Worse: I dropped my pricing to avoid sales calls (letting operations drive strategy instead of solving operationally).

The fix: Return to premium positioning, mechanism-based messaging, and model what I actually teach.

Here's what we were testing:

The Goal: Launch the new Essentialist CEO positioning with a free workshop, convert attendees to the Collective (new $247/month membership community)

The Strategy:

What I Expected: Based on my past webinar performance and the newsletter engagement rates, I projected:

I'd run similar webinars before. I'd regularly sold $5K programs this way. I knew how to do this.

Or so I thought. 😱

The Funnel:

What Worked:

What Flopped:

Here's what made these numbers really alarming:

This wasn't just below industry benchmarks. This was dramatically below MY benchmarks.

Same webinar format. Same promotion strategy. Same me.

Completely different results.

What I used to talk about:

This attracted:

What I started emphasizing:

This mostly attracted:

Here's what I missed:

My actual ideal clients HAVE hit $10K months. They've probably hit $20K or $30K months, too.

Their problem isn't "getting to $10K." Their problem is the chaos and inconsistency of bouncing between $8K and $25K with no predictability or control.

Wrong audience, entirely.

Here's what made the audience mismatch even more obvious:

On the webinar, we went through an assessment based on the 5 Essential Elements—the framework I've developed after working with over 1,000 entrepreneurs to grow their businesses.

The 5 Elements:

Everyone on the call assessed themselves in real-time: Red (struggling), Yellow (inconsistent), or Green (mastered).

Here's what I know from working with 1,000+ entrepreneurs:

And here's what happened on the call:

Multiple people shared in the chat that they were GREEN across 4 or 5 categories.

Yet they were on a call about "hitting consistent $10K months."

The math doesn't math.

Two possibilities:

Either way? Not my ideal client.

I've learned that I do my best work with entrepreneurs who:

The people who rated themselves GREEN in nearly everything? They're either:

This is the other problem with the "$10K months" positioning:

It attracted two opposite extremes:

Neither of these are my people.

My ideal clients?

They're the ones who assessed themselves honestly. Who said:

They're the ones who WANT the diagnosis. Who are ready to hear what's actually blocking them. Who will implement when given surgical precision on their essential next step.

The ones rating themselves green in everything while asking how to hit $10K months?

They need something I don't provide: either foundational business education (if they're actually struggling) or ego management (if they can't be honest with themselves).

Here's what I teach my clients constantly: If you're going to tell your clients to charge premium prices, you have to model that behavior.

And yet, that's exactly what I didn't do.

Sales calls drain me. They're exhausting. After a day of sales calls, I'm wiped out.

So when I started redesigning my business, I knew I didn’t want my long-term growth to depend on taking a high volume of sales calls.

But, instead of figuring out how to structure premium delivery without calls, I changed my entire business model.

I dropped my pricing to $250/month. I changed my positioning to attract "anyone struggling to hit $10K." I removed the qualification mechanism that premium pricing provides.

See the difference?

One is strategic problem-solving. The other is avoidance disguised as strategy.

And here's what that cost me:

When you charge a premium (even if unstated), you attract people who:

When you charge $250/month with no commitment, you attract people who:

The real kicker: Premium pricing is about more than just money. It's also about mindset. When someone invests $2,500, they show up differently than when they spend $250. They implement differently. They engage differently.

By avoiding the operational challenge of premium delivery, I changed more than just my pricing. I changed my entire client experience, my business model, and ultimately, my results.

The pricing wasn't just about money. It was a qualification mechanism. And I removed it to avoid solving the operational challenge.

I let an operational preference dictate my positioning and pricing strategy.

That's backwards.

While the messaging mismatch was the core issue, the technical problems made everything worse.

Yes, my newsletters have excellent deliverability, but my confirmations and follow ups were sent from a new tool and a new domain. So, a HUGE number of emails to improve show-up rates and drive post-webinar conversions went to spam. UGH!

Here's what was broken:

Email Deliverability Crisis:

Post-Registration + Post-Webinar Follow-Ups:

Here's why this matters more than I initially thought:

If I'd had my historical 40-50% show-up rate instead of 20%, I would have had 50-64 attendees instead of 26.

At the same 35% close rate, that's 17-22 sales instead of 9.

That's literally double the revenue from the exact same launch.

But here's the kicker I initially missed: I had 102 people who registered but didn't show up. In my past launches, I'd convert 10-20% of no-shows through follow-up sequences.

That's potentially another 10-20 sales I completely lost because the post-webinar emails hit spam folders.

So we're not talking about doubling revenue. We're talking about potentially tripling it.

The infrastructure problems didn't just hurt attendance - they eliminated an entire revenue stream from people who were interested enough to register but couldn't attend live.

Yes, I would have been converting the wrong audience at higher volume. But it also would have given me much cleaner data about whether the messaging shift was the primary problem or just one of several issues.

What I'm fixing for the relaunch:

The lesson: Even with perfect messaging, broken infrastructure kills results. But broken infrastructure can also mask messaging problems by making everything perform poorly.

I need both the right message AND the right delivery mechanism.

You don't have to do things the way everyone else does them.

You CAN charge premium prices without sales calls.You CAN build leverage without sacrificing quality.You CAN design a business around what actually energizes you.

But you have to solve operational challenges strategically—not abandon your positioning to avoid them.

The hard thing that drains you? That's not the real problem.

The real problem is letting that operational preference drive your strategic decisions.

Figure out how to deliver premium value in a way that works for YOU—while maintaining the positioning that actually attracts the right people.

That's the CEO move.

I'm at a decision point:

Do I double down on trying to convert an audience that can't afford $250?

Or do I have the courage to return to what actually worked—premium positioning that attracts growth-ready entrepreneurs—and figure out the operational model that serves both me and them?

The Essentialist answer is obvious.

But it requires admitting I spent months building in the wrong direction.

Next in this series: The positioning evolution, the pricing decision, and what happens when you stop optimizing for "accessible" and start optimizing for "right-fit."

I'm redesigning everything based on what I learned from this launch and I need your help.

If you read this far, you're clearly invested in this conversation. Which means you're probably exactly who I should be learning from.

Take 2 minutes to tell me about your business →

5 questions. No fluff. Just helping me understand where you actually are, so I can create what you actually need.

In love and growth,
Kasey

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