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The Country Club Illusion: When $15M Still Feels Like You're Drowning

Playing to Win

August 14, 2025

newsletter-title

Welcome to the Latest Newsletter
of Playing to Win!

My newsletter is designed specifically to help business owners like you grow your companies with tried & applied bits of business knowledge, all communicated in actionable, bite-sized chunks. I will share insights and advice aimed at enhancing your business operations, boosting your success, and allowing you to focus more on what truly matters. Let's work together to achieve your goals and make your endeavors a reality.

Key Points of the Newsletter

  • Revenue doesn't mean you’ve figured it out, especially if you’re overleveraged.
  • Most entrepreneurs second-guess themselves daily, even at high income levels.
  • There’s no secret solution, just hard-earned experience and real strategy.

The Country Club Illusion: When $15M Still Feels Like You're Drowning

 
So you’ve got the country club membership, the luxury car, maybe even a second home.

From the outside, it looks like you’ve made it.

But let me ask you something, do you ever find yourself wide awake at 2 A.M., running worst-case scenarios in your head? Wondering if your whole house of cards is about to collapse because of one or two bad decisions?

Yeah. I’ve been there.

I know what it’s like to hit $15 million in revenue and still feel like you’re treading water. Overleveraged. Overcommitted. And no one to talk to about it, because from the outside, you’re “successful.”

Here’s what most won’t admit: You haven’t figured it out. You’ve figured out how to make money, not how to scale something sellable. There’s a difference. A big one.

You’re not focused on the right variables. You’re playing defense instead of offense. You’ve got debt you don’t talk about. Systems that don’t scale. And deep down, you know that one wrong move could send it all crashing.

This isn’t judgment. It’s recognition. I know what goes on behind your eyes because I lived it.

And if you’re looking for a secret solution? I’ll save you some time, there isn’t one. Anyone promising you a magic fix is full of shit.

But what I do have is experience. I’ve walked that tightrope. Built it. Broke it. Rebuilt it stronger. And I can share exactly what I wish someone had told me back when I thought a high revenue number was the finish line.

It’s not.

It’s just the start of a different game, and the rules are harsher.

So if you're waking up second-guessing yourself, just know you're not broken. You're just playing a game no one taught you how to win.

Let’s change that.

Want to build something that scales without breaking you in the process? I’ve been there. Let’s talk. 

Stay tuned for more insights in our next newsletter. Remember, it's the small adjustments that often make the biggest impact on your business's profitability. Here's to your continued success!

Stay driven to push your business forward,
Ryan Niddel