Command Your Brand Podcast Interview

5 Mistakes Coaches Make That Kill Their Success (And How To Actually Build a Real Business)

Most new coaches don’t fail because they don’t have the skills. They fail because they never fully shift their identity into that of a CEO.

In this conversation, I break down the hard truths I’ve seen after coaching hundreds of founders, consultants, and coaches who want to build businesses that scale — but keep getting stuck repeating the same mistakes.

Here’s what we covered:

[02:00] My Origin Story — From Side Hustle to 7-Figure Revenue Enablement
First-gen everything. Corporate career at LinkedIn, Google, Uber, and Tesla. Then full-time into entrepreneurship after Hurricane Maria — bringing Big Tech revenue systems into small businesses.

[07:10] Mistake #1: You Don’t See Yourself as the Expert Yet
Before I can coach you on strategy, we have to stack your receipts. Your experience. Your results. Your authority. If you can’t own your expertise, you’ll sabotage every other part of your business.

[12:30] Mistake #2: You’re Acting Like the Intern, Not the CEO
Are you taking orders and chasing every dollar? Or are you leading with strategic discipline? CEOs say no. They protect their energy and only take aligned opportunities.

[18:40] Mistake #3: You Have Toxic Assumptions About Selling
“I don’t want to be sleazy.” “I don’t want to bother people.” Cool. Then don’t. Selling isn’t about forcing. It’s about inviting people into a transformation they actually want.

[24:20] Mistake #4: You Can’t Tell a Persuasive Story
At the end of the day, every business — every sale — is driven by your ability to influence how people see themselves on the other side of your work. Storytelling is the most important sales skill you’ll ever develop.

[30:10] Mistake #5: Your Systems Are a Mess
You’ve got tools duct-taped together from random courses you bought 3 years ago. Your backend isn’t supporting your front end. And the customer experience is suffering because of it.

[35:00] The Hardest Coaches to Scale? The Healers
Wellness practitioners. Life coaches. Spiritual guides. The ones called to serve from the heart — who struggle to charge what they’re worth, set boundaries, and separate passion from business.

[42:10] If You Want Clients to Take You Seriously, Make Yourself Scarce
Set boundaries. Honor your time. When people know you run tight sessions and expect them to show up prepared, they engage with more intent and get better results.

[48:00] Why Undercharging Actually Hurts Your Clients
If they don’t feel the financial stretch, they won’t stretch themselves. Higher investments create higher commitment and stronger transformation.

[53:30] The Coaches Who Scale Fastest Are The Ones Willing To Watch The Tape
If you want to get great as a coach, don’t just read more books. Record your calls. Transcribe them. Watch yourself. Audit your language. Spot your own patterns. That’s how you level up.

[58:10] The Power of Having Your Own Signature Framework
Your IP becomes your asset. Your framework gives you structure to build coaching programs, consulting packages, digital products, and scalable offers — all anchored on repeatable transformation.

[63:20] My First Coaching Client Story — And Why I’ll Never Forget It
How one life coach went from zero to TEDx stages, multiple published books, and corporate contracts — after anchoring her IP, raising her pricing, tightening her sessions, and letting me challenge her assumptions.

If you’re a coach who’s tired of guessing, exhausted from trading time for dollars, and finally ready to build something scalable and sustainable — this conversation gives you the full blueprint.