The Hustler Has to Die: How to Finally Become a Real CEO | Brett Gilliland
7/15/202646 min
In this episode I sit down with Brett Gilliland, founder and CEO of Elite Entrepreneurs, who has spent the last fourteen years helping business owners make the leap from hustler to real CEO. We dig into why so many founders get stuck right before the ten million dollar mark, and why it almost always comes down to control. Brett walks me through the four systems his company teaches to build a business that doesn't depend on the founder for everything, what a CEO's real job becomes once a leadership team is in place, and how to know when you're still holding onto something you should have let go of months ago. We also get personal, talking about the daily disciplines that keep us both grounded, including his fourteen "I am" statements that he's repeated every single morning for over a decade, and why taking care of yourself first isn't selfish, it's what makes you capable of showing up for everyone else. If you've built something real but feel like you're the bottleneck holding it back, this conversation is for you.
Topics Covered
- Why founders need to change in order to grow their business
- Letting go of control as a business owner
- The difference between a hustler and a real CEO
- What changes once a business hits $10 million
- Building a full leadership team
- The CEO's real job: vision, team, resources
- The four systems Elite Entrepreneurs teaches to scale a business
- Why founders unknowingly sabotage their own growth
- Daily disciplines and morning routines
- Putting yourself first to show up better for others
About Brett Gilliland:
Brett Gilliland is the founder and CEO of Elite Entrepreneurs, a company that gives seven figure business owners the knowledge, systems, and coaching to grow to ten million dollars and beyond. For over a decade, Brett helped lead Infusionsoft's growth from seven million to more than one hundred million dollars in revenue, where he was involved in building the company's Purpose, Values, and Mission, co-created the Elite Forum, and served as VP of Leadership Development. He has spent fourteen-plus years coaching founders and executives on how to move from hands-on hustler to confident, capable CEO. Brett has been married to his wife Sharon for thirty years, and together they have eight children.
Connect with Brett:
Website: https://growwithelite.com LinkedIn: https://www.linkedin.com/in/built2lastchamp/
About Justin:
Justin Colby is the host of The Entrepreneur DNA and The M.O.R.E Show podcasts and a best-selling author. He is a serial entrepreneur and a seasoned real estate investor with over 20 years of experience.
Driven by a passion to help entrepreneurs thrive, Justin created the Entrepreneur DNA community to support business owners in building wealth, systems, and long-term freedom. Through his podcasts, books, education platforms, and hands-on mentorship, he continues to help entrepreneurs scale with clarity and confidence.
Connect with Justin:
- Instagram: @thejustincolby
- YouTube: Justin Colby
- TikTok: @justincolbytsof
- LinkedIn: Justin Colby
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Clips
Transcript preview
First 90 secondsTeasco Hernandez0:00
Hi, I'm Teasco Hernandez. As a parent, I know that being present make all the difference. I have three young sons, and I learned that kids don't just hear our words, they feel them too. The way we respond in tough moments, the sense of security we provide, it all matters. When we help our kids to feel heard and supported, we helping them feel safe and protected. That's why I support First 5 California and their mission to ensure every child has a stronger start in life. Learn more at first5california.com.
Speaker 20:29
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Speaker 30:53
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Brett Gilliland· Guest1:23
There has to be transformation in us as business owners if we wanna take our business to the next level.