People and Culture Make Bigger Companies Fun

Brett Gilliland, founder of Elite Entrepreneurs, joins Greg to discuss how they help ambitious founders navigate the tough leadership journey from $1M to $10M in revenue. Brett shares how co-creating a clear, practical Purpose, Values, and Mission form the foundation of scalable organizations.

He explains why moving from founder-led chaos to aligned leadership teams is the critical step that separates $1M experiments from $10M companies. With clear meeting rhythms, disciplined execution, and strong hiring practices, Elite Entrepreneurs has helped hundreds of founders become happy CEOs and build companies that run without constant founder involvement.

Brett reveals the personal transformation required for founders to evolve into true CEOs who can enjoy their business more as it grows. You can reduce chaos, scale your teams, and rediscover the fun of running your business once you shift focus from “I” to “we.”

Key Takeaways

• Growth Brings Freedom: Founders who learn let go in the right way often rediscover fun, profit, and time.
• Leadership Teams Required: Scaling past $3M–$10M depends on building a capable senior leadership team. 
• Meeting Rhythms Drive Scale: Annual, quarterly, monthly, and weekly cadences keep teams aligned.
• CEO Core Roles: Set the vision, build the team, and secure resources—everything else gets delegated.
• Hiring as Marketing: Culture-fueled job postings act like a “bat signal” for the right candidates.

This Interview Is Perfect For

• SaaS founders at $1–5M in ARR
• Business owners feeling “stuck” at their current stage
• CEOs ready to build their first real leadership team
• Entrepreneurs who want growth and a life

Quote from Brett Gilliland, founder of Elite Entrepreneurs

“All of us get stuck in some way. We know there's a better way. We see other people figuring it out. I should be able to do this, we say, but we just didn't know what to do. 

"You have to do work on your business in a deliberate way. And those who do the work consistently make progress. We help them lay out the path from $1 to 10 million. Here are the things that you do. It's proven, it's practical. 

“Whoever has been consistent with it, quarter after quarter, month after month, week after week, doing the things that we're talking about, they start stacking wins. 

“Then all of a sudden, 18, 24 months later, we're at a place where we've tripled in revenue, we've doubled in team, it's fun, I've got some time back in my life. It does take time, but it's totally doable. I've seen it over and over and over again.

Links

• Brett Gilliland on LInkedIn
• Elite Entrepreneurs on LinkedIn
• Elite Entrepreneurs website

This podcast is sponsored by Designli, a digital product studio that helps entrepreneurs and startups turn their software ideas into reality. From strategy and design to full-scale development, Designli guides you through every step of building custom web and mobile apps. Learn more at designli.co/practical.

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