In this episode of Retained Trust, host Karl Hughes speaks with Jesse Gilmore, founder of Niche in Control and author of The Agency Owner’s Guide to Freedom. Jesse shares his journey from hustle-heavy entrepreneurship to creating a structured program designed to help agency owners reclaim their time and build scalable, founder-independent businesses. They discuss the triggers that lead owners to rethink their roles, how to measure real freedom in business, and why defining success beyond revenue is essential. Jesse also opens up about building his team, recovering from personal loss, and staying aligned with a long-term purpose.

Key Points From This Episode:

[00:00:30] Introduction to Jesse Gilmore and his background as a half-marathon runner and entrepreneur.

[00:01:39] Jesse’s inspiration for writing The Agency Owner’s Guide to Freedom.

[00:02:52] The evolution of agency founders and the Leverage for Growth method.

[00:04:11] Challenges of working with small agency owners and how Niche in Control addresses them.

[00:06:29] Life events as pivotal motivators for agency transformation.

[00:07:57] Rethinking success as freedom, not revenue.

[00:10:22] Why personal freedom must come before financial freedom.

[00:11:24] Breakdown of Jesse’s program structure, including coaching, collaboration, and training.

[00:14:58] Typical bottlenecks for agency growth and where founders often get stuck.

[00:17:12] The personal transformation required to grow beyond hustle mode.

[00:19:17] Applying the 80/20 principle to reclaim time and scale smarter.

[00:21:05] Helping founders identify their unique ability and redesign how they use their time.

[00:24:16] Creating a life event and identity shift to anchor behavior change.

[00:27:13] Measuring business freedom by time away and founder independence.

[00:30:36] What founders should do with the freedom they gain.

[00:32:01] Expanding goals beyond the business into body, being, and balance.

[00:35:24] The CQ (Consistency → Quality → Confidence → Quantity) framework.

[00:38:47] Building mastery through sustained creative practice.

[00:39:59] Jesse’s evolving team and operations structure.

[00:44:16] The impact of personal loss on business clarity and mission.

[00:45:56] Book recommendations: 10x is Easier than 2x, Who Not How, Four Disciplines of Execution, The War of Art.

[00:47:33] Where to learn more about Jesse’s events, book, and program.

Links:

• Jesse Gilmore on LinkedIn: https://www.linkedin.com/in/jessepgilmore
• Niche in Control: https://www.nicheincontrol.com
• Monthly events: https://events.nicheincontrol.com
• Free Guide: https://www.nicheincontrol.com/free-guide
• Karl Hughes on LinkedIn: https://www.linkedin.com/in/karllhughes