What happens when a successful entrepreneur realizes that business achievements aren’t the only measure of a life well-lived? In this episode of Leveraging Success, Jeff Gerhardt sits down with his good friend Trey Sheneman, founder of Herald and author of The Compass Method, to discuss how to make major life and business decisions while keeping family, freedom, and faith at the center.
Trey shares his journey of building a thriving company, navigating opportunities from private equity groups, and balancing work with family responsibilities. Jeff introduces his “Five Column Decision Framework”—Money, Family, Freedom, Passion, and Kingdom —to help evaluate choices that truly matter.
From homeschooling and family priorities to launching a book and guiding a business with impact, Trey opens up about aligning life, work, and kingdom principles. This episode is packed with insights for anyone striving for success that lasts beyond the scoreboard.
[00:00] Intro
[01:12] Meet Trey Sheneman
[02:45] Bear’s 5-year health journey
[07:38] Diagnosis & new season
[11:30] The private equity offer
[15:05] The 5 Columns: Money, Family, Freedom, Passion, Kingdom
[19:35] Why Freedom is the real decider
[24:50] The size lie most entrepreneurs believe
[29:12] Trey’s next-step commitment
[30:34] Closing thoughts – Don’t get opportunity suckered!
Our Guest
Trey Sheneman is the founder of Herald and author of The Compass Method. A faith-driven entrepreneur, he helps leaders and founders grow revenue, scale businesses, and create lasting impact—all while staying true to their values. He also hosts the 10-Minute Masterclass podcast, sharing practical insights on marketing, sales, and leadership.
Resources & Links
Trey Sheneman
https://www.linkedin.com/in/treyshen/
Jeff Gerhardt
https://www.linkedin.com/in/jeffgerhardt/
Resources
https://jeffgerhardt.com/wp-content/uploads/2025/11/Quarterly-Portfolio.pdf
Life Balance Assessment – https://lba.priorityliving.org/
Leveraging Success Podcast- https://www.leveragingsuccesspodcast.com
Hearing God by Dallas Willard
