The Guidelight
The Guidelight — Hosted by Jason Trent
The Guidelight is for leaders like you — business owners, presidents, and CEOs who’ve built something remarkable and are now asking, “What’s next?”
Hosted by Jason Trent, each episode dives beyond the spreadsheets to explore what truly matters when selling, scaling, or reshaping your company — your people, your purpose, and your next chapter.
You’ll hear real stories and expert insights from those who’ve stood where you are, uncovering how to protect what you’ve built while stepping confidently into the future with clarity and peace of mind.
If your company’s EBITDA is between $2 and $10 million, this is your space to gain perspective that goes far beyond the deal. Because your next chapter matters just as much as the one you’ve built.
🎧 Listen. Reflect. Lead with Light.
The Guidelight
Building Legacy with the End in Mind
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Ten years into running his insurance agency, Jason Trent felt done. Burned out. Unsure if he should sell it all and start over.
In this first episode of The Guidelight, Jason shares the mentors, faith, and hard choices that shaped his leadership.
Then on a quiet walk from his barn to the house, he told God, “I can’t do this.” What happened next changed everything and turned his business into a mission that’s now part of one of the largest insurance networks in the Southeast.
If you’ve ever wondered how to build a legacy that lasts and honors God, this is where you start.
Watch The Guidelight: Building Legacy with the End in Mind.
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Jason Trent is an executive coach, relationship builder, and President of Highstreet Guidelight Insurance. As the founder of J. Trent Connect, he helps business leaders navigate change, strengthen relationships, and safeguard their legacy. With decades of experience in mergers and acquisitions, Jason brings clarity and faith-driven purpose to high-stakes decisions, guiding leaders to align their values with their vision.
Connect with Jason Trent:
Linktr.ee: https://linktr.ee/jtrentconnect
LinkedIn: https://www.linkedin.com/company/jtrentconnect/about/
Instagram: https://www.instagram.com/jtrentconnect
Facebook: https://www.facebook.com/profile.php?id=61575862355860
YouTube: https://www.youtube.com/@theguidelightwithjasontrent
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linktr.ee/JTrentConnect