The Guidelight

Jason Trent
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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.

  1. JAN 20

    Change Is Easy, Transitions Are Hard: How Leaders Navigate Business & Life Transitions

    Transitions take time and that’s where leadership is tested.  In this episode, I reflect openly on why navigating transition requires awareness, patience, and a willingness to lead people, not just processes. I share why change may look simple on the surface, but transitions affect identity, purpose, and trust beneath the surface. Drawing from proven transition frameworks and real leadership experience, I explain why resistance often uncertainty asking for clarity.  The three phases every transition moves through are endings, neutral zone, and new beginnings. I talk about why leaders must name what’s ending, create safety in the in‑between, and reinforce meaning before expecting momentum. Transitions succeed when leaders communicate clearly, anchor people to purpose, and model steady faith through uncertainty. If you’re leading a team or growing a brand, watch this episode of The Guidelight to learn how thoughtful leadership can turn difficult transitions. Enjoy this episode? Give us a review and leave a 5-star rating. Jason Trent is the founder of Guidelight Legacy Advisors, where he helps business owners prepare for, execute, and transition through the sale of their life’s work. With over 25 years of experience as an owner, operator, and advisor, Jason understands that an exit is never just a transaction—it is a defining leadership moment that affects identity, family, culture, and legacy. Unlike traditional M&A firms that focus solely on valuation and close, Guidelight Legacy Advisors works upstream, helping owners build transferable businesses and downstream, helping them navigate the personal and strategic realities of life after exit. Through his advisory work and The Guidelight Podcast, Jason equips leaders to move from success to significance with clarity, conviction, and purpose. Connect with Jason Trent: Website: https://guidelightpodcast.com/  Social Media:  LinkedIn: https://www.linkedin.com/in/trent-jason/ https://www.linkedin.com/company/guidelightpodcast      Facebook: https://www.facebook.com/people/The-Guidelight/61575862355860/   Stay Connected. Stay Inspired. Let’s build deeper, stronger relationships—one meaningful connection at a time. 👉 Explore all things JTrent Connect: linktr.ee/JTrentConnect

    26 min

  2. 12/02/2025

    God's Will to Sell: How And When

    One of the biggest questions I hear from faith-driven business owners is simple but heavy: “Is it God’s will for me to sell?”  In this episode, I speak candidly about the truth behind that question and why the real issue is your heart, timing, and willingness to listen to God’s guidance. I walk through the three main paths of transition, selling outright, transferring to your team, or passing it down through family, and why each one requires spiritual clarity, not just strategy. Selling a business is a moment of stewardship. I also share the story of how God shifted my own assignment in 2020. Selling wasn’t in my plan but God made it clear that the mission was bigger than my comfort. When you keep your heart open, God often reveals that the “when” is very different from your expectations. Let’s talk about how to recognize when God is leading you into your next chapter. Tune in to the full episode! Enjoy this episode? Give us a review and leave a 5-star rating. Jason Trent is the president of Highstreet Guidelight Insurance, founder of Guidelight Legacy Advisors, and host of The Guidelight Podcast. With over 25 years of experience in insurance and risk management, Jason is passionate about helping leaders build stronger businesses and enduring legacies. His mission is to merge faith, strategy, and innovation guiding teams to grow not just in profit, but in purpose. As a mentor and community advocate, he champions connection and clarity in an age of digital noise. Through his work and podcast, Jason inspires others to align their growth with values that truly matter. Connect with Jason Trent: Website: https://guidelightpodcast.com/ Linkt.ree: https://linktr.ee/theguidelight YouTube: https://www.youtube.com/channel/UCyXPtmwEwvZ-qJB0uYln7mg Facebook: https://web.facebook.com/people/The-Guidelight/61575862355860/ LinkedIn: https://www.linkedin.com/company/guidelightpodcast/ #FaithDrivenLeadership #BusinessStewardship #GodsPlan Stay Connected. Stay Inspired. Let’s build deeper, stronger relationships—one meaningful connection at a time. 👉 Explore all things JTrent Connect: linktr.ee/JTrentConnect

    13 min

  3. 11/25/2025

    What’s Truly On Your Heart? A Birthday Wish With Purpose

    The most powerful moments with God come when we stop asking for what we want and start listening to what’s already in our hearts. In this episode, I open up about a deeply personal experience, a birthday prayer that turned into a life-changing reminder of what truly matters. While driving home on my birthday, I asked God for a simple wish. At first, I wanted a special word or a deeper sense of His presence. But in that quiet time of prayer, He reminded me that I already have both, His Word and His presence are always with me.   My true wish wasn’t about me at all. It was for God to be magnified and glorified through my life. For His light to shine through me and others, so that more people might come to know Him.  If you’ve ever found yourself searching for purpose or wondering what to ask God for next, this episode will speak to you. Watch NOW! Enjoy this episode? Give us a review and leave a 5-star rating. Jason Trent is the president of Highstreet Guidelight Insurance, founder of Guidelight Legacy Advisors, and host of The Guidelight Podcast. With over 25 years of experience in insurance and risk management, Jason is passionate about helping leaders build stronger businesses and enduring legacies. His mission is to merge faith, strategy, and innovation guiding teams to grow not just in profit, but in purpose. As a mentor and community advocate, he champions connection and clarity in an age of digital noise. Through his work and podcast, Jason inspires others to align their growth with values that truly matter.  Connect with Jason Trent: Website: https://guidelightpodcast.com/ Linkt.ree: https://linktr.ee/theguidelight YouTube: https://www.youtube.com/channel/UCyXPtmwEwvZ-qJB0uYln7mg Facebook: https://web.facebook.com/people/The-Guidelight/61575862355860/ LinkedIn: https://www.linkedin.com/company/guidelightpodcast/  Stay Connected. Stay Inspired. Let’s build deeper, stronger relationships—one meaningful connection at a time. 👉 Explore all things JTrent Connect: linktr.ee/JTrentConnect

    8 min

  4. 11/11/2025

    Transition Well: Top 3 M&A Myths Business Owners Believe

    Transitioning a business is a test of faith, trust, and purpose.  In this episode, Duane Gentry, founder and managing partner of CD Gentry Associates, explores the heart and hope behind selling and buying businesses the right way. With over two decades of experience in buying, selling, and guiding companies, Duane shares powerful lessons about letting go, trusting God’s timing, and preparing your business and your heart for what’s next. We unpack the biggest myths about mergers and acquisitions, from the illusion of being “ready” to sell, to relying on friends over professionals, to believing buyers pay for potential instead of proof. If you lead with faith and believe your business is part of a bigger calling, this episode is for you. We talk about how to honor God in every transition, protect your legacy, and make decisions with peace and clarity. Tune in now and see how faith-led leadership can turn transition into testimony. Enjoy the podcast? Subscribe and leave a 5-star review. Duane Gentry is the founder and managing partner of CD Gentry Associates with over 30 years of experience in business, finance, and entrepreneurship. With a background in banking and Fortune 500 finance, Duane grew his own home services company 20X before selling it successfully in 2018. Since then, he’s led multiple M&A transactions, guiding business owners through buy-side, sell-side, and generational transfer strategies. Holding an MBA and an Executive M&A Certification from Columbia Business School, Duane brings deep expertise in helping entrepreneurs navigate growth and transition with clarity. Beyond business, he is passionate about mentoring young leaders and serving his community through charitable and mission-driven initiatives.  Connect with Duane Gentry: Website: https://www.cdgentryassociates.com/     LinkedIn: https://www.linkedin.com/in/duane-gentry-6b734a30/ Jason Trent is the president of Highstreet Guidelight Insurance, founder of Guidelight Legacy Advisors, and host of The Guidelight Podcast. With over 25 years of experience in insurance and risk management, Jason is passionate about helping leaders build stronger businesses and enduring legacies. His mission is to merge faith, strategy, and innovation guiding teams to grow not just in profit, but in purpose. As a mentor and community advocate, he champions connection and clarity in an age of digital noise. Through his work and podcast, Jason inspires others to align their growth with values that truly matter.  Connect with Jason Trent: Website: https://www.hsip.com/agency-directory/guidelight-insurance   LinkedIn: https://www.linkedin.com/in/trent-jason/ https://www.linkedin.com/company/guidelight-insurance/     Instagram:     X: https://www.linkedin.com/company/guidelight-insurance/   Facebook: https://www.facebook.com/people/The-Guidelight/61575862355860/    Stay Connected. Stay Inspired. Let’s build deeper, stronger relationships—one meaningful connection at a time. 👉 Explore all things JTrent Connect: linktr.ee/JTrentConnect

    26 min

  5. 11/04/2025

    Authentic Leadership: Why It Matters More Than Ever

    True leadership starts from the heart, not the spotlight.  In this episode, I step away from the usual polish to talk about something deeper: authenticity. Authenticity begins with God. Before we can lead others, we must be real with Him laying down our burdens and trusting His plan. When I handed Him my worries about family, work, and faith, peace followed.   At home and in leadership, authenticity means presence. It’s choosing to listen, pause, and connect when life feels crowded. It’s showing up as someone willing to care. In our teams and ministries, authenticity is leading with transparency and hope. It’s reminding people that even in hard seasons, God’s promises never waver. The Psalms show us that honesty with God always brings us back to hope.  Tune in now and let’s lead with authenticity that transforms hearts and strengthens faith. Jason Trent is the president of Highstreet Guidelight Insurance, founder of Guidelight Legacy Advisors, and host of The Guidelight Podcast. With over 25 years of experience in insurance and risk management, Jason is passionate about helping leaders build stronger businesses and enduring legacies. His mission is to merge faith, strategy, and innovation guiding teams to grow not just in profit, but in purpose. As a mentor and community advocate, he champions connection and clarity in an age of digital noise. Through his work and podcast, Jason inspires others to align their growth with values that truly matter.  Connect with Jason Trent: Website: https://www.hsip.com/agency-directory/guidelight-insurance   LinkedIn: https://www.linkedin.com/in/trent-jason/ https://www.linkedin.com/company/guidelight-insurance/     Instagram:     X: https://www.linkedin.com/company/guidelight-insurance/   Facebook: https://www.facebook.com/people/The-Guidelight/61575862355860/    Stay Connected. Stay Inspired. Let’s build deeper, stronger relationships—one meaningful connection at a time. 👉 Explore all things JTrent Connect: linktr.ee/JTrentConnect

    17 min

  6. 10/28/2025

    Peace of God: 5 Reasons You’re Missing It & How To Find It

    How often do you feel like you’re missing the peace of God? In this episode of The Guidelight, Jason shares the five reasons we drift away from God’s peace and how we can overcome these stumbling blocks to draw closer to Him again. When pride, doubt, and fear take over, God is still there. Waiting for you in the silence, ready to show you His truth. The question is, are you truly seeking His kingdom first? You don’t have to control everything. Let go, forgive, and heal. God isn’t finished with you yet. Anchor into Him and let His peace fill your heart. Learn more in The Guidelight podcast: Peace of God: 5 Reasons You’re Missing It & How To Find It Enjoy this episode? Give us a review and leave a 5-star rating. Jason Trent believes the strongest businesses — and the most meaningful lives — are built on relationships, not transactions. As a leader, advisor, and storyteller, his purpose is to help others see what’s possible when faith and leadership walk hand in hand. Through decades of experience guiding business owners and CEOs, Jason has seen the tension between growth and grounding — the chase for success that too often drifts from God’s greater calling.  That conviction inspired The Guidelight Podcast, where he sits down with entrepreneurs, community leaders, and changemakers to uncover the stories, principles, and faith that illuminate their journey. As the founder of Guidelight Capital Advisors and President of Highstreet Guidelight Insurance, Jason continues to help others steward both their companies and their calling. His approach blends business acumen with heart — challenging leaders to think beyond profit toward purpose, legacy, and impact. Whether behind a microphone or across a table, Jason’s mission remains the same: to shine light on what matters most, and to remind others that leadership rooted in love changes everything. Connect with Jason Trent: Website: https://guidelightpodcast.com/  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/channel/UCyXPtmwEwvZ-qJB0uYln7mg   #PeaceOfGod #SeekHisKingdom #ForgiveAndHeal   Stay Connected. Stay Inspired. Let’s build deeper, stronger relationships—one meaningful connection at a time. 👉 Explore all things JTrent Connect: linktr.ee/JTrentConnect

    24 min

  7. 10/21/2025

    Authority and Faith: Leading Under God’s Direction

    As a leader, do you ever struggle with the authority that God has given you? In this episode of The Guidelight, Jason Trent explores what it truly means to walk in authority — its purpose, its power, and the frustrations that sometimes come with it. Inspired by a simple yet profound question from his daughter — “Why do we pray in Jesus’ name?” — Jason reflects on how Jesus’ authority covers us and how He invites us to do life with Him. He also shares how God led him to start this podcast and how surrendering his own strength allowed him to rest in the Lord’s authority. Watch The Guidelight: Authority and Faith: Leading Under God’s Direction Enjoy the podcast? Subscribe and leave a 5-star review. 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/channel/UCyXPtmwEwvZ-qJB0uYln7mg   #FaithLeadership #GodsAuthority #WalkInFaith Stay Connected. Stay Inspired. Let’s build deeper, stronger relationships—one meaningful connection at a time. 👉 Explore all things JTrent Connect: linktr.ee/JTrentConnect

    10 min

  8. 10/14/2025

    When Is the Right Time to Sell Your Business? The Truth About Maximizing Value

    A brand is simply a promise, and a good brand is a promise kept. In this episode, Jason Trent shares a conversation with Kit Garren, Founder of IPM and tonsofrentals.com, about preparing your business for an exit and unlocking its full potential and value. As a brother in Christ, Kit shares insights on the time value of money, how business owners weigh risks and uncertainties, and the difference between financial and strategic buyers. He also dives into how building a strong brand adds value to your business and how faith can guide growth and leadership. Selling your company isn’t the end, but the beginning of new opportunities. As a leader, remember that your business is your legacy. Watch The Guidelight: When Is the Right Time to Sell Your Business? The Truth About Maximizing Value   Enjoy this episode? Give us a review and leave a 5-star rating! Kit Garren, MPM, RMP, is the Founder of IPM/tonsofrentals.com with over 30 years of executive experience as founder and CEO of a real estate management company that specializes in single-family homes, duplexes, property owner associations, condominium associations, and other residential investment properties. The success of the brand was built upon a strong foundation that "our purpose must transcend our product." The team of professionals understands and embraces this truth. That foundational principle, blended with the ever-present pursuit of innovation, lean principles, and technology, elevated IPM/tonsofrentals.com to its current success. Today, IPM/tonsofrentals.com is part of the Associa/Rhome family of companies operating throughout the U.S., Mexico, and Canada, for which he now serves as Vice President of Acquisitions. LinkedIn: https://www.linkedin.com/in/kit-garren-mpm-rmp-865040a/  Visit his website: https://www.rhomepm.com/about  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/channel/UCyXPtmwEwvZ-qJB0uYln7mg   #BusinessLegacy #FaithInBusiness #ExitStrategy   Stay Connected. Stay Inspired. Let’s build deeper, stronger relationships—one meaningful connection at a time. 👉 Explore all things JTrent Connect: linktr.ee/JTrentConnect

    26 min
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About

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.

Information

  • Creator
    Jason Trent
  • Years Active
    2025 - 2026
  • Episodes
    16
  • Rating
    Clean
  • Copyright
    © 2026 The Guidelight
  • Show Website
    The Guidelight