Great leaders don’t get it right every time. They get better over time. In this episode, I tackle one of the most critical questions a founder will ever face, “When is the right time to sell?”

I walk through five clear signs that test your timing, valuation, and mission alignment.

Are you burned out or is the assignment complete? Has growth turned into maintenance mode? Are silent warning signs showing up in your health, marriage, or spiritual life? Are you tempted by a hot market and peak multiples? Or are you waiting too long and risking enterprise value, succession strength, and legacy impact?

Selling too early can cost a mission. Waiting too long can cost value. The right exit strategy requires clarity, wise counsel, and alignment with purpose.

Tune in to this episode of The GuideLight, walk through the five signs with me, and make sure your next move protects both your business and your calling.

Enjoy the podcast? Subscribe and leave a 5-star review!

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:

Websites:
https://guidelightlegacy.com/
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

Great leaders don’t get it right every time. They get better over time. In this episode, I explore how moments of misalignment can become powerful turning points, and why real leadership growth starts with refocusing your aim, not carrying shame.

I reflect on the true meaning of “missing the mark,” a phrase rooted in the language of archery. Most leaders don’t wake up trying to make poor decisions. We lead with good intentions, but distraction, pressure, and misplaced focus can pull our aim off center. When that happens, the solution is to refocus on the target.

I share lessons drawn from leadership, faith, and even the trail why looking at what you want to avoid often leads you straight into it. Strong leaders learn to set their eyes on what matters most: purpose, identity, truth, wisdom, culture, and stewardship. These anchors help leaders adjust their aim and move forward with clarity.

Learn how realigning your focus can help you lead with clarity, conviction, and renewed purpose. Watch this episode of The Guidelight.

Enjoy the podcast? Subscribe and leave a 5-star review!

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

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

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

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

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

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

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