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.

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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/

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