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
Serial Entrepreneurship: When to Start, When to Sell, and When to Stay Focused
Use Left/Right to seek, Home/End to jump to start or end. Hold shift to jump forward or backward.
When is it time to start something new — and when is it time to stay the course?
In Part 2 of my conversation with Dave Streen, we unpack the realities of serial entrepreneurship. Dave has launched multiple companies, brought over 100 products to market, and bought and sold businesses across industries. But this isn’t about chasing ideas. It’s about discipline, timing, and alignment.
Serial entrepreneurship is powerful, but without focus, it becomes an expensive distraction.
Before you make your next move, listen to this conversation — it may save you from starting the wrong thing or walking away too soon.
Dave Streen is a serial entrepreneur, author, and speaker known for building businesses that prioritize simplicity, leverage, and freedom. He is the innovator behind EdgyTools®️ and the founder of We Help Authors™, where he supports entrepreneurs in turning their ideas and expertise into impactful books. Dave also hosts the Authors Summaries Podcast, where he explores key insights from influential thinkers and creators. Through his work, he helps business owners design companies that are easy, lucrative, and fun — without sacrificing focus or fulfillment.
Connect with Dave Streen:
Website: https://davestreen.com/
Instagram: https://www.instagram.com/davestreen
LinkedIn: https://www.linkedin.com/in/davestreen/
Facebook: https://www.facebook.com/dave.streen
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/
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