In this enlightening episode of Inside Personal Growth, host Greg Voisen welcomes entrepreneur, leadership coach, and sailor David J. Greer, author of Wind In Your Sails: Vital Strategies That Accelerate Your Entrepreneurial Growth. What unfolds is more than a discussion about business—it’s a vulnerable, inspiring, and deeply practical conversation about the inner journey of being a founder.From confronting burnout and addiction to navigating massive business transitions and finding peace on the open sea, David’s story is both relatable and transformational.
When Achievement Isn’t Enough
David shares how, after building a wildly successful tech company, he found himself unfulfilled—trapped in the expectations of external success and disconnected from his sense of purpose. Despite having the “perfect” life on paper, including financial success and industry recognition, something was missing.
That turning point came when David and his wife decided to homeschool their children and sail 5,000 miles across the Mediterranean. It was during this time away from the grind that he began to uncover the deeper truths about leadership, clarity, and joy.
The Real Reason Entrepreneurs Burn Out
One of the most powerful insights from the episode is that many entrepreneurs suffer not because they’re doing too little—but because they’re trying to do it all. As David explains, many founders are the original architects of their businesses. They build every system, wear every hat, and slowly become the bottleneck to their own company’s growth.
He emphasizes a core mistake that sinks businesses: refusing to let go.
“The most limiting factor for most companies is the founder themselves,” David says.
His advice? Trust your team. Hire people smarter than you—and then actually let them lead.
Self-Awareness Over Strategy
Greg and David explore the connection between emotional intelligence and business resilience. David openly discusses his battle with alcoholism, a struggle he kept hidden even as he coached others. It wasn’t until he named the problem out loud that he began the path to recovery.
“Half the battle is naming the brutal fact,” David shares. “Once it’s out in the open, you can begin to heal, grow, and lead with integrity.”
This principle applies to founders facing hard decisions: layoffs, pivots, or admitting when a vision no longer works. As David puts it, you can’t outgrow your business if you’re still pretending everything is fine.
Reconnecting with Purpose and Energy
Burnout doesn’t always mean you hate your work—it can mean you’ve simply lost your why. David helps founders reconnect with the reason they started their businesses in the first place. He recommends asking yourself:
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Why did I start this?
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What brings me joy in the business today?
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What have I let go of that used to energize me?
And perhaps most importantly: How can I take care of myself so I can show up fully for others?
David breaks life into three categories—career, relationships, and self—and challenges leaders to intentionally invest in all three. Without caring for the self, the rest eventually collapse.
Learn More from David J. Greer
If you’re a founder, executive, or entrepreneur feeling stuck or overwhelmed, David offers real-world wisdom, coaching, and encouragement from someone who’s lived both the highs and lows.
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Get your copy of Wind In Your Sails
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Visit his website: CoachDJGreer.com
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Follow on Instagram
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Connect on LinkedIn
He even offers a free one-hour coaching session to help you get clarity on your next step.
Final Reflection
David’s episode is a reminder that leadership is not about perfection—it’s about presence. It’s about facing the hard truths, letting go of control, and learning to sail with the wind rather than against it.
Whether you’re navigating rough waters or feeling adrift in your business, David J. Greer offers a compass, a sail, and the wisdom to help you catch the wind again.
“When your sails feel deflated, take a step back. Breathe. And remember—you don’t have to sail alone.” – David J. Greer
You may also refer to the transcripts below for the full transcription (not edited) of the interview.
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