Turning Self-Doubt to Self-Discovery with Dan Henderson

Today I'm speaking with Leadership Coach Dan Henderson, who spent years building a career in business—founding companies, working in venture capital, and leading major acquisitions - until an undiagonosed discovery changed the trajectory of his career and set him on a journey—not just of understanding himself, but of reframing his entire story.

In this conversation, Dan shares how he transformed what he once saw as a deficit into his greatest strength. We dive into the emotional landscape of leadership, the power of finding community, and why the stories we tell ourselves—especially the ones about not being ‘enough’—deserve to be challenged. Thanks for listening!

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Bio

Dan Henderson spent nearly three decades building and successfully exiting high-growth businesses as a founder, venture investor, and corporate development executive. He played key roles in companies like FastSoft (acquired by Akamai) and BeClose (incubated at Alarm.com), led global M&A for 3Pillar Global, and invested in startups that achieved valuations in the hundreds of millions.

Now an ICF-accredited leadership coach and Founder of Gravity Insights he helps business leaders navigate growth, blind spots, and work-life balance with insight from his own journey. He also volunteers as a business advisor, plays fiddle in an award-winning bluegrass band, and lives in Falls Church, VA, with his family and an assortment of pets.