Finding Your Purpose: Justin Davis on Reinventing Yourself After Success
What happens after you’ve built successful companies, achieved financial success, and reached the milestones you once dreamed about?
For many entrepreneurs, that question arrives quietly. The business is growing, the career looks impressive, yet something feels missing. In this episode of the Rebellious Times Podcast, Justin Davis, founder of Eleven Dunbar, shares an honest conversation about finding your purpose after success, navigating grief, rebuilding your identity, and reconnecting with what it truly means to be human.
Finding Your Purpose Often Begins With Letting Go
Justin’s career reads like many founders would dream of. Multiple successful startups. Six acquisitions. Leadership roles in technology. Yet behind those achievements came burnout, loss, failed ventures, personal grief, and a profound question:
“If I’m no longer the CEO… who am I?”
Instead of immediately launching another company, Justin chose something much harder. He paused. He spent months reflecting on his identity outside of work, discovering that purpose isn’t something you achieve—it’s something you uncover.
Success Doesn’t Protect You From Transformation
One of the most powerful moments in our conversation is Justin’s honesty about failure. He openly discusses winding down his previous company while simultaneously dealing with family illness, personal loss, and the end of important relationships.
Rather than viewing these experiences as setbacks, Justin now sees them as necessary chapters in his own transformation. Sometimes life’s biggest breakthroughs begin when the identity we’ve built no longer serves us.
Curiosity Creates Better Relationships
Long before becoming a founder, Justin discovered something that would shape his career: genuine curiosity.
Whether speaking with customers, colleagues, or complete strangers, he believes the best conversations come from asking thoughtful questions rather than trying to impress people with your own answers.
That mindset became the foundation for Eleven Dunbar, a community built around meaningful conversations, vulnerability, creativity, and authentic human connection.
Chapters
00:00 Introduction and Justin’s background
03:08 Justin shares his early entrepreneurial roots
08:16 Lessons from Cisco and early sales experiences
12:42 The importance of work ethic and kindness
13:45 The art of connection and curiosity
17:54 Closing his previous company and personal loss
21:18 Healing, grief, and self-discovery
23:08 Building Eleven Dunbar
42:57 Advice for entrepreneurs seeking a fuller life
44:29 Community and shared curiosity
47:46 Understanding human frequency
55:17 The caterpillar, cocoon and butterfly
58:46 Living authentically and serving others
01:00:17 Closing remarks
Why Human Connection Matters in the Age of AI
Artificial intelligence became an unexpected topic throughout our discussion.
Justin doesn’t see AI as something opposed to humanity. Instead, he argues that AI is one of humanity’s greatest creations. The challenge isn’t resisting technology; it’s making sure we don’t lose the qualities that technology can never replace—empathy, curiosity, creativity, community, and authentic relationships.
It’s a refreshing perspective in a world that often frames AI as either salvation or catastrophe.
The Caterpillar, Cocoon, and Butterfly
Perhaps my favourite idea from the conversation was Justin’s metaphor for personal growth.
Life isn’t a straight line.
Sometimes we’re the caterpillar, searching for something more.
Sometimes we’re inside the cocoon, letting go of old identities, habits, and expectations.
Eventually, if we’re willing to do the work, we emerge as the butterfly—not because we’ve become perfect, but because we’ve become more authentic.
And then the cycle begins again.
For anyone navigating change, uncertainty, or a search for greater meaning, this conversation offers a reminder that transformation isn’t something to fear. It’s part of being human.
Justin Davis links:
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