What does it take to go from scrubbing junk out of donated cars at 18 to running a $10 million nonprofit as CEO at 30? In Episode 14 of the Glovisor Podcast, Colin Weatherwax shares the raw, unexpected story of how he rose through the ranks, not by chasing titles, but by treating every role as a learning opportunity, until a sudden tragedy made him the leader nobody saw coming.
The Inside Hire Nobody Saw Coming
Here's the thing: most people believe career growth means hopping between companies, collecting titles along the way. Colin's story flips that script entirely. He started at the bottom, literally cleaning donated cars, and spent over a decade learning every function of one organization. No shortcuts, no politics, just showing up, mastering each role, and earning trust season after season.
When the moment came, he was ready, not because he was groomed with the title in mind, but because he had quietly built competence in every corner of the organization.
Leading Through Crisis: Trial by Fire
Colin's first month as CEO was unlike anything most leaders face. His mentor and boss suddenly passed away, and days later he stepped in as interim CEO facing:
A pending lawsuit he inherited with zero warning
A board he had never met, now looking to him for answers
Finances he did not fully understand yet, with millions at stake
You know what I mean? Most new CEOs get an onboarding plan. Colin got a storm. And his response is the masterclass: he did not pretend to have all the answers. He reached out. He hired three business coaches on his own dime, because he understood that asking for help is a sign of strength, not weakness.
Key Man Insurance: The Lesson Every Owner Needs
One of the most practical takeaways from this episode is Colin's passionate explanation of key man insurance, coverage that protects a business when a critical person, a founder, CEO, or irreplaceable leader, is suddenly lost. If your organization would face serious financial or operational damage from losing one key individual, you need this policy.
Colin's firsthand experience of inheriting a crisis after the sudden death of his mentor taught him something every business owner should hear: succession planning and key person coverage are not optional extras. They are the difference between an organization that survives a shock and one that collapses. This lesson became the seed for his move into the insurance world as an entrepreneur.
The Framework: How to Rise From Entry-Level to CEO
Colin's climb distills into a repeatable playbook for anyone starting at the bottom:
Treat every role as tuition. You are not just doing a job; you are learning how the whole machine works.
Show up consistently. Reliability over time builds the trust that titles cannot buy.
Learn adjacent functions. Volunteer for cross-training, understand finance, operations, and people, not just your lane.
Hire coaches before you feel ready. Growth accelerates when you invest in your own development, especially during transitions.
Lead with humility in crisis. Admit what you do not know, gather advisors fast, and act with the information you have.
A Scenario You Might Recognize
Picture a 22-year-old employee grinding through entry-level work, wondering if she should jump ship for a $5K raise elsewhere. Colin's story suggests the better question: where can I learn the most in the next five years? Loyalty to one organization, when matched with curiosity and initiative, can compound into opportunities jumpers rarely see: the insider who knows every system becomes the obvious choice when leadership is needed.
Of course, loyalty only pays when paired with growth. Show up, learn everything, and let the compounding do its work.
Reflection During Career Transitions
Colin also opens up about what reflection actually looked like during his hardest transitions: concrete practices, not vague journaling. Processing grief while running an organization required intentional pauses, honest self-assessment, and leaning on his coaches to separate personal pain from professional decisions. That emotional discipline is what allowed him to lead well while healing.
Connect and Go Deeper
Connect with Colin Weatherwax on LinkedIn. Mention Glovisor when you reach out, and if you would like a personal introduction or have questions about working with him, contact us, and we will happily connect you.
Ready to accelerate your own leadership journey? Explore our books at store.glovisor.com, master the system with our guided online course, or go deeper with personalized 1-on-1 coaching at Glovisor.com.
Watch the full episode with Colin Weatherwax
Conclusion
Colin Weatherwax's story dismantles the myth that leadership is something you chase. It is something you grow into, one role, one lesson, one kept commitment at a time. Whether you are scrubbing cars or steering a $10 million organization, the formula holds: show up, learn everything, hire support, and be ready when the room calls your name.