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Conversations with Christopher Weible

Today we’d like to introduce you to Christopher Weible.

Hi Christopher, so excited to have you on the platform. So before we get into questions about your work-life, maybe you can bring our readers up to speed on your story and how you got to where you are today?

Chris Weible is a lifelong entrepreneur who started his first business running a neighborhood landscaping company at a young age. After studying musical theatre, he moved to New York City, where he developed the confidence, communication, and relationship-building skills that would later define his career.

Chris went on to build and operate a successful personal training business for 12 years and, in his 20s, led a network marketing organization of more than 50 independent business owners. Years of relying on relationships—not ads or cold leads—to grow his income shaped him into an expert networker who understands how trust and referrals drive sustainable business success.

Today, Chris runs a multi-line insurance practice specializing in health, life, Medicare, long-term care, and supplemental insurance. Coming from a family of insurance professionals—his mother, father, and sister are all licensed agents—Chris combines deep industry knowledge with real-world entrepreneurial experience to help individuals and self-employed business owners protect what they’ve worked so hard to build.

We all face challenges, but looking back would you describe it as a relatively smooth road?
Definitely not. Entrepreneurship has been anything but a straight line for me. For more than a decade, I’ve pursued self-employment with a clear vision—to create freedom, provide incredible experiences for my family, and build a lifestyle that isn’t limited by someone else’s ceiling. What people don’t always see are the long seasons of uncertainty, inconsistent income, and constant reinvention that came with that pursuit.

There were years of grinding without guarantees, learning lessons the hard way, and investing time and money into myself before seeing meaningful returns. I’ve experienced the pressure of being responsible not just for my own success, but for the well-being of my family. That pressure forced me to develop discipline, resilience, and the ability to build relationships and opportunities from scratch.

The rewarding part is that those struggles built the foundation for where I am today. I’m just beginning to live out the dreams that once felt distant—creating flexibility, making memories with my family, and building a business that aligns with my values. The journey hasn’t been easy, but it’s made the success far more meaningful.

Thanks for sharing that. So, maybe next you can tell us a bit more about your work?
What role does supplemental insurance play in your work with clients?

As a wealth protector and strategist, my role is to help clients prepare for the moments that can quietly steal their wealth. Supplemental insurance is one of the most powerful tools we use because it puts money directly into people’s pockets when they need it the most.

Health insurance covers doctors and hospitals. Supplemental insurance covers life—lost income, deductibles, out-of-pocket costs, travel for care, childcare, rent, and everyday bills that don’t stop when a diagnosis or accident happens. When the unexpected hits, these policies provide cash benefits that give families options instead of panic.

Why do you advocate so strongly for supplemental coverage?

Because I’ve seen what happens without it. One medical event can derail years of hard work, especially for self-employed business owners and families living on earned income. Supplemental coverage acts as a financial shock absorber. It protects savings, keeps people out of debt, and prevents medical situations from turning into long-term financial crises.

My job isn’t to sell policies—it’s to help clients keep the money they’ve worked so hard to build.

What would you say have been one of the most important lessons you’ve learned?
My mom taught me early on that the only difference between you and the person ahead of you is time and practice. With enough reps and commitment, there’s no limit to what you can accomplish.

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