Ditch the Dread: Business Insurance Explained by a Pro You’ll Like
Update: 2025-08-07
Description
Most business leaders treat insurance like a checkbox—until it becomes their biggest blind spot. In this episode of the Business Roundtable Podcast, David W. Carr sits down with Dillon Hawkins of HUB International to tackle the topic nobody talks about—but everyone needs to understand.
This isn’t a boring breakdown of policy types. It’s a candid conversation about how your insurance strategy reflects your leadership, your culture, and your future readiness.
Dillon shares the behind-the-scenes view on how brokers really pitch your business to carriers, the questions leaders should be asking (but usually aren’t), and how insurance can actually become a competitive advantage when it’s used proactively.
Whether you’re a founder, operator, or HR lead, this episode will challenge how you think about risk—and show you how to stop leaving your business exposed.
In this episode:
Connect with Dillon Hawkins of HUB Fort Worth
LinkedIn: https://www.linkedin.com/in/dillon-hawkins-hubintl/
Subscribe to the Business Roundtable Podcast
Become a supporter of this podcast: https://www.spreaker.com/podcast/business-roundtable--6049255/support.
Watch more episodes on YouTube and subscribe here:
https://www.youtube.com/@steward_your_business
Connect with Steward Your Business:
Website: https://stewardyourbusiness.com
LinkedIn: https://www.linkedin.com/in/davidwcarr
This isn’t a boring breakdown of policy types. It’s a candid conversation about how your insurance strategy reflects your leadership, your culture, and your future readiness.
Dillon shares the behind-the-scenes view on how brokers really pitch your business to carriers, the questions leaders should be asking (but usually aren’t), and how insurance can actually become a competitive advantage when it’s used proactively.
Whether you’re a founder, operator, or HR lead, this episode will challenge how you think about risk—and show you how to stop leaving your business exposed.
In this episode:
- The “narrative” your broker presents to underwriters—and why it matters
- How to shift from reactive renewals to proactive strategy
- Hidden gaps in coverage that could cost you everything
- Why most insurance advisors don’t ask the right questions—and how Dillon does
- The power of true collaboration between leaders, consultants, and insurance pros
Connect with Dillon Hawkins of HUB Fort Worth
LinkedIn: https://www.linkedin.com/in/dillon-hawkins-hubintl/
Subscribe to the Business Roundtable Podcast
Become a supporter of this podcast: https://www.spreaker.com/podcast/business-roundtable--6049255/support.
Watch more episodes on YouTube and subscribe here:
https://www.youtube.com/@steward_your_business
Connect with Steward Your Business:
Website: https://stewardyourbusiness.com
LinkedIn: https://www.linkedin.com/in/davidwcarr
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