Ditch the Dread: Business Insurance Explained by a Pro You’ll Like episode artwork

EPISODE · Aug 7, 2025 · 30 MIN

Ditch the Dread: Business Insurance Explained by a Pro You’ll Like

from Business Roundtable · host David W. Carr

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:The “narrative” your broker presents to underwriters—and why it mattersHow to shift from reactive renewals to proactive strategyHidden gaps in coverage that could cost you everythingWhy most insurance advisors don’t ask the right questions—and how Dillon doesThe power of true collaboration between leaders, consultants, and insurance prosListen now and turn this overlooked area into a growth lever.Connect with Dillon Hawkins of HUB Fort Worth LinkedIn: https://www.linkedin.com/in/dillon-hawkins-hubintl/Subscribe to the Business Roundtable PodcastBecome a supporter of this podcast: https://www.spreaker.com/podcast/business-roundtable--6049255/support.Connect with Steward Your Business:Book a Leadership Clarity Call: https://calendar.stewardyourbusiness.com/ccCall: +1 909.404.9865Website: https://stewardyourbusiness.comLinkedIn: https://www.linkedin.com/in/davidwcarrWatch more episodes  and subscribe on YouTube:https://www.youtube.com/@steward_your_business

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:The “narrative” your broker presents to underwriters—and why it mattersHow to shift from reactive renewals to proactive strategyHidden gaps in coverage that could cost you everythingWhy most insurance advisors don’t ask the right questions—and how Dillon doesThe power of true collaboration between leaders, consultants, and insurance prosListen now and turn this overlooked area into a growth lever.Connect with Dillon Hawkins of HUB Fort Worth LinkedIn: https://www.linkedin.com/in/dillon-hawkins-hubintl/Subscribe to the Business Roundtable PodcastBecome a supporter of this podcast: https://www.spreaker.com/podcast/business-roundtable--6049255/support.Connect with Steward Your Business:Book a Leadership Clarity Call: https://calendar.stewardyourbusiness.com/ccCall: +1 909.404.9865Website: https://stewardyourbusiness.comLinkedIn: https://www.linkedin.com/in/davidwcarrWatch more episodes  and subscribe on YouTube:https://www.youtube.com/@steward_your_business

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Ditch the Dread: Business Insurance Explained by a Pro You’ll Like

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This episode is 30 minutes long.

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This episode was published on August 7, 2025.

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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...

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