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Ever wondered how a lack of insurance could spell disaster for your contracting business? Buckle up as we bring you an insider's account unraveling the complexities of contractor insurance and why skimping on it isn't an option. This episode isn't just cautionary tales—though we've got those too—but a treasure trove of personal experiences and hard-earned wisdom that will guide you to secure your business's future. From the pitfalls of underinsurance to the nuances of general liability and workers' compensation, we dissect the insurance landscape to ensure you're prepared for whatever comes your way. Whether you're flying solo or managing a team, our discussion underscores the importance of having all the right shields up before you step onto the job site.
Navigating the onboarding jungle with new vendors can be a high-wire act, balancing stringent insurance demands with the flexibility needed to foster growth. In this candid conversation, we share strategies for giving promising contractors the opportunity to prove their mettle—insurance in hand or not. Delving into the details, we discuss the perks of providing a "short runway" for newcomers and how exceptions for smaller trades can benefit your business. Join us as we also cover the symbiotic relationship between contractors and vendors: setting clear insurance expectations from the get-go, helping them thrive for mutual gain, and cultivating loyalty that translates into efficiency on the job. Tune in to gain invaluable insights that will empower you to craft a supportive, collaborative, and protected work environment.
Join us January 11–13 in Nashville for the Chart the Course 2026 Planning Retreat. Sign up now and get three free coaching sessions before the event to finish 2025 strong and hit 2026 with a clear game plan. At the retreat, you’ll tackle systems, hiring, marketing, and leadership alongside ambitious contractors, leaving with a blueprint for growth. Spots are limited—visit prostruct360.com to learn more!
Have a question or an idea to improve the podcast?
Email us at [email protected]
Want to learn more about our software or coaching?
Visit our website at ProStruct360.com
By ProStruct3605
1818 ratings
Ever wondered how a lack of insurance could spell disaster for your contracting business? Buckle up as we bring you an insider's account unraveling the complexities of contractor insurance and why skimping on it isn't an option. This episode isn't just cautionary tales—though we've got those too—but a treasure trove of personal experiences and hard-earned wisdom that will guide you to secure your business's future. From the pitfalls of underinsurance to the nuances of general liability and workers' compensation, we dissect the insurance landscape to ensure you're prepared for whatever comes your way. Whether you're flying solo or managing a team, our discussion underscores the importance of having all the right shields up before you step onto the job site.
Navigating the onboarding jungle with new vendors can be a high-wire act, balancing stringent insurance demands with the flexibility needed to foster growth. In this candid conversation, we share strategies for giving promising contractors the opportunity to prove their mettle—insurance in hand or not. Delving into the details, we discuss the perks of providing a "short runway" for newcomers and how exceptions for smaller trades can benefit your business. Join us as we also cover the symbiotic relationship between contractors and vendors: setting clear insurance expectations from the get-go, helping them thrive for mutual gain, and cultivating loyalty that translates into efficiency on the job. Tune in to gain invaluable insights that will empower you to craft a supportive, collaborative, and protected work environment.
Join us January 11–13 in Nashville for the Chart the Course 2026 Planning Retreat. Sign up now and get three free coaching sessions before the event to finish 2025 strong and hit 2026 with a clear game plan. At the retreat, you’ll tackle systems, hiring, marketing, and leadership alongside ambitious contractors, leaving with a blueprint for growth. Spots are limited—visit prostruct360.com to learn more!
Have a question or an idea to improve the podcast?
Email us at [email protected]
Want to learn more about our software or coaching?
Visit our website at ProStruct360.com

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