The Insurance Perspectives Podcast

In this episode of the Insurance Perspectives Podcast , Brad Boldt sits down with two members of the HawkSoft leadership team: Jake Dunbar, Director of Product Support, and Greg Fish, Director of IT and Information Security. Together they pull back the curtain on one of HawkSoft's defining core values, Sense of Community. They trace its origins back to the early days of the company and explor...

In this episode of the Insurance Perspectives Podcast, host Brad Boldt sits down with Brad Kaplan, president and CEO of Kaplan Insurance Agency. The discuss how Brad's friendship with Andy Priesman led him to become one of Cover Desk's earliest and most enthusiastic adopters, why specialization is the key to getting the most out of virtual staff, and how Cover Desk's accounting feat...

In this episode of the Insurance Perspectives Podcast, Brad Boldt sits down with Andy Priesman, CEO and founder of Cover Desk, and Kelsey Tenallion, Sr. Director of Business Development of Cover Desk, to talk about how Cover Desk can benefit an independent agent. Andy shares the origin story of Cover Desk, from hiring his first virtual assistant (VA) at Greenway Insurance in 2016 to building a 1,7...

In this episode of the Insurance Perspectives Podcast, host Brad Boldt sits down with Ashley Winebrenner, a third-generation insurance professional at Dwyer Insurance Agency in London, Ohio. Ashley shares her winding path to insurance — from working for a CRM company and traveling the world, to nursing school, to stumbling into her dad's agency "just temporarily" and never leaving....

In this episode of the Insurance Perspectives Podcast, Brad Boldt sits down with Jason Larsen, CEO and Risk Advisor at First State Insurance Agency Southwest, to discuss his rapid journey from outside the insurance industry to agency owner. Jason shares how an unexpected career transition led him into insurance during the COVID era, and how strong mentorship, structure, and a willingness to learn...

In this episode of the Insurance Perspectives Podcast, host Brad Boldt sits down with Jesse Villafranca, owner of Evergreen Insurance, to share the story of building an independent insurance agency from the ground up. Jesse walks through his journey of starting with almost nothing, opening Evergreen Insurance at age 33, and growing it into a respected, community‑focused agency. This conversation d...

In this episode of the Insurance Perspectives podcast, host Brad Boldt sits down with Darrin DeFouw, Director of Partner Integrations at HawkSoft, to explore his 20‑year journey with the company and his new role building and maintaining HawkSoft’s partner ecosystem. Darrin shares what it was like joining HawkSoft as one of the company’s first employees, how his experience across every department s...

In this episode of the Insurance Perspectives podcast, host Brad Boldt is joined by Michael Ley, HawkSoft Director of Networks, to discuss choosing the right network and conducting effective technology audits. Michael shares practical guidance on how agencies should evaluate networks, identify red flags in contracts, and avoid common mistakes that can lead to costly exits or misalignment. The conv...

In this episode of the Insurance Perspectives podcast, host Brad Boldt sits down with Dirk and Beth Zeigler of Zeigler Insurance to discuss the realities of building and running an independent insurance agency as a married couple. Dirk and Beth share their journey from the early days of starting the agency out of necessity, through the leap from a captive model to independence, and into the long‑t...

In this episode of the Insurance Perspectives podcast, Megan Ashmead Pacella and Kim Ashmead Leyens share insights on managing family dynamics within their independent insurance agency. They discuss the evolution of their agency, the challenges and rewards of working with family, and strategies for effective partnership and leadership. Takeways Multi‑generation agencies succeed with clear successi...

In this episode of the Insurance Perspectives podcast, Brad Boldt speaks with Dee and Jackie Zampella of EAB Insurance Group about leading and modernizing a family‑owned independent insurance agency. They discuss working together as a family, leadership, agency technology, and how tools like HawkSoft helped modernize operations while preserving a strong, client‑first culture. Takeaways Running a f...

In this episode of the Insurance Perspectives podcast, Brad Boldt interviews David and Grayson Carothers from Florida Risk Partners, exploring the unique dynamics of working with family in the insurance industry. They discuss the evolution of their agency, the onboarding process of Grayson into the business, and the importance of mentorship and building relationships with clients. The conversation...

In this episode of the Insurance Perspectives podcast, host Brad Boldt sits down with Dean Bowen of Patriotic Insurance Group to explore how Sembley functions inside a real independent agency. Dean shares his journey into the insurance industry, what it was like joining his family’s agency, and how Sembley has transformed their workflows. The conversation highlights the practical, day‑to‑day impac...

In this episode of the Insurance Perspectives podcast, Brad Boldt sits down with Dean Bowen and Joe Ems to explore how Sembley is transforming insurance workflows. They discuss Sembley's mission to eliminate duplicate data entry, streamline ACORD and supplemental forms, leverage document‑reading AI, and deeply integrate with systems like HawkSoft, AgencyZoom, and Canopy Connect. Listeners get...

In this episode of the Insurance Perspectives podcast, Brad Boldt interviews Linda Fisher, founder of Cardinal Insurance Group. They discuss the agency's growth strategies, the challenges faced during the hard market, and the importance of restructuring and departmentalization. Linda shares insights on leveraging technology and AI to enhance efficiency and the role of mentorship in developing...

In this episode of the Insurance Perspectives podcast, Brad Boldt sits down with Billy Wagner to discuss Brightway Insurance's focus on team development, culture, and strategies for growth in 2026. Billy shares insights on building a high-performing team, the importance of a positive culture, the rigorous hiring process for A-players, and the comprehensive benefits offered to employees. He em...

In this episode of the Insurance Perspectives podcast, Brad Boldt interviews Michael Cruz, founder of Foresight Insurance, discussing the agency's growth strategies, their implementation of a four-day work week, and the challenges faced in the insurance market. Michael shares insights on productivity, client retention, and the role of technology and AI in enhancing agency operations. The conv...

In this episode of the Insurance Perspectives podcast, Brad Boldt sits down with Dale Steinke, Director of Agent for the Future Advisors at Liberty Mutual, to discuss the transformative role of AI in the insurance industry. Dale emphasizes the importance of independent agents adapting to technological advancements, particularly AI, to enhance their business operations. He shares insights from his...

In this episode of the Insurance Perspectives podcast, Brad Boldt sits down with HawkSoft leadership, Sean Hawkins and Matt Aman, to discuss the evolving role of artificial intelligence (AI) in the insurance industry and at HawkSoft. The conversation begins with an overview of HawkSoft's approach to AI, emphasizing the importance of understanding its limitations and potential pitfalls. They e...

In this episode, the conversation revolves around the integration of Cara at LeDoux Insurance. Host Brad Boldt interviews the agency's principal, Dawn Roberts, about her experience and how Cara has transformed their operations by improving call handling and client interactions. The discussion also covers the agency's history, the challenges faced in customer service, best practices for i...

In this episode of the Insurance Perspectives podcast, Brad Boldt sits down with Nikhil Kansal, co-founder and CTO of Cara, to talk about how Cara helps independent agents. They discuss the transformative role of AI in the insurance industry, focusing on Cara AI's capabilities to automate back-office tasks, enhance client interactions, and streamline the quoting process. The conversation high...

In this episode of the Insurance Perspectives podcast, host Brad Boldt chats with Jeff Arnold to discuss the integration of AI in the insurance industry. Jeff shares his journey from a failed acting career to becoming a successful insurance agency owner, emphasizing the importance of using AI to enhance customer service and operational efficiency. The conversation explores the balance between leve...

In this episode of the Insurance Perspectives podcast, Brad Boldt welcomes Amrish Singh to discuss Liberate and its transformative impact on the insurance industry. They explore the mission of Liberate, its differentiating factors, the importance of data ownership, and how AI enhances human capabilities in insurance agencies. The conversation also touches on the integration with HawkSoft, the chal...

In this episode of the Insurance Perspective podcast, Brad Boldt hosts Chris Fitts and Scott Smith to discuss Fitts Insurance Agency's experience with Jump Suit Group. The conversation covers the evolution of the agency, the challenges of transitioning leadership, the importance of technology solutions, and the benefits of automation in client communication. Chris emphasizes the value of buil...

In this episode of the Insurance Perspectives podcast, Brad Boldt welcomes Scott Smith and Chris Fitts to discuss the role of Jump Suit Group in providing digital marketing and lead generation services for independent insurance agents. The conversation covers the importance of a strong digital presence, the challenges faced by independent agents, and the need for realistic expectations in digital...