The Insurance Perspectives Podcast

Hosted by HawkSoft

Business TechnologyInterviews guests

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Episodes

120

Latest episode

Jun 2026

Language

EN-US

About the show

The Insurance Perspectives podcast provides honest, open, and transparent conversations with members of the independent insurance space about technology partners, mental health, building a tech stack, and more.

Listen to episodes

60 recent

June 16, 2026Episode 12420 min

Growing and Leading in a Family Agency with Ashley Winebrenner

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. Now 14 years in, Ashley is an inaugural member of HawkSoft's Taking Flight Program and is preparing to one day take over the agency her great-grandfather founded in 1931. She opens up about the joys and challenges of working with a parent, navigating a paper-vs-digital standoff, and what it means to carry the weight of a nearly 100-year family legacy.TakeawaysYour path doesn't have to be straight. Sometimes you stumble into your purpose.Working with family is a gift, even when it's hard.Change takes patience. Move the agency forward without leaving people behind.Solve the problem before buying the tool.Community closes the knowledge gap. You don't have to figure it out alone.Legacy is both a burden and a privilege.Learn more about Dwyer Insurance Agency:https://www.dwyerinsuranceagency.com/https://www.facebook.com/DwyerInsAgencyTo get in touch with today's guest, reach out below:Ashley Winebrenner (click here)Brad Boldt (click here)________________________________________________________________________If you’re looking to reach out to HawkSoft, please email marketing@hawksoft.com. For more information on HawkSoft, visit:https://www.hawksoft.com/https://www.facebook.com/hawksofthttps://x.com/HawkSofthttps://instagram.com/hawkSoftMusic by AudioCoffee(Denys Kyshchuk): https://www.audiocoffee.net/

June 9, 2026Episode 12319 min

Building a Growth-Focused Agency with Jason Larsen

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 helped him step into leadership quickly. He opens up about the challenges of leading through a hard insurance market, building team culture across multiple locations, and balancing growth with thoughtful decision‑making.Takeaways:Strong mentorship can accelerate leadership readiness and ownership transitions.Clear structure and documentation are essential for sustainable agency growth.Culture is built through everyday moments, not just big initiatives.Technology should enhance workflows through integration, not complexity.Community involvement builds trust and long‑term client relationships.Serving people well ultimately drives agency growth.Learn more about First State Insurance Agency Southwest:https://firststateinsurance.net/https://www.facebook.com/Firststateinsurancesw/https://www.instagram.com/firststateinsuranceagency/To get in touch with today's guest, reach out below:Jason Larsen (click here)Brad Boldt (click here)________________________________________________________________________If you’re looking to reach out to HawkSoft, please email marketing@hawksoft.com. For more information on HawkSoft, visit:https://www.hawksoft.com/https://www.facebook.com/hawksofthttps://x.com/HawkSofthttps://instagram.com/hawkSoftMusic by AudioCoffee(Denys Kyshchuk): https://www.audiocoffee.net/

June 2, 2026Episode 12220 min

Growing a Values‑Driven Agency with Jesse Villafranca

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 dives into family‑first leadership, mentoring the next generation (including bringing his son into the agency), and why doing the right thing for employees and clients always pays dividends.TakeawaysValues and family drive long‑term agency successStaying paperless early created lasting efficiencyLeadership evolves from client service to team developmentMentoring the next generation strengthens continuityCommunity and relationships fuel sustainable growthDoing the right thing builds trust and loyaltyLearn more about Evergreen Insurance:https://evergreen-insurance.com/https://www.facebook.com/EvergreenInsurancehttps://www.instagram.com/evergreenvanwa/To get in touch with today's guest, reach out below:Jesse Villafranca (click here)Brad Boldt (click here)________________________________________________________________________If you’re looking to reach out to HawkSoft, please email marketing@hawksoft.com. For more information on HawkSoft, visit:https://www.hawksoft.com/https://www.facebook.com/hawksofthttps://x.com/HawkSofthttps://instagram.com/hawkSoftMusic by AudioCoffee(Denys Kyshchuk): https://www.audiocoffee.net/

May 26, 2026Episode 12119 min

Getting to Know HawkSoft's New Director of Partner Integrations with Darrin DeFouw

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 shaped his perspective, and why partner integrations play a critical role in solving real‑world agency problems. TakeawaysPartner integrations solve agency problems holistically.HawkSoft carefully vets partners for quality and fit.Agencies retain full ownership of their data.Cloud architecture enables better, faster integrations.Technology should support real agency workflows.Learn more about HawkSoft and the Partner Program:https://www.hawksoft.com/https://www.hawksoft.com/about/partners/https://www.facebook.com/hawksoft/https://www.instagram.com/hawksoft/To get in touch with today's guest, reach out below:Darrin DeFouw (click here)Brad Boldt (click here)________________________________________________________________________If you’re looking to reach out to HawkSoft, please email marketing@hawksoft.com. For more information on HawkSoft, visit:https://www.hawksoft.com/https://www.facebook.com/hawksofthttps://x.com/HawkSofthttps://instagram.com/hawkSoftMusic by AudioCoffee(Denys Kyshchuk): https://www.audiocoffee.net/

May 19, 2026Episode 12024 min

Choosing a Network and Auditing Tech with Michael Ley

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 conversation concludes with a discussion on technology audits and how agencies can assess their current tech stack, avoid “shiny object syndrome,” and ensure new tools actually support workflows and growth goals.TakeawaysInterview multiple networks before committing.Always review contracts and exit terms.Strong networks offer more than commissions.Annual tech audits reduce waste and improve ROI.Assign a tech owner to drive adoption.New tech should support clear workflows.Integration and training matter more than price.Learn more about HawkSoft:https://www.hawksoft.com/https://www.hawksoft.com/networks/https://www.facebook.com/hawksoft/https://www.instagram.com/hawksoft/To get in touch with today's guests, reach out below:Michael Ley (click here)Brad Boldt (click here)________________________________________________________________________If you’re looking to reach out to HawkSoft, please email marketing@hawksoft.com. For more information on HawkSoft, visit:https://www.hawksoft.com/https://www.facebook.com/hawksofthttps://x.com/HawkSofthttps://instagram.com/hawkSoftMusic by AudioCoffee(Denys Kyshchuk): https://www.audiocoffee.net/

May 12, 2026Episode 11938 min

Family Dynamics with Dirk and Beth Zeigler

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‑term growth of a community‑focused agency. They open up about the challenges of working alongside a spouse, setting boundaries between work and home, navigating major business decisions together, and learning to trust each other’s strengths.TakeawaysWorking with a spouse requires clear role separation and strong communication.Setting boundaries between work and home helps protect both the business and the marriage.Mentorship and business coaching can accelerate growth and clarity in leadership roles.Shared values and community involvement strengthen agency culture and client trust.Empowering both partners as true owners leads to long‑term sustainability.Learn more about Zeigler Insurance:https://www.zeiglerinsurance.com/https://www.facebook.com/zeiglerinsurance/https://www.instagram.com/zeiglerins/To get in touch with today's guests, reach out below:Dirk Zeigler (click here)Beth Zeigler (click here)Brad Boldt (click here)________________________________________________________________________If you’re looking to reach out to HawkSoft, please email marketing@hawksoft.com. For more information on HawkSoft, visit:https://www.hawksoft.com/https://www.facebook.com/hawksofthttps://x.com/HawkSofthttps://instagram.com/hawkSoftMusic by AudioCoffee(Denys Kyshchuk): https://www.audiocoffee.net/

May 5, 2026Episode 11836 min

Family Dynamics with Ashmead Insurance Associates

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.TakewaysMulti‑generation agencies succeed with clear succession and communication.Family hires need mentorship, not shortcuts.Open communication reduces legacy and leadership pressure.Strong teams smooth leadership transitions.Family becomes an advantage when trust aligns goals.Learn more about Ashmead Insurance Associates:https://ashmeadins.com/https://www.facebook.com/AshmeadInsurancehttps://www.instagram.com/ashmeadinsurance/https://www.linkedin.com/company/ashmead-insurance-associates/To get in touch with today's guests, reach out below:Megan Ashmead Pacella (click here)Kim Ashmead Leyens (click here)Brad Boldt (click here)________________________________________________________________________If you’re looking to reach out to HawkSoft, please email marketing@hawksoft.com. For more information on HawkSoft, visit:https://www.hawksoft.com/https://www.facebook.com/hawksofthttps://x.com/HawkSofthttps://instagram.com/hawkSoftMusic by AudioCoffee(Denys Kyshchuk): https://www.audiocoffee.net/

April 28, 2026Episode 11738 min

Family Dynamics with Dee and Jackie Zampella

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.TakeawaysRunning a family‑owned insurance agency requires clear roles and accountabilityModernizing systems can improve efficiency without losing cultureTechnology works best when teams are involved and changes roll out graduallyStrong community relationships drive long‑term agency successClear processes make agencies easier to scale and protect against E&O riskLearn more about EAB Insurance Group:https://www.facebook.com/EABInsuranceGrouphttps://www.linkedin.com/company/eabinsurance/To get in touch with today's guests, reach out below:Dee Zampella (click here)Jackie Zampella (click here)Brad Boldt (click here)________________________________________________________________________If you’re looking to reach out to HawkSoft, please email marketing@hawksoft.com. For more information on HawkSoft, visit:https://www.hawksoft.com/https://www.facebook.com/hawksofthttps://x.com/HawkSofthttps://instagram.com/hawkSoftMusic by AudioCoffee(Denys Kyshchuk): https://www.audiocoffee.net/

April 21, 2026Episode 11637 min

Family Dynamics with David and Grayson Carothers

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 highlights the challenges and rewards of family-run businesses, emphasizing the significance of clear communication and understanding in maintaining both personal and professional relationships.TakeawaysClear rules and boundaries are essential when working with family.Customer service experience is invaluable in the insurance industry.Mentorship plays a crucial role in onboarding new family members.Patience is necessary for both learning and teaching in a family business.It's important to let family members find their own path in the business.Success in family business requires open communication and trust.Learn more about Florida Risk Partners:https://www.facebook.com/FloridaRiskPartners/https://www.instagram.com/flriskpartners/https://www.linkedin.com/company/florida-risk-partners/To get in touch with today's guests, reach out below:David Carothers (click here)Grayson Carothers (click here)Brad Boldt (click here)________________________________________________________________________If you’re looking to reach out to HawkSoft, please email marketing@hawksoft.com. For more information on HawkSoft, visit:https://www.hawksoft.com/https://www.facebook.com/hawksofthttps://x.com/HawkSofthttps://instagram.com/hawkSoftMusic by AudioCoffee(Denys Kyshchuk): https://www.audiocoffee.net/

April 14, 2026Episode 11531 min

Sembley Pt. 2 - Dean Bowen

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 impact of Sembley, including streamlined intake processes, simplified ACORD creation, reduced manual work, and improved client communication.TakeawaysSembley makes ACORD creation fast, standardized, and far less manual.Custom intakes help simplify complex and E&S submissions.Sembley keeps data consistent across tools.Clients benefit from cleaner, more complete intakes with fewer follow‑ups.Onboarding was smooth, and the team adopted Sembley quickly.Learn more about Patriotic Insurance Group:https://patrioticinsurancegroup.com/https://www.facebook.com/patrioticinsurancegrouphttps://www.linkedin.com/company/patriotic-insurance-group/To get in touch with today's guests, reach out below:Dean Bowen (click here)Joe Ems (click here)Brad Boldt (click here)More information about Sembley:https://sembley.com/linkedin.com/company/sembley ________________________________________________________________________If you’re looking to reach out to HawkSoft, please email marketing@hawksoft.com. For more information on HawkSoft, visit:https://www.hawksoft.com/https://www.facebook.com/hawksofthttps://x.com/HawkSofthttps://instagram.com/hawkSoftMusic by AudioCoffee(Denys Kyshchuk): https://www.audiocoffee.net/

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