Family Dynamics with Ashmead Insurance Associates

Cover Desk Pt. 2 - Brad Kaplan

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 feature has allowed his agency to reclaim 15 hours of his month. He also shares the agency's unique niche of insuring performing arts theaters across the country through what they call the "Red Carpet Program." Takeaways * Specialize your VAs the same way you specialize your staff. * Virtual Assistants (VA) handle the back-end so licensed people can focus on coverage conversations. * Add responsibilities gradually. Dump too much at once and nobody wins. * Cover Desk handles the IT, onboarding, and tech setup. * Just put your toe in the water when it comes to adopting a VA. The investment is low, the upside is high, and you'll find more work for them than you expect. Learn more about Kaplan Insurance Agency: https://www.kaplaninsuranceagency.com/ [https://www.kaplaninsuranceagency.com/] https://www.facebook.com/KaplanInsuranceAgency [https://www.facebook.com/KaplanInsuranceAgency] https://www.linkedin.com/company/kaplan-insurance-agency-inc-/ [https://www.linkedin.com/company/kaplan-insurance-agency-inc-/] To get in touch with today's guests, reach out below: * Brad Kaplan (click here [https://www.linkedin.com/in/bradkaplan1/]) * Andy Priesman (click here [https://www.linkedin.com/in/andy-priesman-6286834/]) * Kelsey Tenaillon (click here [https://www.linkedin.com/in/kelsey-tenaillon-3a0683a2/]) * Brad Boldt (click here [https://www.linkedin.com/in/brad-boldt-00318278/]) More information about Cover Desk: https://coverdesk.com/ [https://coverdesk.com/] https://www.facebook.com/coverdesk [https://www.facebook.com/coverdesk] https://www.linkedin.com/company/coverdesk/ [https://www.linkedin.com/company/coverdesk/] ________________________________________________________________________ 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.hawksoft.com/] https://www.facebook.com/hawksoft [https://www.facebook.com/hawksoft]https://x.com/HawkSoft [https://x.com/HawkSoft]https://instagram.com/hawkSoft [https://instagram.com/hawkSoft] Music by AudioCoffee(Denys Kyshchuk): https://www.audiocoffee.net/

Cover Desk Pt. 1 - Andy Priesman and Kelsey Tenaillon

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 1,700-person operation. He and Kelsey break down what Cover Desk does differently: in-office infrastructure, end-to-end foundational training, and a client success team that supports agencies well past onboarding. They also get practical about the top duties VAs handle, what makes agencies succeed or fail with virtual staff, and their other services that make Cover Desk more than just a VA provider. Takeaways * Cover Desk started as a solution to Andy's own staffing problem. * VAs can outperform local hires when given the right training and support. * You don't need perfect SOPs to start. Cover Desk will help you build them. * Training matters. Agencies that don't invest time upfront won't succeed with any hire. * Cover Desk is more than VAs — shared services, accounting, claims, and automation are all services they offer. * Treat your VA like a team member, not a task machine. Learn more about Cover Desk: https://coverdesk.com/ [https://coverdesk.com/] https://www.facebook.com/coverdesk [https://www.facebook.com/coverdesk] https://www.linkedin.com/company/coverdesk/ [https://www.linkedin.com/company/coverdesk/] To get in touch with today's guests, reach out below: * Andy Priesman (click here [https://www.linkedin.com/in/andy-priesman-6286834/]) * Kelsey Tenaillon (click here [https://www.linkedin.com/in/kelsey-tenaillon-3a0683a2/]) * Brad Kaplan (click here [https://www.linkedin.com/in/bradkaplan1/]) * Brad Boldt (click here [https://www.linkedin.com/in/brad-boldt-00318278/]) More information about Kaplan Insurance Agency: https://www.kaplaninsuranceagency.com/ [https://www.kaplaninsuranceagency.com/] https://www.facebook.com/KaplanInsuranceAgency [https://www.facebook.com/KaplanInsuranceAgency] https://www.linkedin.com/company/kaplan-insurance-agency-inc-/ [https://www.linkedin.com/company/kaplan-insurance-agency-inc-/] ________________________________________________________________________ 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.hawksoft.com/] https://www.facebook.com/hawksoft [https://www.facebook.com/hawksoft]https://x.com/HawkSoft [https://x.com/HawkSoft]https://instagram.com/hawkSoft [https://instagram.com/hawkSoft] Music by AudioCoffee(Denys Kyshchuk): https://www.audiocoffee.net/

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. Takeaways * Your 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.dwyerinsuranceagency.com/] https://www.facebook.com/DwyerInsAgency [https://www.facebook.com/DwyerInsAgency] To get in touch with today's guest, reach out below: * Ashley Winebrenner (click here [https://www.linkedin.com/in/ashley-winebrenner-8655281b/]) * Brad Boldt (click here [https://www.linkedin.com/in/brad-boldt-00318278/]) ________________________________________________________________________ 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.hawksoft.com/] https://www.facebook.com/hawksoft [https://www.facebook.com/hawksoft]https://x.com/HawkSoft [https://x.com/HawkSoft]https://instagram.com/hawkSoft [https://instagram.com/hawkSoft] Music by AudioCoffee(Denys Kyshchuk): https://www.audiocoffee.net/

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://firststateinsurance.net/] https://www.facebook.com/Firststateinsurancesw/ [https://www.facebook.com/Firststateinsurancesw/] https://www.instagram.com/firststateinsuranceagency/ [https://www.instagram.com/firststateinsuranceagency/] To get in touch with today's guest, reach out below: * Jason Larsen (click here [https://www.linkedin.com/in/jason-larsen-94a01b1a6/]) * Brad Boldt (click here [https://www.linkedin.com/in/brad-boldt-00318278/]) ________________________________________________________________________ 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.hawksoft.com/] https://www.facebook.com/hawksoft [https://www.facebook.com/hawksoft]https://x.com/HawkSoft [https://x.com/HawkSoft]https://instagram.com/hawkSoft [https://instagram.com/hawkSoft] Music by AudioCoffee(Denys Kyshchuk): https://www.audiocoffee.net/

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. Takeaways * Values and family drive long‑term agency success * Staying paperless early created lasting efficiency * Leadership evolves from client service to team development * Mentoring the next generation strengthens continuity * Community and relationships fuel sustainable growth * Doing the right thing builds trust and loyalty Learn more about Evergreen Insurance: https://evergreen-insurance.com/ [https://evergreen-insurance.com/] https://www.facebook.com/EvergreenInsurance [https://www.facebook.com/EvergreenInsurance] https://www.instagram.com/evergreenvanwa/ [https://www.instagram.com/evergreenvanwa/] To get in touch with today's guest, reach out below: * Jesse Villafranca (click here [https://www.linkedin.com/in/jesse-villafranca-99699b7/]) * Brad Boldt (click here [https://www.linkedin.com/in/brad-boldt-00318278/]) ________________________________________________________________________ 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.hawksoft.com/] https://www.facebook.com/hawksoft [https://www.facebook.com/hawksoft]https://x.com/HawkSoft [https://x.com/HawkSoft]https://instagram.com/hawkSoft [https://instagram.com/hawkSoft] Music by AudioCoffee(Denys Kyshchuk): https://www.audiocoffee.net/