Rough Notes Front Cover, October 2025: Jackson Rollo, Rollo Insurance

In this Halloween-themed episode of Stuff About Money They Didn’t Teach You in School, host Erik Garcia, CFP®, ChFC®, BFA™ is joined by Dr. Matt Morris and first-time guest Stephanie Osborn for a fun and insightful conversation about fear, especially the fear of money. The trio starts by sharing their thoughts on scary movies (and why Erik can’t stand them) and explores some New Orleans lingo about what it really means to call someone “scary.” From there, they draw parallels between the things that spook us on screen, and the real-life anxieties people feel around money. As the discussion unfolds, they unpack why money can be so intimidating and how fear often leads to poor, or no financial decisions at all. The group explores the antidote to financial fear: identifying what’s truly important to you, Erik’s first pillar of financial security. Matt shares personal stories about how that focus has helped him overcome financial stress, while Erik and Stephanie offer practical strategies like setting small goals, celebrating wins, and building fierce accountability. Tune in for a lighthearted, meaningful conversation that’ll leave you a little less afraid of your finances—and maybe a little more ready to face your own money monsters. Episode Highlights: Erik kicks off the episode by sharing his fear of scary movies and how “scary” means something different in New Orleans. (03:38) Matt recalls childhood memories of terrifying films like Children of the Corn and Blair Witch Project, explaining why uncertainty makes horror so effective. (04:57) Stephanie admits she used to love scary movies but can’t handle them anymore, naming Scream as her favorite from the ’90s. (05:48) Erik transitions the conversation to the episode’s main topic about how money can be just as scary as horror movies and introduces Stephanie as a first-time guest. (08:00) Matt explains how financial anxiety often stems from the unknown, similar to fear in horror films, and why some people hide from their finances. (09:00) Stephanie cites statistics about Americans feeling anxious and stressed about money, and Matt discusses how confidence and financial literacy help reduce fear. (10:00) Erik and Matt break down three major financial fears: not having enough, fear of debt, and fear of the unknown. (24:00) Matt shares how fear can lead to poor or avoidant financial decisions and explains the importance of awareness and communication in relationships. (27:00) Erik introduces “knowing what’s important to you” as the antidote to financial fear and anxiety, connecting values to practical money habits. (36:00) Matt offers personal examples of aligning money with values, like saving for family travel and using insurance for peace of mind. (39:00) Stephanie adds that identifying where fear comes from and checking in regularly can help manage anxiety and prevent “fear paralysis.” (51:00) Erik concludes by encouraging listeners to identify what matters most, create action steps, and check in consistently to keep fear from controlling their finances. (56:00) Key Quotes: “None of us want to be fear driven. We don't want to make decisions just based out of fear. Our fears are frequently misaligned with reality.” - Dr. Matt Morris “I feel like people with money are always concerned about money, and people without money are always concerned about money. They always want to have more or they fear that they don't have enough.” - Stephanie Osborn “When you stop long enough to determine what’s most important to you, you can start making conscious decisions to align your money with those things.” - Erik Garcia, CFP®, ChFC®, BFA™ Resources Mentioned: Dr. Matt Morris Matt Morris & Associates Stephanie Osborn Erik Garcia, CFP®, BFA Xavier Angel, CFP®, ChFC, CLTC Plan Wisely Wealth Advisors

The Executive Sessions: Ryan Westerman, President at AndDone Executive Sessions are all about humanizing the C-suite, and this one does just that. Jason sits down with Ryan Westerman, President at AndDone, to talk about his path from physics major to payments innovator, the lessons that shaped his leadership, and how AndDone is changing the way agents get paid. What starts as a career story unfolds into an honest look at communication, responsibility, and the human side of leading a growing company. Key Topics: Ryan’s journey from physics and public administration to leading a fintech company in insurance How a Pepsi bottling job sparked his entry into payment facilitation and technology innovation The birth of AndDone and its mission to simplify premium collection for agents Why Ryan believes technology and business models must evolve together Lessons from early mentors on communication, clarity, and explaining ideas that inspire buy-in The human side of executive leadership and carrying the weight of others’ livelihoods What’s next for payments, AI, and data in the insurance ecosystem Reach out to: Ryan Westerman Jason Cass Visit Website: AndDone IPFS Agency Intelligence Produced by PodSquad.fm

In this new episode of Insurance Shoptalk, join host Eric Stein and guest Jim Urseth, president of Reliable Premium Management (RPM), for a deep-dive into their pay-as-you-go solutions. RPM has many unique offerings, including a pay-as-you-go general liability program billed by payroll instead of the company’s revenue. Their pay-as-you-go offerings also include Workers’ Compensation programs, with superior options, flexibility, and benefits like easy implementation, a simplified audit experience, and pay-as-you-go insurance premiums to minimize the upfront costs of Workers’ Compensation. To learn more about RPM and their pay-as-you-go solutions, find them online at https://reliablepremium.com/. About Insurance Shoptalk: Join host Eric Stein on a journey through the dynamic world of commercial property and casualty insurance. With over 25 years of experience in the industry, Eric brings a wealth of knowledge and insights to every episode. Insurance Shoptalk is your premier destination for in-depth discussions on the latest industry trends, technology impacts, interviews with leading experts, and much more. If you enjoyed this episode of Insurance Shoptalk, follow us on our social media pages to learn the latest on commercial insurance industry.

When clarity meets compassion, leadership becomes legacy. Jason Cass sits down with Jason Sanders, COO and Senior Vice President at IPFS, for an Executive Session that uncovers how a people-first mindset can shape an entire organization. From starting in the mailroom to building one of the industry’s most respected leadership programs, Jason shares how structure, service, and culture drive both his success and IPFS’s future. Key Topics: Jason’s rise from the mailroom to COO at IPFS and what he learned at every level The creation of IPFS’s Leadership Development Program and its impact on culture Why clarity and transparency are essential traits of great leadership How mentorship shaped his philosophy that “clarity is kindness” The role of rhythm, discipline, and family in sustaining leadership energy Giving back through community service and serving on the Children’s Mercy Hospital board The vision for a more agile, future-ready IPFS that’s more than just premium finance Reach out to: Jason Sanders Jason Cass Visit Website: IPFS Agency Intelligence Produced by PodSquad.fm

In this episode of Insurance Shoptalk, explore the world of human resources (and more!) with host Eric Stein and special guest host Ryan Floyd. Eric and Ryan talk with David Ainsworth and David Bell from Zynergia, a trusted HR partner that offers a variety of services, including payroll, benefit management, risk management, and more. They discuss Zynergia’s the coverage, features, and benefits of their unique programs, especially their PEO and Workers’ Compensation offerings. To learn more about Zynergia and their services, please find them online at https://zynergiahr.com/ About Insurance Shoptalk: Join host Eric Stein on a journey through the dynamic world of commercial property and casualty insurance. With over 25 years of experience in the industry, Eric brings a wealth of knowledge and insights to every episode. Insurance Shoptalk is your premier destination for in-depth discussions on the latest industry trends, technology impacts, interviews with leading experts, and much more. If you enjoyed this episode of Insurance Shoptalk, follow us on our social media pages to learn the latest on commercial insurance industry.

In this episode of Stuff About Money They Didn’t Teach You in School, Erik Garcia, CFP®, ChFC®, BFA™, and Xavier Angel, CFP®, ChFC®, CLTC, tackle one of the most important yet often overlooked financial topics: long-term care. The conversation kicks off with a laugh as Erik shares how Xavier nearly got himself kicked out of a professional study group for challenging the conventional wisdom around long term care insurance. That sets the stage for a lively discussion about why this issue matters so much, even if it is not the kind of thing people want to chat about at a cocktail party. Between sobering stats about rising care costs and Xavier’s candid story of his aunt currently in a long term care facility, this episode keeps things engaging while shining a light on a subject that is too often ignored. But ignoring the problem does not make it go away. With the average nursing home room now costing well into six figures annually, long term care planning is a reality everyone needs to address. Erik and Xavier unpack the complexity, explaining why traditional policies may not be as reliable as they seem, why the financial planning around it can be so tricky, and how thinking in terms of cash flow might change the conversation entirely. Along the way, Erik lightens the mood with a surprisingly fitting analogy about chickens and eggs, reminding us that financial planning can be both practical and a little entertaining. Tune in, lean in, and be sure to share this episode with someone who may need a nudge to plan wisely for their future. Episode Highlights: Erik emphasizes why long term care matters, even for younger listeners, due to its inevitable impact on families. (01:12) Erik unpacks the challenges retirees face when fixed incomes meet rising care costs. (03:01) Xavier explains how some advisors buffer rate hikes by quoting higher premiums upfront. (04:00) Xavier shares a personal story to define long-term care as more than just insurance, it’s physical and emotional support. (06:56) Xavier discusses the national costs of care and why planning for it is essential. (11:00) Erik outlines the risks of asset depletion and reduced income after losing a spouse. (13:38) Xavier explains how women statistically need care longer and why planning must consider longevity. (14:18) Erik highlights why long-term care planning must include income replacement strategies. (16:17) Xavier warns against “one-size-fits-all” insurance solutions in client conversations. (17:36) Erik uses a chicken-and-egg analogy to explain sustainable income planning. (21:53) Erik encourages listeners to focus on income streams over lump sums in planning for future care. (24:36) Xavier shares a case study about a client who prioritized legacy over self-care and why that needed to change. (25:39) Erik urges listeners to talk with aging parents now about their long-term care plans. (27:00) Key Quotes: “ As a planner, I'm always thinking about how does this affect you long term, not just today, but what happens 10 years from now? Because if we're doing your planning today, I'm still doing your planning 10 years from now.” - Xavier Angel, CFP®, ChFC®, CLTC “Even though you may not necessarily be taking direct action to solve a potential financial problem today or in the future, having the conversation about it is actually starting to solve the problem.” - Erik Garcia, CFP®, ChFC®, BFA™ “We are financial planners. We love helping people solve financial problems, and we love helping people make financial decisions that are in alignment with what is most important to them.” - Erik Garcia, CFP®, ChFC®, BFA™ Resources Mentioned: Erik Garcia, CFP®, BFA Xavier Angel, CFP®, ChFC, CLTC Plan Wisely Wealth Advisors

What shapes a leader who has spent decades at the highest levels of business? Jason sits down with Frank Friedman, CEO & President at IPFS, for an Executive Session that blends personal stories with industry insight. From mentors who made a difference to premium financing, payments innovation, and the future of insurance tech, this conversation highlights the human side of leadership. Key Topics: Early career mistakes that shaped Frank’s leadership style The mentors who stood behind him during pivotal moments Lessons from decades at Deloitte and a global COO role The pace of technology change, from the dot-com bubble to AI How IPFS and AndDone are innovating payments and financing Why consolidation and automation will define the next decade Frank’s perspective on AI’s impact on jobs and efficiency The books and history that inspire Frank’s worldview A defining 9/11 experience that reshaped Frank’s perspective on unity Reach out to: Frank Friedman Jason Cass Visit Website: IPFS Agency Intelligence Produced by PodSquad.fm

What happens when a State Farm agent decides he’s not cut out for the captive world and instead builds a tech empire supporting $2B in premium? Jason Cass sits down with Austin Moorhead, Founder of Lava Automation to unpack that journey.  Key Topics: Austin’s leap from State Farm to automation and his “lightbulb moment” with Keap Growing from a side project into 350+ virtual assistants powering $2B in premium Balancing hard work, family, and redefining success in the agency tech space Why AI hype feels like past industrial shifts and what it really means for agencies How LAVA approaches SOC 2 certification and data security in the AI era Turbo Dial’s customizable VoIP and HubSpot’s growing role in larger agencies Why lead generation remains the great separator for top-performing agencies Optimizing websites for ChatGPT and AI-driven search, not just Google Fear, valuations, and why relationships still anchor the future of independent agents Reach out to: Austin Moorhead Jason Cass Visit Website: Lava Automation Agency Intelligence Produced by PodSquad.fm

In this episode of Front Cover: A Rough Notes Podcast on the Agency Intelligence Podcast Network, Jason Cass sits down with Jackson Rollo, President at Rollo Insurance, the agency featured on the October 2025 front cover of Rough Notes Magazine.  Key Topics: The honor of being featured on the Rough Notes Magazine front cover Carrying forward a family agency legacy while creating new impact Jackson’s journey from aspiring attorney to agency president The “God, Family, Country” framework shaping their culture Why investing in a Director of Culture transformed their agency Building unity through quarterly leadership book studies Lessons from Good to Great and embracing healthy debate Scaling from 60 to 275 employees while preserving culture AI as a tool for growth, not replacement, in the insurance industry Balancing rapid expansion with staying true to core values Reach out to: Jackson Rollo Jason Cass Visit Website: Rollo Insurance Rough Notes Magazine Produced by PodSquad.fm

We’re bringing back a powerful Executive Session with Ryan Hanley, who at the time of this recording was CMO at Linqura (and is now the company’s President). In this replay, Ryan opens up about his journey from small-town beginnings to industry leadership, sharing raw insights on humility, resilience, and the seasons of business leadership. He and Jason dig into AI’s role in reshaping insurance, why data accuracy and security can’t be overlooked, and the surprising parallels between leading a company and raising a family. Key Topics: Navigating the seasons of leadership and evolving roles as businesses grow. Why shedding your ego is essential to leveling up as an entrepreneur. How diverse career experiences create unmatched perspective and adaptability. The three human roles that remain in an AI-driven insurance future. Linqura’s mission is to make every agent a specialist with real-time insights and data. How parenting challenges mirror leadership—building resilience through real talk. What true culture building looks like (and what it doesn’t). Reach out to:  Ryan Hanley Jason Cass Visit Website: Linqura Agency Intelligence Produced by PodSquad.fm