Agency Intelligence: The Insurance Podcast Network

In this episode of Front Cover: A Rough Notes Podcast on the Agency Intelligence Podcast Network, Jason Cass sits down with Diane Keil-Hipp, Chief Operations Officer at Knight Insurance Group, the agency featured on the March 2026 front cover of Rough Notes Magazine.  Key Topics: Landing on the front cover of Rough Notes Magazine, a goal Knight set five years in advance How a 165-year history shapes Knight Insurance's identity and culture Revitalizing Toledo's Warehouse District and leading the Warehouse District Association Why private equity's impact on a local competitor pushed Knight toward employee ownership How Knight's ESOP rewards both salary and tenure for long-term staff The five stakeholders Knight serves and why no decision can benefit one at another's expense Maintaining three levels of carrier relationships and a formal Carrier of the Year award Why live phone answers and relationship-first practices still drive Knight's growth Diane's PhD dissertation on the three internal factors that cause organizations to decline Knight's three core values: enduring relationships, relentless focus, and exceptional standards Reach out to: Diane Keil-Hipp Jason Cass Visit Website: Knight Insurance Group Rough Notes Magazine Produced by PodSquad.fm

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® begin a two-part series on how wealth is actually built and why it often looks boring in real life. In Part 1, they tackle three common myths that derail people before wealth ever has a chance to compound. From the belief that wealth is built by luck or big breaks, to the assumption that it is reserved for the privileged few, to the misconception that a high income guarantees financial success, Erik and Xavier unpack the cultural narratives that cause people to quit too early. Drawing on research, real-life stories, and years of experience in financial planning, they explain why wealth is more accessible than most people believe but slower than most people expect. They emphasize that financial success is less about flashy wins and more about mindset, discipline, and intentional decision-making over time. If you have ever felt behind, discouraged, or tempted to chase the next big move, this episode reframes what real wealth-building looks like and sets the stage for Part 2, where they reveal the three ingredients that consistently build lasting wealth. Episode Highlights: Erik mentions that the episode was inspired by conversations at a business conference about what leads people to grow wealth and the myths they tell themselves along the way. (01:30) Erik discusses the idea that wealthy people made their money overnight through one big deal or a viral moment, noting these are exceptions rather than the rule. (06:40) Xavier shares that the average age of a successful business founder is 45, and how that statistic brought visible relief to a business owner who feared she was too late. (10:55) Erik mentions that eight out of ten wealthy people are first-generation, meaning wealth is more accessible than most believe, but requires patience and consistency. (16:20) Erik defines wealth as optionality: having low debt, financial margin, and the freedom to use money for what is most important rather than being backed into a corner. (21:35) Xavier discusses the discouragement that comes when progress feels invisible, reminding listeners that wealth is forming beneath the surface long before the outside world sees it. (26:10) Xavier shares the bonus myth that a high income is required to build wealth, and Erik shares the story of a woman who built a five-million-dollar estate while never earning much money. (29:30) Key Quotes: “Experience and industry familiarity were more important than just pure intelligence when it comes to building wealth. It's a slow grind sometimes to build wealth. It's not overnight.” - Erik Garcia, CFP®, ChFC®, BFA™ “If you're following the right processes, if you're taking the right steps of what it leads to be successful, then it's going to come with time.” - Erik Garcia, CFP®, ChFC®, BFA™ “ Wealth is built in the gaps between what you make and what you keep, and the behavior matters more than the income alone.” - Xavier Angel, CFP®, ChFC®, CLTC® Resources Mentioned: ⁠Erik Garcia, CFP®, ChFC®, BFA™⁠ ⁠Xavier Angel, CFP®, ChFC®, CLTC®⁠ ⁠Plan Wisely Wealth Advisors

In this episode, Jason Cass and Joel Poythress discuss the evolution of telecommunications, the impact of AI on customer interactions, and the future of communication technology. They explore how AI is transforming the industry, the importance of sentiment analysis, and the potential for voice prints in authentication. The conversation also touches on security concerns, the decline of voicemail, and the role of AI in enhancing business reputation and efficiency. Key Topics: The Evolution of Telecommunications and AI The Future of Communication: AI and Transcription AI's Role in Customer Interaction and Sentiment Analysis The Importance of AI in Business Reputation Innovations in Call Technology and Features The Future of Voicemail and Communication Security Concerns in Data and Voice Technology Voice Prints and Authentication The Future of Human Interaction in Business Calls Lightning Round: Quickfire Questions on AI and Communication Reach out to: Joel Poythress Jason Cass Visit Website: Lightspeed Voice Agency Intelligence Produced by PodSquad.fm

Healthcare costs are no longer just a line item — they’re a growing liability for employers. In this episode of Insurance Shoptalk, host Eric Stein sits down with Brandy Thompson, CEO of BenefitBay, to explore how ICHRA (Individual Coverage Health Reimbursement Arrangements) is reshaping the way larger employers approach employee benefits. With renewal volatility, self-funded risk exposure, fiduciary pressure, and increasing administrative burden, many CFOs and HR teams are feeling squeezed from every direction. Brandy breaks down how a defined contribution model can restore budget control, preserve pre-tax advantages, and give employees true plan choice across multiple carriers — all while significantly reducing internal administration. The conversation covers: • How ICHRA works for groups 200+ lives • Why large employers are moving away from traditional self-funded models • How employees can shop plans based on their own doctors and prescriptions • The role of technology in simplifying enrollment and payroll coordination • How brokers and P&C agents can expand advisory value in the benefits space If you work with CFOs, HR leaders, or growing organizations facing healthcare cost pressure, this episode offers a fresh perspective on a rapidly evolving market. Watch now and learn how this model is changing the benefits conversation. #InsuranceShopTalk #EmployeeBenefits #ICHRA #HealthcareStrategy #CFOInsights #AgencyGrowth #InsuranceIndustry

Insurance agencies don’t just need more people — they need smarter operations. In this episode of Insurance Shoptalk, Eric Stein sits down with Travis MacMillian of Xceedance to unpack how automation, AI, and strategic back-office support can completely transform the way property & casualty agencies operate. From policy checking and COI management to remarketing, loss runs, endorsements, accounting reconciliation, and even claims coordination — Travis explains how agencies can eliminate repetitive portal work, reduce manual data entry, and create 30%+ more operational capacity without stacking on more headcount. This isn’t about replacing people. It’s about removing friction — so principals can put more in their pocket, pay producers and CSRs more, and build a modern digital footprint that supports real growth. If you’re tired of adding bodies just to keep up with volume, this conversation will shift your thinking. #InsuranceShopTalk #AgencyAutomation #InsurTech #InsuranceOperations #AgencyGrowth #DigitalInsurance #PAndC New boost

In this episode of the Agency Intelligence Podcast, Jason Cass and Andy Mathisen discuss the evolution of lead generation in the insurance industry, focusing on innovative strategies and tools like Homebot that bridge the gap between real estate and insurance. They explore the importance of personalization, data analytics, and building relationships with referral partners to enhance agency growth. The conversation also touches on the challenges and opportunities in the current market, emphasizing the need for agents to adapt and leverage technology effectively. Key Topics: Andy’s Journey in Insurance and Lead Generation Homebot: Bridging Real Estate and Insurance The Importance of Homeowner Engagement Leveraging Data for Insurance Agents Understanding MLS and Its Value Automation and Connecting Professionals Final Thoughts on Collaboration and Success Leveraging Homebot for Real Estate Connections Engagement Strategies for Insurance Agents The Dance Floor: A Lighthearted Interlude Navigating the Challenges of Lead Generation Building Relationships with Referral Partners Event Planning: The Trials and Tribulations Reach out to: Andy Mathisen Jason Cass Visit Website: Homebot Agency Intelligence Produced by PodSquad.fm

Too many insurance producers are playing Pat-A-Cake with their insurance careers. They're not taking seriously the need to focus, to get prepared, to see what works and pivot as needed, etc. They're just wingin' it, throwing mud against the wall to see what sticks. But you don't want to play Pat-A-Cake with your commission check. In this episode, host Charles Specht explains what both producers and agency leaders need to do to get serious about winning in order to build a $1,000,000 or more Book of Business. ---------- PS --->>> The next cohort of the "PERMISSION PRODUCER SCHOOL" will be starting on February 16, 2026. Find out more information by visiting: www.PermissionProducerSchool.com You won't want to miss out on this one! Key Topics: Playing Pat-A-Cake with prospecting, scripting, and career shows up in your commission check Winging it without researching carriers, appetites, and competitors is patty cake business Why prospects say no: you failed to articulate your value compared to your fee Recording yourself prospecting reveals where you lose attention and energy in your script Agency owners can't afford to let producers wing it when hiring costs too much Creating cold call scripts, one-liners, and differentiation statements eliminates amateur behavior What no really means: you haven't helped them understand the value of moving forward yet Tracking social media and email analytics helps dominate your space instead of guessing Permission Producer School teaches how to dominate with broker of record letters and full marketplace exclusivity Reach out to  Charles Specht Visit: Permission Producer School Permission Network Produced by PodSquad.fm

In this milestone episode of Stuff About Money They Didn’t Teach You in School, Erik Garcia, CFP®, ChFC®, BFA™, and co-host Xavier Angel, CFP®, ChFC®, CLTC®, reflect on what they’ve learned after reaching 100 episodes of honest, practical money conversations.  This episode looks back at why the podcast started, the gaps in financial education that inspired it, and the themes that kept showing up again and again in conversations with clients, guests, and listeners. Erik and Xavier share the biggest money lessons reinforced over the past 100 episodes, the moments that challenged their thinking, and why behavior, mindset, and consistency matter far more than financial hacks or headlines. They also pull back the curtain on what it really takes to stay consistent, grow personally and professionally, and keep showing up for meaningful conversations about money. Episode Highlights: Xavier explains that his dress code changed in 2020 when he joined the firm after Erik's dad told him he could relax and wear polos instead of formal attire. (03:35) Erik discusses his podcasting history, including 65 episodes of Building Us with Dr. Matt Morris during COVID, before starting Stuff About Money. (06:10) Erik shares that the hardest part of podcasting isn't coming up with topics but maintaining consistency with recording every two weeks. (09:35) Erik explains the podcast is part of their vision to resource people for wise financial decisions and reinforce behaviors that lead to success. (11:25) Xavier highlights compounding interest as the most popular response when guests are asked what they wish they knew about money 20 years ago. (12:30) Xavier recalls Billy Williams' advice that stuck with him: if you can't pay for it twice, you can't afford it. (19:50) Erik discusses the responsibility of sharing information on the podcast since they're talking about money topics that could change people's lives. (24:20) Erik explains he pushes back against giving prescriptive advice because personal finance is as much personal as it is finance. (26:10) Erik shares three simple things to build wealth: spend less than you make, save as much as you can, and don't do anything foolish. (28:50) Erik announces two future episode series ideas: interviewing faith leaders about money and exploring emotions like greed and fear that drive financial decisions. (31:15) Xavier shares his key takeaway for listeners: if something is uncomfortable and hard, keep moving forward with intentionality instead of stopping. (33:15) Erik and Xavier announce they'll start doing solo episodes beginning in February to share personal experiences and lessons independently. (37:00) Key Quotes: "Our vision here of the firm is to really resource people to make wise financial decisions. The podcast is part of that vision." - Erik Garcia, CFP®, BFA "Most financial decisions are not made on spreadsheets. They're made with emotions." - Erik Garcia, CFP®, BFA "If something is uncomfortable, it's hard, and if it's hard, keep moving forward. Don't stop doing what you're doing. Make it comfortable." - Xavier Angel, CFP®, ChFC, CLTC Resources Mentioned: Erik Garcia, CFP®, BFA Xavier Angel, CFP®, ChFC, CLTC Plan Wisely Wealth Advisors

In this episode of the Millionaire Insurance Producer Podcast, host Charles Specht discusses the challenges insurance agents face in prospecting and securing exclusive access to markets. He emphasizes the importance of understanding the insurance buyer's perspective, the necessity of Micro-Niching to stand out, and the common issue of agents presenting only one quote in their proposals. Charles advocates for positioning yourself as a "multiple quote option producer" to build trust and ultimately win clients' business through exclusivity. TAKEAWAYS: Prospecting can be frustrating when clients seek multiple quotes. Insurance buyers often don't understand the process or the agents. Micro-Niching helps agents stand out and build trust. Agents should present multiple options to clients. A strong marketing summary is crucial for success. Positioning is key to winning clients' trust. Clients prefer agents who show them multiple options. Understanding the client's perspective is essential. Agents need to change the perception of their role in the market. The Permission Producer School offers valuable training for agents. Moreover, the next cohort of the "PERMISSION PRODUCER SCHOOL" will be starting on February 16, 2026. Find out more information by visiting: www.PermissionProducerSchool.com You won't want to miss out on this one! 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 Andrew Cowan and Dave Taylor of FirstMark Insurance Group, the agency featured on the February 2026 front cover of Rough Notes Magazine.  Key Topics: From Farmers agents to independent: Andrew and Dave's leap into FirstMark in 2013 Bootstrapping for seven years and choosing people over profit to fuel growth Transitioning to 100% remote operations after COVID showed it could work Four guiding principles: positive attitude, confidence, pursuit of excellence, and thoughtful and kind Choosing ideal clients who value advice and coverage over cheap pricing Teaching agents to reframe price conversations around the three things clients deserve Three-tier training system: foundation agents, journeymen, and tenured producers Using Microsoft Teams, EZLynx, and Sales Center for remote coaching and pipeline management Building a leadership team and moving to EOS with a COO as integrator Service model that frees agents to grow by adding client care teams to relationships Reach out to: Andrew Cowan Dave Taylor Jason Cass Visit Website: FirstMark Insurance Group Rough Notes Magazine Produced by PodSquad.fm

In this solo episode of the Stuff About Money podcast, Erik Garcia CFP®, BFA™, ChFC®, reflects on King Cake season in New Orleans, an annual reminder that some things are wonderful precisely because they don’t last forever. Between questionable calorie intake and the collective sugar coma that sweeps the city, Erik is grateful that King cake is a season, not a lifestyle. That rhythm sparks a bigger conversation about money and how so much of our financial stress comes from forgetting that money, too, has seasons. Erik breaks down the three financial seasons he most often discusses with clients: laying the foundation, building on that foundation, and eventually spending down and distributing assets. Each season comes with different demands, priorities, and emotional pressures, and many “bad” financial decisions are only bad because they’re made in the wrong season of life. He also explores how these seasons show up for business owners, from startup to growth to exit. If money feels tight, confusing, or heavier than expected, this episode offers clarity, perspective, and a reminder that you’re probably not doing it wrong. You may just be in a different season. If it resonates, follow the show and share it with someone who could use that reminder. Episode Highlights: Erik discusses three financial phases: laying a foundation, building on it, and spending down your accumulated assets. (04:15) Erik shares his biggest financial mistake: trying to accumulate in five years everything that took his parents decades to build. (05:35) What makes a financial decision bad isn't always the decision itself, but making it in the wrong season of life. (07:45) The foundation-laying season is characterized by tight margins, high demands, and competing financial priorities like homeownership, transportation, and student loan repayment. (09:25) Erik explains that restraint doesn't mean selling yourself short, but preparing yourself for the future, and making hard decisions early makes transitions easier. (12:50) Regardless of income level, clients face a common challenge: people tend to spend or tie up their money in proportion to what they earn. (16:10) Not spending every dollar isn't a sign of missing out on life; it's good stewardship and wise money management. (18:30) Erik mentions that most small businesses fail not because they're bad ideas, but because they run out of cash. (22:00) Financial seasons have beginnings and endings, making it valuable to pause and reflect on where you currently are in your money journey. (24:50) Erik discusses the value of working with a financial planner who understands your values and the season of life you're in. (26:10) The reality that seasons are temporary makes having trusted guidance in your financial life incredibly valuable. (27:15) Key Quotes: “Restraint doesn't mean that you're selling yourself short. You're preparing yourself for the future.” - Erik Garcia CFP®, BFA™, ChFC® “Making good decisions that are in alignment with your values, that are in alignment with the season that you're in. It's important.” - Erik Garcia CFP®, BFA™, ChFC® “I love the fact that more and more people aren't just quitting or retiring completely, that they recognize they have something still to give. There's meaning, and there's purpose in working.” - Erik Garcia CFP®, BFA™, ChFC® Resources Mentioned: Erik Garcia, CFP®, BFA Xavier Angel, CFP®, ChFC, CLTC Plan Wisely Wealth Advisors

In this episode of the Agency Intelligence Podcast, host Jason Cass welcomes guests Daniel Garzella, CEO of Darkhorse Insurance Brokers and Jason Massey, Vice President of Finance and Accounting at Insurance Accountants to discuss the unique challenges of insurance accounting. Daniel shares his journey from running a retail brokerage to founding an insurance accounting company, highlighting the difficulties he faced in finding suitable accounting solutions tailored to the insurance industry. Jason Massey, with a background in corporate accounting at American Express, joins Daniel to provide insights into how their firm addresses the specific needs of insurance agencies, emphasizing the importance of understanding agency management systems and the complexities of insurance accounting. The conversation delves into the significance of accurate financial reporting and the common pitfalls that insurance agents encounter, such as not knowing their numbers and the challenges of scaling their businesses. Both guests stress the importance of leveraging technology, including AI, to enhance efficiency and accuracy in accounting processes. As they prepare for the upcoming Indy Tech event, they express excitement about connecting with independent agencies and sharing their expertise in solving the industry's accounting challenges. Key Topics: The Journey to Founding an Insurance Accounting Company Understanding the Unique Needs of Insurance Accounting The Importance of Technology in Accounting Common Mistakes Made by Insurance Agents Transitioning from Captive to Independent Insurance Leveraging AI in Insurance Accounting Key Financial Metrics for Agency Success Final Thoughts and Looking Ahead to IndieTech Reach out to: Daniel Garzella Jason Massey Jason Cass Visit Website: Insurance Accountants Darkhorse Insurance Brokers  Garzella Group Agency Intelligence Produced by PodSquad.fm

This episode of the Agency Intelligence Podcast is a heartfelt tribute to Walt Gdowski, a significant figure in the insurance industry and the former CEO of Rough Notes.  Jason Cass and Roger Sitkins reflect on Walt's life, his contributions to the industry, and the personal memories they shared with him. They discuss his leadership style, his commitment to community service, and the high standards he set for the industry. The conversation highlights the importance of relationships in business and the lasting impact Walt had on those around him. Key Topics: Walt Gdowski was a pivotal figure in the insurance industry. He modernized Rough Notes, making it a trusted resource. Walt was known for his generosity and mentorship. He believed in the power of relationships in business. Walt's leadership style combined authority with influence. He launched the Rough Notes Community Service Award in 2000. Walt was an avid golfer and a licensed pilot. He had a significant impact on independent agents and brokers. Walt's legacy is a high standard for the industry. He was a gregarious and fun-loving individual who cared deeply about others. Reach out to: Roger Sitkins Jason Cass Visit Website: The Rough Notes Company Agency Intelligence Produced by PodSquad.fm

There are definitely things that the most highly successful insurance producers do in order to ensure victory when selling insurance. Some are easier than others, but almost all of them can be done by new(er) producers as well. If you want to build a $1,000,000 or more Book of Business, you need to begin implementing these things the most successful producers do. What are these things, you ask? Well, that's what host Charles Specht will teach you about in this podcast episode. Moreover, be sure to check out www.PermissionProducerSchool.com as the next cohort will begin on February 16, 2026. Go to www.PermissionProducerSchool.com to learn more and get registered for the upcoming cohort for producer school (virtual sales training). And, be sure to pre-register before all of the spaces are gone. Happy prospecting! Key Topics: How successful producers generate business through referrals and centers of influence instead of cold prospecting Why top producers only work through broker of record letters and never blind quote The importance of being micro-niched to know which carriers you need to be competitive Pre-qualifying accounts by calling underwriters before meetings to avoid wasted time and market blocks Three essential guardrails for the quoting process: securing markets, defining savings thresholds, and preventing quote sharing Using the Broker Of Record letter request in first meetings to measure relationship strength Permission Producer School training for building a million-dollar book through the permission sales framework Reach out to  Charles Specht Visit: Permission Producer School Permission Network Produced by PodSquad.fm

In this episode of Stuff About Money They Didn’t Teach You in School, Xavier Angel, CFP®, is joined by Shannon Mehaffey Ory, Owner and Senior Care Consultant at Avila Senior Advisors, for an honest conversation about something every family will face but few feel prepared for: caring for aging parents. Whether care needs change slowly or arrive overnight after a fall, hospitalization, or diagnosis, Xavier and Shannon unpack why families often find themselves making major financial and care decisions under stress, emotion, and time pressure, usually without a plan. With over a decade of experience across senior housing, memory care, home care, and mission-based work with the homebound and aging, Shannon brings clarity to a confusing and emotionally charged process. Together, she and Xavier walk through six essential things families need to understand about long-term care, including why crisis-based decisions are the most expensive, why Medicare assumptions can be dangerous, and how understanding care options like assisted living, memory care, and skilled nursing changes everything. At the heart of this episode is a simple but powerful truth: early planning gives families options, peace of mind, and the ability to honor their loved one’s wishes. If you have aging parents, or hope someone will one day advocate well for you, this is a conversation worth starting now. If this episode resonates, follow the show and share it with someone who needs to hear it before life forces their hand. Episode Highlights: Shannon shares her background in Health Administration with a concentration in senior housing and her experience working across multiple states in assisted living, memory care, and sitter agencies. (03:04) Shannon explains how care needs can change overnight with an example of a healthy client whose wife fell after a medication change. (07:50) Shannon discusses the differences between sitter agencies and private independent sitters, recommending getting names ahead of time through church or friends. (13:30) Shannon describes dementia as a journey and explains factors that determine whether someone should stay home or move to memory care. (18:42) Shannon explains independent living retirement communities, including buy-in fees and how residents can lock in monthly rates as their needs increase. (22:01) Shannon defines activities of daily living (ADLs) including bathing, dressing, hygiene, feeding, and transfers. (26:36) Xavier discusses the importance of aligning care needs with financial ability and how crisis-based decisions become the most expensive. (32:42) Shannon discusses how clients discover VA benefits they had no idea they had access to, making senior living possible. (37:22) Shannon shares her main takeaway that there are options available for aging parents, including resources not widely known to the public. (42:48) Key Quotes: “Every family is unique in what they're experiencing and what their needs are, and they do need accompaniment through that to figure out what is available for them specifically.” - Shannon Mehaffey Ory “A lot of people forget what their long-term care insurance policies included, and adult children have no idea their parents have this, and finding that out means a whole world is possible to them that the children didn't know was possible.” - Shannon Mehaffey Ory “The benefit of independent living is you don't have any maintenance. You probably can pay an extra fee for housekeeping. You have a ton of social opportunities, lovely dining. People go on trips together in independent living communities all the time.” - Shannon Mehaffey Ory Resources Mentioned: Shannon Mehaffey Ory Avila Senior Advisors Erik Garcia, CFP®, BFA Xavier Angel, CFP®, ChFC, CLTC Plan Wisely Wealth Advisors

In this episode of Insurance Shop Talk, host Eric Stein introduces a game-changing workers’ compensation opportunity for P&C agents in Ohio and surrounding states. With Ohio’s monopolistic system long limiting agent participation, a newly approved Alternate Employer Organization (AEO) program now allows agents to earn ongoing commission while delivering meaningful cost savings and improved claims management for their clients. Eric breaks down how the program works, who it’s best suited for, and—most importantly—the practical sales strategy agents can use to position it with existing clients and prospects. From pay-as-you-go billing and simplified claims handling to real-world savings examples, this webinar offers a clear roadmap for agents looking to unlock new revenue and strengthen client retention in a competitive market.

In this episode of Insurance Shoptalk, host Eric Stein sits down with Walter Sabrin of Venture Employer Services for a wide-ranging conversation on the realities of hiring, recruiting, and retaining talent in today’s insurance agency environment. Drawing on decades of experience, Walter breaks down why agencies should always be recruiting, how internal referral programs and small-scale job fairs can deliver outsized results, and why traditional job boards often fail to reach the best candidates. The discussion also explores proactive headhunting, building a recruiting pipeline for future needs, leveraging nearshore and remote talent to reduce costs while increasing productivity, and the importance of communication, training, and career progression in improving retention. Together, Eric and Walter share practical, real-world insights that agency owners can use to strengthen their teams, adapt to a changing workforce, and build a sustainable hiring strategy for the future.

In this episode of Front Cover: A Rough Notes Podcast on the Agency Intelligence Podcast Network, Jason Cass sits down with Jeff and Eboné Granger, Managing Partners at Granger Financial, the 2022 Rough Notes Magazine Agency of the Year.  Key Topics: The significance of being featured on the front cover of Rough Notes Magazine Building the agency from the ground up during COVID and scaling intentionally over time Expanding beyond insurance into multiple financial service verticals to better serve clients Creating a culture centered on mission, legacy, and long-term impact Using community service as a core business driver, not a side initiative Developing and retaining talent through an ownership mindset, culture, and values Reach out to: Jeff Granger Eboné Granger Jason Cass Visit Website: Granger Financial Rough Notes Magazine Produced by PodSquad.fm

In this episode of Stuff About Money They Didn’t Teach You in School, Erik Garcia is joined by Miles Clark, Senior Analyst at Nasdaq Dorsey Wright, to explore a simple but important question: what’s better—time in the market or timing the market? The conversation opens with a long-term look at how markets have behaved over multi-decade periods and what that data can teach investors when they’re deciding what to do with new money, especially when markets are sitting at or near all-time highs. From there, Erik and Miles walk through three common investor approaches: investing a lump sum right away, waiting for a pullback, or easing in over time. They discuss which experiences tend to lead to better long-term outcomes and why those results often surprise people. The conversation also touches on momentum, relative strength, and market breadth, including what it means when market leadership becomes narrow and valuations stretch. The episode wraps up with Miles’ thoughts on what matters most heading into 2026, what investors tend to worry about too much, and what deserves more attention moving forward. If you found this episode helpful, follow the show and share it with someone who’s still waiting for the “right” time to invest. Episode Highlights: Miles discusses a study showing "Average Joe," who invests $500 monthly regardless of market conditions, outperforms market timers by about $1 million. (07:25) Miles breaks down market breadth through a football analogy: it tells investors whether the market is on offense or defense. (13:20) Miles mentions that in core-dominated markets, the real risk isn't beating the benchmark but simply keeping up with it. (18:55) Miles discusses how Dorsey Wright applies relative strength to identify which assets to hold, focusing on sustained trends rather than short-term news. (22:45) Miles explains how momentum investing rotated out of tech in 2022 into energy and utilities, then back into tech for 2023-2024. (29:30) Erik emphasizes that risk capacity matters more than risk tolerance, which is often driven by emotions about current market conditions. (36:25) Key Quotes: "We don't necessarily have to focus on protecting against the entire market washout. We really just need to protect ourselves against where we're over-concentrated in our portfolios." - Miles Clark "In core-dominated markets, a lot of the risk is actually just not keeping up with the benchmark because it is so strong." - Miles Clark "Finding and earning positive relative strength is just trying to pick those assets that are doing relatively better towards the up or downside than their benchmark." - Miles Clark Resources Mentioned: Miles Clark Nasdaq Dorsey Wright Erik Garcia, CFP®, BFA Xavier Angel, CFP®, ChFC, CLTC Plan Wisely Wealth Advisors

What if every phone call your agency receives could tell you exactly how customers feel and how your team is performing? Jason Cass sits down with Winston Smith, CEO of Bridge Insure and Magellan Insure, to unpack how call intelligence is reshaping agency operations. The discussion explores why phone systems are more than dial tone, how real insights surface from everyday conversations, and why focusing on customer happiness and employee productivity creates a clearer picture of agency performance. Key Topics: The evolution of Bridge and the launch of Magellan Why phone systems are an untapped intelligence source Using call transcription to surface meaningful insights Measuring customer satisfaction through real conversations Evaluating employee performance with service standards Real time alerts for negative customer experiences Connecting phone data to revenue and premium impact Contrarian perspectives on AI in insurance agencies Reach out to: Winston Smith Jason Cass Visit Website: Bridge Insure Magellan Insure Agency Intelligence Produced by PodSquad.fm