Stuff About Money: Episode 99: Should You Wait to Invest When the Market Feels Expensive?

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

In this solo episode of Stuff About Money They Didn't Teach You in School, Xavier Angel, CFP®, ChFC®, CLTC, steps behind the mic to wrestle with a tough truth: planning isn’t optional, not if you want control over your future. Fresh off his conversation with Giovanni Arenas about Gio’s life-threatening condition and remarkable double lung transplant, Xavier gets another call that hits just as hard. A dear friend's cancer has returned, and with it comes the realization that he never put proper business succession plans in place. It is a moment that reveals not just financial vulnerability but emotional fallout, the kind that compounds heartbreak when families are already hurting. Xavier digs deeper into why waiting to plan is one of the costliest decisions a business owner can make. He lays out how proactive planning protects the people you care about most and why delaying those decisions hands your future over to circumstances instead of intention. This episode is an honest call to action: don't wait until life forces your hand. If the message resonates, share the episode with someone who needs the nudge, and make sure you're following the show for more conversations that help you take control before life does it for you. Episode Highlights: Procrastination is a bill that silently compounds, delaying tasks makes them harder to complete, and weighs you down. (01:00) Time is the most valuable asset when building wealth. Every year of waiting meant losing opportunity, not just time. (01:30) Xavier references his previous episode with Giovanni Arenas about his double lung transplant and how quickly life can change. (02:30) Xavier shares a personal story: A close friend's rapidly progressing cancer forced immediate business and family decisions no one was prepared for. (04:10) Xavier outlines action steps: Create a will, establish an estate plan (not just for the wealthy), and build a business continuation plan. (07:10) Planning documents are acts of love and gifts of clarity that ensure your intentions, not others' emotions, guide what happens next. (07:50) Key Quotes: “Procrastination doesn't just slow you down. It widens the gap between where we are today and where we want to be.” - Xavier Angel, CFP®, ChFC®, CLTC “Planning isn't when life is perfect. Planning isn't when life happens, planning now it matters.” - Xavier Angel, CFP®, ChFC®, CLTC “ Take that first step today, no matter how small. Start planning today. Start the conversation, get the documents in place. Build the plan that protects the people and the legacy you want to fulfill your future self and your family will thank you later.” - Xavier Angel, CFP®, ChFC®, CLTC Resources Mentioned: Erik Garcia, CFP®, BFA Xavier Angel, CFP®, ChFC, CLTC Plan Wisely Wealth Advisors

I know you probably work only on signed BOR ... right? Well, sometimes you might be tempted to offer quotes to a prospect (aka: Non-Client; someone who doesn't trust you yet) who won't sign the BOR over to you. Should you still work on that account and offer a quote, or should you push the "pause button" and try again next year? Well, it all depends on whether or not you can get the prospect to give you three things first.  In this episode, host Charles Specht shares what three things you should do in order to increase your Quote-to-Bind rate by other 25% or more. Give a listen, subscribe, and let Charles explain. And, visit our newly updated website at: https://permissiongroup.com Key Topics: Why second place in insurance sales pays zero commission The three critical things you must secure before offering any quote How to demand exclusive access to the carriers you need to compete Getting objective commitments on what you must accomplish to win the business Why prospects must agree not to share your numbers with other agents How agents lose 20-30% of business when prospects share quotes behind their backs Why it's your fault, not the insured's, when you get used in quoting The reminder system that reinforces commitments throughout the sales process Why insurance buyers prefer one trusted agent but don't know how to choose How agency leaders can boost profits by requiring BOR letters over blind quotes Reach out to  Charles Specht Visit: Permission Network Produced by PodSquad.fm

Pressure on agency call volume has never been higher, and the gap between what teams can handle and what clients expect is widening fast. In this Executive Sessions conversation, Jason Cass sits down with Francisco Lopes, Founder and CEO of Sonant AI, to unpack how AI voice technology is transforming call handling, reducing repetitive tasks, and freeing teams to focus on higher-value work. Their discussion breaks down real adoption challenges, workflow design, routing logic, and the future impact of AI on agency operations and client experience. Key Topics: AI phone agents purpose-built for insurance operations Improving call latency, clarity, and conversational flow Differences in inbound versus outbound AI call performance Workflow design that reduces repetitive staff tasks Routing logic tied to AMS data and team roles Increasing task capacity through automated call handling Adoption hurdles and the tension between personal touch and AI Future impact of agentic systems on agency productivity How AI reshapes efficiency, staffing, and client communication Reach out to: Francisco Lopes Jason Cass Visit Website: Sonant AI Agency Intelligence Produced by PodSquad.fm

Where does agency efficiency go when AI begins handling the repetitive steps teams have battled for years? Jason Cass explores that shift with Jackson Fregeau, Co-Founder and CEO of Quandri, as they break down how a renewal intelligence platform can analyze policies, trigger quoting based on premium changes, and create contextual client communication automatically. Their discussion highlights how these capabilities free up staff to spend more time with clients while opening the door to new levels of retention and operational scale. Key Topics: Evolution from RPA to AI-driven capabilities Building a renewal intelligence platform for agencies Policy analysis across key coverage variables Automated quoting triggered by premium change thresholds Personalized communication for retention and cross-sell Shifts from personal lines to small commercial automation Differences in margin and complexity across business segments Trust, accuracy, and model limits in production workflows AI adoption timing, economic cycles, and industry expectations Reach out to: Jackson Fregeau Jason Cass Visit Website: Quandri Agency Intelligence Produced by PodSquad.fm

In this solo episode of the Stuff About Money podcast, host Erik Garcia, CFP®, ChFC®, BFA™ sits down for a candid one-on-one about goals. Not the shiny, New-Year’s-resolution kind, but the messy, honest kind we whisper to ourselves when no one’s listening. Erik shares two personal moments that reshaped how he thinks about goal setting, including the year Dr. Matt Morris bluntly told him, “You just made a bad goal,” and the overly ambitious golf objective that nearly convinced him to quit the game altogether. These stories spark a bigger conversation about why we so often overestimate what we can accomplish in the short term and underestimate what we’re capable of over the long haul. In the second half of the episode, Erik unpacks a healthier, more realistic framework for pursuing goals — especially financial ones. Instead of obsessing over hitting a number by a certain date, he encourages listeners to think of goals as direction and objectives as the checkpoints that keep them moving forward. Erik explores why grace, awareness, and better-designed goals lead to more progress and less burnout. If this episode resonates with you, share it with someone who needs a fresh perspective on goal setting, and make sure you’re following the show for more conversations that help you move toward a wiser, more intentional financial life. Episode Highlights: Erik discusses why traditional goal-setting frameworks and New Year’s resolutions aren’t the focus, emphasizing the frustration goals often create. (01:10) Erik shares the moment Dr. Matt Morris looked at him and said he had simply made a bad goal, reframing how he viewed falling short. (02:30) A reminder surfaces about how people consistently overestimate short-term capacity and underestimate long-term potential. (04:00) Erik explains why he now treats goals as directions rather than destinations, using the New York-to-England swimming analogy. (05:30) Erik shares how an overly ambitious summer golf goal led to frustration and helped him rethink the difference between goals and objectives. (07:00) Financial goal setting follows the same pattern, as unrealistic expectations often lead to shame, frustration, or giving up entirely. (09:10) Two core takeaways: create better directional goals and recognize the bias of misjudging short- and long-term potential. (10:40) Why having someone walk alongside you, such as a financial planner, helps maintain direction and adjust objectives over time. (11:40) Erik encourages listeners to share the episode and continue reframing their approach to goal setting. (13:40) Key Quotes: “ I've stopped treating goals like a destination, like something I have to reach. Instead, I think of them like a direction.” - Erik Garcia, CFP®, ChFC®, BFA™ “  You're not failing your goals, your goals just might need a reframe. Fix the direction, adjust the objectives, and trust the long-term journey.” - Erik Garcia, CFP®, ChFC®, BFA™ “ Set better goals, not bigger ones, not more detailed ones. Better ones. Goals that orient you long-term, meaningful directional goals, and then backfill that with objectives that guide your ” - Erik Garcia, CFP®, ChFC®, BFA™ Resources Mentioned: Erik Garcia, CFP®, BFA Xavier Angel, CFP®, ChFC, CLTC Plan Wisely Wealth Advisors

Leadership is shaped in the moments when uncertainty meets opportunity. Jason Cass sits down with Doug McElhaney, Chief Strategy Officer at Applied Systems, for an Executive Sessions discussion at the Applied Conference, where Doug breaks down how strategic clarity guides agencies through rapid technological change. Drawing from his years at McKinsey and his work at Applied Systems, he shares the decisions, mentors, and personal experiences that continue to influence his approach to leadership and industry impact. Key Topics: Understanding strategy through hard-to-reverse decisions Top-down thinking and identifying value-producing objectives Overcoming analysis paralysis in agency decision-making Mentorship philosophies and leadership growth Mindsets that shape personal and professional confidence People-driven execution of technology and data Navigating industry transformation and accelerating change Insurance access, protection gaps, and real-world impact Bold thinking and envisioning long-term industry progress Reach out to: Doug McElhaney Jason Cass Visit Website: Applied Systems 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 Mark Rodgers, Founder of Trailstone Insurance, the agency featured on the December 2025 front cover of Rough Notes Magazine.  Key Topics: Mark’s reaction to being selected for the Rough Notes Magazine front cover  Trailstone’s growth from a small agency to a large operation after shifting strategy in 2017–2018 Building automation in 2019 and writing more than 50 million in new personal lines premium Moving from purchased leads to strong inbound through social media, YouTube, and referral partners A sales process centered on homeowner targeting, education, and retention systems Operating fully inside HubSpot for AMS, CRM, communication, and workflow management Leveraging offshore teams, automation, and Traction accountability charts to support scale and culture Reach out to: Mark Rodgers Jason Cass Visit Website: Trailstone Insurance Rough Notes Magazine Produced by PodSquad.fm

What happens when experience, resilience, and strategic discipline converge inside a rapidly evolving insurance ecosystem? Jason Cass sits down with Ashim Khurana, COO of Cogneesol, for an Executive Sessions conversation that explores how a 25-year industry leader balances instinct, data, technology, and people. Drawing from work across global operations, insurance services, and Cogneesol’s transition into IT-enabled solutions, Ashim breaks down the mindset required to lead teams, solve problems, and build systems that stand up to change. Key Topics: Early influences and lessons from past mentors Transition from instinct-driven work to data-informed decision-making Evolution from BPM services into technology-led solutions Strategic thinking versus operational execution AI use cases and why processes must be fixed first Supporting agents, carriers, MGAs, and legal service clients Leadership strengths, weaknesses, and personal growth The role of global operations and continuous adaptation Travel, culture, and perspective gained across markets Reach out to: Ashim Khurana Jason Cass Visit Website: Cogneesol Agency Intelligence Produced by PodSquad.fm