John Thompson is here today to talk about how the future is reinventing taxes. He discusses his diverse career path from technology and programming into finance, tax services, and nonprofit work, highlighting his long-term involvement with the Financial Health Network and their efforts to improve consumer financial health. He explains how H&R Block has evolved from serving primarily low- and middle-income clients to addressing more complex financial needs, and how automation and technology are changing tax preparation and accounting. Thompson emphasizes the importance of personal finance fundamentals, daily cash-flow systems, and awareness in managing income, debt, and budgeting amid rising costs and structural challenges like housing and healthcare.

We discuss...

• John Thompson shares his career journey from technology and programming into finance, tax services, and nonprofit work.
• He highlights his 25-year relationship with the Financial Health Network and their mission to improve consumer financial health.
• John explains how research on bridging taxes and banking for underbanked populations inspired practical programs at H&R Block.
• He describes the evolution of H&R Block from serving primarily low- and middle-income clients to addressing more complex financial needs.
• Automation and technology in tax preparation are allowing professionals to focus on higher-value advisory services rather than data entry.
• Thompson emphasizes the importance of daily personal finance systems to manage cash flow, spending, saving, and debt.
• Challenges like inflation, housing affordability, student loans, and healthcare costs create structural barriers to financial health.
• Thompson discusses how banks and financial institutions are experimenting with different models to serve both underbanked and community-focused customers.
• He points out that for many simple tax filers, future trends may simplify filing to automated or postcard-level processes.
• Thompson stresses the importance of taking timely financial actions at key moments, like tax season, raises, or job changes.
• He highlights upcoming policy and product changes, such as the retirement savings match in 2027–2028 and child savings accounts starting in 2025.
• Thompson underscores that financial resilience requires both structural solutions and disciplined personal money management.

Today's Panelists:

• Kirk Chisholm | Innovative Wealth
• Barbara Friedberg | Barbara Friedberg Personal Finance

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For more information, visit the show notes at https://moneytreepodcast.com/reinventing-taxes-john-thompson-772

This could be your best trade of the year! Join us as we share December secrets for your portfolio. We also talk about the shifting narratives around climate change, deregulation, and rising energy demand driven by AI. We also explore expectations for low energy prices through the election cycle, concerns about an AI-driven bubble, the continued K-shaped economy, and tactical investing insights such as exploiting year-end tax-loss selling, watching beaten-down sectors, monitoring insider buying, and recognizing mutual-fund distribution dips.

We discuss...

• Political climate influences environmental narratives, pointing out that media references to "climate crisis" suddenly dropped as energy demand pressures changed.
• The explosion of AI data centers has quietly forced policymakers to pivot from anti-energy rhetoric to encouraging more electricity production and deregulation.
• How AI companies are now some of the largest new consumers of electricity, making cheap, abundant power a strategic priority for the tech sector.
• Energy prices are being politically managed to stay low into the midterm elections to keep inflation optics favorable.
• While AI valuations are stretched, there's unlikely to be an immediate bubble burst because capital flows and earnings momentum remain supportive.
• How end-of-year tax-loss harvesting creates forced selling in beaten-down stocks, temporarily pushing prices below fair value.
• Mutual funds selling to raise cash for capital-gains distributions can generate artificial dips that offer tactical buying windows for informed investors.
• Insider-buying activity is a useful signal in December, since executives often buy when their stock is mispriced due to seasonal pressures.
• A simple long-term Bitcoin approach: buy when it collapses on fear, hold through chop, and scale out when it becomes euphoric and parabolic.
• Concerns about the systemic risk attached to MicroStrategy's leveraged Bitcoin balance sheet and how a sharp BTC drawdown could spark forced selling.
• How crypto ETFs, institutional custody, and Wall Street participation may reduce volatility over time but also increase susceptibility to coordinated market moves.
• How markets today reward patience, skepticism, and tactical opportunism more than blind buy-and-hold in all sectors.

Today's Panelists:

Kirk Chisholm | Innovative Wealth Douglas Heagren | Mergent College Advisors

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For more information, visit the show notes at https://moneytreepodcast.com/best-trade-of-the-year-771

Larry Kriesmer shares how his career evolved from life insurance to options-driven wealth management, explaining that supervisory limitations at his former firm pushed him to launch his own RIA focused on option-based strategies. He and the host discuss the industry's longstanding discomfort with options, the differences among custodians, and the surge in option-centric ETFs driven by investor demand for income, downside buffers, and more predictable outcomes. Larry explains why he favors synthetic long exposure to the S&P 500, how options can create defined risk in ways traditional 60/40 portfolios cannot, and why repeated market shocks have increased interest in structures that limit drawdowns. He also stresses that while options can be powerful, they require real understanding—especially given the asymmetric risks—and that most investors are best served using simple strategies or working with experienced professionals.

• Larry Kriesmer shares his background transitioning from life insurance into wealth management and ultimately founding his own RIA due to options-related supervision limitations at his prior firm.
• We highlight how many insurance and brokerage firms restrict options usage because supervisors often lack the necessary licensing or comfort with the risks.
• Early-career experiences show how compliance departments often misunderstand options and overburden advisors executing client-driven trades.
• Larry explains that custodians also vary widely in their options competency, noting TD Ameritrade's historically advanced approach compared to more conservative platforms like Schwab and Fidelity.
• He describes how the growth of option-based ETFs and structured strategies reflects rising demand for income, risk buffers, and outcome-based portfolio design.
• Why options are resurging in popularity despite being decades old, tying it to investor frustration with unpredictable markets, multiple major drawdowns, and the need for more controlled outcomes.
• Larry outlines his discovery of options through studying indexed annuities, which showed him how options could define downside risk and reshape portfolio construction.
• He explains his core strategy of staying synthetically long the S&P 500 at all times, avoiding market timing, and focusing on capturing upside while limiting drawdowns.
• The conversation touches on potential expansion of his strategy into other sectors or international markets, though the S&P remains his primary exposure due to its self-healing nature.
• Larry critiques modern portfolio theory as outdated and insufficient for managing real downside risk, arguing that a bond-plus-options structure can outperform a traditional 60/40 on a risk-adjusted basis.
• You discuss how 2022 exposed the limitations of conventional diversification when both stocks and bonds fell simultaneously.
• Larry emphasizes that while options can be powerful tools, investors must deeply understand which side of the contract's risk they are assuming to avoid catastrophic losses.
• He concludes that most investors should pursue education but ultimately rely on professionals or ETF structures if they want to safely incorporate options into their portfolios.

Today's Panelists:

• Kirk Chisholm | Innovative Wealth
• Barbara Friedberg | Barbara Friedberg Personal Finance
• Phil Weiss | Apprise Wealth Management

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For more information, visit the show notes at https://moneytreepodcast.com/strategies-for-modern-investors-lawrence-kriesmer-770

There are financial opportunities in Latin America, silver and more and today we are going to share them with you! We also talk holiday shopping trends and the struggles of retailers in our current economy. We also dive into "confuse-opoly" industries like furniture, mattresses, and healthcare where pricing is intentionally opaque, share personal experiences with overpriced goods, and discuss how margins, supply, and consumer behavior shape retail dynamics. Today we discuss...

• Buying a new house and becoming newly attentive to pricing, noting how Black Friday sales have expanded so much that they no longer feel special.
• How holiday traditions and retail behavior have shifted, with Christmas decorations and sales appearing earlier each year.
• How perpetual discounts dilute the meaning of sales and reflect retailers' struggles in a weakening, K-shaped economy.
• Constant "sale" pricing makes it impossible for consumers to know real value, especially in industries like furniture.
• We share anecdotes about mattress shopping and how identical products are given different names across stores to prevent direct price comparisons.
• Market charts prompt discussion on growth vs. value investing, highlighting value's long-term underperformance and its historical cyclicality.
• We compare current market dynamics to the late 1990s tech bubble, noting similarities in speculation and skepticism toward value investing.
• Latin America's unusually low valuations and strong relative performance this year are examined as a potential opportunity.
• Emerging markets often struggle with consistency due to currency issues, political instability, and uneven economic development.
• We emphasize the importance of evaluating assets in relative terms—stocks vs. dollars, gold vs. currencies, and region vs. region.
• How relative performance charts reveal where capital is flowing, using gold, silver, and mining stocks as examples of cycle progression.
• Copper miners' potential breakout is highlighted as a key signal for commodity sector strength.
• Markets ultimately reflect where limited investor capital is being allocated at any given moment.

Today's Panelists:

• Kirk Chisholm | Innovative Wealth
• Barbara Friedberg | Barbara Friedberg Personal Finance
• Phil Weiss | Apprise Wealth Management

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For more information, visit the show notes at https://moneytreepodcast.com/opportunities-in-latin-769

A bull market in cash is coming! Gary Zimmerman, founder and CEO of Max, explains how he discovered major inefficiencies in the cash-deposit market and built a platform that helps clients earn higher yields while staying fully FDIC-insured. We explore how broker-dealer incentives shaped the "always be invested" mindset, why RIAs take a more fiduciary approach to cash, and how most advisors dramatically underestimate how much cash clients actually hold in outside bank accounts.

We also dive into the strategic role of cash in portfolios, the psychology and behavioral finance behind loss aversion, and why many investors keep cash in low-yield big banks despite far better options.

We discuss...

• Gary Zimmerman shares his path from aspiring biochemist to investment banker and ultimately founder of Max.
• Gary describes how Max helps advisors and clients earn higher yields on cash while staying fully FDIC-insured.
• The conversation highlights the structural differences between broker-dealers and fiduciary RIAs in how they treat cash.
• Cash is both the "worst" asset class (low returns) and the "best" (strategic flexibility and optionality).
• Gary emphasizes that many advisors are unaware of large "held-away" cash balances clients keep at big banks.
• Research shows high-net-worth households keep roughly 25% of their liquid assets in cash—far above portfolio models.
• Behavioral finance plays a major role as clients publicly want risk but privately hoard cash for emotional comfort.
• Cash helps investors sleep better, reduce loss-aversion anxiety, and feel less trapped in work or life decisions.
• Gary explains that deposit pricing inefficiency exists because large banks don't need or want more deposits.
• The system also keeps client deposits below insurance limits by spreading funds across multiple banks.
• They explore how most households either have no emergency reserve or keep excessive idle cash earning too little.
• Cash reserve needs vary dramatically by life stage, career stability, and complexity of financial obligations.
• Senior professionals may need years of cash cushion because job searches take longer at higher levels.
• Behavioral mistakes in downturns often stem from being over-invested relative to one's psychological risk capacity.
• Gary argues that post-pandemic money-supply expansion suggests more inflation is still embedded in the system.

Today's Panelists:

• Kirk Chisholm | Innovative Wealth
• Diana Perkins | Trading With Diana

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For more information, visit the show notes at https://moneytreepodcast.com/bull-market-in-cash-gary-zimmerman-768

The economy is breaking, and today we discuss the signs. We explore the challenges of navigating today's markets, highlighting the volatility and skepticism around AI-driven companies, overinflated stock valuations, and earnings season dynamics where "beating expectations" often masks underlying realities. It's important to be cautious investors over high P/E ratios, unsustainable growth, and market timing. You need to focus on risk management over speculation. Critical thinking is also imperative while evaluating data and it's important to question assumptions and focus on market behavior rather than blindly trusting reported numbers.

We discuss...

• Volatility in November and the flat performance in October, with a mixed outlook for the remaining six weeks of the year.
• Historical trends in presidential cycles, noting that the second year is statistically the worst for stock market performance, while years one, three, and four tend to perform better.
• The impact of earnings season on markets and how companies often beat expectations by managing guidance strategically, which can mislead retail investors.
• The market's reaction to AI-related companies, the skepticism around reported growth, revenue, and inter-company financing "shenanigans."
• Historical parallels to the late 1990s internet bubble, where vendor financing inflated revenues before companies ultimately collapsed.
• The difficulty of individual stock investing, noting that growth rates slow as companies mature and valuations often contract over time.
• The risk of focusing on long-term predictions without timing, being "right too early" can result in significant opportunity costs and losses.
• Michael Burry's recent hedge fund moves, his short positions on AI-related stocks like Nvidia and the implications for investors skeptical of inflated earnings.
• Timing is critical in investing, caution with high-growth sectors and risk management rather than speculative bets are needs.
• Investors should not blindly trust government or corporate data, but instead focus on market behavior and price trends to assess reality.
• There's importance in distinguishing between what is factually true and what the market believes.
• Apply critical thinking, question assumptions, and focus on present market realities rather than speculative long-term projections.

Today's Panelists:

• Kirk Chisholm | Innovative Wealth
• Phil Weiss | Apprise Wealth Management

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For more information, visit the show notes at https://moneytreepodcast.com/the-economy-is-breaking

John Bartleman, the CEO of TradeStation, is here today to talk about how AI will transform the future of trading. John shares his background and the evolution of TradeStation from early backtesting software to a full-service broker, while explaining how its roots in systematic trading differentiated it from competitors. He outlines major industry shifts, along with the benefits and challenges of dark pools and institutional order flow. We also dive into how AI is transforming trading, as John describes his own use of MCP-enabled AI agents for research, portfolio analysis, trade structuring, and more. AI may radically reshape fintech analytics and asset management, enabling traders to work more efficiently and pushing the industry toward fewer traditional money managers and more AI-driven decision systems.

We discuss...

• Record money market fund levels are being widely misinterpreted, as the balances often represent defensive positioning rather than pent-up buying power.
• Many investors mistakenly assume large cash balances automatically signal a coming equity influx, ignoring the behavioral reasons people hold cash.
• The tariff headline created rapid swings in futures markets, revealing how sensitive positioning is ahead of the election.
• A sharp crypto drawdown triggered widespread stop-loss cascades across major tokens, amplifying downside pressure in a classic liquidity vacuum.
• Seasonal trends typically provide a tailwind this time of year, but macro uncertainty is preventing markets from fully leaning into the pattern.
• Investors are observing a notable rotation away from mega-cap tech and toward value-oriented and small-cap sectors.
• The dispersion between the top seven tech stocks and the rest of the index remains near historic extremes.
• Elevated cash levels and volatility suggest institutional investors are selectively adding risk rather than buying broadly.
• Market breadth is improving modestly, but not enough yet to signal a durable trend reversal.
• Short-term traders are capitalizing on intraday volatility spikes driven by headlines and algos.
• Longer-term investors remain focused on earnings resilience and margin stability across sectors.
• Companies with global exposure are expressing concern about potential policy shifts after the election.
• Energy and industrials are gaining attention as potential beneficiaries of a reflationary environment.
• Tech remains bifurcated between AI-driven leaders and more traditional software names experiencing deceleration.
• Crypto markets continue to influence risk appetite, even among investors who do not directly hold digital assets.

Today's Panelists:

• Kirk Chisholm | Innovative Wealth
• Barbara Friedberg | Barbara Friedberg Personal Finance
• Diana Perkins | Trading With Diana

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For more information, visit the show notes at https://moneytreepodcast.com/the-future-of-trading-john-bartleman-766

The stock market is broken! Today we talk about a broad range of economic, market, and behavioral topics, beginning with the cognitive bias of sunk costs and how it affects personal decisions, investing, and business choices, emphasizing the importance of recognizing losses and cutting them early. We also explore recent market signals, including distress in the credit and auto-loan markets, and the K-shaped economy. We also critique media and policy narratives, pointing to propaganda around climate change and the pivot to nuclear energy. It's important to be aware and prudent in your observations in uncertain times. We also remark on the rising cost of living, currency devaluation (the end of the penny), and market performance trends.

We discuss...

• Sunk cost bias was illustrated with examples in plumbing repairs, investing in stocks like QQQ, and hiring ineffective marketers in business.
• People often continue bad relationships or investments due to the psychological discomfort of admitting mistakes.
• Non-decisions are still decisions, and it's important to consciously choose a path rather than defaulting to inaction.
• The conversation shifted to propaganda in media and politics, including discussions about global warming and COVID messaging.
• Nuclear energy is the only scalable solution for energy needs if climate change is real, and that AI and technology interests influenced the shift in media focus.
• We discussed deliberate and coincidental market messaging, citing examples of Fed statements and past financial crises like 2008.
• Michael Burry's recent fund positions and put options on Nvidia and Palantir were discussed as a signal for investors to pay attention, though not necessarily to follow blindly.
• Extreme caution in investing is recommended, particularly in markets or sectors one does not fully understand, such as the stressed auto-loan market.
• Signs of market stress were highlighted, including unusual moves in the SOFR rate and subprime auto-loan distress, though not on the scale of the 2008 mortgage crisis.
• The K-shaped economy was explained, where asset holders benefit from price inflation while those without assets see income stagnation and rising expenses.
• Rising housing costs and mortgage challenges were linked to declining fertility rates and generational effects on college and workforce participation.
• Indicators of market sentiment, including CNN's Fear and Greed Index, were analyzed, with a caution not to follow them blindly as they often lag or mislead.
• Observations were made on shifting consumer behaviors, including declining cash usage and businesses refusing pennies as payment.
• Future discussion topics were teased, including REIT investment opportunities and year-to-date market performance insights.

Today's Panelists:

Kirk Chisholm | Innovative Wealth Douglas Heagren | Mergent College Advisors

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For more information, visit the show notes at https://moneytreepodcast.com/stock-market-is-broken

Mark Salisbury shares the secrets to spending less on the cost of college! As the founder of TuitionFit, explains how the college pricing and financial aid system is designed to favor schools over families. He describes how emotional marketing, opaque pricing, and complex financial aid forms create confusion and limit families' leverage. he outlines how students and parents can regain control by defining their price range first, using resources like TuitionFit and net price calculators, and strategically managing assets, timing, and financial disclosures. He also covers how income, savings, and family structure affect aid, and more!

We discuss...

• Mark Salisbury explains how the college pricing system is intentionally vague, designed to benefit schools rather than families.
• This conversation exposes how the financial aid process operates like a hidden marketplace where families unknowingly pay vastly different prices for the same education.
• Mark explains the difference between a school's sticker price, discount rate, and net price, emphasizing that the last is what truly matters.
• He details how the FAFSA and CSS Profile collect information that can be used by colleges to assess a family's financial "willingness to pay."
• Timing and disclosure of assets can dramatically impact how much financial aid a family receives.
• Families with business ownership structures may have advantages in how assets and income are reported.
• Fnancial aid formulas often penalize savings while rewarding debt.
• Salisbury argues that families should start with their budget first, then find schools that fit within that price range—rather than applying and hoping for aid.
• Tools like TuitionFit help families compare real financial aid offers and discover the true market price for college.
• He advises against oversharing financial information before admission decisions are made to preserve negotiation leverage.
• Negotiating college costs is compared to buying a car—where informed consumers who know their target price get better deals.
• Transparency and data sharing among families are key to fixing the broken college pricing system.
• Mark calls for systemic reform to make higher education pricing fairer, more transparent, and tied to real market value.

Today's Panelists:

• Kirk Chisholm | Innovative Wealth
• Douglas Heagren | Mergent College Advisors
• Diana Perkins | Trading With Diana
• Jack Wang | Smart College Buyer

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For more information, visit the show notes at https://moneytreepodcast.com/secrets-to-spending-less-on-the-cost-of-college-mark-salisbury-764

Should the S&P go higher? Today we discuss that and more in this wide-ranging episode. We talk the markets, and warn that investors often cling to bad positions instead of reassessing when wrong, noting that current valuations are stretched and the market appears overextended. There is rising corporate caution during earnings season, weak performance among consumer staples and cyclicals, and the growing dominance of the "Magnificent Seven" tech stocks in driving the S&P 500's gains. AI-related capital expenditures and record margin debt levels suggest heightened risk, so you should remain defensive and patient as market conditions soften despite entering a historically strong seasonal period.

We discuss...

• New York City's election of a socialist-leaning mayor and question how it might impact the city's historically capitalist foundation.
• Drawing a parallel to investing, we stress the need to reassess assumptions when investments go against you instead of clinging to them.
• The current market is overextended, with valuations significantly above historical trends and a concentration in a few large tech stocks.
• Consumer cyclicals and staples, normally defensive areas, have underperformed, suggesting caution for risk-averse investors.
• The "Magnificent Seven" tech stocks are disproportionately driving the S&P 500's performance, masking weakness in the broader market.
• AI-related capital expenditures are rising sharply, but returns on these investments remain minimal, highlighting potential overhype.
• Margin debt has reached record levels, indicating elevated risk if market sentiment shifts.
• Earnings season shows that even companies beating expectations may see stock declines, signaling that much of the positive news is already priced in.
• Weak market breadth—many stocks declining while a few outperform—indicates fragility and higher potential volatility.
• While a correction is possible, seasonal trends historically make late November through January a strong period for markets.
• Inflation is picking up modestly, while interest rates are being lowered, creating a complex environment for fixed-income investors.
• Private credit and real estate markets are showing early signs of stress, particularly as products are increasingly marketed to retail investors.
• Investors are advised to watch for opportunities in mispriced assets but remain cautious due to market overvaluation and potential downside risks.
• Overall, the discussion emphasizes patience, caution, and careful risk management amid uncertainty in politics, markets, and emerging technologies.

Today's Panelists:

Kirk Chisholm | Innovative Wealth Douglas Heagren | Mergent College Advisors

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For more information, visit the show notes at https://moneytreepodcast.com/should-the-sp-500-go-higher-763

Lily Vittayarukskul shares her remarkable journey from working at NASA in her teens to founding a company that innovates with AI to transform long-term care planning. We explore why long-term care remains one of the most misunderstood and underserved areas in wealth management, despite being one of the biggest retirement risks. We break down how long-term care works, who needs it most, the pros and cons of self-funding versus insurance products, and why many families fail to plan until it's too late.

We discuss...

• Lily Vittayarukskul shared her early fascination with aerospace engineering, including work recognized at age 12 and a role at NASA's JPL by 16.
• A personal long-term care event in her family at age 16 prompted her pivot from aerospace to healthcare.
• She built technical expertise in genetics and AI at Berkeley before founding a company focused on long-term care solutions.
• The ideal candidates for long-term care planning are typically 40–60 years old, upper-middle-class individuals with $2–5 million in assets.
• Many financial professionals avoid long-term care due to its complexity, morbid nature, and time-consuming conversations.
• Traditional long-term care policies and hybrid/lump-sum products each have advantages depending on individual circumstances and predicted care needs.
• Self-funding long-term care is an option, but many clients are risk-averse and ultimately prefer a structured insurance plan.
• Lily's company uses decades of data to predict long-term care events and costs, helping advisors map policies to individual client needs.
• Long-term care planning is as much about protecting family members and legacy as it is about financial strategy.
• Conversations about long-term care should start with a professional, involve spouses, and eventually include children or trusted family members.
• Many clients struggle with the emotional and logistical burdens of caregiving, which can impact their own health and quality of life.
• The topic is often avoided culturally because it forces acknowledgment of aging, mortality, and potential loss of autonomy.

Today's Panelists:

• Kirk Chisholm | Innovative Wealth
• Barbara Friedberg | Barbara Friedberg Personal Finance
• Douglas Heagren | Mergent College Advisors

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For more information, visit the show notes at https://moneytreepodcast.com/transform-long-term-care-lily-vittayarukskul-762