Money Tree Investing

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:

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:

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:

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:

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: