Elliot Holland joins us to explore the realities of building and sustaining a high-quality, trust-driven professional business in an era dominated by AI hype, declining marketing efficiency, and algorithmic noise. We discuss skepticism around AI's real-world impact especially in high-stakes financial decisions. We also talk marketing and content strategy, why sensationalism and clickbait may win algorithms but will always repel discerning clients. We also unpack our frustrations with modern marketing platforms like Google, Facebook, and HubSpot as they grow increasingly expensive and benefit from opacity while delivering lower-quality data. The most important thing is authentic conversations, patience, and thoughtful content aimed at a small, qualified audience that can outperform viral reach.

We discuss...

• Sustaining a professional services business increasingly depends on trust, judgment, and human relationships rather than scale, speed, or technological hype.
• There's septicism that AI will meaningfully disrupt high-stakes, people-to-people work, arguing it is largely rebranded machine learning with limited real-world adoption so far.
• Discerning clients value nuance, experience, and improvisational thinking that cannot be captured in static data sets or automated workflows.
• AI is a productivity aid for summaries and surface-level tasks, but not a substitute for deep expertise, critical thinking, or accountability.
• YouTube and podcasts are trust-building tools rather than growth hacks, with success measured by client conversion quality instead of view counts.
• Algorithms reward "nonsense about nonsense," making platforms misaligned with professionals selling high-trust, high-ticket services.
• Marketing metrics such as views, impressions, and engagement were described as misleading compared to tracking clicks, conversations, and actual revenue outcomes.
• Google, Facebook, and HubSpot are operating as "confuse-opolies," benefiting from complexity, opacity, and user lock-in rather than clear results.
• The rising difficulty of marketing has forced business owners to either deeply understand marketing themselves or risk wasting capital on underqualified vendors.
• Elliott explained restructuring his marketing around specialized vendors, strict performance accountability, and personal ownership of customer persona definition.
• Long-form, unscripted conversations often deliver more value than polished, optimized content designed for algorithms.
• Future marketing success will favor authenticity, clarity, and long-term relationship-building over funnels, gimmicks, and viral reach.

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For more information, visit the show notes at https://moneytreepodcast.com/ai-hype-and-clickbait-are-failing-elliott-holland

Today we're sharing the tax loss selling secrets you need to know before 2026! We also talk understanding personal strengths and psychological limits in investing. It's good to avoid shiny-object strategies like day trading and prioritize risk management through diversification. We explore how market structure, valuations, and historical data suggest future returns may be lower and more volatile, making stress-testing portfolios and aligning risk with temperament essential. Remember long-term success comes from discipline, education, adaptability, and thoughtful strategy rather than chasing returns in overheated markets.

We discuss...

• Successful goal-setting focuses on small, repeatable actions over time rather than unrealistic short-term outcomes.
• Investors must design strategies that align with their psychological makeup, risk tolerance, and time availability rather than copying what appears profitable for others.
• Stop-loss orders can be dangerous in volatile or less-liquid markets due to slippage and market maker behavior, often leading to worse-than-expected exits.
• Markets can remain expensive longer than expected, making flexibility and balanced positioning more important than precise market timing.
• Concentration in high-performing assets like AI stocks or precious metals can lead to severe losses if momentum reverses sharply.
• Historical examples showed that long periods of weak or flat equity returns are normal following valuation extremes.
• Diversification across asset classes, regions, and styles was highlighted as essential for retirement sustainability and long-term wealth preservation.
• Static portfolios such as traditional 60/40 allocations were questioned, with an emphasis on active monitoring and adjustment as conditions change.
• Precious metals typically move in sequence, with gold leading, followed by silver and then platinum, often ending in unsustainable parabolic moves.
• Misuse of statistics, such as confusing average with median net worth, can distort perceptions of wealth and financial reality.
• Investment performance should be evaluated using geometric averages rather than arithmetic means to reflect true compounded returns.
• Emotional states like greed and fear often peak near market extremes and should signal the need for reevaluation rather than increased risk-taking.
• Political, macroeconomic, and election-cycle dynamics can temporarily suppress or amplify commodity prices, particularly in energy markets.
• Long-term success in investing depends less on prediction and more on preparation, adaptability, and disciplined execution of a well-structured plan.

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/tax-loss-selling-secrets-777

Sallyann Della Casa, CEO Dubai-based "community as a service" GLEAC, joins us to share her personal journey and how collaborative leadership will thrive in our AI-drive future. She explains how access to networks, proximity to experience, and "quiet capital" are often more powerful than credentials alone in shaping opportunity, leadership, and career outcomes. We explore inequality driven by access rather than ability, leadership and gender mental models, and examines why modern society struggles to produce widely respected leaders. We also education and AI, arguing that traditional schooling is outdated, overly focused on memorization, and ill-suited for a world where AI can outperform humans on hard skills, while human skill can thrive in areas AI can't. AI will reshape leadership, investing, and management and future leaders will succeed by combining learning agility, deep expertise, strong networks, and the ability to co-lead alongside AI.

We discuss...

• Sally Ann Della Casa shares her personal story to illustrate how proximity, networks, and early access often determine life outcomes more than raw talent.
• The concept of "quiet capital" is a mix of social trust, reputation, networks, and deep domain knowledge that drives real-world success.
• The discussion examined inequality as a function of access and networks rather than intelligence or effort.
• Leadership was debated through the lens of mental models, including gender expectations, risk tolerance, and the loneliness of decision-making.
• Modern society struggles to identify and develop respected leaders across business, politics, and culture.
• Education systems are outdated, overly focused on memorization, and misaligned with how people actually learn and collaborate.
• AI was framed as a forcing function that will finally push education to prioritize human skills like judgment, creativity, curiosity, and critical thinking.
• The risks and benefits of AI are discussed, emphasizing that AI reflects human biases and represents the "gray average," not top-tier insight.
• The importance of context, storytelling, and lived experience are highlighted as something AI cannot replace.
• Leadership in the future is more agile, less hierarchical, and increasingly collaborative with AI tools and agents.

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/collaborative-leadership-in-an-ai-driven-world

Should you be buying this precious metal this Christmas? Find out what it is today as we reflect on how instant gratification, social media, and shifting consumer behavior mirror broader economic changes. We also talk practical year-end investing discipline, including portfolio "hygiene," investor psychology alignment, rule-based decision making, and tax-loss harvesting strategies. We explore assesing holdings as if investing fresh today, managing oversized winners and stagnant losers, watching natural market turning points around year-end, while also exploring inflation trends, shrinkflation, housing affordability, and generational cost pressures. We also urge listeners to use the final weeks of the year to review risks, taxes, family financial clarity, and opportunities ahead. Thoughtful preparation, not momentum or emotion, drives long-term investment success.

We discuss...

• The importance of year-end portfolio assessment, emphasizing reviewing holdings as if investing fresh today to determine alignment with investor psychology.
• Manage oversized winners, stagnant losers, and follow disciplined, rule-based investment practices rather than ego-driven decisions.
• Tax-loss harvesting is a key strategy, including the special advantage that crypto is treated as property and not subject to the 30-day wash-sale rule.
• Monitoring natural market turning points, particularly around year-end, to identify potential buying opportunities in beaten-down assets.
• Gold's leadership in the rally, silver's sharp recent gains, and the implications of JP Morgan shifting from short to long silver positions.
• Basel III banking regulations and the possibility of global banks increasing gold holdings if U.S. deficits rise above projected thresholds.
• Strategies for buying gold and silver, emphasizing buying for weight to minimize premiums and potentially profiting from historical spreads in coin pricing.
• Have caution with rare coin premiums, only experienced investors should consider numismatic factors, otherwise stick to weight-based purchases.
• Inflation indicators, using Campbell's Soup can pricing as a proxy for quality-adjusted inflation over decades.
• Shrinkflation and the rising cost of essentials for younger generations, noting housing, insurance, and other expenses have outpaced wages.
• Recent trends in housing, including declining new home prices but smaller home sizes, illustrating hidden inflation and cost pressures.

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/santa-clause-rally-ahead-775

Economist George Economou joins us today to share why stocks and gold are soaring in the modern global market. He talks about his global outlook on markets amid rising economic and geopolitical uncertainty, AI-driven growth narratives, stock buybacks, and deep investor anxiety fueled by a multipolar world. We also chat on trade tensions, and escalating conflicts across the globe. He explained how falling interest rates continue to prop up U.S. and European stocks despite stretched valuations, why gold is surging as central banks and investors hedge geopolitical risk, and why tariffs are unlikely to succeed economically over the long run.

We discuss...

• George Economou outlined his background as a Greece-based macroeconomist, financial consultant, academic, and economics educator.
• Rising tariffs, shifting trade policies, and the growing independence of BRICS nations are major sources of macro instability.
• Europe is particularly vulnerable, with echoes of pre-2008 risks despite strong headline equity performance.
• U.S. equity markets are being driven by AI-led profit growth, excess liquidity, and falling interest rates rather than pure fundamentals.
• European equity strength is largely attributed to corporate stock buybacks rather than underlying economic health.
• Falling interest rates globally were highlighted as a key driver pushing investors away from bonds and into equities.
• Gold prices were said to be surging due to geopolitical uncertainty and aggressive central bank accumulation, especially by BRICS nations.
• Geopolitical risks involving Russia–Ukraine, the Middle East, and China–Taiwan are central drivers of market anxiety.
• Tariffs are a political tool aimed at reshoring U.S. production, but one that economic theory suggests will be inefficient long term.
• AI investment is comparable to early smartphone adoption, requiring heavy upfront spending before productivity gains become visible.
• CEOs' frustration with AI returns is linked to poor implementation rather than a lack of long-term potential.
• Extremely high global equity valuations are attributed to investors avoiding bonds and real estate due to unattractive risk-reward dynamics.
• Sustained market valuations is questioned, with the warning that expensive assets eventually decline when buyers step away.

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/stocks-and-gold-are-soaring-george-economou-774

The Federal Reserve tipped it's hand for a bull market. Today we discuss the details. We talk economic divergence, as decades of debt-fueled growth and asset inflation have benefited boomers and asset owners while leaving younger generations locked out of housing and upward mobility, creating frustration and political volatility. The U.S. economy is fundamentally leveraged by pulling future earnings forward and this could be an eventual but unpredictable global financial reset.

We also talk the near-term debt panic but don't get nervous as deficits are the true risk. We also talk practical investing takeaways around market cycles, sentiment, tax-loss selling, Santa Claus rally dynamics, and the importance of patience, diversification, and avoiding extreme, fear-driven decisions.

We discuss...

• We highlight generational economic disparities, noting younger people struggle with housing affordability and wealth accumulation compared to boomers.
• Economic frustration among younger generations is linked to the appeal of populist political figures who speak to lived experiences.
• The U.S. economy is heavily leveraged, with future earnings being pulled forward to maintain growth and consumption.
• We warn of a potential global financial reset, while emphasizing that timing and specifics are uncertain.
• Central banks' accumulation of gold is a signal of perceived systemic risk and preparation for a global reset.
• Debt itself can be manageable, but the ongoing growth of deficits is the real problem.
• Concerns about foreign countries dumping U.S. bonds were dismissed as largely impractical due to mutual economic harm.
• Market reactions to Fed rate cuts are analyzed, showing how assets like stocks, silver, the dollar, and Treasury yields respond differently.
• It's important to analyze market cycles and sentiment, rather than relying on GDP or simplistic economic indicators.
• Tax-loss selling and end-of-year market dynamics are discussed as opportunities to buy undervalued assets with lower downside risk.
• The Santa Claus rally and January market patterns are historically strong indicators for short-term gains.
• Focus on sectors or assets that were beaten down, watch early January flows, and avoid extreme, fear-driven moves.

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/the-federal-reserved-tipped-its-hand-773

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