Money Tree Investing

Get new ideas every week from Money Tree Investing Podcast! Come find out why our smart listeners love us. We find the top minds of investing and personal finance to join us on our show. Our guests and panelists talk about investing and personal finance ideas like how to find great investment ideas, building passive income, investing in real estate, financial independence, alternative investments, personal finance, money management, retirement, and finding new investment trends that are not yet mainstream.

Medicare Madness Solved with Sylvia Gordon 03/27/2026

Medicare Madness Solved with Sylvia Gordon Medicare madness solved! Join us as Sylvia Gordon demystifies retirement planning, explaining how Medicare and Social Security actually work, highlighting key age milestones and emphasizes that there is no one-size-fits-all strategy. Descisions depend heavily on individual health, finances, and lifestyle goals. We break down Medicare’s complex structure, contrasts private Medicare Advantage plans with traditional coverage, and explores common (and costly) misconceptions while also addressing broader systemic issues such as rising healthcare costs, doctor shortages, and policy uncertainty. Personalized planning is the most important thing you can do as there is no one-size-fits-all set up. Early education and understanding nuanced rules like spousal and ex-spousal Social Security benefits can help you avoid leaving money on the table. We discuss... Sylvia Gordon explained her background training insurance agents and simplifying retirement topics through short-form educational content. Many people misunderstand that taking Social Security early permanently reduces benefits and that Medicare does not begin at the same time. There is no universal “rule of thumb” for claiming Social Security, as decisions depend on the individuals goals. Medicare enrollment at 65 is optional if you continue working with qualifying employer coverage, which can prevent unnecessary costs. Prescription drug coverage now includes a capped out-of-pocket maximum, though costs have shifted for many users. Healthcare system challenges such as doctor shortages and low Medicare reimbursement rates were discussed as reasons providers limit Medicare patients. Rising healthcare costs and inefficiencies are major pressures on the long-term sustainability of retirement systems. Future changes to Social Security and Medicare are likely to include higher retirement ages and reduced benefits due to demographic trends. Policy changes are often phased in gradually to avoid political backlash and protect current retirees. The conversation explored potential reforms like lowering drug prices and reducing U.S. subsidization of global pharmaceutical costs. Medical tourism and international drug purchasing are discussed as cost-saving strategies not typically covered by Medicare. Medicare generally does not cover alternative or functional medicine, requiring out-of-pocket spending for those services. Incentives within healthcare, such as provider bonuses and system constraints, can influence treatment recommendations. Many retirees miss benefits or make suboptimal decisions due to lack of education and reluctance to discuss finances within families. Starting retirement planning in your 50s, and helping parents navigate the system, can improve outcomes and understanding. Today's Panelists: Kirk Chisholm | Phil Weiss | Douglas Heagren | Follow on Facebook: Follow LinkedIn: Follow on Twitter/X: For more information, visit the full show notes at /episode/index/show/moneytreeinvesting/id/40568905

WAR… And No Market Crash… Is That Bullish or Bearish… Let’s Find Out 03/25/2026

WAR… And No Market Crash… Is That Bullish or Bearish… Let’s Find Out WAR… and no market crash… Are we in a bear market or a bull market? Rapidly shifting narratives, once centered on a soft landing, rate cuts, and strong consumers, have been disrupted by war, oil volatility, and weakening economic data, creating widespread uncertainty and “busted brackets” for investors. Markets are behaving irrationally, often reacting more to expectations and propaganda than clear fundamentals, making prediction unreliable and reinforcing the importance of scenario-based thinking rather than conviction. There will either be a quick end to the conflict that could drive lower oil, falling rates, and a rebound in bonds and staples, or a prolonged war leading to higher inflation, economic strain, and limited upside across most assets. With elevated correlations, fragile financial systems, and a stalled market that has gone largely sideways, traditional diversification may not provide protection. The key takeaway is caution and avoiding emotional decisions! As always, adaptability and risk management matter more than trying to predict outcomes in a highly unstable environment. We discuss... Markets are behaving like March Madness, with unpredictability, momentum shifts, and broken narratives replacing earlier optimism around a soft landing. Geopolitical conflict and unclear information flows are driving volatility, making it difficult to distinguish truth from market-moving narratives. The market appears to be pricing in a short-lived conflict, despite ongoing uncertainty and mixed signals. Traditional diversification is less reliable as correlations between stocks and bonds have increased in recent years. Energy has emerged as the primary outperformer, while most other sectors struggle amid rising costs and uncertainty. Financial system risks are building, particularly in private credit and banking exposure, signaling potential stress beneath the surface. Consumer strength is weakening as higher costs and debt begin to pressure spending behavior. Housing remains a major concern, with rising supply and weak demand due to elevated mortgage rates. Market movements often contradict headlines, reinforcing the need to observe price action rather than rely on media narratives. “Buy the dip” strategies are risky in uncertain or potentially bearish environments. Sitting in cash or staying defensive can be a strategic choice when market direction is unclear. Predictions from Wall Street are often overly optimistic and fail to account for downside risks. Volatility and confusion in markets are often the result of mispriced uncertainty rather than clear economic deterioration. Successful investing in this environment requires adaptability, patience, and disciplined risk management rather than bold predictions. Today's Panelists: Kirk Chisholm | Douglas Heagren | Follow on Facebook: Follow LinkedIn: Follow on Twitter/X: For more information, visit the full show notes at /episode/index/show/moneytreeinvesting/id/40598415

Navigating Today’s Investment Landscape with Elliott Holland 03/20/2026

Navigating Today’s Investment Landscape with Elliott Holland Elliott Holland is back with us to help us explore today's investing landscape. We discuss concerns about illiquidity, continuation funds, and efforts to expand private equity access into retirement accounts such as 401(k)s, as those moves may be driven by a need for liquidity rather than investor benefit. We also talk how investor psychology, ego, and exclusivity often influence capital allocation, while experienced investors should focus instead on fundamentals like who has better information in a transaction and whether there are multiple ways to win in an investment. We dive into emerging areas like search funds, small business acquisitions, and roll-up strategies, highlighting both their potential and risks. There is importance to patience in investing, as technologies like AI may reshape research, decision-making, and competitive advantages for investors and business owners. We discuss... Whether private equity still deserves its reputation as producing the smartest investors and best returns in finance. Private equity returns have declined over the past decade and in many cases barely outperform the S&P 500. Mezzanine debt is highlighted as an alternative that has historically produced better returns with less risk and shorter lockups than private equity. Continuation funds and other mechanisms allow private equity firms to extend holding periods when they cannot find buyers. Some private equity firms are struggling with liquidity because they cannot exit deals at the valuations they promised investors. Illiquid investments with mediocre returns may not be worth the long lockup periods required. How exclusivity and the desire to invest alongside prestigious managers can lead investors to overlook fundamentals. How Wall Street often profits regardless of whether the underlying investments succeed. The Stanford model of funded search funds is historically producing strong reported returns. Increased competition for small business deals may be inflating prices and reducing returns. In some cases sellers may misrepresent financial performance to attract inexperienced buyers. Roll-ups can work when a larger buyer eventually acquires the combined platform at a premium valuation. Real estate is an example where multiple exit paths can justify accepting illiquidity. Periods of market stress often create the best opportunities for patient investors. Investors often regret not having enough capital ready during market downturns. The conversation also examines how smaller investors may have advantages over large institutions in finding niche deals. How new technologies and economic changes may create opportunities for the next generation of investors. AI is described as a productivity tool that can accelerate research and idea development, though AI outputs are not always reliable and require human judgment. Experienced professionals who combine domain knowledge with AI tools may gain a major advantage. Leaders should ensure someone within their organization is actively monitoring AI developments. Investors and entrepreneurs should stay curious, patient, and disciplined while adapting to changing markets and technologies. Today's Panelists: Kirk Chisholm | Barbara Friedberg | Phil Weiss | Follow on Facebook: Follow LinkedIn: Follow on Twitter/X: For more information, visit the full show notes at /episode/index/show/moneytreeinvesting/id/40458645

Private Credit Could Be The Next Black Swan 03/18/2026

Private Credit Could Be The Next Black Swan Private credit could be the next black swan and we're going to break it down for you. We also discuss the ongoing war and how geopolitical uncertainty is affecting financial markets, investor psychology, and economic conditions. Misinformation, AI-generated content, and media bias make it difficult to know what is actually happening amidst the "fog of war", which increases market uncertainty. Markets have reacted with volatility rather than a sharp crash, highlighting unexpected moves such as a stronger U.S. dollar, mixed performance across sectors, and spikes in oil prices that could fuel inflation. Risk management is of the upmost importance during uncertain periods and investors should reassess their theses, reduce exposure when necessary, and consider holding cash until clearer trends emerge. We also talk broader economic risks including rising credit balances, potential policy mistakes by central banks, and structural concerns in areas like private credit and financial sector exposure. We discuss... The ongoing war has created uncertainty and a wide range of opinions about its political and economic implications. The S&P 500 has only modestly declined so far, suggesting markets have not fully priced in the potential risks. Traditional market expectations have been challenged, such as the U.S. dollar strengthening instead of weakening. Oil prices have spiked due to geopolitical tensions, raising concerns about inflation and broader economic impacts. Energy has been the strongest-performing sector while many other sectors have struggled. Risk management should come before return-seeking when uncertainty is high. Investors should not hesitate to move to cash when market conditions become unclear. Crowded trades in war-related assets like energy, defense, and gold could reverse if sentiment shifts. The potential for consumer stress is highlighted, including rising credit card balances and higher costs from energy prices. Rising mortgage rates are a factor that could freeze housing activity during the spring selling season. Geopolitical risk is increasingly being priced into markets after years of relative stability. The current environment may represent a shift away from the low-rate, liquidity-driven market regime of the past decade. Policy mistakes by governments or central banks could become a bigger risk than the war itself. There are potential risks in the private credit sector, particularly due to limited regulation and transparency. Private credit has replaced some traditional bank lending since the 2008 financial crisis. Redemption freezes in private credit funds could signal stress in the system. Patience, discipline, and careful portfolio management are essential during periods of geopolitical and economic uncertainty. Today's Panelists: Kirk Chisholm | Douglas Heagren | Follow on Facebook: Follow LinkedIn: Follow on Twitter/X: For more information, visit the full show notes at /episode/index/show/moneytreeinvesting/id/40500160

Wall Street Secrets… Pros and Cons of Alternative investments 03/13/2026

WAR… Huge Impacts On Your Portfolio If You Don’t Do This 03/11/2026

Wall Street Blind Spots… Old School Investing Still Works… 03/06/2026

Wall Street Blind Spots… Old School Investing Still Works… Jose Mayora, author of Wall Street’s Blind Spots, a new book about the realities of value investing in a market dominated by mega-cap growth stocks, explains that true value investing is not about low P/E ratios but about buying businesses at a meaningful discount to intrinsic value. He emphasizes disciplined, bottom-up research, geographic and sector diversification, and concentrated portfolios to uncover overlooked opportunities. We also explore the psychological challenges of investing through crashes and euphoric markets, the tension between patience and performance when managing other people’s money, and the risks of over-investment. We discuss... Jose Mayora shares his background in investment banking, economics, earning the CFA, and co-founding DeVita Valley Growth Fund with a disciplined value-oriented philosophy. The discussion highlights how traditional value strategies have lagged during the dominance of mega-cap tech stocks, particularly the “Magnificent Seven,” over the past decade. Mayora emphasizes that avoiding high-multiple stocks purely on valuation optics can cause investors to miss strong businesses compounding at high rates. The conversation underscores the importance of remaining impartial and avoiding confirmation bias from sell-side research, headlines, or popular narratives. Mayora argues that concentrated portfolios of 10–16 positions are more realistic for true value investing, as finding dozens of genuine bargains in expensive markets is unlikely. We examine how broad market crashes create opportunity because markets become indiscriminate, often punishing high-quality companies alongside weaker ones. Historical examples like Google during the 2008–2009 crisis illustrate how strong businesses temporarily trade at compelling valuations during downturns. The psychological challenge of buying low-quality “junk” stocks for sharper rebounds versus sticking with durable high-quality companies is debated. They discuss how long recoveries—such as after the dot-com crash—can test investor patience even when valuations are compelling. Mayora explains that maintaining close communication and philosophical alignment with investors helps navigate inevitable periods of underperformance. They debate missed opportunities in large-cap tech and the difficulty of staying disciplined when high-momentum stocks dominate returns. Today's Panelists: Kirk Chisholm | Barbara Friedberg | Douglas Heagren | Marc Walton | Follow on Facebook: Follow LinkedIn: Follow on Twitter/X: For more information, visit the show notes at /episode/index/show/moneytreeinvesting/id/40182085

Sector Rotation: Using A Firehose To Fill A Dixie Cup 03/04/2026

The Silver Rocket... The Silver Party Is Just Beginning 02/27/2026

Investment Success Secrets… The Magic Of Seasonality 02/25/2026

The Family Private Enterprise Model with Tom Hoffman 02/20/2026

The Family Private Enterprise Model with Tom Hoffman Tom Hoffman shares the Family Private Enterprise Model for business succession. As an attorney and CPA at Knox Law Firm, Tom discusses his 30+ years of experience in business succession, complex estate planning, and asset protection, focusing on how families can successfully transition businesses across generations. He explains that while most owners want to keep their companies in the family, few heirs are truly prepared to lead, making clarity of goals, fairness (not necessarily equality), and strong communication essential to preserving family harmony. Tom outlines common pitfalls such as forcing children into roles they don’t want or failing to define objectives early. He also contrasts selling versus retaining the business, highlighting tax implications, the risks of dissipating liquid wealth, the role of family offices and trusts in preserving capital, and the broader community impact of keeping businesses local. We discuss... While about 70% of owners want to keep their business in the family, only 20–25% of children are typically prepared to lead it. Succession planning should start with clearly defining the family’s goals rather than jumping straight into structural decisions. Fairness in dividing assets does not always mean equality, especially when some children work in the business and others do not. Lack of communication is the primary driver of family conflict during transitions. “Self-realization” conversations help family members come to their own conclusions about what is fair, preserving harmony. Outside consultants and counselors are often necessary when emotional, mental health, or substance issues complicate planning. Forcing children into leadership roles they do not want can create long-term personal and business damage. Hiring a professional outside CEO can dramatically improve performance and free the senior generation from daily operations. Professionalized management often increases EBITDA significantly and expands the pool of qualified leadership talent. Even if the business is eventually sold, building a strong management team substantially increases valuation. Family offices and multigenerational trusts can help preserve and strategically deploy large pools of liquid wealth. The “family private enterprise model” offers an alternative to selling by keeping ownership while professionalizing operations. Succession planning is a process that requires coaching, buy-in, and intentional cultural transition rather than a one-time transaction. Today's Panelists: Kirk Chisholm | Barbara Friedberg | Follow on Facebook: Follow LinkedIn: Follow on Twitter/X: For more information, visit the show notes at /episode/index/show/moneytreeinvesting/id/40026260

Exclusive Update: The Run is Hot Economy is Here 02/18/2026

Future Technology... How To Invest In The Future 02/13/2026

Dump Your Tech... This Sector Is Booming... 02/11/2026

Hard Assets and Smart Debt with Ben Reinberg 02/06/2026

Hard Assets and Smart Debt with Ben Reinberg Commercial real estate veteran Ben Reinberg shares how he uses hard assets and smart debt to strengthen his investing portfolio. He shares his journey from starting in his early 20s to building a national hard-asset portfolio across industrial, office, retail, multifamily, and medical real estate. We talk the importance of the “ability to hold” assets through cycles by avoiding over-leverage, maintaining reserves, and structuring smart debt. Ben outlines where commercial real estate sits in the current cycle, highlighting looming debt maturities, distressed opportunities, and the potential for attractive buying conditions over the next few years. We discuss... Ben Reinberg explains how he built wealth starting in his early 20s by focusing on hard assets, particularly commercial real estate, as a long-term strategy for cash flow and financial control. He emphasizes the importance of becoming a true expert in a specific asset class rather than spreading focus too broadly. He shares lessons from his first industrial deal, including managing tenant loss, repositioning assets, and creating value through active ownership. A central theme was the “ability to hold,” meaning structuring investments to survive any market cycle without being forced to sell. He stressed using smart debt, avoiding over-leverage (generally keeping loan-to-value around 65%), and maintaining ample reserves. The discussion highlighted why medical office real estate is recession- and pandemic-resilient, with high tenant renewal rates and stable cash flow. Reinberg explained how inflation, tariffs, and rising costs affect tenants and property operations across different real estate sectors. The episode explored how real estate acts as an inflation hedge through rent growth, escalators, and long-term asset appreciation. They discussed the current commercial real estate downturn, driven by higher rates, falling values, and large amounts of debt coming due. Reinberg argued that the next few years may present some of the best commercial real estate buying opportunities in decades. He warned investors to be cautious, underwrite deals conservatively, and focus on tenant quality and market fundamentals. We have an optimistic outlook for 2026–2028, expecting lower rates, increased liquidity, more transactions, and improving economic stability. Today's Panelists: Kirk Chisholm | Barbara Friedberg | Douglas Heagren | Follow on Facebook: Follow LinkedIn: Follow on Twitter/X: For more information, visit the show notes at /episode/index/show/moneytreeinvesting/id/39708760

Silver CRASHED... What Happened & What's Next 02/04/2026

Growing Global Debt and the Future of the Global Economy with Jean-Baptiste Wautier 01/30/2026

How To Profit In The Run It Hot Economy 01/28/2026

College Without Crushing Debt with Shellee Howard 01/23/2026

The Best Ways to Invest in the Run It Hot Economy 01/21/2026

Secret Franchising Profits For Investors 01/16/2026

2026 Predictions... This is What Will Outperform in 2026 01/14/2026

Investing in Bitcoin in 2026 01/09/2026

2025 Wrap Up... Year End Surprises 01/07/2026

2025 Wrap Up... Year End Surprises There are a lot of year end surprises in store with the 2025 wrap up. The year has come to an end and we are here to discuss everything from year-end reflections and personal anecdotes to a broad market outlook. We focused on the recent surge and volatility in precious metals, especially silver, explaining how futures-market leverage and exchange rule changes (like margin requirement hikes) are used to cool speculative excess, why parabolic price moves are unhealthy, and why investors should be cautious in the near term even if long-term fundamentals remain bullish. We also talked government fraud, rising debt costs, aging demographics, deglobalization, and higher-for-longer rates, arguing that bad asset allocation now carries real risk and diversification with assets like precious metals still matter. We discuss... We challenge simplistic economic cause-and-effect narratives, arguing that inflation, tariffs, and monetary policy outcomes are highly contextual and often misrepresented by official government data. Past periods of QE and low inflation were cited to illustrate how money printing can offset deflation rather than automatically cause inflation, reinforcing skepticism toward consensus forecasts. Large-scale government fraud is pervasive, rarely punished, and structurally embedded, with the prediction that no high-level figures will face consequences in ongoing public scandals. Precious metals, particularly silver, were a major focus due to extreme recent price volatility, including sharp multi-day gains and losses while most investors were disengaged over the holidays. The mechanics of futures markets were explained in detail, emphasizing how leverage works, why margin requirements matter, and how exchanges can legally change rules to stabilize markets. Recent increases in margin requirements for silver, gold, platinum, and palladium were highlighted as a deliberate attempt by exchanges to flush out speculative leverage and cool “animal spirits.” Governments and exchanges can escalate interventions dramatically if needed, including forcing cash settlement or changing delivery rules, which would materially alter market dynamics. Banks’ growing discomfort with holding U.S. Treasuries and their shift toward gold are a quiet but significant signal about long-term confidence in fiat systems. The contrast between gold (central-bank owned) and silver (primarily investor and industrial owned) explains differing market behaviors and intervention risks. The hosts argued that the era of “cheap mistakes” is over, meaning poor allocation decisions now result in permanent capital loss, not just missed opportunity. AI enthusiasm should be thought of skeptically as large language models are becoming commoditized quickly, lack durable moats, and resemble past tech bubbles. Be cautious, diversify, be skeptical of narratives, have respect for market structure, and prepare for a year where volatility exposes complacency. Today's Panelists: Kirk Chisholm | Douglas Heagren | Follow on Facebook: Follow LinkedIn: Follow on Twitter/X: For more information, visit the show notes at /episode/index/show/moneytreeinvesting/id/39620935

Why AI Hype and Clickbait Are Failing Serious Business Owners with Elliot Holland 12/31/2025

Why AI Hype and Clickbait Are Failing Serious Business Owners with Elliot Holland 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. Follow on Facebook: Follow LinkedIn: Follow on Twitter/X: For more information, visit the show notes at /episode/index/show/moneytreeinvesting/id/39153580

Year End Tax Loss Selling Secrets You Must Know 12/31/2025

Collaborative Leadership in an AI-Driven World 12/26/2025

Collaborative Leadership in an AI-Driven World 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 | Barbara Friedberg | Phil Weiss | Follow on Facebook: Follow LinkedIn: Follow on Twitter/X: For more information, visit the show notes at /episode/index/show/moneytreeinvesting/id/39478725

CAUTION… Santa Clause Rally Ahead 12/24/2025

Why Stocks and Gold Are Soaring in a World Full of Risk with George Economou 12/19/2025

The Federal Reserved Tipped It’s Hand For a Bull Market In… 12/17/2025

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