Money Tree Investing

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

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For more information, visit the full show notes at https://moneytreepodcast.com/todays-investing-landscape-elliott-holland-800

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 | Innovative Wealth Douglas Heagren | Mergent College Advisors

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For more information, visit the full show notes at https://moneytreepodcast.com/the-next-black-swan-799

Jade Miller is here to discuss the pros and cons of alternative investments. Jade shares her journey to becoming the CEO of the Alternative & Direct Investment Securities Association (ADISA), her background in private markets, and ADISA's role in advocating for and expanding access to alternatives for financial advisors and investors.

We explore the growing push to include alternative investments in 401(k) plans, investor misunderstanding, and potential regulatory challenges. We also talk the importance of thorough due diligence, common red flags, and the need for greater transparency from fund managers.

We discuss...

• Jade Miller discusses her background in private markets, primarily real estate, and her transition to becoming the first CEO of the ADISA.
• ADISA's mission is to advocate for alternative investments, provide education and due diligence standards, and connect financial advisors with alternative investment managers.
• The alternatives industry is shifting from limited access for wealthy investors toward broader availability, including potential inclusion in 401(k) retirement plans.
• Large institutional managers are likely to dominate 401(k) alternative offerings rather than smaller private fund sponsors.
• Liquidity constraints and fund structures such as interval and tender-offer funds will likely shape how alternatives are implemented inside retirement plans.
• Illiquid investments in retirement accounts can carry a higher risk of fraud or poor diligence because the capital is often locked up for long periods.
• Increased transparency and reporting expectations from investors are pushing alternative fund managers to provide more detailed disclosures.
• Financial advisors play a key role in helping investors assess alternative opportunities and navigate complex investment structures.
• Unrealistically high projected returns and lightly vetted crowdfunding deals can be major warning signs for investors.
• Real estate is highlighted as a foundational alternative asset due to its tangible nature, income potential, and long-term demand.
• Alternative investments can offer meaningful tax advantages, including depreciation benefits, opportunity zone incentives, and oil and gas deductions.
• Roth conversion strategies can sometimes be enhanced through private investments that temporarily reduce valuation during development stages.
• Investors and financial advisors who ignore alternative investments risk falling behind as the asset class becomes a larger part of diversified portfolios.

Today's Panelists:

• Kirk Chisholm | Innovative Wealth
• Barbara Friedberg | Barbara Friedberg Personal Finance
• Marc Walton | Forex Mentor Pro

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There's war in the middle east and there will be huge impacts on your portfolio! Today we talk about how war-related uncertainty and conflicting economic signals are creating unusual market behavior, making it difficult for investors to interpret short-term movements. Broad market declines across many asset classes can indicate de-leveraging rather than money simply rotating elsewhere, and geopolitical tensions, rising oil prices, weakening job data, and potential stagflation risks are adding pressure to the economy.

While some sector rotation into energy, commodities, and defensive assets is occurring, be wary that wartime conditions disrupt normal market trends, making strategies like "buying the dip" risky. Now is the time for risk management as preserving capital during periods of uncertainty is often more important than trying to time short-term market moves.

We discuss...

• How misinformation, AI-generated content, and limited reliable sources make it difficult to understand what is actually happening during geopolitical conflicts.
• How negative political messaging often backfires psychologically because the human brain tends to ignore the word "not" and focus on the core concept.
• The unusually volatile week in markets, where prices swung sharply day-to-day despite ongoing geopolitical tensions.
• Markets do not always react logically to major events like wars, with assets sometimes moving in unexpected directions.
• A key explanation for broad market declines was de-leveraging, where leveraged positions are unwound and excess liquidity effectively disappears from the system.
• Investors rarely know the full reasons behind short-term market movements because many institutional trades occur behind the scenes.
• "Buying the dip" works in bull markets but can lead to significant losses during bear markets or uncertain environments.
• During wartime conditions traditional market frameworks often break down, making predictions especially unreliable.
• Reduce risk exposure and avoid aggressive trades until geopolitical uncertainty becomes clearer.
• Recent economic data show job losses and rising unemployment, which adds pressure to an already fragile economic outlook.
• Capital is rotating into defensive areas such as energy, commodities, defense stocks, and gold.
• Market rotations are normal in healthy markets but can become distorted when geopolitical shocks occur.
• Holding cash can be a strategic decision during uncertain markets rather than a missed opportunity.
• How falling interest rates could eventually lower mortgage rates and trigger more activity in the housing market.
• Investors should focus on protecting capital and managing downside risk during periods of extreme uncertainty.

Today's Panelists:

Kirk Chisholm | Innovative Wealth Douglas Heagren | Mergent College Advisors

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For more information, visit the full show notes at https://moneytreepodcast.com/investors-are-fleeing-into-this-sector-797

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 | Innovative Wealth
• Barbara Friedberg | Barbara Friedberg Personal Finance
• Douglas Heagren | Mergent College Advisors
• Marc Walton | MarcWalton.com

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For more information, visit the show notes at https://moneytreepodcast.com/wall-street-blind-spots-jose-mayora-796

There is a sector rotation happening and today we're here to discuss it! We also touch on the sudden U.S. conflict with Iran as this is not the time to start reacting emotionally to early headlines, misinformation, and media fear cycles. Keep in mind historical market reactions to prior military strikes; while volatility typically spikes, equity drawdowns have historically been modest and short-lived unless oil supply or credit markets break down.

We also highlight that markets are driven more by liquidity and capital flows than headlines and investors should focus on historical patterns, sector positioning, bond duration strategy, and risk management rather than panic, while closely watching oil prices, credit spreads, and bond yields for signs of deeper systemic stress.

We discuss...

• The concept of the "fog of war," warning listeners not to trust early reports, viral videos, or emotionally charged headlines.
• Media outlets monetize fear and that investors should avoid panic-driven decisions.
• Historical data from past U.S. military strikes was reviewed, showing that market drawdowns are typically modest and short-lived.
• Oil prices spiked on geopolitical risk, but the move was framed as a fear premium rather than confirmed supply disruption.
• The U.S. dollar was expected to strengthen in the short term as capital seeks safe-haven assets.
• Sector rotation was highlighted, with money moving out of mega-cap tech and into energy, materials, and defensive sectors.
• Utilities, staples, and healthcare were identified as traditional late-cycle or risk-off sectors.
• If capital exits large tech allocations, there are limited sectors large enough to absorb those flows without major price distortions.
• Bonds were presented as increasingly attractive if interest rates begin to decline.
• Long-duration bonds tend to benefit most when yields fall due to the inverse price-yield relationship.
• Lower mortgage rates were projected as a possibility, which could reignite housing demand but also drive home prices higher again.
• Markets are driven more by liquidity and money flows than by headlines or fundamentals alone.
• Investors should focus on second- and third-order effects rather than reacting to the immediate shock of war.
• Credit spreads, bond yields, and oil prices are key indicators to monitor for signs of systemic stress.
• Remain disciplined, historically grounded, and risk-aware rather than emotionally reactive.

Today's Panelists:

Kirk Chisholm | Innovative Wealth Douglas Heagren | Mergent College Advisors

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For more information, visit the full show notes at https://moneytreepodcast.com/sector-rotation-795

The silver party is just beginning as precious metals expert David Morgan shares his journey from early fascination with silver coin debasement to becoming a long-time financial analyst focused on the silver market. Morgan argues that silver is widely misunderstood as merely speculative, emphasizing instead its critical industrial role in AI, EVs, solar, and advanced technologies amid a structural supply deficit and declining mine output. We explore alleged market manipulation through paper derivatives and "spoofing," the growing influence of physical demand over futures pricing, and why mining stocks may be significantly undervalued relative to rising silver prices. We also deep dive into Bitcoin's impact on precious metals demand, skepticism around crypto's "freedom" narrative, and broader reflections on monetary systems, inflation, and personal responsibility in navigating an uncertain financial future.

We discuss...

• David shares how the removal of silver from U.S. coinage sparked his lifelong interest in sound money and finance.
• He argues silver is strategically indispensable due to rising industrial demand from AI, EVs, solar, and advanced technologies.
• Global silver supply has been flat to declining since 2016, creating a multi-year structural deficit.
• Most silver is produced as a byproduct of base metal mining, limiting the incentive to increase supply.
• David explains that silver trades largely as a paper derivatives market, which can suppress price discovery.
• Recent price spikes may signal a shift from paper-driven pricing to physical supply constraints in industrial bars.
• Retail investors have largely been selling into strength, while industrial demand has driven the latest rally.
• Mining stocks appear undervalued relative to higher silver prices, offering potential leverage to the upside.
• The discussion highlights how value investors and major funds may eventually rotate into precious metals equities.
• David suggests Bitcoin has evolved away from its original decentralization narrative and is now institutionally influenced.

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-silver-party-is-just-beginning-david-morgan-794

Do you want to know investment success secrets? Look no further than today's discussion! The long-dominant "buy the Magnificent 7 and forget it" tech trade is fading, with sector rotation favoring energy, materials, and staples while technology and discretionary lag. Drawing on presidential cycle data, it seems markets often experience weakness and corrections in midterm years before potential strength later, though today's backdrop of sticky inflation, high debt, and constrained Federal Reserve policy could challenge historical norms. Liquidity over politics is the true market driver and power preservation incentives may shape fiscal and economic decisions and highlights opportunities in defensive sectors and fixed income if rates fall. As always, disciplined investing is the most important: avoid ego, abandon rigid outcome-based predictions, adopt scenario-based thinking, respect price action, and define in advance when you are wrong.

We discuss...

• The long-standing strategy of simply buying mega-cap tech stocks is breaking down as sector leadership rotates.
• Energy, materials, and staples are outperforming while technology and discretionary stocks lag, signaling possible market-top behavior.
• Historical sector rotation patterns suggest markets may be transitioning from expansion toward a late-cycle phase.
• Midterm presidential years historically bring volatility and frequent 10–20% corrections before potential recovery.
• Liquidity is framed as the primary force driving market cycles.
• Today's environment of sticky inflation, high debt, and constrained Federal Reserve policy may weaken the reliability of historical patterns.
• Defensive sectors and fixed income could benefit if growth slows and interest rates decline.
• Political incentives around power preservation may influence fiscal decisions and economic optics heading into elections.
• Investors are warned not to blindly "buy the dip," especially in volatile assets like crypto.
• The hosts stress that price action ultimately determines whether an investment thesis is right or wrong.
• Ego and overconfidence are identified as major threats to long-term investing success.
• Outcome-based thinking is discouraged in favor of scenario-based planning across multiple probable outcomes.
• Behavioral research shows experts often double down when wrong, reinforcing the importance of flexibility.
• Successful investing requires humility, adaptability, risk management, and clearly defined exit strategies.

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.cominvesting-success-secrets-793

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 | Innovative Wealth
• Barbara Friedberg | Barbara Friedberg Personal Finance

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For more information, visit the show notes at https://moneytreepodcast.com/family-private-enterprise-model-tom-hoffman-792

The run is hot economy is here! Today we talk markets, and debunk alarmist headlines about rising Japanese bond yields. We also talk about a significant market rotation: expensive mega-cap tech stocks are faltering while capital flows into "boring" sectors like staples, industrials, energy, healthcare, and utilities, with international markets also outperforming. Watch out about chasing falling tech names or trying to pick bottoms in areas like crypto. Diversification is always the way to go so understand sentiment cycles and focus on where money is flowing rather than where it has already been. Successful investing is about discipline, context, and avoiding emotional decisions.

We discuss...

• Japan's 10-year government bond yield rising from near 0% to over 2%, which has sparked global concern.
• Because most Japanese government debt is owned domestically—by the central bank and pensions—the systemic risk narrative may be exaggerated.
• Market headlines often amplify short-term moves without proper historical framing.
• A large percentage of U.S. stocks are trading at very high price-to-sales ratios, exceeding even dot-com-era levels in some measures.
• Companies like Apple have high valuations despite limited recent earnings growth, raising questions about sustainability.
• Rotations are normal cycles in markets, where leadership shifts rather than the entire market collapsing.
• Utilities and staples—traditionally "boring" sectors—have recently outperformed while software and high-beta tech stocks have sold off sharply.
• International markets, particularly emerging markets and Europe, have outperformed the U.S. year-to-date.
• Heavy AI-related capital expenditures announced by large tech firms may have contributed to investor concerns.
• We compare crypto cycles to past tech bubbles, noting that true bottoms often occur when sentiment disappears and investors stop paying attention.
• Focus on where capital is flowing now rather than chasing sectors based on past performance.
• Diversification, patience, and understanding market cycles are essential for long-term investing success.

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/run-it-hot-economy-is-here-791