Money Tree Investing

Latest Episodes:

The Billionaires Know About This Hidden Bull Market… Do You? Sep 24, 2025

Show notes

This week we cover the hidden bull market that the billionaires know about. Are you in on it? We also cover the Fed's recent rate cut and how markets reacted with little real impact, highlighting skepticism about the Fed's effectiveness and the risks its policies create for wealth disparity and asset inflation. We emphasize the importance of questioning financial "half-truths" as outcomes often depend on assumptions rather than blanket rules. Gold, silver, and mining stocks are strong but under-appreciated trends, while tariffs are having far less economic impact than public debate suggests.

We discuss...

The Fed's latest rate cut had almost no real impact on markets, revealing investor skepticism about monetary policy effectiveness.
Fed policies have unintentionally widened the wealth gap by inflating asset prices that primarily benefit the wealthy.
Asset bubbles created by easy money policies pose future risks for average investors who lack diversification.
The idea that Roth IRAs are always better than traditional IRAs is a half-truth since tax outcomes depend on future income and assumptions.
Financial advice that paints with broad strokes often fails to account for personal circumstances.
Gold has surged in value, reflecting distrust in fiat currencies and central bank credibility.
Silver and mining stocks are also strengthening, though they lag behind gold and remain overlooked.
Precious metals serve as both a hedge against inflation and a store of value when trust in the Fed declines.
Tariffs are often overblown in the media, with real economic impact being far less dramatic than public debate suggests.
The bigger risk to markets is not tariffs but systemic distortions caused by prolonged monetary policy intervention.
Investors should prepare for volatility, especially given how fragile sentiment has become.
Timing is critical in retirement planning, as retiring during a market downturn can devastate portfolios.
Critical thinking is essential for navigating half-truths in financial media and mainstream narratives.
Complacency is dangerous in today's environment of uncertainty and shifting economic conditions.
Owning tangible assets like real estate, commodities, or productive businesses is one of the best hedges against inflation and Fed-driven distortions.

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/hidden-bull-market-749

Inside the World's First Crypto Mortgage with Josip Rupena Sep 19, 2025

Show notes

Josip Rupena talks about how his company Milo, created the world's first Crypto mortgage. Josip shares how his background in investment banking led him to found his company, which solves financing challenges for high-net-worth international clients and later Bitcoin holders who struggle to qualify for traditional mortgages despite significant wealth.

He explains how Milo created the world's first crypto mortgage in 2022, allowing clients to buy U.S. real estate without selling Bitcoin. Josip highlights that Milo's products give clients flexibility, preserve upside in both real estate and Bitcoin, and address gaps left by legacy financial institutions in a changing economy.

We discuss..

How Josip's career in investment banking exposed him to the challenges high-net-worth individuals face when trying to access traditional lending, especially international clients with wealth but no U.S. credit history.
He founded Milo to address these gaps, initially focusing on helping global investors buy U.S. real estate without relying on outdated borrower requirements set by legacy banks.
Traditional banks are reluctant to serve clients outside narrow profiles—such as W-2 earners with U.S. tax records—leaving wealthy entrepreneurs and international investors underserved.
In 2022, Milo pioneered the first crypto mortgage, allowing Bitcoin holders to directly purchase U.S. real estate without liquidating their coins.
By using Bitcoin as collateral, clients can avoid triggering capital gains taxes while continuing to benefit from potential long-term appreciation.
Milo structures its loans with institutional partners and securitization, bridging the gap between innovative lending products and traditional capital markets.
Crypto-backed loans offer borrowers quick access to liquidity while being overcollateralized to protect Milo and its investors from volatility risks.
Milo's approach demonstrates how fintech can expand financial inclusion by designing products around real client needs rather than forcing clients into rigid bank standards.
By enabling clients to hold both real estate and Bitcoin, Milo gives them a way to compound upside across two asset classes while maintaining flexibility and financial control.

Today's Panelists:

Kirk Chisholm | Innovative Wealth
Douglas Heagren | Mergent College Advisors
Diana Perkins | Trading With Diana

Follow on Facebook: https://www.facebook.com/moneytreepodcast

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For more information, visit the show notes at https://moneytreepodcast.com/crypto-mortgage-with-josip-rupena

The Silent Bull Market That No One Is Talking About Sep 17, 2025

Show notes

There's a silent bull market right now that no one is talking about. Gold has had a powerful breakout and silver's lagging but still strengthening. Gold has surged from $2,000 to $3,600 since 2023, driven largely by central bank buying amid global distrust of U.S. reserves. Investors should approach metals through ETFs rather than individual picks unless you have deep expertise. We also talk the likelihood of rate cuts under political pressure, persistent "slow burn" inflation from tariffs and supply issues, de-dollarization, and the need for diversification beyond passive index funds. Inflation isn't dead, passive portfolios are under strain, and active allocation to precious metals may be one of the most underpriced opportunities available.

We discuss...

Gold has staged a historic breakout, climbing from around $2,000 in 2023 to roughly $3,600, with central bank buying acting as the primary driver.
Global distrust in the U.S. dollar and concerns about the credibility of U.S. reserves are pushing sovereign nations toward gold accumulation.
Unlike gold, silver remains more dependent on retail participation and industrial demand, leaving it lagging but positioned for potential catch-up.
Silver faces supply constraints that limit downside, with demand tied to solar, electronics, and other industrial uses, making it a dual-purpose metal.
Mining stocks were highlighted as structurally poor businesses due to high costs and weak capital discipline, yet they are soaring as leveraged plays on rising metals.
Junior miners offer the most explosive upside but come with extreme risks, making them closer to speculative lottery tickets than investments.
For most investors, ETFs and broad metals exposure were recommended as the safer approach compared to individual mining stock selection.
Inflation is not "dead" but a persistent, slow-burn phenomenon fueled by tariffs, supply chain issues, and ongoing policy shifts.
Political pressure makes interest rate cuts increasingly likely, regardless of whether inflation is fully under control.
A broader theme of de-dollarization is accelerating gold's role in global reserves as nations seek alternatives to U.S. dominance.
Passive index funds were critiqued as over-reliant on historical correlations that no longer hold, leaving portfolios vulnerable.
The hosts concluded that gold, silver, and related hard assets remain one of the most underpriced and overlooked opportunities for active investors today.

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/silent-bull-market-747

Investing in Legacy Businesses Beats Chasing Tech Trends with Travis Jamison Sep 12, 2025

Show notes

Today's Panelists:

Kirk Chisholm | Innovative Wealth
Douglas Heagren | Mergent College Advisors
Diana Perkins | Trading With Diana

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Travis Jamison shares his journey from serial entrepreneur to full-time investing in legacy businesses, explaining that while tech is great for building, it's risky for investing. He allocates capital into small, decades-old businesses via search funds, independent sponsors, and roll-ups, aiming for diversification, steady cash flow, and multiple expansion.

Travis views AI less as a direct investment opportunity and more as a tool for operating businesses that are resilient to technological change. AI's rapid evolution makes predicting its exact impact nearly impossible, so investors should approach private businesses with careful bet sizing, strong due diligence, and awareness of risks.

We discuss...

Travis Jamison transitioned from serial entrepreneur to full-time investor after several liquidity events.
He avoids investing in tech startups due to disruption risks despite believing they're great for building wealth.
His capital allocation focuses on small, boring, decades-old businesses that are hard to kill and generate steady returns.
He participates in search funds, independent sponsor deals, and roll-ups, rather than angel or venture investing.
He targets companies in the $4–30 million enterprise value range, often in industries like HVAC, pool services, and rehab centers.
Roll-ups allow him to buy add-on companies cheaply, combine them, and benefit from multiple expansion.
He diversifies across industries to avoid concentration risks and aims to build a portfolio of around 30 small businesses.
He sees the lower middle market as more attractive than larger private equity deals due to lower entry multiples.
He views business as the most fun game to play and continues investing for identity and enjoyment, not just money.
For AI, he invests in companies largely unaffected by it, seeing boring businesses as safer than trying to pick AI winners.
AI should be viewed as a powerful leverage tool, allowing individuals and businesses to achieve far greater output with fewer resources.
Blue-collar industries like HVAC, plumbing, and construction are less exposed to AI disruption in the near term, making them relatively safer sectors.
Many companies deliberately keep their AI use quiet to avoid tipping off competitors or losing their edge.
Because the long-term trajectory of AI is unpredictable, investors should avoid over-concentration and treat exposure as part of a balanced portfolio.
The most effective strategy is to swing at the "easy pitches"—investments with clear fundamentals—rather than forcing deals in uncertain or hype-driven areas.

For more information, visit the show notes at https://moneytreepodcast.com/investing-in-legacy-businesses-travis-jamison-746

You Are Probably Missing The Biggest Bull Market Right Now… Here is How You Play It Sep 10, 2025

Show notes

You may be missing the biggest bull market right now. Today we share how you can make sure you're a part of it. We talk market trends as we hit September, which has historical weakness for stocks and the tendency for markets to defy consensus expectations. Equities and commodities like oil and natural gas have been lackluster, gold has quietly entered a strong bull market, driven largely by central bank buying rather than retail investors. Investor psychology, price action, and historical cycles shape opportunities in gold and silver markets. We also talk about cultural and global perspectives, noting that Americans tend to favor stocks and dollars over gold.

We discuss...

September was noted as historically one of the weakest months for stocks, often followed by a rebound later in the year.
Markets often defy consensus expectations, meaning heavy selling sentiment could set up a surprise rally.
Gold has entered a strong bull market, driven by consistent central bank buying rather than retail investors.
Silver has lagged behind gold but is positioned for a potential breakout as individual investors enter the market.
Precious metals tend to move in cycles, with gold leading, then silver, followed by miners and junior miners.
Mining stocks can outperform in bull markets but generally have poor business models and higher risks.
Central banks' distrust of the financial system underpins their growing gold accumulation.
Kirk emphasized that gold miners, though risky and often unprofitable, can deliver exponential upside in bull markets.
Junior miners were described as the most volatile and speculative plays, offering high risk and high reward.
Futures markets were highlighted as distorting bullion's true value and price signals.
Central banks are steadily accumulating gold instead of treasuries, signaling waning trust in U.S. debt.
U.S. bonds are losing their safe-haven status compared to previous cycles.
Political uncertainty, including figures like Trump, adds to market unpredictability.
Diversification was stressed as key, since risks are already embedded across today's financial markets.

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-biggest-bull-market-right-now-745

Living and Investing Overseas with Global Real Estate Sep 05, 2025

Show notes

Kathleen Peddicord shares her experience living investing overseas. Her journey took her from publishing to becoming an authority on global real estate investing. She discusses why she prefers real estate over stocks while also outlining challenges such as lack of MLS systems, legal complexities, and cultural differences. Kathleen explained how to evaluate markets, avoid overpaying, plan exit strategies, and select properties with unique value rather than cookie-cutter developments. She stressed the importance of freehold title, sound property rights, and turnkey management solutions, while also addressing issues of safety, infrastructure, and research hurdles in foreign markets.

We discuss...

Kathleen Peddicord began her career in publishing with Agora but developed lifelong interests in global diversification and real estate investing.
She prefers real estate over stocks because it offers stability, control, personal use, and both cash flow and appreciation potential.
International real estate yields vary widely, with Panama highlighted as a safe haven market where she has achieved strong rental returns.
A major challenge abroad is the lack of MLS systems, requiring investors to do extensive legwork to determine fair property values.
Ensuring freehold title is essential to avoid risks of losing property to unclear or cooperative land ownership structures.
Investors should plan their exit strategy before buying and avoid cookie-cutter developments that force competition solely on price.
Properties with unique features, amenities, or historical value are better positioned to hold and increase resale value.
Turnkey solutions with property and rental management are crucial for those who don't live locally.
Legal systems, language barriers, and cultural differences add complexity compared to U.S. real estate.
Safety perceptions are relative, and many international markets can feel safer than U.S. cities depending on the context.
Choosing a country to invest in requires matching personal goals, budget, and lifestyle priorities to the market options.
Visiting potential markets in person is essential, as spreadsheets and research alone can't capture whether a location will feel right.
Success stories, like a couple thriving in Portugal, show the upside of international moves, while failures, like an unhappy relocation to Belize, highlight the importance of fit and flexibility.
Small surprises—such as homes without hot water—illustrate the cultural adjustments investors must be prepared for.

Today's Panelists:

Kirk Chisholm | Innovative Wealth
Phil Weiss | Apprise Wealth Management
Douglas Heagren | Mergent College Advisors

Follow on Facebook: https://www.facebook.com/moneytreepodcast

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For more information, visit the show notes at https://moneytreepodcast.com/living-and-investing-overseas-kathleen-peddicord-744

Wall Street Is Selling Beer, Beaches, and Barbecue… Here's How You Can Invest Sep 03, 2025

Show notes

Wall Street is selling beer, beaches, and barbecue. Want to invest? We also dove into the concerns about the reliability of government data. Investors should focus less on headline data and more on long-term directional trends, since recessions matter less to portfolios than actual corporate performance. We also talk labor markets, employment revisions, and rate-cut predictions, highlighting inconsistencies and the limited value of forecasts.

Debt structures like extended auto loans and creative mortgages stress the importance of cash flow flexibility and smart loan structuring rather than simply chasing the lowest rate. Kirk also shares his experience getting an offer accepted on a home during a time of market peaks.

We discuss...

Corporate earnings compared to government data; how companies manage expectations to appear consistently successful.
Investors should focus on long-term directional trends rather than short-term or inaccurate data points.
Whether recessions truly matter for investors compared to corporate earnings growth.
Labor market data showed employment revisions and a slowdown in job gains, raising concerns about real job strength.
Predictions of interest rate cuts are inconsistent and unreliable.
Consumer behavior trends, including retail and food service spending, suggested tightening conditions.
Rising delinquency rates in student loans and credit cards signaled growing consumer financial strain.
Mortgages and auto loans showed fewer delinquencies since they are collateralized and prioritized by borrowers.
There is importance in structuring debt with maximum flexibility and focusing on cash flow management.
A home should be viewed as a personal expense rather than an investment.
Housing markets are peaking in many areas, with Massachusetts showing declining rents and prices.
Mortgage strategies discussed include recasting loans and making lump-sum payments to reduce monthly payments or shorten maturity.
Using a home equity line of credit strategically can accelerate mortgage payoff and improve cash flow.
Globally, fertility rates in developed countries are below replacement level, indicating shrinking populations.
Growth in population is concentrated in parts of Africa, South America, and select Asian regions.
Macro trends impacting markets include protectionism, geopolitical tensions, and reserve currency diversification.
Policy rewrites under Trump are shaking up traditional approaches, sometimes positively by encouraging change.
Many U.S. housing markets are seeing declining sales as buyers and sellers are unwilling to compromise.
Tariffs, especially on metals, could spike short-term costs across industries but are expected to normalize over the long term.
Unexpected macroeconomic events, such as new technologies or policy changes, can disrupt markets before adjustments occur.

Today's Panelists:

Kirk Chisholm | Innovative Wealth Douglas Heagren | Mergent College Advisors

Follow on Facebook: https://www.facebook.com/moneytreepodcast

Follow LinkedIn: https://www.linkedin.com/showcase/money-tree-investing-podcast

Follow on Twitter/X: https://x.com/MTIPodcast

For more information, visit the show notes at https://moneytreepodcast.com/wall-street-is-selling-beer-743

The Risks and Rewards of Investing in Fine Art Aug 29, 2025

Show notes

Philip Hoffman is here to share his journey from CPA to investing in fine art. He founded The Fine Art Group, where he advises wealthy families on art investing, valuations, lending, and education. He outlines the global art market as a $60 billion industry with only $6–10 billion considered truly investable, highlights the risks and pitfalls of treating art as an asset class without expert guidance, and shares cautionary tales of investors losing millions by buying discounted works without due diligence, contrasted with success stories where expertise and timing led to strong returns.

We discuss...

Philip Hoffman began his career as a CPA at KPMG, later became CFO and youngest board director at Christie's, and eventually founded The Fine Art Group.
His firm advises wealthy families across 28 countries on art transactions, valuations, education, and art-backed lending.
Investable art includes high-value works, jewelry, vintage cars, and luxury items like Hermès handbags, while most antiques and collectibles fall outside this category.
Investors can access art through funds, private credit against art, direct ownership, or syndication with others.
Hoffman emphasizes that art buyers should use reputable advisors, much like when purchasing real estate, to avoid costly mistakes.
A client once spent $4 million on 40 polo paintings by an unknown artist with no resale market, ultimately finding them worthless.
Using an advisor costs a fraction of an artwork's price but can prevent costly mistakes.
Even seasoned collectors often misjudge valuations; in one example, most experts mistook a $1M Monet for a $10M Monet.
Condition issues, provenance gaps, and theft risks make professional due diligence essential in high-value purchases.
Current market conditions—with top-tier art down 20–30% from recent highs—make this one of the best times in decades to buy blue-chip works.
Wealthy collectors often allocate about 5% of their portfolio to art, balancing enjoyment with investment.
The black market exists, but high-profile stolen works are nearly impossible to sell through reputable channels.
Damage usually devastates value, though rare cases like Banksy's shredded artwork increased in worth due to notoriety.
Mishandling in storage, shipping, or moving can ruin artworks, highlighting the importance of professional logistics.
Over decades, disciplined art investors with good advisors typically achieve strong compounded returns comparable to or exceeding equities.

Today's Panelists:

Kirk Chisholm | Innovative Wealth
Phil Weiss | Apprise Wealth Management
Douglas Heagren | Mergent College Advisors

Follow on Facebook: https://www.facebook.com/moneytreepodcast

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For more information, visit the show notes at https://moneytreepodcast.com/investing-in-fine-art-philip-hoffman-742

Government Data Is Fake… Here Is the Solution Aug 27, 2025

Show notes

Private Market Investing vs. Public Markets: Where the Real Opportunities Lie Aug 22, 2025

Show notes

Mark Flickinger shares his journey from engineering and building small businesses to working in private market investing at BIP Capital, where he helps both entrepreneurs and high-net-worth investors achieve their goals. He explains that private markets have grown as many high-quality companies remain private longer, creating opportunities for alpha that are less available in public markets, especially as IPO thresholds have risen. Flickinger highlights trends in alternatives, noting that while AI attracts attention, compelling private businesses can now be accessed at lower entry costs.

We discuss...

Mark Flickinger combines his engineering background with investment expertise to support both business owners and high-net-worth investors.
Private markets have grown in importance as alternatives, moving beyond hedge funds to include a wide range of private companies.
Value creation that once happened in small-cap public stocks is now largely occurring in private companies.
Only one out of ten U.S.-based companies with $100 million or more in revenue is public, leaving most growth in private markets.
Entrepreneurs increasingly stay private due to regulatory burdens and the ability to grow without going public.
Business development companies (BDCs) were created to simplify private market investing for U.S.-based companies and investors.
Entrepreneurs are increasingly using a hybrid approach of equity and debt to raise capital without overly diluting ownership.
Taking on a partner or investor is worthwhile if they bring expertise and add significant value to the business.
Debt can be advantageous if the business grows faster than the interest cost, making leverage an effective tool.
Capital should be taken strategically to overcome growth hurdles, not just for the sake of raising funds.
Many business owners excel in specific phases of growth and benefit from focusing on their strengths rather than the CEO role.
The private credit market is likely to expand further, while banks continue to reduce direct lending to businesses.
A robust AI plan is now a key factor in evaluating a company's long-term potential, beyond just naming conventions.