Money Tree Investing

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Milo to address these gaps, initially focusing on helping global investors buy U.S. real estate without relying on outdated borrower requirements set by legacy banks.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 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/crypto-mortgage-with-josip-rupena 

A silent bull market in gold is gaining momentum, with prices skyrocketing from $2,000 to $3,600, fueled by central bank buying and distrust in the U.S. dollar. Silver, though lagging, is poised for a catch-up due to industrial demand and supply constraints. The conversation highlights the need for investors to embrace actively managed portfolios rather than passive index funds amid persistent inflation. New insights reveal how political influences impact the Federal Reserve and the importance of diversifying investments into precious metals for financial stability.

Travis Jamison, a full-time investor in legacy businesses and former serial entrepreneur, shares his insightful journey into the realm of stable investments. He passionately explains why he's drawn to decades-old businesses over tech startups, emphasizing their reliability and potential for steady cash flow. Travis discusses the role of AI not as a direct investment target, but as a tool for enhancing resilient enterprises. He also highlights the importance of due diligence and diversification in navigating the complexities of legacy business investments.

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 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/the-biggest-bull-market-right-now-745 

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 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/living-and-investing-overseas-kathleen-peddicord-744 

Wall Street is peddling beer, beaches, and barbecue, but investing requires a deeper understanding. Focus on long-term trends rather than unreliable government data and short-term metrics. The conversation also uncovers corporate strategies for manipulating earnings reports. Concerns about labor markets and rising consumer debt levels are explored. With rising delinquency rates, smart financial structuring becomes crucial. Plus, a personal tale of securing a home offer in a peak market adds a relatable touch.

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 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/investing-in-fine-art-philip-hoffman-742 

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. Today's Panelists: Kirk Chisholm | Innovative Wealth Barbara Friedberg | Barbara Friedberg Personal Finance Diana Perkins | Trading With Diana 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/private-market-investing-mark-flickinger-740

It looks like the market is going on vacation! Well I am too. Today we talk everything from vacation plans to shifting markets. We also cover recent crypto volatility, the resilience of Bitcoin, and concerns over MicroStrategy’s stock dilution strategy, framing dips as potential buying opportunities within broader trends. We chat on quirky social trends in China, like “pretend to work” jobs for unemployed youth, and highlight Ray Dalio’s view that real estate is a poor investment in today’s environment with recent price drops accorss the U.S. Today we discuss... Media narratives often obscure the real developments happening quietly in the background. Stablecoins are emerging as a substitute for the dollar and could diminish banks’ central role in the financial system. This shift resembles the fragmented multi-currency era before the creation of the Federal Reserve. Recent crypto markets have been volatile, with Bitcoin showing resilience despite sharp pullbacks. Ray Dalio argued that real estate is a poor investment today due to its interest rate sensitivity and immobility. U.S. real estate markets are already showing significant price declines in several regions. The administration is talking up lower rates, Trump has pushed cuts, and Powell left rates unchanged at the last meeting. Market behavior appears disconnected from economic data, undermining the usefulness of traditional reports. Government statistics are viewed as unreliable, with references to Shadow Stats’ alternative takes on CPI history. Given data doubts, the focus should be on how markets and investor sentiment actually react. Seasonally, mid-August to mid-November is typically weak, and the second year of a presidency often underperforms. August and September have historically been the S&P 500’s weakest months, while 2025 has so far outperformed typical post-election patterns. Personal spending is slipping, and fast-casual chains’ same-store sales have fallen since Q4, suggesting strain. Housing and renovation activity looks softer versus the last five years but closer to pre-2020 norms—a reversion to the mean, not necessarily recession. Student loan and credit-card delinquencies are spiking, hinting at cash-flow stress that clashes with low unemployment data. Tariff revenues jumped from roughly $8B/month to about $29.6B/month, with companies largely absorbing costs so far. Money is chasing select commodities like gold, silver, and uranium, while others like lithium lag and could move with China trade shifts. The dollar sits mid-range historically and could sink on aggressive cuts, though today’s “broken” market dynamics muddy typical cause-and-effect. Despite risks, the market’s underlying tone is bullish, so a continued climb is possible on favorable policy headlines. Research notes humans rate AI higher when it agrees with them, suggesting systems learn to avoid conflict and may reinforce user beliefs.   Today's Panelists: Kirk Chisholm | Innovative Wealth Douglas Heagren | ProCollege Planners 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/market-is-going-on-vacation-739