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.

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 We also education and AI, arguing that traditional schooling is outdated, overly focused on memorization, and ill-suited for a world where AI can outperform humans on hard skills, while human skill can thrive in areas AI can't. AI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 Education systems are outdated, overly focused on memorization, and misaligned with how people actually learn and collaborate.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

Reinventing Taxes to Make Them Work for You with John Thompson 12/12/2025

This December Secret Could Be Your Best Trade of the Year 12/10/2025

Options Strategies for Modern Investors with Lawrence Kriesmer 12/05/2025

Breaking News… HUGE Opportunities in Latin America, Silver and Biotechnology 12/03/2025

The Bull Market In Cash Is Coming... 11/28/2025

More Shocking Signs... The Economy Is Breaking 11/26/2025

More Shocking Signs... The Economy Is Breaking The economy is breaking, and today we discuss the signs. We explore the challenges of navigating today’s markets, highlighting the volatility and skepticism around AI-driven companies, overinflated stock valuations, and earnings season dynamics where “beating expectations” often masks underlying realities. It's important to be cautious investors over high P/E ratios, unsustainable growth, and market timing. You need to focus on risk management over speculation. Critical thinking is also imperative while evaluating data and it's important to question assumptions and focus on market behavior rather than blindly trusting reported numbers. We discuss... Volatility in November and the flat performance in October, with a mixed outlook for the remaining six weeks of the year. Historical trends in presidential cycles, noting that the second year is statistically the worst for stock market performance, while years one, three, and four tend to perform better. The impact of earnings season on markets and how companies often beat expectations by managing guidance strategically, which can mislead retail investors. The market’s reaction to AI-related companies, the skepticism around reported growth, revenue, and inter-company financing “shenanigans.” Historical parallels to the late 1990s internet bubble, where vendor financing inflated revenues before companies ultimately collapsed. The difficulty of individual stock investing, noting that growth rates slow as companies mature and valuations often contract over time. The risk of focusing on long-term predictions without timing, being “right too early” can result in significant opportunity costs and losses. Michael Burry’s recent hedge fund moves, his short positions on AI-related stocks like Nvidia and the implications for investors skeptical of inflated earnings. Timing is critical in investing, caution with high-growth sectors and risk management rather than speculative bets are needs. Investors should not blindly trust government or corporate data, but instead focus on market behavior and price trends to assess reality. There's importance in distinguishing between what is factually true and what the market believes. Apply critical thinking, question assumptions, and focus on present market realities rather than speculative long-term projections. Today's Panelists: Kirk Chisholm | Phil Weiss | Follow on Facebook: Follow LinkedIn: Follow on Twitter/X: For more information, visit the show notes at /episode/index/show/moneytreeinvesting/id/39165035

How AI will Transform the Future of Trading with John Bartleman 11/21/2025

The Stock Market Is Broken… K Shaped Economy 11/19/2025

Secrets To Spending Less On The Cost Of College 11/14/2025

Secrets To Spending Less On The Cost Of College Mark Salisbury shares the secrets to spending less on the cost of college! As the founder of TuitionFit, explains how the college pricing and financial aid system is designed to favor schools over families. He describes how emotional marketing, opaque pricing, and complex financial aid forms create confusion and limit families’ leverage. he outlines how students and parents can regain control by defining their price range first, using resources like TuitionFit and net price calculators, and strategically managing assets, timing, and financial disclosures. He also covers how income, savings, and family structure affect aid, and more! We discuss... Mark Salisbury explains how the college pricing system is intentionally vague, designed to benefit schools rather than families. This conversation exposes how the financial aid process operates like a hidden marketplace where families unknowingly pay vastly different prices for the same education. Mark explains the difference between a school’s sticker price, discount rate, and net price, emphasizing that the last is what truly matters. He details how the FAFSA and CSS Profile collect information that can be used by colleges to assess a family’s financial “willingness to pay.” Timing and disclosure of assets can dramatically impact how much financial aid a family receives. Families with business ownership structures may have advantages in how assets and income are reported. Fnancial aid formulas often penalize savings while rewarding debt. Salisbury argues that families should start with their budget first, then find schools that fit within that price range—rather than applying and hoping for aid. Tools like TuitionFit help families compare real financial aid offers and discover the true market price for college. He advises against oversharing financial information before admission decisions are made to preserve negotiation leverage. Negotiating college costs is compared to buying a car—where informed consumers who know their target price get better deals. Transparency and data sharing among families are key to fixing the broken college pricing system. Mark calls for systemic reform to make higher education pricing fairer, more transparent, and tied to real market value. Today's Panelists: Kirk Chisholm | Douglas Heagren | Diana Perkins | Jack Wang | Follow on Facebook: Follow LinkedIn: Follow on Twitter/X: For more information, visit the show notes at /episode/index/show/moneytreeinvesting/id/38959345

Should The S&P 500 Go Higher? 11/12/2025

Using AI to Transform Long-Term Care with Lily Vittayarukskul 11/07/2025

The Stock Market Bubble Is Getting Bigger... This Is When It Will Pop 11/05/2025

The Stock Market Bubble Is Getting Bigger... This Is When It Will Pop The stock market bubble is going to pop! And we're going to tell you when. In today's episode we discuss that price is the ultimate indicator of market truth. Charts, narratives, and data often distort reality, while price alone reflects what investors truly believe. Don't overcomplicate investing with speculative indicators, fear-based “chart crimes,” and emotional herd behavior, especially in areas like AI stocks that echo the dot-com bubble. Fundamentals and narratives often mislead, while disciplined attention to price direction and risk management yields better results. We discuss... Price is the purest and most reliable truth in markets, capturing the collective judgment of all participants and filtering out misleading narratives. Investors often get trapped by "chart crimes," forcing technical patterns or trends that confirm what they want to see rather than what the market is actually showing. Investors often believe that deeper analysis means better insight, but in truth, simplicity and clarity around price direction outperform complex models. There are strong parallels between the current AI investment boom and the late-1990s dot-com bubble. Euphoric narratives around transformative technologies tend to overinflate valuations before reality catches up. AI enthusiasm is driving herd behavior, where investors fear missing out on perceived “once-in-a-lifetime” gains, leading to speculative excess and distorted valuations. Most investors misjudge risk, confusing volatility with opportunity, and failing to respect the message that price declines are often early warnings of deeper structural problems. There are under-appreciated risks building in private markets, especially private credit and private equity, which have grown rapidly outside the scope of traditional regulation. Private credit lacks transparency, liquidity, and oversight, creating potential systemic vulnerabilities if credit conditions tighten or defaults rise. In contrast, regulated banks, though unpopular, are more transparent and stress-tested, making them safer in relative terms despite their public scrutiny. Investors chasing yield in private markets are ignoring the lessons of past crises, mistaking the illusion of stability for real safety. Liquidity is an often-overlooked advantage, allowing investors to act decisively when market conditions change instead of being trapped in illiquid positions. Stay grounded in simplicity, price truth, and discipline, avoid the noise of narratives, the allure of complexity, and the comfort of consensus thinking. Today's Panelists: Kirk Chisholm | Follow on Facebook: Follow LinkedIn: Follow on Twitter/X: For more information, visit the show notes at /episode/index/show/moneytreeinvesting/id/38906240

Investing Into Space is No Longer Science Fiction 10/31/2025

Investing Into Space is No Longer Science Fiction Have you thought about investing into space? Mark Boggett, CEO of Seraphim, shares the investment opportunities in the rapidly expanding space industry. He explains how innovations led by SpaceX dramatically lowered launch costs and increased access to space, catalyzing growth in satellite constellations and data-driven applications for defense, climate, and communications. He emphasizes that near-term investment potential lies in defense and climate-related uses of satellite data, rather than speculative ventures like space travel or asteroid mining. He also highlights the growing importance of sustainability, debris management, and more. We discuss... Mark Boggett is a career technology investor who founded Seraphim Space, the world’s first space-focused investment fund. Seraphim Space operates a global accelerator, a private venture fund, and a publicly listed growth fund on the London Stock Exchange. Boggett shifted focus to space investing after recognizing how technologies like AI, telecommunications, and 3D printing were transforming the sector. SpaceX revolutionized space access by reducing launch costs from $86,000 to $1,000 per kilogram and dramatically increasing launch frequency. Smaller, cheaper satellites now enable massive constellations that provide real-time Earth observation and global connectivity. Investment opportunities in space fall into three categories: upstream (launch and satellites), downstream (data and applications), and in-space (future lunar and interplanetary activities). The most investable areas today are defense and climate-related satellite data applications rather than speculative space travel or mining. The falling cost of launch is paving the way for large-scale space infrastructure, including future data centers powered by solar energy. Space debris is an emerging challenge, driving new industries focused on monitoring, avoiding, and removing defunct satellites. Regulatory changes now require satellite operators to deorbit defunct satellites within five years, accelerating growth in orbital cleanup services. Defense is a major driver of demand for satellite technology in intelligence, communications, navigation, and asset protection. The “in-space” category includes lunar landers, space stations, and eventual habitation or mining ventures, though these remain long-term prospects. NASA’s new funding model relies on private companies like Axiom Space and Voyager to build commercial space stations. Boggett concludes that while long-term prospects like lunar mining are exciting, the current trillion-dollar opportunity lies in satellites, data, and communication serving Earth-based customers. Today's Panelists: Kirk Chisholm | Phil Weiss | Douglas Heagren | Follow on Facebook: Follow LinkedIn: Follow on Twitter/X: For more information, visit the show notes at /episode/index/show/moneytreeinvesting/id/38776220

Record Levels Of Money Market Funds Does Not Mean What You Think 10/29/2025

How to Use Puerto Rico’s Act 60 to Growth Your Wealth 10/24/2025

Earnings Season Investing Secrets 10/22/2025

Earnings Season Investing Secrets Today we dive into earnings season investing secrets. Learn the investing secrets that will grow your wealth as we dive into market analysis highlighting accounting red flags and potential overvaluation risks. Financial engineering often signals late-cycle behavior recessions, though unpopular, are necessary to clear economic “dead wood.” We also examined current earnings trends in the financial sector, technical market patterns like resistance and support levels in small caps and metals, and the importance of balancing fundamental and technical analysis. We also talk investor psychology—how emotion, bias, and sentiment often drive poor timing and decision-making in markets. We discuss... The Kolbe test, which measures instinctive strengths and natural problem-solving styles rather than personality or intelligence. Businesses use Kolbe results to build better teams by pairing complementary working styles. We also talked current market conditions, drawing comparisons between today’s tech boom and the late-1990s dot-com bubble. How Nvidia’s vendor financing arrangements resemble accounting maneuvers from the dot-com era, raising concerns about inflated revenues and future write-down risks. The hosts noted signs of late-cycle behavior in markets, including excessive optimism, overleveraged valuations, and creative corporate accounting. Recessions serve an essential economic function by clearing out inefficiencies and “dead wood,” creating healthier long-term growth. A segment focused on earnings season, particularly the uneven performance in the financial sector and what it signals about underlying economic momentum. We analyzed technical market patterns, such as key resistance and support levels in small-cap indexes and precious metals. How gold and silver might act as contrarian signals or safe havens amid market uncertainty. The discussion emphasized the interplay between fundamental and technical analysis, stressing that investors should use both to form a complete market view. They highlighted the danger of emotional decision-making, noting that fear and greed often lead investors to buy high and sell low. The episode closed by underscoring the importance of maintaining discipline and objectivity, especially during euphoric or panic-driven market phases. Today's Panelists: Kirk Chisholm | Phil Weiss | Follow on Facebook: Follow LinkedIn: Follow on Twitter/X: For more information, visit the show notes at /episode/index/show/moneytreeinvesting/id/38702045

College Planning Strategies For Families 10/17/2025

Invest In Anything But The S&P 500… 10/15/2025

Tasty Options Strategies For 2025 10/10/2025

Tasty Options Strategies For 2025 JJ Kinahan, CEO of TastyTrade shares some tasty option strategies for 2025. JJ shares his journey from floor trader at the CBOE to CEO of TastyTrade under IG North America. He discusses the evolution of the brokerage industry—from the days of shouting in trading pits to today’s retail-driven, commission-free environment—and how access to education has empowered individual investors. JJ emphasizes the importance of starting small, defining risk, and learning gradually when trading. We also talk why certain option types are miscategorized as “risky,” the influence of retail investors since the meme stock era, and how futures trading offers hedging and round-the-clock opportunities. We discuss... JJ Kinahan discusses his journey from being a floor trader on the CBOE to leading roles at ThinkorSwim and TD Ameritrade, and now serving as CEO of TastyTrade under IG North America. The real differentiator for traders now is education, not access, and that platforms like TastyTrade prioritize teaching users how markets actually work. The conversation highlights how TastyTrade continues that mission by combining content, community, and trading functionality in one ecosystem. JJ stresses the importance of understanding “defined risk” in options trading—knowing exactly how much you can lose before entering a trade. Calendar spreads can help traders take advantage of time decay and volatility differences between expiration cycles. JJ notes that the “meme stock” era of 2020–2021 changed market dynamics by bringing millions of new retail participants into the market. JJ warns that while accessibility is great, it can lead to overconfidence, so risk control and continuous learning are critical. JJ shares insights on how professional traders manage emotions and avoid letting losses dictate decision-making. Traders who survive long-term tend to manage downside risk far better than they chase upside potential. The conversation explores how automation and data analytics have reshaped trading, but that human intuition still matters in volatile environments. Building good habits—like journaling trades, reviewing setups, and setting stop levels—is key to developing consistency. He encourages investors to find strategies that fit their personality, risk tolerance, and time commitment rather than copying others. JJ leaves listeners with a simple message: focus on learning, define your risk, and don’t let one trade define your trading journey. 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/38512320

This Bull Market Is Crashing… And No One Is Talking about It 10/08/2025

The Finances of Athletes and NFL Players with Hillary Seiler 10/03/2025

The Finances of Athletes and NFL Players with Hillary Seiler Hillary Seiler joins us today to discuss the finances of athletes and NFL players. She shares her journey from personal financial struggles in college to building a career helping athletes, students, and employees improve their financial wellness. She shares how supporting friends who went pro in the NFL led her into creating financial literacy programs for professional teams, eventually expanding into universities and corporate America. She talks the lack of financial education for athletes, the misconceptions around their earnings, and the systems now in place to protect players from going broke. We discuss... Hillary is a financial education coach who began working with pro athletes and later expanded to universities and corporate America. She was inspired by her own financial struggles during her mother’s illness, which gave her perspective on money management. The NFL now mandates financial education sessions for rookies and younger players to prevent bankruptcy and poor financial decisions. Many athletes face misconceptions about their earnings, with most NFL players earning far less than the public assumes. Financial downfall is often tied to lack of education, poor money management, divorce, and being targeted for bad investments. Hillary teaches athletes to evaluate deals by requiring full business plans and consulting financial advisors before investing. Support systems and career planning are critical to helping athletes adjust to life after sports and avoid identity loss. Studies show Olympic silver medalists often stay motivated while gold medalists can struggle with depression and identity loss after reaching the pinnacle. Professional athletes and military veterans face similar challenges when retiring, often losing their sense of purpose. There has been debate about requiring athletes to save in pensions or annuities, but concerns remain about limiting free will. The NFL and NBA encourage saving with strong 401k matching programs, but players cannot access funds until age 45. The Pro Athlete Community (PAC) helps retired athletes manage money and avoid financial pitfalls. Despite education programs, some athletes still make costly mistakes or fall for scams, learning lessons the hard way. For more information, visit the show notes at h /episode/index/show/moneytreeinvesting/id/38430865

Your Financial Advisor Hates This Bull Market 10/01/2025

Your Financial Advisor Hates This Bull Market Your financial advisor hates this bull market! Find out what it is as we talk the recent market conditions as well as the potential upcoming government shutdown, noting that while shutdowns once spooked markets, investors have become largely desensitized as they rarely have major lasting effects outside of government employees and contractors. Shutdowns have historically been used as political tools, sometimes causing GDP drag and reputational costs, but now often register as background noise. We also chat about seasonal and cyclical inflection points—like quarter-ends, tax-loss selling, and earnings season—that can drive short-term volatility. It's important to keep your perspective, recognizing political drama as a “circus,” and instead focusing on underlying market cycles. Today we discuss... Government shutdowns used to trigger fear in markets but now typically cause little more than short-term noise. Politicians increasingly use shutdowns as leverage tools in budget negotiations rather than genuine fiscal concerns. Past shutdowns have shown temporary GDP drag but very little lasting structural harm to markets. Markets tend to quickly recover after shutdown drama fades, reinforcing investor desensitization. The real drivers of volatility now are cyclical factors like quarter-end portfolio adjustments and tax-loss harvesting. Earnings season consistently creates inflection points for markets, often outweighing political headlines. Seasonal forces can exaggerate short-term market swings, particularly in September and October. Positioning between defensive stocks and growth stocks is more critical for risk management than reacting to shutdown fears. Broader global market trends often matter more than U.S. political events. U.S. small-cap stocks have underperformed compared to large caps and international equities, reflecting structural weaknesses. Investors should focus on long-term positioning rather than reacting to short-lived shutdown volatility. Shutdowns reveal the widening gap between political theater and actual economic fundamentals. Short-term market noise from shutdowns can actually create opportunities for disciplined investors. Shutdowns are best understood as temporary disruptions, not trend-defining events. Today's Panelists: Kirk Chisholm | Follow on Facebook: Follow LinkedIn: Follow on Twitter/X: For more information, visit the show notes at /episode/index/show/moneytreeinvesting/id/38420475

End of Life Planning: Creating a Legacy That Lasts with Dr. Kimberly Harms 09/26/2025

The Billionaires Know About This Hidden Bull Market… Do You? 09/24/2025

Inside the World’s First Crypto Mortgage with Josip Rupena 09/19/2025

Inside the World’s First Crypto Mortgage with Josip Rupena 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 | Douglas Heagren | Diana Perkins | Follow on Facebook: Follow LinkedIn: Follow on Twitter/X: For more information, visit the show notes at /episode/index/show/moneytreeinvesting/id/38267640

The Silent Bull Market That No One Is Talking About 09/17/2025

Money Tree Investing

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