Money Tree Investing

Money Tree Investing Podcast
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Oct 10, 2025 • 1h 13min

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 | Innovative Wealth Barbara Friedberg | Barbara Friedberg Personal Finance 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/tasty-options-strategies-for-2025   
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Oct 8, 2025 • 57min

This Bull Market Is Crashing… And No One Is Talking about It

Doug Agrin, a seasoned investment expert, explores the current bull market dynamics that many are overlooking. He discusses the lasting impact of the government shutdown on market trends and highlights the ongoing surge in precious metals like gold and silver. Doug also critiques the dangers of misinterpreting data, urging critical evaluation in finance. He warns about private equity's overleveraging and the risks it poses to businesses and communities, cautioning against short-term gains at the expense of long-term stability.
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Oct 3, 2025 • 1h 37min

The Finances of Athletes and NFL Players with Hillary Seiler

Hillary Seiler, a financial education coach for professional athletes, shares her journey from personal financial struggles to empowering others. She discusses the lack of financial education in sports and how the NFL now mandates rookie financial sessions to prevent bankruptcy. Hillary emphasizes the importance of evaluating investment deals, the role of branding in NIL deals, and the complexities around post-career transitions. Her insights highlight how athletes can protect their wealth and navigate their financial futures effectively.
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Oct 1, 2025 • 46min

Your Financial Advisor Hates This Bull Market

Doug Hagren, an investment professional known for his market insights, discusses the evolving impact of government shutdowns on the markets. He explains how these shutdowns, once feared, now cause minimal disruption due to investor desensitization. The conversation shifts to seasonal factors driving volatility, such as quarter-end adjustments and tax-loss selling. Additionally, Doug highlights the significance of the upcoming earnings season as a key market inflection point, overshadowing political drama and impacting investment strategies.
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Sep 26, 2025 • 55min

End of Life Planning: Creating a Legacy That Lasts with Dr. Kimberly Harms

Dr. Kimberly Harms, a grief counselor, death doula, and life coach, shares her journey from dentistry to supporting families through end-of-life planning. She highlights how avoiding conversations about death can lead to conflict and emphasizes the importance of clear wills and healthcare directives. Dr. Harms discusses creating a meaningful legacy, focusing on love, resilience, and life skills for future generations. She encourages open family discussions about death to prevent misunderstandings and offers practical tips to prepare emotionally and practically.
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Sep 24, 2025 • 45min

The Billionaires Know About This Hidden Bull Market… Do You?

Discover the hidden bull market in gold, silver, and mining stocks that billionaires are capitalizing on! Learn how recent Fed actions have had minimal impact on markets and may exacerbate wealth gaps. Challenge common financial assumptions, like the so-called superiority of Roth IRAs over traditional ones. Delve into the limited effects of tariffs on the economy and the rising distrust in fiat currencies as seen in gold's surge. Plus, the importance of personal research in financial matters takes center stage!
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Sep 19, 2025 • 1h 5min

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 | 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 
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12 snips
Sep 17, 2025 • 44min

The Silent Bull Market That No One Is Talking About

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.
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Sep 12, 2025 • 1h 7min

Investing in Legacy Businesses Beats Chasing Tech Trends with Travis Jamison

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.
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Sep 10, 2025 • 55min

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

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 

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