Investing in Legacy Businesses Beats Chasing Tech Trends with Travis Jamison
Money Tree Investing
Today's Panelists: Kirk Chisholm | Douglas Heagren | Diana Perkins | Follow on Facebook: Follow LinkedIn: Follow on Twitter/X: 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...
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You Are Probably Missing The Biggest Bull Market Right Now… Here is How You Play It
Money Tree Investing
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Living and Investing Overseas with Global Real Estate
Money Tree Investing
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...
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Wall Street Is Selling Beer, Beaches, and Barbecue… Here’s How You Can Invest
Money Tree Investing
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...
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The Risks and Rewards of Investing in Fine Art
Money Tree Investing
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...
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Government Data Is Fake… Here Is the Solution
Money Tree Investing
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Private Market Investing vs. Public Markets: Where the Real Opportunities Lie
Money Tree Investing
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...
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Looks Like the Market is Going on Vacation… Me Too
Money Tree Investing
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... Douglas Heagren | ...
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The Singularity Paradox with Anders Indset
Money Tree Investing
Anders Inset is here to share on this new work The Singularity Paradox. He shares his journey from capitalist and athlete to author and shares the concept of the technological singularity and the associated risks of creating godlike, self-improving machines without fully understanding their implications. He argues for developing “artificially human intelligence” rooted in human biology to preserve humanity in the face of exponential technological growth. The discussion covers the profound transformations such advancements could bring, from curing diseases and achieving abundant energy to...
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Is Private Equity Destroying Your Favorite Consumer Products?
Money Tree Investing
Douglas Heagren | Follow on Facebook: Follow LinkedIn: Follow on Twitter/X: For more information, visit the show notes at
info_outlineToday we go down the AI rabbit hole. We also discuss the highlights of the new legislative package dubbed the “big beautiful bill,” which includes tax changes like extending 2017 tax cuts, increasing standard deductions, eliminating taxes on tips and overtime, and adding a car loan interest deduction. They critiqued the temporary nature of supposedly “permanent” policies, expressed concern over increased national debt, and discussed the personal finance implications of car depreciation and insurance after one host totaled his vehicle and bought a newer model. We also talk about the potential of lower interest rates.
We discuss:
- The recent (and short-lived) Israel-Iran conflict and it's comparisons to past rushed declarations of victory.
- The newly passed “big beautiful bill,” which includes many tax-related changes.
- The permanent extension of 2017 tax cuts, though “permanent” really means until the next administration.
- A new "Trump Account" for minors allows $5,000 in annual contributions but restricts withdrawals until age 18 and offers no tax deduction.
- Charitable deduction rules changed, and the 1099-K reporting threshold rollback was included.
- Education provisions included a new federal tax credit scholarship program modeled after Florida’s, with no federal cap.
- Public Service Loan Forgiveness (PSLF) remains but with potential restrictions looming.
- Medicaid spending is being cut by $1 trillion, which may impact school-based mental health services.
- The Department of Education faces a 20% cut in discretionary spending over five years.
- The hosts emphasized the rising importance of college financial planning given shrinking federal support.
- Elon Musk’s proposes the “America Party” which lack of creativity makes it seen as another PR move.
- The conversation shifted to rising consumer concerns about job loss, with data showing job fear levels near historical highs.
- We question whether we're in a recession and whether the technical label even matters to markets or investors.
- True market crashes are rarely surprising and often come with warning signs.
- Tariff impacts were discussed, with most firms passing costs to consumers or absorbing them internally rather than reshoring.
- Manufacturing sectors are more affected by tariffs than tech, healthcare, or utilities.
- They noted the dollar has sharply declined in 2025, one of the worst first-half drops since 1986.
- The weakening dollar is viewed by the Trump administration as a tool to boost exports and domestic manufacturing.
Today's Panelists:
Kirk Chisholm | Innovative Wealth
Douglas Heagren | ProCollege Planners
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For more information, visit the show notes at https://moneytreepodcast.com/ai-rabbit-hole-729