loader from loading.io

My Housing Debacle – What Not To Do When Buying A House

Money Tree Investing

Release Date: 08/06/2025

Investing in Legacy Businesses Beats Chasing Tech Trends with Travis Jamison show art 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...

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

Money Tree Investing

Follow on Facebook: Follow LinkedIn: Follow on Twitter/X: For more information, visit the show notes at  

info_outline
Living and Investing Overseas with Global Real Estate show art 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...

info_outline
Wall Street Is Selling Beer, Beaches, and Barbecue… Here’s How You Can Invest show art 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...

info_outline
The Risks and Rewards of Investing in Fine Art show art 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...

info_outline
Government Data Is Fake… Here Is the Solution show art Government Data Is Fake… Here Is the Solution

Money Tree Investing

info_outline
Private Market Investing vs. Public Markets: Where the Real Opportunities Lie show art 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...

info_outline
Looks Like the Market is Going on Vacation… Me Too show art 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 | ...

info_outline
The Singularity Paradox with Anders Indset show art 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...

info_outline
Is Private Equity Destroying Your Favorite Consumer Products? show art 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_outline
 
More Episodes

Here's what not to do when buying a house! Today we explore my experience with buying a home. We also talk about what it means to be "anti-fragile" in markets that look stable but are actually full of hidden risks. We unpack why markets feel eerily calm despite cracks under the surface, point to red flags like rising margin debt and overvalued equities, and question the rosy government data that doesn’t match what businesses are actually seeing. We also touch on the Fed’s latest rate hold, the performative nature of their messaging, and why Japan might be the next weak link in the global system.

We discuss...

  • We talk about how fragile markets can appear strong but collapse under pressure, while anti-fragile strategies are built to withstand shocks.
  • There’s growing skepticism around official data on inflation, unemployment, and job growth, which often don’t match real-world experiences.
  • We flag early warning signs like record-high margin debt and stretched market valuations that suggest hidden fragility.
  • The Buffett Indicator is flashing red, pointing to historically high levels of overvaluation.
  • We discuss how investors often chase all-time highs without considering the risks beneath the surface.
  • The Fed paused interest rate hikes again, but its messaging feels more performative than predictive.
  • Government job growth is outpacing private sector job growth, raising questions about the true health of the economy.
  • Markets are euphoric about all-time highs, but this sentiment overlooks growing risks and valuation distortions.
  • There’s a widespread misunderstanding of the difference between correlation and causation in market data and recessions.
  • Long-term market growth trends can be distorted by short-term performance comparisons, leading to misleading “chart crimes.”
  • Used car prices remain high, partly due to ongoing shortages and strong demand, especially for 2–3-year-old vehicles.
  • Housing affordability has worsened dramatically, with mortgage costs far outpacing rent, making ownership financially unappealing.
  • Personal experience with deceptive sellers reflects broader issues in the housing market’s transparency and ethics.
  • As interest rates fall, more inventory may hit the housing market, but price drops are likely in many regions.
  • Homeownership is a personal expense, not an investment, due to ongoing maintenance, taxes, and volatility.
  • Homeownership comes with hidden costs and liabilities that are often underestimated by buyers.
  • The financial burden of owning—repairs, maintenance, interest—can reduce or erase the perceived gains over time.

Today's Panelists:

Kirk Chisholm | Innovative Wealth
Douglas Heagren | Mergent College Advisors

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

For more information, visit the show notes at https://moneytreepodcast.com/what-not-to-do-when-buying-a-house-735 

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

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