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. Today 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.
"Cash is not trash... Cash is King" - Kirk Chisholm
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Today's Guest: Kirk Chisholm
Kirk Chisholm is a Wealth Manager and Principal at Innovative Advisory Group, an independent Registered Investment Advisor located in Lexington, MA. He has been providing wealth management services to individuals, executives, entrepreneurs, and their families since 1999. He is an outside the box thinker, risk manager, inflation expert, blogger, podcaster, and all-around interesting guy. Kirk is dedicated to developing lasting relationships with all of his clients and their families. One of the benefits of working with Kirk is his patience, empathy, and his ability to provide clear and easy-to-understand explanations to complex financial topics.
Kirk developed a unique philosophy for the wealth management industry called Risk Management First. The medical field has a similar way of thinking of “first do no harm”. This philosophy focuses on risk management for clients in all aspects of their lives in ways the industry does not address. Risk management does not stop with investments. It also requires working closely with other professionals to address areas of their financial lives not currently being met.
In 2008, Kirk co-founded Innovative Advisory Group to address the needs not being addressed by the wealth management industry. It started with specializing in alternative assets held in retirement accounts (i.e. self directed IRAs/401ks). Then the company expanded into the specialization of college funding (i.e. planning, strategy, and paying the least possible for a high quality education), Risk Management First, exit planning for business owners, advanced planning (estate, tax, etc), and providing practice management and leadership training to other financial advisors, accountants and attorneys.
Kirk's Online Presence:
Today's Panelists
- Kirk Chisholm | Innovative Wealth
- Douglas Heagren | Mergent College Advisors






