Learn From My Previous Investment Mistakes
Oct 22, 2025In this incredibly candid episode titled "Learn From My Previous Investment Mistakes," Terry Wheeler gets real about the financial blunders of his past the "scary investments" so you can secure your future without making the same costly errors. 🛑
Terry covers three illiquid investment blunders and the one common mistake you need to address right now as the market nears its peak:
Illiquid REITs & BDCs: Why did investments that were perfect in theory turn into decade-long traps with only modest (or negative) returns? The answer is fees and illiquidity. Learn why you must prioritize control.
The Scaled Tax Lien Strategy: An example of a good idea ruined by flawed implementation. Terry explains the dangers of boutique investments that try to scale too fast.
The Biggest Lesson: Market Defense! Relive the pain of the 2001 and 2008 crashes. Terry explains that his biggest mistake was not having a heavy enough concentration in protected positions near the market top.
👉 Actionable Takeaway: Terry advocates for Defined Outcome Investing to protect your gains and ensure you're positioned to "buy the dip" when the current bull run inevitably ends. Find out how to achieve most of the upside with critical downside protection. Don't wait to get crushed. Learn from these mistakes and take action today!
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