HeyJaredLeibel on FIRE
The Financial Independence and Retirement show dedicated to helping you build the life of your dreams, as fast as possible, with as little stress as possible
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- Sep 8, 2026
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- Jul 7, 2026
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Downside Protection Products Explained: Counterparty Risk, Structured Notes, Buffered UITs, and CDs (opens the original)
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The episode compares downside-protection tools and how much they rely on an institution’s solvency. It explains that flex options cleared by the Options Clearing Corporation reduce counterparty risk, market-linked CDs provide FDIC-insured principal protection up to $250,000, and buffered unit investment trusts (UITs) hold assets in a legally separate trust, limiting issuer solvency concerns even though principal isn’t guaranteed. Structured notes are described as loans to an issuing bank with si
How Buffers, RILAs, and Structured Notes Can Limit Downside While Staying Invested (opens the original)
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Leibel Sternbach of Yields4You explains how downside-protection strategies use option-based contracts to trade limited upside for defined protection, including how buffers work when markets fall beyond the buffered amount. He describes buying downside protection and offsetting its cost by selling upside participation, then compares approaches such as fixed index annuities (with strong downside protection but limited upside), registered index linked annuities that let investors dial protection le
The Only Real Hedge Against Market Volatility: How Options Work Like Insurance (opens the original)
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The episode explains that the primary way to protect against major market declines is through contracts like those used by insurance companies—options—framed with a real estate analogy. Just as a homebuyer’s deposit secures the right to buy or sell a house at a set price by a certain date, options provide the right to buy or sell assets at specified prices within specified timeframes. The discussion focuses on using these contracts to “lock in” value while still keeping upside, and why accessing
Is Your Retirement Portfolio More Concentrated Than You Think? (opens the original)
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Is Your S&P 500 Fund Riskier Than You Think? Protecting Your Retirement From Market Drops YouTube Description The S&P 500 may contain 500 companies, but that doesn’t necessarily mean your retirement portfolio is as diversified as you think. In this episode of Leibel on FIRE, Leibel Sternbach explains how a small group of large companies—many tied to the artificial intelligence boom—now represents a significant portion of the S&P 500. While that concentration has helped drive impressive market re
The Real Roth Conversion Question: How, When, and Whose Tax Bill Are You Lowering? (opens the original)
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Freddie Bell interviews Leibel Sternbach about his upcoming Amazon release, The 30-Day Roth Conversion Handbook, arguing the key Roth decision isn’t simply whether to convert, but how, when, and whose long-term tax bill to reduce (you, your spouse, heirs, or charity). Sternbach explains he wrote the book to scale his mission of helping one million people retire securely, drawing on client stories and his father’s death at 63 without a plan. He discusses required minimum distributions that can su
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