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You are here: Home / Archives for optionality

558 Plus: SpaceX IPO, Equity REITs, Preferred Stock, Option Income, Managed Futures, Optionality, and AI Writing

June 13, 2026 by David Stein · Updated June 23, 2026

In Plus episode 558, David provides a short update on the SpaceX IPO, he reviews his income strategy holdings, and considers whether now is a good entry point for equity REITs, preferred stock, option income, and managed futures. Finally, we discuss a recent piece on energy optionality that was written mostly using AI and whether that detracted from the piece's credibility. Become a Member If you would like to listen to this episode of Money For the Rest of Us Plus, you can do so by … [Read more...]

Filed Under: Money Plus Tagged With: AI, equity REITs, managed futures, optionality, options writing, preferred stocks

492: The Power of Optionality: Small Bets, Big Payoffs

September 4, 2024 by David Stein · Updated September 20, 2024

In this episode, we explore the concept of optionality—how small, strategic decisions can lead to outsized rewards with limited downside risk. From ancient philosophy to modern financial strategies, discover how recognizing and seizing options can unlock opportunities in both life and investing. Topics covered include: Show Notes Antifragile by Nassim Nicholas Taleb—Penguin Random House The Wisdom Of Finance: Discovering Humanity in the World of Risk and Return by Mihir … [Read more...]

Filed Under: Podcast Tagged With: call options, optionality, options, options writing, put options

268: How To Better Manage Risk

September 11, 2019 by David Stein · Updated May 20, 2021

What are the three steps to better manage risk and get what you really want. In this episode you’ll learn: Why goods and services that lessen risk tend to cost more.What is the three-step process for assessing and managing risk.Why defining the risk-free option or asset is critical to managing risk.Why immediate annuities are the retirement risk-free option rather than a conservative investment portfolio.What are the two types of risk and how do we mitigate them.What is the … [Read more...]

Filed Under: Podcast Tagged With: hedging, idiosyncratic risk, insurance, optionality, risk, risk management, Schrager (Allison), systemic risk

164: Optionality—When To Keep Your Options Open and When To Commit

July 12, 2017 by David Stein · Updated March 12, 2024

How to use the asymmetric payoff of options, trial and error, and commitments to better yourself financially and in other areas of your life. In this episode you’ll learn: Show Notes Story of Thales of Miletus by Aristotle in Politics Antifragile: Things That Gain From Disorder - Nassim Nicholas Taleb The Wisdom of Finance: Discovering Humanity in the World of Risk and Return by Mihir Desai Bartleby, the Scrivener: A Story of Wall Street by Herman … [Read more...]

Filed Under: Podcast Tagged With: Aristotle, Desai (Mihir A.), optionality, options, Taleb (Nassim Nicholas), Thales

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