Markets, Taxes, and the Hidden Risk

“What if the very tool meant to protect your portfolio is quietly doing the opposite?” In this episode, the discussion challenges common assumptions about stop losses, market timing, and protecting against major downturns. The conversation explores why disciplined selling can be easier than smart re-entry—and how that gap changes investor outcomes. Shifting from risk to structure, the episode examines alternative approaches like buffered strategies, structured notes, and tax-efficient planning tools that aim to reshape downside exposure rather than react to it. The broader theme questions whether traditional tactics still fit an environment where valuations, taxes, and volatility collide in unexpected ways.The Prosper Podcast is the podcast version of Prosper with Keith Singer, the weekly radio program featuring Keith Singer and David Friedland of Boca Raton, Florida based Singer Wealth Advisors. Keith and David discuss various financial topics and investment opportunities many people may not know about, and how they relate specifically to retirement planning.