The Retirement Risk Nobody Is Talking About

The Hidden Bridge to Tax-Free Wealth

"Where is the $49 trillion that the IRS hasn’t taxed yet?" Discover what most retirees overlook about shifting tax laws, and why trusting today’s tax code could be costly tomorrow. Keith Singer and David Friedland peel back decades of history and reveal little-known strategies used by savvy investors to protect their retirement from government levers and legislative surprises. Find out why the ‘bridge’ to tax-free wealth has been in plain sight all along—yet almost nobody crosses it. 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.

The Price WAS Right and the Harbor Pilot

Did you know nearly half of your S&P 500 fund is concentrated in just two sectors? This episode of Prosper with Keith Singer challenges conventional wisdom around asset allocation, revealing overlooked imbalances and “bets” many investors didn’t realize they were making. Keith and David break down how massive shifts in energy investment, inflation, and retirement planning demand a new mindset—and why navigating the transition from accumulation to income calls for specialized guidance. What does it truly mean to get your ship safely home? You may rethink your own plan by the end. 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.

Beating Taxes: The Advisor Advantage

Is your advisor helping you win the tax game—or just keeping score? Many successful investors are losing thousands by separating tax planning from their investment strategy, all while believing a dusty will is enough to safeguard their legacy. Keith Singer and David Friedland reveal strategies the wealthiest quietly use to earn more, keep more, and ensure their wealth lands where they intend. Discover the five overlooked pillars that can transform how your money works for you—before and after you're gone. 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.

The Retirement Risk Nobody Is Talking About

“Does your retirement plan survive a 35% drop?” Today, Keith Singer and David Friedland dig into a provocative question raised by legendary investor Paul Tudor Jones—what if the market is more vulnerable than ever? Discover how historic stock market valuations, sequence of returns risk, and the hidden dangers of 'riding out' downturns could impact anyone within 10 years of retirement. Solutions and real client stories highlight just how much the investment landscape has changed—and why hope alone isn’t a strategy. 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.

Engineering Tax Alpha: Keeping More of Your Wealth

“Did you know the tax you pay on investment gains isn’t set in stone—it can be engineered?” This episode dives into the world of ‘tax alpha,’ unveiling strategies once reserved for billionaires and now accessible to more investors. Keith and David expose not only how the affluent keep more of what they earn, but also why growing wealth makes you a prime target—from sophisticated scams to intimate betrayals. Explore the hidden levers of tax efficiency and the critical safeguards that can make or break a legacy—with real stories that reveal what many never see coming. 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.