The Prosper Podcast

What if picking the “right” investments is just a fraction of what it takes to secure your retirement? In this episode, Keith Singer and David Friedland dissect the most overlooked threats—taxes, healthcare costs, legacy gaps—and reveal how true wealth management is about integration, not just asset allocation. The conversation uncovers surprising connections between financial planning pillars, ex...

How does a 4.2% inflation rate threaten not only your wallet, but your entire retirement plan? In this episode, Keith Singer and David Friedland expose the hidden layers of damage inflation can cause—from rising everyday costs to sneaky tax and Medicare traps most never see coming. With high-impact stories and actionable insights, this episode journeys through the pitfalls and advanced strategies...

Keith and David discuss the difference between an investment advisor whose job is to help grow portfolios, and a retirement advisor who helps turn portfolio resources into income for retirement. They also look at vehicles which can help provide protected growth and avoid the volatility of the stock market. The Prosper Podcast is the podcast version of Prosper with Keith Singer, the weekly radio pr...

What would you do if you became a millionaire overnight? In this episode, Keith Singer and David Friedland examine the sudden wealth created by the SpaceX IPO and uncover why most windfalls are less secure than they appear. Explore the emotional rollercoaster, the hidden dangers of concentrated wealth, and the little-known strategies the truly wealthy use to protect, diversify, and preserve new fo...

“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 exam...

“Does $150 oil really break economies—or is this just headline panic?” In a week swollen with viral predictions and market twists, Prosper dives deep into what’s true and what’s spun, revealing how seasoned investors respond when fear collides with facts. Keith Singer and David Friedland calmly unpack the difference between supply shocks and market realities, challenge conventional wisdom, and sha...

"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 ‘br...

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—...

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. Disc...

“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 an...

“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...

“What if the real winners in artificial intelligence aren’t the companies everyone’s watching?” Discover why the foundation of AI’s explosive growth lies far below the tech giants, and how overlooked sectors could hold the keys to portfolio resilience. The episode explores the intricate five-layer structure behind AI, exposes gaps in typical energy investing, and guides listeners through the cruci...

How can you protect your portfolio when market darlings stumble and volatility returns? This episode dives into the surprising risks of stock concentration, the overlooked normalcy of market downturns, and the contrasting realities faced by retirees and accumulators. Uncover tools that offer exposure with protection, and explore a century-old tax strategy the “informed” have used for generations....

What happens when you wait for lower rates—and they never arrive? This episode exposes the common misconceptions behind Federal Reserve moves and why the bond market truly sets the tone for mortgages, investments, and your financial plan. Join Keith Singer as he unpacks the hidden forces dictating interest rates, reveals pitfalls in conventional income strategies, and explores innovative ways to p...

What if the real danger to your retirement isn’t market losses, but the way you turn savings into income? In this eye-opening episode, Keith Singer and David Friedland reveal why so many retirees stumble—despite years of diligent wealth-building—by mistaking growth planning for income planning. Discover the critical distinction that most advisors overlook, the silent threat called “sequence of ret...

Are you missing out on tax "free bridges" and making costly estate planning errors without realizing it? This episode, Keith Singer and David Friedland share eye-opening stories—from the high-earning executive paying unnecessary taxes to a grieving partner locked out of her late loved one's assets—illustrating how easy it is for even diligent people to miss crucial details. Learn why planning (not...

Keith has a chat with Christopher Zook, the founder and chairman of Kaz Investments, a Houston based institutional firm with a broad based network of world wide investments. They focus on the boom in energy, especially as it relates to the growing demand for power usage by AI, as well as other areas where private equity can bring good returns. The Prosper Podcast is the podcast version of Prosper...

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.

Did you know that a single investment could potentially wipe out tens of thousands from your tax bill—and that your retirement savings may be quietly growing a debt to Uncle Sam? This episode of Prosper with Keith Singer rips the lid off powerful but overlooked tax strategies, from oil and gas deductions to the IRA “time bomb” most high earners never see coming. Keith and David dig deep into legal...

Keith and David discuss numerous ways to save on what you owe to the IRS, including Roth conversions, private investments, structured notes and more, as well as how to obtain reports from their office which explain these strategies. 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 bas...

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 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.

Keith and David take a look at why various professional believe 2026 may provide good market returns, then turn their attention to why being too conservative to avoid market volatility can actually make you lose money to inflation due to lack of returns. The Prosper Podcast is the podcast version of Prosper with Keith Singer, the weekly radio program featuring Keith Singer and David Friedland of B...

Keith and David talk with Michael Lavy, the Chief Investment Officer for Singer Wealth Advisors, about the types of long term investment strategies institutions use and how they can help retirees in managing their financial goals. 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...

Tesla is known for its electric cars, but they are into many other things that could change society in coming years. Keith and David discuss how the company is into manufacturing robots, as well as AI, energy storage and more. They also take a look at one of their favorite investment platforms, structured notes, and how they could bring smarter growth with predictability and much less volatility t...