The Prosper Podcast

“Who really owns your retirement savings, and why are so many families shocked by the answer?” The Prosper Podcast dives into the hidden math behind traditional IRA advice, uncovering the IRS’s silent partnership and...

"Are you sure you need a financial advisor—or are you in the rare group who doesn’t?" In this candid episode, Keith Singer and David Friedland reveal why some self-sufficient investors may not benefit from hiring their...

What drives someone to turn childhood deprivation into enormous success? In this moving premiere of Rags to Riches, entrepreneur Von Malone shares an astonishing journey—from a poverty-stricken village in Vietnam and a...

What if the real fortunes aren’t made the day a company goes public—but years before, where most investors never look? This episode of Prosper peels back the curtain on how today’s wealth creation is shifting out of...

What would you do if you suddenly won millions—but your prize wasn’t just a check, it was a major choice? This episode of Prosper with Keith Singer unpacks the story of a lottery winner facing a deceptively simple...

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...

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...

“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...

“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...

"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...

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...

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...

“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...

“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...

“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...