The Prosper Podcast
The podcast version of the Prosper radio program heard each weekend throughout South Florida. Keith Singer and David Friedland discuss up-to-date financial topics, as well as investment strategies that many investors may be unaware of. Singer Wealth Advisors is an SEC registered investment advisory firm.
Episodes
October 13, 2026 • 26 mins
Is your money growing faster than a Big Mac? Discover why the “silent tax” of inflation can quietly erode your nest egg—without ever sending you a bill. Keith Singer and David Friedland reveal why even a well-written estate plan can fall short and how everyday decisions may leave your loved ones or favorite charities missing out. From menu changes to financial missteps, this episode explores the hidden threats to ...
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October 3, 2026 • 25 mins
What if the expense that derails your retirement isn’t the one you planned for? Join Keith Singer and David Friedland as they untangle the real costs of health care—and reveal why long-term care is the elephant in the retirement room. Get insights into navigating Medicare, tax traps, and hybrid investment options, plus a candid look at how emerging risks like AI could impact your portfolio. Discover the planning moves m...
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September 26, 2026 • 25 mins
Is there a way to turn a looming tax bill into an investment advantage? Discover the little-known Opportunity Zone changes, the surprising rules for capital gains, and why your IRA isn’t as private as it seems. Keith Singer and David Friedland unpack new strategies, reveal overlooked pitfalls, and share timely insights for those navigating high-stakes financial decisions—all without giving away the most powerful tools a...
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September 19, 2026 • 25 mins
“What could derail a perfect retirement plan?” Discover the hidden dangers lurking in old 401ks, income strategies, Social Security timing, and long-term care. This episode dives deep on four challenges that can reshape your financial future and the surprising questions every retiree should ask—before it’s too late. The conversation sets a thought-provoking mood as experts discuss overlooked decisions and ga...
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September 12, 2026 • 25 mins
Is the IRS quietly positioned to claim a bigger share of your retirement legacy than you ever realized? This episode unpacks the seismic changes reshaping IRA inheritance and reveals a looming deadline that could reshape your capital gains strategy for years. Listen in as Keith Singer and David Friedland explore overlooked tax traps, clever strategies, and the little-known moves that could safeguard your financial future against sh...
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September 5, 2026 • 25 mins
How can paying twice as much for a stock alter your financial future? Keith Singer and David Freeland uncover surprising truths at the intersection of stock valuations and retirement planning. Discover why the current market’s “CAPE ratio” could spell challenge—or opportunity—for investors, and explore strategies even the pros debate when markets are unusually expensive. The episode’s candid, dat...
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August 29, 2026 • 25 mins
What does it take to turn tortillas and adversity into billion-dollar deals? In this episode, Fernando DeLeon recounts the trials and triumphs that shaped his path from humble beginnings to remarkable wealth. Discover the mindset, strategies, and pivotal moments that defied all expectations. From spelling bees to Wall Street, every twist reveals new lessons—yet the biggest game-changers remain just beneath the surface.
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August 15, 2026 • 27 mins
“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 how recent law changes upend decades-old strategies. Keith Singer and David Friedland reveal overlooked pitfalls and introduce a new framework for maximizing family wealth—while warning against ...
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August 15, 2026 • 28 mins
"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 firm and outline the evidence behind DIY success. The discussion dives into behavioral pitfalls, defensive insurance strategies, and overlooked legal documents that shape financial security. The show&rsqu...
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August 1, 2026 • 26 mins
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 harrowing escape attempt, to building thriving businesses in America. Amid tales of near-impossible odds, resilience, and reinvention, listeners are invited to reflect on both hidden struggles and overlooked op...
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July 25, 2026 • 24 mins
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 reach of the traditional stock market, revealing the strategies, opportunities, and crucial risks few advisors discuss. From the SpaceX IPO frenzy to little-known paths for accessing growth and managin...
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July 18, 2026 • 26 mins
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 decision: steady income for life, or an enticing lump sum now. Discover the unseen pitfalls, tax troubles, and psychological hurdles in choosing the right payout, and learn why this dilemma isn’t just fo...
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July 11, 2026 • 26 mins
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, exposes commo...
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July 4, 2026 • 29 mins
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 for protecting your wealth in...
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July 1, 2026 • 27 mins
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 program featuring Keith Singer...
The Prosper Podcast is the podcast version of Prosper with Keith Singer, the weekly radio program featuring Keith Singer...
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June 20, 2026 • 22 mins
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 fortunes—for now and for future...
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June 13, 2026 • 25 mins
“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 ...
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June 6, 2026 • 25 mins
“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 share pr...
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May 30, 2026 • 25 mins
"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 ta...
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May 23, 2026 • 26 mins
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 nav...
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