Episodes

  • Four Retirement Pitfalls That Cost Thousands

    Four Retirement Pitfalls That Cost Thousands
    Sep 19 2026
    “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 gaps, leaving key details open and inviting listeners to reflect on their own 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.
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    25 mins
  • Outmaneuvering Taxes: IRAs, Opportunity Zones & Risk

    Outmaneuvering Taxes: IRAs, Opportunity Zones & Risk
    Sep 12 2026
    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 shifting laws and skyrocketing market risks—all without relying on yesterday’s conventional wisdom. What’s at stake may be more than just your nest egg.

    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.
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    25 mins
  • High Valuations, Tough Questions: Stock Market Reality

    High Valuations, Tough Questions: Stock Market Reality
    Sep 5 2026
    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, data-driven discussion invites you to question long-held investment habits, while hinting at ways to weather turbulent times—without ever giving away the ending.

    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.
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    25 mins
  • Self-Made Success: Billionaire Insights Unveiled

    Self-Made Success: Billionaire Insights Unveiled
    Aug 29 2026
    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.

    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.
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    25 mins
  • Do You Really Need a Financial Advisor?

    Do You Really Need a Financial Advisor?
    Aug 15 2026
    "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’s tone is refreshingly honest, challenging old assumptions and leaving crucial details—and surprises—for curious listeners to discover.

    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.
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    28 mins
  • Rethinking IRA Strategies for a New Era

    Rethinking IRA Strategies for a New Era
    Aug 15 2026
    “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 blanket solutions and quick fixes. Tune in for a clear-eyed look at the real risks, bracket gaps, and income-building options that could redefine your financial future, but be prepared—some truths may surprise you.

    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.
    Show More Show Less
    28 mins
  • From Mud Floors to Million-Dollar Ventures

    From Mud Floors to Million-Dollar Ventures
    Aug 1 2026
    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 opportunities on the path to prosperity. Uncover the roots of determination that can spark a life-changing transformation.

    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.
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    27 mins
  • The Real Money is Made Before the IPO

    The Real Money is Made Before the IPO
    Jul 25 2026
    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 managing taxes, Keith Singer unpacks what truly separates ordinary investors from the ultra-wealthy. Find out where the next wave of growth is happening—and why knowing your options might rewrite your financial future.

    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.
    Show More Show Less
    25 mins