Episodes

  • 72. Aging in place vs long-term care

    72. Aging in place vs long-term care
    Jun 28 2026
    This week, Leo sits down with Sam Morocco, RICP®, Retirement Income Specialist at Gem Young Wealth Advisors, to discuss one of the most important planning decisions many families will face: Aging in Place vs. Long-Term Care. As people live longer and healthcare needs evolve, understanding your options becomes increasingly important. Leo and Sam explore the benefits and challenges of remaining at home as you age, the realities of long-term care costs, and why having a plan in place before a crisis occurs can make all the difference.
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    54 mins
  • 71. The realities of skilled nursing, rehabilitation, and long-term care.

    71. The realities of skilled nursing, rehabilitation, and long-term care.
    Jun 23 2026
    Leo Daprile sits down with Clint Ansell and Tiffany Crane from Maplecrest Skilled Nursing and Rehabilitation Center to discuss the realities of skilled nursing, rehabilitation, and long-term care. Together, they break down the differences between aging in place, assisted living, and skilled nursing care, helping families better understand when each option may be appropriate. Leo, Clint, and Tiffany explore common misconceptions about long-term care facilities, the services available to residents, and what families should consider when making care decisions for a loved one. Whether you're planning ahead or currently navigating these choices, this conversation provides valuable insight into one of the most important decisions families may face as they age
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    54 mins
  • 70. Long-term care planning

    70. Long-term care planning
    Jun 15 2026
    Leo Daprile sits down with Attorney Joseph Johnson to discuss the legal considerations surrounding aging in place and long-term care planning. Together, they explore the critical legal documents that can help protect you and your loved ones, including wills, trusts, powers of attorney, and healthcare directives. Leo and Attorney Joseph Johnson discuss common mistakes families make when planning for the future, the importance of having difficult conversations before a crisis occurs, and how proper legal planning can provide peace of mind while preserving your wishes. Whether you're preparing for your own future or helping aging parents navigate theirs, this conversation offers valuable insights into creating a plan that protects both your family and your legacy.
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    54 mins
  • 69. Future care needs

    69. Future care needs
    Jun 6 2026
    Leo Daprile sits down with Stephen Daprile to discuss the financial realities of aging in place and planning for future care needs. Together, they explore the costs associated with remaining in your home as you age, how those expenses compare to assisted living and long-term care options, and the importance of creating a financial strategy before a health event or crisis occurs. Leo and Stephen discuss how proper planning can help protect assets, maintain independence, and provide greater flexibility when making important healthcare and lifestyle decisions. Whether you're planning for yourself or helping a loved one navigate the future, this conversation offers valuable insights into preparing financially for the next chapter of life.
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    54 mins
  • 68. Life Insurance

    68. Life Insurance
    May 31 2026
    Leo sits down with Stephen Daprile and Sam Morocco for an important conversation on life insurance and the role it plays in your overall financial plan. They break down the different types of life insurance, how to determine what coverage is right for you, and why it’s not just about protection—but also about creating stability and flexibility for the future. You’ll also hear common misconceptions, planning strategies, and how life insurance can support your goals as you work toward a work optional lifestyle.
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    54 mins
  • 67. How insurance goes in your financial plan

    67. How insurance goes in your financial plan
    May 31 2026
    Leo sits down with Stephen Daprile and Denny White for a powerful conversation on how insurance fits into your overall financial plan. From protecting your assets to managing risk, they break down why insurance isn’t just a standalone product—it’s a key piece of building a strong, well-rounded strategy. You’ll hear how the right coverage works alongside your investments and planning to help keep everything on track. They also share common gaps people overlook and why aligning your insurance with your financial goals is essential to building and maintaining a work optional lifestyle.
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    54 mins
  • 66. Buying based on Price

    66. Buying based on Price
    May 18 2026
    Leo sits down with Denny White, Chief Revenue Officer at Gem Young Insurance, for an important conversation on buying insurance based on price vs. understanding the full picture. They break down why choosing the cheapest option isn’t always the best decision, how insurance company “report cards” can help you evaluate carriers, and what really matters when it comes to protecting your assets. You’ll learn how to look beyond price, avoid common mistakes, and make more confident decisions that align with your long-term goals and your path toward a work optional lifestyle.
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    54 mins
  • 65. Medicare

    65. Medicare
    May 11 2026
    Leo sits down with Jerald “Jerry” Balestrino, Risk Management Advisor and Senior Health Advisor at Gem Young Insurance, to talk all things Medicare. From understanding your options to avoiding common mistakes, Jerry breaks down what you need to know to make confident decisions about your healthcare coverage. They’ll also cover important updates and how Medicare fits into your overall financial plan. Whether you’re approaching eligibility or just want to better understand your coverage, this episode provides clear, practical insight to help you stay informed and protected—while supporting your path toward a work optional lifestyle.
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    54 mins