The Gem-Young Wealth Cast with Leo Daprile

Hosted by iHeart (WKBNAM)

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Episodes

300

Latest episode

Jun 2026

Language

EN-US

About the show

Conversations with Leo Daprile of Gem-Young.

Listen to episodes

60 recent

June 15, 202653 min

70. Long-term care planning

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.

June 6, 202653 min

69. Future care needs

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.

May 31, 202653 min

68. Life Insurance

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.

May 31, 202653 min

67. How insurance goes in your financial plan

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.

May 18, 202653 min

66. Buying based on Price

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.

May 11, 202653 min

65. Medicare

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.

May 4, 202653 min

64. Insurance Claims

Leo sits down with Denny White, Becky Olsavsky, and Kim from the Gem Young Insurance team to talk all things insurance claims—what really happens when you file a claim and how to navigate the process with confidence. From the first call to final resolution, the team breaks down what to expect, common mistakes to avoid, and how having a dedicated service team can make all the difference during stressful situations. You’ll gain insight into how claims are handled behind the scenes and why working with a team that knows you and your coverage matters when it counts the most—all while helping protect your path toward a work optional lifestyle.

April 26, 202653 min

63. Stephen Daprile

Leo Daprile sits down with Stephen Daprile to recap the most important insights from the series and how you can apply them to your own financial future. It’s all about clarity, confidence, and creating a plan that works for you.

April 22, 202653 min

62. Ryan LeStrange

Leo Daprile is joined by Ryan LeStrange to discuss key financial strategies, current trends, and how to stay focused on building a strong financial future. From market insights to practical planning tips, this episode is all about helping you stay on track.

April 22, 202653 min

61. Phil Blancato

Leo Daprile is joined by Phil Blancato, President & CEO of Ladenburg Thalmann Asset Management and Chief Market Strategist at Osaic. Together, they dive into the current state of the markets, economic trends shaping investor behavior, and what it all means for your financial future.