The Gem-Young Wealth Cast with Leo Daprile
Conversations with Leo Daprile of Gem-Young.
Episodes
June 15, 2026 • 53 mins
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 hav...
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June 6, 2026 • 53 mins
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 ...
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May 31, 2026 • 53 mins
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 stra...
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May 31, 2026 • 53 mins
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 ...
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May 18, 2026 • 53 mins
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 ...
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May 11, 2026 • 53 mins
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&rs...
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May 4, 2026 • 53 mins
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’l...
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April 26, 2026 • 53 mins
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.
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April 21, 2026 • 53 mins
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.
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April 21, 2026 • 53 mins
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.
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April 4, 2026 • 52 mins
Leo Daprile is joined by Glenn Dorsey, SVP and Head of Client Portfolio Management at Clark Capital Management Group. Together, they break down what’s happening in today’s markets, key trends investors should be paying attention to, and how to stay focused on your long-term goals in a constantly shifting environment.
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March 28, 2026 • 53 mins
Leo Daprile is joined by Stephen Daprile, President of Gem Young Wealth, to wrap up our special client series on the work-optional lifestyle.
After hearing real stories from clients living this stage of life, Leo and Stephen take a step back to discuss what truly goes into building a work-optional future. They explore why retirement planning is never cookie-cutter, why understanding each client’s goals and definition of succe...
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March 21, 2026 • 53 mins
Leo Daprile sits down with Stephanie Schuler — a widow who is embracing the work-optional lifestyle with purpose and intention. Stephanie shares how thoughtful financial planning has given her the freedom to focus on what matters most: spending meaningful time with family, traveling, and being present for the newest little members of her growing family. Her story is one of resilience, strength, and the power of designing the ...
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March 14, 2026 • 54 mins
Leo Daprile sits down with Randy Reese to reflect on his first year living the work-optional lifestyle.After choosing to scale back from his full-time career last year, Randy transitioned to working just one day a week — and is even considering adding a little more. In this honest and practical conversation, Randy shares what the adjustment has really been like, including the benefits, the challenges, and the unexpected surpr...
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March 7, 2026 • 53 mins
Leo Daprile sits down with Gary Wakeford to discuss what it truly means to live a work-optional lifestyle. Gary has reached retirement age and has the financial freedom to step away from work entirely — yet he chooses to continue working because he genuinely enjoys what he does. Together, Leo and Gary explore the role of purpose in retirement, how financial independence creates freedom of choice, and why today’s definit...
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March 1, 2026 • 53 mins
Leo Daprile sits down with Denny White, Chief Revenue Officer, and Kimberly Cheshire, Director of Operations at Gem-Young Insurance and Wealth Advisors. In this conversation, Denny and Kimberly join us to share valuable insights on today’s insurance landscape, the importance of strong coverage, and how exceptional service plays a key role in protecting individuals, families, and businesses.
Together, we’ll explore timel...
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February 22, 2026 • 53 mins
Leo Daprile sits down with Samuel G. Morocco, RICP®, Retirement Income Certified Professional with Gem-Young Insurance and Wealth Advisors. In this conversation, Sam joins us to share valuable insights on building a work optional lifestyle, key strategies for retirement income planning, and what individuals should be keeping in mind as they work toward greater financial freedom.
Together, we’ll explore real-world planning per...
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February 16, 2026 • 53 mins
Leo Daprile sits down with Denny White, Chief Revenue Officer, and Vince Armeni, Risk Management Advisor with Gem-Young Insurance and Wealth Advisors. In this conversation, Denny and Vince join us to share valuable insights on today’s insurance landscape, key trends impacting coverage, and what individuals and business owners should be keeping an eye on moving forward.
Together, we’ll explore timely insurance updates, r...
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February 16, 2026 • 53 mins
Leo Daprile sits down with Jerald Balestrino, Risk Management Advisor and Senior Health Advisor with Gem-Young Insurance. In this conversation, Jerry joins us to share valuable insights on Medicare, key coverage options, and what individuals should be keeping in mind as they approach retirement.
Together, we’ll explore important Medicare updates, real-world planning perspectives, and practical takeaways to help you stay infor...
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February 1, 2026 • 53 mins
Leo Daprile sits down with Elizabeth McConville, Sr. Regional Investment Specialist (Central) with AssetMark Asset Management. In this conversation, Elizabeth joins us to share valuable insights on today’s financial landscape, key trends shaping the markets, and what investors should be keeping an eye on as we move forward.
Together, we’ll explore timely market updates, real-world investment perspectives, and practical ...
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