The Gem-Young Wealth Cast with Leo Daprile

85. Ryan LeStrange In this episode of the Gem Young Wealthcast, Leo Daprile welcomes Ryan LeStrange of CIBC to discuss the firm’s expanding resources, including the addition of a new portfolio manager and income tax strategist. They explore CIBC’s approach to tax management, including asset location, thoughtful tax-loss harvesting, and recognizing capital gains based on each client’s individual circumstances.

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84. In this episode of the Gem Young WealthCast, Leo Daprile is joined by Stephen Daprile to explore whether ChatGPT can really manage your retirement, where AI can be a valuable financial tool, and why human experience, judgment, and personalized planning still matter.

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In this episode of the Gem Young WealthCast, Leo Daprile is joined by Stephen Daprile to discuss the new realities of retirement, from creating dependable income and managing inflation to rising healthcare costs, investing for longevity, and enjoying retirement with confidence.

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In this episode of the Gem Young WealthCast, Leo Daprile is joined by Stephen Daprile to discuss five financial moves to consider before year-end, including portfolio reviews, tax planning, RMDs, charitable giving, and your overall financial strategy.

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In this episode of the GemYoung Wealthcast, Leo Daprile sits down with Stephen Daprile and Sam Morocco to discuss how life insurance fits into a comprehensive financial plan and why it's an essential tool for protecting your family, preserving your legacy, and creating long-term financial security.

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In this episode of the GemYoung Wealthcast, Leo Daprile is joined by Sam Morocco, RSSA® (Registered Social Security Analyst®) to discuss the importance of Social Security planning and how making informed decisions today can have a lasting impact on your financial future.

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In this episode of the GemYoung Wealthcast, Leo Daprile sits down with Denny White and Vince Armeni to discuss the recent storms, the insurance claims process, and how homeowners can better protect themselves before and after damage occurs.

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Medicare can feel overwhelming—but it doesn't have to be.
In this episode of the GemYoung Wealthcast, Leo Daprile is joined by Jerry Balestrino, Medicare Specialist at Gem Young Insurance, to break down the latest Medicare updates and help you better understand your options.

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In this episode of the GemYoung Wealthcast, Leo Daprile sits down with Nancy Zimbardi and Jerry Balestrino to discuss how Gem Young Insurance works alongside Gem Young Wealth Advisors to provide a truly client-focused experience. From home, auto, and umbrella coverage to Medicare, life insurance, business insurance, and financial planning, discover how having one trusted team can simplify your life and help ensure every piece of your financial picture works together.

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This week, Leo Daprile welcomes Glenn Dorsey, CFA®, CAIA®, SVP, Head of Client Portfolio Management, for another edition of the Quarterly Market Update on the Gem Young Wealthcast.
Together, they discuss the latest market performance, economic trends, and the factors shaping today's investment landscape. Glenn shares his perspective on navigating uncertainty, identifying long-term opportunities, and why staying committed to your financial plan is more important than trying to time the market.

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This week, Leo Daprile sits down with Stephen Daprile, President of Gem Young Insurance & Wealth Advisors, for another edition of our Quarterly Market Update.
In this episode, Leo and Stephen discuss the latest market activity, economic developments, and the importance of keeping a long-term perspective when building your financial plan. Rather than reacting to headlines, they share practical insights to help you stay focused on your goals through every stage of the market cycle.

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This week, Leo Daprile welcomes Elizabeth McConville, Sr. Regional Investment Specialist, Central at AssetMark Asset Management, for the latest Quarterly Market Update on the Gem Young Wealthcast.
Together, they break down the current market environment, discuss the economic trends shaping today's investment landscape, and provide valuable perspective on what investors should consider as they plan for the future.

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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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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...

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...

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...

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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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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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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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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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 coun...

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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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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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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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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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 success matters, and how going deeper into every financial plan makes all the difference.
This conversation highlights the philosophy behind the planning — and the commitment to helping clients create freedom, flex...

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 next chapter of life on your own terms.

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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 surprises that come with creating more balance.

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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 definition of retirement looks very different from generations past.

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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 timely insurance updates, real-world operational and service perspectives, and practical takeaways to help you stay informed and confident in navigating your insurance needs.

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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 perspectives, practical takeaways, and the steps you can take to feel more confident in designing a future where work becomes a choice—not a necessity.

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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, real-world risk management perspectives, and practical takeaways to help you stay informed and confident in protecting what matters most.

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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 informed and confident in your healthcare and financial journey.

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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 takeaways to help you stay informed and confident in your financial journey.

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Leo Daprile sits down with Stephen Daprile, President of Gem Young Wealth Advisors, for an insightful discussion on today’s market environment. Leo and Stephen break down what’s driving the markets, how economic trends may impact investors, and what this means for long-term financial planning. Whether you’re navigating volatility or looking ahead to future opportunities, this episode offers valuable perspective to help you stay informed and confident.

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Leo Daprile sits down with Glenn Dorsey, SVP and Head of Client Portfolio Management at Clark Capital, for an in-depth discussion on today’s market environment. Glenn shares insight into current market trends, portfolio positioning, and how investors can navigate ongoing volatility with a disciplined, long-term approach. From risk management to investment strategy, this conversation provides valuable perspective for investors looking to stay informed and confident in their financial decisions.

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Leo Daprile sits down with Phil Blancato, President and Chief Executive Officer of Ladenburg Thalmann Asset Management and Chief Market Strategist at Osaic, for our latest Quarterly Market Update. We discuss recent market activity, key economic developments, and the trends investors should be paying attention to as we move forward. Phil provides timely insight and clear perspective to help listeners better understand today’s market environment and what it could mean for their financial plans.

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Leo Daprile sits down with Shelby Anderson, Senior Wealth Planner with Clark Capital Management Group. Together, Leo and Shelby discuss the role charitable giving plays in comprehensive wealth planning, strategies for giving more intentionally, and how donors can maximize impact while staying aligned with their personal values and legacy goals. This conversation highlights how smart philanthropy can create meaningful change—for both individuals and the communities they care about.

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Leo Daprile sits down with Bob Hannon, President of the United Way of Youngstown and the Mahoning Valley. Bob brings deep insight into the mission, impact, and community-focused work of United Way right here in the Mahoning Valley.

Together Leo and Bob explore the power of charitable giving, how contributions are directed to support local families, and the real-world difference that strategic philanthropy makes in our community.

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Leo Daprile sits down with Sam Morocco, Retirement Income Certified Professional . An eye-opening conversation about one of the most meaningful — and often overlooked — ways to give: gifting life insurance.

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