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, flexibility, and confidence in the next chapter of life.
If you want to understand what it really takes to build a work-optional future, this is an episode you won’t want to miss.

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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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