Tax Smart Retirement Podcast

What if planning forward is the wrong way to retire? This episode flips the script on traditional retirement planning by exploring a “reverse engineering” approach, starting with your end goal and working backward to build a strategy. The conversation breaks down why relying on investments alone can miss key factors, and how taxes, income timing, healthcare, and estate planning all int...

What happens when life throws a curveball right before retirement? Charles Winfrey breaks down practical strategies to stay on track, whether you’re facing a sudden layoff, questioning your readiness, or looking to maximize your long-term tax efficiency. This episode explores how to realistically assess your financial position, avoid costly mistakes during income gaps, and use tools like Rot...

Welcome to The Tax-Smart Retirement Podcast, the go-to podcast for anyone looking to take charge of their financial future. Hosted by Charles Winfrey of The Rollover Company, each episode dives into the essentials of 401(k) planning, lump-sum pensions, and IRAs with straightforward information and practical advice. Charles brings his experience as a financial advisor to the mic, making complex top...

What happens when the paycheck stops, but life doesn’t? In this episode, Charles Winfrey of The Rollover Company breaks down the realities of retirement planning beyond just saving money. With decades of experience helping pre-retirees and retirees, Winfrey explains why building a sustainable income strategy is critical to maintaining your lifestyle. From navigating taxes and healthcare cost...

Social Security is evolving and understanding how it works today is critical for your retirement future. In this episode, Charles Winfrey breaks down the current state of Social Security, including the financial pressures facing the system and what they could mean for future benefits. Learn how taxes can impact your Social Security income, why up to 85% of benefits may be taxable depending on your...

Tax planning isn’t one-size-fits-all, especially when retirement, athletic careers, and legacy goals collide .   In this episode, Charles Winfrey breaks down how proactive tax strategies can help retirees preserve income, athletes manage short high-earning windows, and families protect wealth for future generations. From navigating required distributions and Social Security taxes to str...