HeyJaredRetire With Ryan
If you're 55 and older and thinking about retirement, then this is the only retirement podcast you need. From tax planning to managing your investment portfolio, we cover the issues you should be thinking about as you develop your financial plan for retirement.
- Indexed episodes, last 90 days
- 13
- Latest publication
- Sep 29, 2026
- Audience
- Checking…
- Earliest in this view
- Jul 7, 2026
Latest episodes
What If I Retire Right Before A Market Crash? #325 (opens the original)
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What should you do if the stock market crashes right after you retire? In this episode, I discuss what happens if you experience a major market decline in your early retirement years, explain the concept of sequence of return risk, and share a few strategies to safeguard your hard-earned nest egg and maintain peace of mind. You will want to hear this episode if you are interested in... [01:20] What to do if the stock market crashes right after retiring [04:09] Sequence of return risk explained [
What Happens To My HSA When I Enroll In Medicare? #324 (opens the original)
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How much have you thought about Health Savings Accounts (HSAs) and what happens to them once you enroll in Medicare? Whether you're nearing age 65, wondering if you can keep contributing to your HSA, or curious about how you can use your HSA funds in retirement, this episode covers it all. I explain the rules around HSA contributions after enrolling in Medicare, the types of medical expenses you can pay for tax-free, and what happens to your HSA if there's still money in it after you pass away.
5 Tax Mistakes To Avoid In Your Initial Retirement Years, #323 (opens the original)
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As you transition into retirement, tax planning might not be at the top of your to-do list—but overlooking it can lead to costly mistakes. This week, I break down the five biggest tax pitfalls new retirees face, from unexpected taxes on Social Security benefits to costly Medicare premium surcharges and missed Roth conversion opportunities. I'm also sharing a few of my favorite strategies to avoid unnecessary state taxes and manage your retirement distributions with confidence. You will want to h
5 Year Roth IRA Rule People Get Wrong, #322 (opens the original)
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Roth IRAs are a powerful retirement tool, much loved for their promise of tax-free growth and withdrawals. But embedded in the rules for Roth IRAs are two little-understood 5-year rules. Misunderstanding these can trip up even savvy savers, potentially exposing your hard-earned gains to taxes and early withdrawal penalties. This week I'm giving you an expert breakdown to clarify how the rule works and bust some common misconceptions. You will want to hear this episode if you are interested in...
4 Best Options To Pay For Long-Term Care, #321 (opens the original)
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Long-term care coverage is an essential, yet often misunderstood, aspect of retirement planning in the United States. Although many people will require some form of long-term care as they age, most are unprepared for the high costs and limited coverage options available. On the show this week, I'm debunking common myths like the notion that Medicare will fully cover all long-term care costs and taking a deep dive into the four main ways retirees can pay for these expenses. You will want to hear
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