Best James Conole, CFP® Podcasts (2024)

1
Early Retirement Health Insurance Strategies | Roth Conversions vs. ACA Subsidies 33:36

1h ago33:36

33:36

Healthcare subsidies are like a tax break and should always be optimized, right? That seems like an easy question that should have a straightforward answer. But the correct answer is, “It depends.” Cole from Move Health is back, as he and James explain how advanced premium tax credits work, when you might not want to take them, and why it’s imperat…

1
Health Insurance Options for Early Retirement 29:25

7d ago29:25

29:25

We meet many people who are in a position to retire early. But when they think about healthcare in retirement and not being eligible for Medicare until age 65, they feel stuck, even though they’re ready for retirement in every other way. Cole Craven of Move Health Partners chats with James about the healthcare options that are available for early r…

1
Should I Invest in My Health Savings Account? 27:16

2h ago27:16

27:16

Are you using your Health Savings Account to its full potential? HSAs are great for covering immediate healthcare costs, but with careful planning, they can also become a strategic part of your long-term wealth plan. This week, Scott Frank, founder of Stone Steps Financial, and Meg Bartelt, founder of Flow Financial Planning, LLC, take on HSAs, sha…

1
Everything You Need to Know About Medicare: Q&A with a Medicare Expert 42:21

14d ago42:21

42:21

Drew Shockley of MOVE Health Partners joins James to address questions about Medicare. He overviews the Medicare system, explains Parts A, B, C, and D, and breaks down what Medicare does and doesn’t cover, who is covered, and when/why you might want alternative coverage. Questions Answered: I’m 65, still working and qualify for Medicare, but I have…

1
What Should You Do With Your Stock Portfolio? 25:35

39m ago25:35

25:35

Deciding what to do with your stocks can prove to be a problem, challenge, and opportunity all at once. With a huge portfolio in front of you, what can you do to slim it down? This week, Scott Frank, founder of Stone Steps Financial, and Meg Bartelt, founder of Flow Financial Planning, LLC, provide insights on how to cut down on your stocks to achi…

1
How to Prepare for Retirement Within 5 Years: 401k, Savings & Investment Changes 30:28

23d ago30:28

30:28

Graham and his wife are in their early 50s and plan to retire in 5 years. He wonders if they should continue maxing out their 401ks, how their investments should change, and what they should do with savings accounts to best prepare for their retirement goals. James addresses these questions, Graham’s biggest risk as he nears retirement, and potenti…

1
What Should You Do With Your Pile of Cash? 23:09

5d ago23:09

23:09

Is your cash currently sitting under your mattress, withering away with inflation? While stashing your cash seems like a safe bet, it limits your access to investment opportunities. With inflation rising, the value of your cash may not have the longevity you hoped for. If you currently have a pile of cash and are asking yourself, “Well…what now?” t…

1
Is It Possible To Actually Reach FIRE? 25:34

1d ago25:34

25:34

What does being financially independent mean to you? Those chasing FIRE (Financial Independence, Retire Early) are choosing to live frugally now to achieve early retirement. FIRE is a means to unlock a life where work is optional and the freedom of choice reigns supreme. Scott Frank, founder of Stone Steps Financial, and Meg Bartelt, founder of Flo…

1
How Can You Avoid Surprises Next Tax Season? 26:07

4h ago26:07

26:07

Does your anxiety spike every time tax season rolls around? The possibility of receiving an unexpected tax bill can bring a sense of dread to the entire month of April. We all have to pay taxes, but we don’t have to stress about them. Scott Frank, founder of Stone Steps Financial, is joined by Meg Bartelt, founder of Flow Financial Planning, LLC, t…

1
How to Know When You Should Stop Saving for Retirement (and What to Do Next) 31:23

29d ago31:23

31:23

Drew, a burnt-out, financially responsible 40-something father of two, hopes he can scale back from his stressful job and still be okay when it’s time to retire. James offers a practical and philosophical take as he tackles Drew’s question. He demonstrates how to determine when Drew and his wife will be in a good position to fully retire. He also c…

1
3 Simple Steps to Determine If You Can Retire 21:19

1M ago21:19

21:19

How do you know if you can retire? It seems straightforward, but the answer is far from simple. Beyond portfolio balances and age thresholds, there are other things to consider. James explains his three-step test to determine your retirement readiness. By pulling together principles from the 4% Rule, straight-line projection, and a Monte Carlo anal…

1
Tax Planning for Widowed Retirees: How to Optimize Your Tax Strategy 21:54

1M ago21:54

21:54

Jennifer, 54, plans to retire soon. Her husband, 70, is retired, on Social Security, and dealing with some severe health issues. Jennifer worries about possibly becoming single in retirement, which could result in a higher tax bracket for her. Jennifer is considering whether to convert her traditional accounts to Roth to lower future taxes or to ch…

1
Lump Sum vs. Annuitization: Tax Implications for Your Non-Qualified Annuity 17:43

2M ago17:43

17:43

Joe is planning for retirement and wants to minimize his tax burden, especially on the interest earned from his three annuities. James explains that non-qualified annuities are purchased with post-tax money and offer tax deferral on growth until withdrawal. When taking out funds, the principal is tax-free, but earnings are taxed at ordinary income …

1
At What Age Should I Work with a Financial Advisor? 24:02

2M ago24:02

24:02

Deciding to work with a financial advisor is about more than how much you've stashed away. It's also about determining whether an advisor's benefits outweigh the costs. In your higher earning years, finances become more complex. More money means more decisions and more chances to make mistakes or miss out on opportunities. That's where a quality ad…

1
Sell, Rent, or Borrow? Best Ways to Use Home Equity in Retirement 24:48

2M ago24:48

24:48

Listener Ray is wondering what to do with his home as he embarks on a nomadic, van-life journey in retirement. Should he sell it to finance his travels or retain it for potential appreciation and cash flow? James explores the nuances of home ownership as an asset versus an investment. He considers cash flow and leverage as he looks at Ray’s three o…

1
Pay ZERO Capital Gains Tax vs Roth Conversions in Retirement: How to Determine Which is Best 34:55

2M ago34:55

34:55

Listener Drew asks about a tax strategy for juggling capital gains and Roth conversions. While it can be a complicated question – especially when large accounts are involved – James provides some general guidelines that can be helpful for anyone with similar gnarly tax strategy challenges in retirement. In this episode, we’ll cover the extent to wh…

1
Tax-Smart Strategies for Wealth Transfer: Secure Your Family's Future 28:25

3M ago28:25

28:25

James responds to listener Jerry’s question about the optimal time to distribute inheritance or charitable gifts: before or after passing away. James walks listeners through four important things to consider when it comes to gifting and inheritance: your gifting goal, whether you have a strong desire to see the assets gifted within your lifetime, t…

1
Roth Conversion Strategies to Protect Your Spouse's Future Tax Burden 35:14

3M ago35:14

35:14

A listener says, “Eventually, one spouse will pass before the other, which will often catapult the survivor into a significantly higher tax bracket. Shouldn’t a Roth strategy take this into account?” James explores several factors that could positively and negatively impact a survivor’s tax liability and what to consider when creating a Roth conver…

1
Should I Fund my Retirement Needs by Purchasing an Annuity? 19:17

3M ago19:17

19:17

Jason and his wife face a crucial decision: whether to purchase an annuity or pursue traditional investments as they prepare for a full-time, slow-travel retirement. With a diverse array of income sources, including pensions, 401k, property sales, and Social Security, they estimate their monthly expenses at $7,500. James analyzes their situation, e…

1
How Should I Invest Bucket #1 of my Retirement Portfolio (3 Bucket Strategy) 26:01

3M ago26:01

26:01

The "Three Bucket Strategy" is a popular retirement income planning method. The first bucket covers immediate expenses in retirement. Listeners John and Donna are seeking advice on constructing their first bucket. With $1.6 million in assets and pension incomes, they aim to retire in 2026. James analyzes their needs, income sources, and portfolio a…

1
At What Point Should I Take the Tax Hit on Unrealized Gains? 31:07

4M ago31:07

31:07

Benjamin, nearing retirement at 65, faces a familiar dilemma with his taxable account housing expensive mutual funds. Despite their underperformance, converting to low-cost index funds entails a significant tax hit due to long-held appreciable value. James explains weighing the immediate tax consequences against the risk of holding onto underperfor…

1
Maximize Your Early Retirement: Should You Save to 401k or Brokerage Accounts? 32:08

4M ago32:08

32:08

Typical retirement strategies assume a retirement age of over 60. With an earlier retirement goal, a careful look is required to determine what strategies will create the best outcome. James responds to a listener’s question about where to invest as he anticipates an early retirement. James walks through the steps of Root’s Sequoia System to explor…

1
Safe Withdrawal Rate Myths: Debunking 3 Common 4% Rule Mistakes 20:00

4M ago20:00

20:00

The 4% rule helps us understand how much we can safely take out of our portfolio each year without running out of money in retirement. Yet, as simple as the 4 percent rule seems, the practical implications are drastically misunderstood. I explore the three common mistakes people make when applying this rule and how to avoid them. Questions Answered…

1
Secrets to a Happy Retirement: What the Research Shows 31:21

4M ago31:21

31:21

Retirement is not just about financial readiness; it's also about finding purpose, passion, and personal growth. James and guest Cynthia Meyer debunk the arrival fallacy, the illusion that reaching retirement will bring lasting happiness. Having structure in retirement and pursuing your passions is vital to feeling fulfilled. Although it's easy to …

1
What's the Right Roth Conversion Amount to Avoid a Tax Nightmare in the Future? 26:40

4M ago26:40

26:40

Sammy, a 51-year-old retiree, is seeking advice on how much she should convert from her traditional IRA to a Roth IRA each year to avoid jumping tax brackets and minimize the taxation of her social security benefits. James analyzes Sammy's current financial situation and offers guidance on approaching the tax planning aspect of her retirement strat…

1
How to Maximize Social Security Spousal Benefits 20:07

5M ago20:07

20:07

James addresses a common concern for a couple approaching retirement through a listener’s question. Listener Rob plans to collect Social Security early at 62, raising questions about his wife’s retirement. Understanding Social Security strategies to avoid potential losses during retirement is important. James explains the intricacies of spousal ben…

1
Bond Ladders in 2024: How to Build a Bond Portfolio for Your Retirement 35:16

5M ago35:16

35:16

As one listener prepares for an early retirement, James discusses the situation, covering how to build a bond ladder based on non-retirement funds. James provides a different way of looking at the stock-to-bond conversation. Learn how to determine the appropriate amount to have a bond ladder and whether you should own individual bonds or bond funds…

1
3 Ways to Protect Against Sequence of Return Risk in Retirement 26:43

5M ago26:43

26:43

James explores the concept of sequence of return risk in retirement planning. Most people are unaware of how risky this is, as it doesn’t become an issue until you begin living off your portfolio. Responding to a listener’s inquiry about early retirement, James dives into the potential impact of market timing on retirement outcomes. Learn three act…

1
Should We Sell Stocks to Make a Large Purchase? 21:46

5M ago21:46

21:46

Should you sell long-term stocks for a real estate investment? I walk through one listener’s question and explain what you need to consider before making such a decision. Aside from the obvious–is it a good financial investment–you also need to consider if it's a good emotional decision. Learn: ➡ The tax implications: how are capital gains taxed di…

1
Am I Crazy For Paying My Financial Advisor $25k/year? 30:20

6M ago30:20

30:20

When you’re doing well financially, paying advisor fees might seem unnecessary. So do you need an advisor if you’re already in a good place? Having a successful retirement isn’t just about not running out of money; it’s about what more you can do. Through a real-life client story, I explain how having an advisor’s perspective to implement the right…

1
When Should You Collect Social Security if Your Spouse is Much Older? 20:39

6M ago20:39

20:39

James addresses a listener's question regarding Social Security strategies in retirement. Sasha, aged 59, seeks advice on when to start collecting Social Security, considering her husband's benefits and their overall retirement plan. James emphasizes the importance of considering spousal benefits, survivor benefits, and age gaps in making this deci…

1
Roth IRA Tax-Free Withdrawals: 5-Year Rule Explained 19:44

6M ago19:44

19:44

James explores the nuanced aspects of Roth IRAs, shedding light on intricacies that can confound even experienced investors. Through a listener question from Manfred, a retiree contemplating a $50,000 conversion from a 401k to a Roth account, James dissects the crucial five-year holding period and the order in which contributions, conversions, and …

1
Retire Happy: How to Navigate Your Retirement Transition with Joe Kuhn 40:20

6M ago40:20

40:20

When we think of retirement, it often evokes dreams of leisure, relaxation, and the freedom to pursue one's passions. Yet, the decision to retire is not merely about leaving a career; it's about embarking on a new chapter filled with purpose and fulfillment. Joe Kuhn, a seasoned retiree and creator of the "Joe Kuhn Loves Retirement" YouTube channel…

1
Tax-Loss Harvesting Strategies to Maximize Your Benefit and Avoid Costly Mistakes 25:23

7M ago25:23

25:23

Tax loss harvesting is a strategy that investors use to reduce their tax bill. However, there are many misconceptions about tax loss harvesting, including when it's valuable and how to do it effectively. James debunks some of the most common myths about tax loss harvesting and explains how to use this strategy to your advantage. Questions Answered…

1
How to Teach Your Adult Children to Plan for Retirement 26:58

7M ago26:58

26:58

James walks through a framework of how you ensure that your legacy goals include more than just leaving a chunk of money to your kids when you're gone. He explains the key concepts that can help your child develop strong money management skills. From starting early to diversifying your investments, learn how you can help set your child up for finan…

1
Is Your Portfolio Big Enough to Benefit From Roth Conversions? 21:31

7M ago21:31

21:31

What are the benefits of Roth conversions in retirement planning? James addresses questions about when Roth conversions become worthwhile. This episode explores key factors: Changes in tax bracket Spousal scenarios Impact of portfolio size on tax savings Potential tax savings tend to increase with a higher portfolio balance but be careful not to ta…

1
Does It Ever Make Sense to Purchase an Annuity? 26:06

7M ago26:06

26:06

Have you ever wondered if purchasing an annuity makes sense for you? There are two conflicting opinions from financial advisors: some advocate for annuities while others advise against them. James explores the concept of being a fiduciary and the challenges of understanding the financial advisory industry. He covers when annuities may be a suitable…

1
Pretax vs Roth- Which is Better for You If You're in the 24% Tax Bracket? 22:08

8M ago22:08

22:08

If you're in a high tax bracket now and expect to remain in a high tax bracket after retirement, should you prioritize pre-tax retirement accounts or Roth retirement accounts for individuals? James answers this and discusses various factors to consider in making this decision, including current and future tax brackets, required minimum distribution…

1
Here's How a Pension Should Change Your Investment Strategy 25:38

8M ago25:38

25:38

James debunks common misconceptions about retirement portfolio allocation and explains how to factor in your pension, social security, and other fixed-income sources into your plan. He discusses the importance of dividends in assessing investment performance, risk capacity and tolerance, and how mastering them can help determine your optimal retire…

1
Your Retirement Roadmap: A 5-Step Plan to Retirement Readiness 26:43

8M ago26:43

26:43

In this episode, James emphasizes the importance of having a well-thought-out financial plan for retirement, rather than relying solely on the size of your investment portfolio. Financial security doesn't come from a specific portfolio number but from having a comprehensive plan. Using a listener's question, James walks through a step-by-step appro…

1
How to Break Up with Your Financial Advisor 19:10

8M ago19:10

19:10

In this episode James explores signs that may indicate it's time to move on from a current financial advisor and discusses the professional and respectful ways to handle this transition. There are three core aspects to consider when contemplating the change: Deciding to Leave: The first step involves recognizing signs that it may be time to move on…

1
Spend Guilt-Free: How to Shift from a Savings to Spending Mindset in Retirement 28:26

8M ago28:26

28:26

One of the most ironic things about retirement spending is that the people who have saved the most money are often the same ones that have the most difficult time spending that money. We often think that if we save up enough money or build up enough of a portfolio that in retirement it will open up unlimited fun and enjoyment. The reality is, for t…

1
Donor Advised Funds - The Secret Weapon for Tax-Efficient Charitable Giving 24:28

9M ago24:28

24:28

The majority of people who participate in some level of charitable giving in retirement aren't getting a tax deduction for any of it. While external reasons should drive charitable giving, you should absolutely look to maximize the tax effectiveness of any giving you're already doing. In this episode, James covers how to optimize your tax benefits,…

1
The Tax-Smart Way to Consolidate Your Retirement Accounts 24:49

9M ago24:49

24:49

By the time you get to retirement, it is not uncommon to have many different accounts at multiple different institutions. You may be wondering, "How do I begin the process of consolidating everything without paying a bunch in taxes or penalties?" In this episode, James covers three types of taxes you're likely to encounter when consolidating: ordin…

1
The Retirement Portfolio Shift- How to Make the Transition Smoothly 20:15

9M ago20:15

20:15

It’s common knowledge to have a different portfolio allocation before retirement than you actually have in retirement. But how and when do we actually go about making that change? This episode is based on a listener question: Alan, has a portfolio mix weighted too heavily in stocks. As he shifts into retirement, he is looking to have a new allocati…

1
Are Adjustable Rate Mortgages Right for You in a High Interest Rate Environment? 22:23

9M ago22:23

22:23

Are short-term savings using an adjustable rate mortgage worth the risk of rate hikes? In this podcast, we cover how adjustable rate mortgages (ARMs) work, how they differ from fixed-rate mortgages, and the reality of their adjustment periods. James uses a real-life scenario to dive into the comparison of adjustable and fixed-rate mortgages. Learn …

1
How Rising Interest Rates Should Impact Your Pension Decision (Lump Sum vs Annuity) 26:04

10M ago26:04

26:04

How can rising interest rates impact your pension value? In this week's episode, we analyze a real-life scenario from our listener, Mark, who is weighing the pros and cons of an early retirement, a higher lump sum, or a commit to an annuity. Learn how to calculate the imputed returns of an income annuity and how to determine if taking the lump sum …

1
What's the Best Way to Fund a Remodel During Retirement? 32:01

10M ago32:01

32:01

If you’re retired, you can’t wait around for the next bonus or stock to vest when you have a large expense. When you’re on a fixed income it’s more important than ever to find the best way to pull funds for large expenses. In today’s episode, James explains how to find the best way to pay for large expenses in retirement while answering a listener’…

1
Here's the Right Way to Determine How Much Individual Stock to Hold 28:06

10M ago28:06

28:06

How much of your portfolio is safe to hold in one individual stock? While 5% or 10% is typically recommended, rules of thumb like these are often irrelevant and harmful. The right answer depends upon your specific situation. James explains the right way to determine how much individual stock you should hold based on your situation. Questions Answer…

1
Ask Yourself This Question to Transform Your Retirement 16:19

10M ago16:19

16:19

What do you think is the key to a successful retirement? By asking yourself the right questions and being intentional about using money to enrich life, you can live more presently in the moment and enjoy a meaningful and successful retirement. James explains the most important question to ask yourself so that you can transform your retirement. Ques…

Podcasts Worth a Listen

James Conole, CFP® Podcasts

Podcasts Worth a Listen

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