Best James Conole Cfp Podcasts (2025)

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How Much Can I Spend In Retirement with a $2 Million Portfolio? 13:19

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1h ago13:19

13:19

A retirement story that challenges everything you thought you knew about what’s possible in your golden years. Meet Michael and Lisa: a couple in their early sixties with $2 million saved who are worried about running out of money too soon. Their initial plan looked bleak, but three simple adjustments reshaped their retirement outlook without worki…

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There’s More to Saving for Retirement Than Knowing How Much Money You’ll Need 16:03

1h ago16:03

16:03

“How much money do I need to save in order to retire – what’s my number?” It’s one of the most common questions financial advisors get, and we understand why. People want a goal, something they can work toward to help them feel more at peace about how they’re saving. As is often the case in financial planning, when people ask for their number, the …

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Top 5 Social Security Secrets Every 60-Year-Old Needs to Know 12:19

4d ago12:19

12:19

The hidden complexities of Social Security could cost retirees tens of thousands over a lifetime. While it may seem like a simple income source, the right strategy can dramatically improve your financial security. Claiming isn’t one-size-fits-all. Protecting a spouse, guarding against longevity risk, or maximizing investments each call for a differ…

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Retiring at 65 Might Be Too Late (Here’s Why) 9:37

8d ago9:37

9:37

Most retirement plans focus on money alone, but the equation is incomplete without factoring in healthspan. Lifespan is how long someone lives, but healthspan is the number of years spent in good physical and cognitive health. The gap is significant. The average American lives to 77, but healthspan often ends around 66. This creates a retirement pa…

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Inside Root’s Growth Plan (And the Promise Refuse to Break) │ Root Talks 17:47

5d ago17:47

17:47

What happens when growth changes a company? We’ve all seen it—your favorite restaurant expands and suddenly the quality slips. The connection feels lost. But does growing always mean losing what made you special? At Root, we think about growth differently. We use “anti-goals” to define what we never want to become, with checks in place so expansion…

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Getting Clients to Open Up: A Framework for Financial Advisors 24:09

6d ago24:09

24:09

Advisors often face a gap between what clients ask for and what they truly need. Retirement projections and tax strategies are important, but beneath them is a deeper desire for clarity, purpose, and a meaningful life. In this episode of Root Ready, James shares a framework that builds trust and guides conversations beyond the numbers. Research sho…

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How to Avoid the Widow’s Tax (Before It’s Too Late) 17:30

7d ago17:30

17:30

When one spouse passes away, the survivor often faces what is known as the “widow’s tax.” It is not an official IRS tax, but the impact of moving from married to single tax brackets. A couple earning $120,000 in the 12 percent bracket can see the surviving spouse pushed into the 24 percent bracket with the same income. This tax bracket compression …

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Pre-Tax, After-Tax, Roth: How Should You Distribute Your 401(k) Contributions? 17:33

12d ago17:33

17:33

People often think of their 401(k) as the set-it-and-forget-it retirement account. You set your contribution amount, get your employer match, and leave it alone. But what if your company gives you pre-tax, after-tax, and Roth IRA options? It’s a nice problem to have, but things can get complicated pretty quickly. In this episode, we’re answering a …

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They Gave Up the ‘Traditional’ Retirement to Live the Life They Always Wanted: The Retirement Travelers 38:39

14d ago38:39

38:39

Redefining retirement with purpose and adventure John and Bev retired at 55, sold almost everything, and traded their dream home for two backpacks, golf clubs, and a life of full-time travel. Since then, they have visited 107 countries and all 50 states as “The Retirement Travelers.” Their journey began during COVID, when cancelled plans led to an …

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The Hidden Cost of Financial Optimization (And How to Avoid It) 17:43

24d ago17:43

17:43

What if the “financially optimal” choice doesn’t actually lead to your best life? This conversation explores the balance between optimizing money and optimizing happiness. We break down the Five Types of Wealth—financial, time, social, mental, and physical—and show why sometimes the decision that looks inefficient on paper may actually be the smart…

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The #1 Way to Be a Standout Team Member 25:44

20d ago25:44

25:44

Becoming an extraordinary financial advisor takes more than technical skill—it requires mastering teamwork. This episode breaks down the five pillars of collaboration: trust, listening, influence, respect, and care. These qualities shape how you show up for colleagues and clients and determine the impact you make as a team member. Strategies for re…

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When Money Isn’t Enough: The 5 Types of Wealth You Need Before Retiring 21:24

26d ago21:24

21:24

When the numbers say you can retire, but you can’t step away. Many people with the financial means to retire keep working, telling themselves one more year will make the plan even stronger. But at what cost to your time, health, and relationships? This episode explores “the good pickle,” where chasing more financial security comes at the expense of…

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A Meaningful Conversation About Money with Former NYT Columnist Carl Richards 23:32

28d ago23:32

23:32

Whether you know him as “The Sketch Guy” from his decade-long run as a NY Times columnist or you’ve heard him on a podcast, if you’re interested in the world of finance, you probably know who Carl Richards is. He has also written multiple books, including The Behavior Gap, The One-page Financial Plan, and his forthcoming book of sketches, titled si…

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Here's How Early Retirement Will Impact Your Social Security Benefit 17:13

1M ago17:13

17:13

Thinking about retiring early and worried it might hurt your Social Security benefits? Good news: it probably won’t. A common myth is that you have to work into your 60s to get the most out of Social Security. In reality, benefits are based on your 35 highest-earning years—not the age you stop working. This episode breaks down how benefits are calc…

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Does Your Spouse Really Know the Financial Plan? Why That Matters │ Root Talks 16:48

1M ago16:48

16:48

Money conversations fall short when only one spouse is at the table. It’s easy to treat financial planning like another household task to divide and conquer, but unlike errands, your financial plan is the blueprint for your shared future. What we’ve seen time and again is that the person sleeping next to you often holds the key to your blind spots.…

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Why You Feel Busy But Get Nothing Done 20:47

1M ago20:47

20:47

Ever end the day feeling busy but not productive? You’re not alone. In this episode, we tackle the productivity paradox that plagues so many advisors—being in constant motion without meaningful progress. Robert Brault said it best: “We are kept from our goal not by obstacles, but by a clear path to a lesser goal.” Lesser goals feel urgent, familiar…

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Can You Retire Without $1 Million? The Truth Might Surprise You 16:36

1M ago16:36

16:36

Forget the myth that you need a million dollars to retire. What really matters is creating sustainable cash flow—not hitting a magic number. Retirement success comes down to three things: your expenses, guaranteed income (like Social Security or pensions), and the gap your savings need to fill. For some, that gap is smaller than expected. Real exam…

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The Good, the Bad, and the Ugly of the OBBBA 21:06

1M ago21:06

21:06

With the OBBBA now signed into law, we’re sitting down to walk through the good, the bad, and the ugly. The biggest takeaway is that the new bill has opened the door to some great tax planning opportunities, but you have to act soon! Most of the OBBBA’s changes expire in four years, so you have a little time and space to consider doing a Roth conve…

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The #1 Way to Ruin Your Retirement (Most People Do This) 7:11

2M ago7:11

7:11

Can a children’s poem change how you think about retirement? In this episode, we unpack the hidden wisdom in Shel Silverstein’s “Smart” and how it reflects a common retirement planning mistake: trading time and well-being for wealth you may no longer need. We explore why it’s hard to step away from accumulation mode—even after reaching financial in…

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How to Know If You’re Ready to Retire (Hint: It’s Not Just About Money) 17:07

2M ago17:07

17:07

The hardest part of retirement isn’t always financial, it’s psychological. For many, stepping away from work isn’t a light switch, but a dimmer that adjusts over time. This episode of Root Talks unpacks what makes the retirement decision so complex, especially for high-achieving professionals whose identity is tied to their careers. Through a real-…

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How Great Advisors Help Clients Face the Fear of Retirement 25:08

2M ago25:08

25:08

Some clients are more than financially ready to retire, but still can’t bring themselves to do it. The real issue often isn’t the numbers. It’s the fear of losing identity, structure, and purpose after decades of work. In this episode of Root Ready, James explores how to support clients who feel stuck at the edge of retirement—not because they can’…

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This Is Why Financially Ready People Struggle to Retire 11:51

2M ago11:51

11:51

Even with a strong financial plan in place, many professionals find themselves hesitating at the retirement decision—stuck in the cycle of “just one more year.” The numbers say it’s possible, yet the fear of leaving behind a paycheck, a title, or a sense of purpose keeps them working long past the point of “enough.” This episode reframes retirement…

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Am I Behind? Rethinking Retirement Catch-Up Strategies 30:02

2M ago30:02

30:02

Do you ever feel like you're behind on retirement? A 41-year-old listener with over $230,000 saved and a 50%+ savings rate, certainly did. In this episode, we explain why starting late doesn't mean finishing last, especially when you're making such incredible strides! We dive into the numbers, the idea of being "behind" and the importance of the ri…

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What Should You Do With Your 401k When You Retire? 16:25

2M ago16:25

16:25

Your 401(k) is likely your largest retirement asset—so the decisions made about it can have a lasting impact. This episode explores the pros and cons of keeping a 401(k) versus rolling it over to an IRA. Learn when it makes sense to stay in a 401(k), especially for those retiring between ages 55 and 59½, when a special IRS rule allows penalty-free …

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DIY vs. Financial Advisor: How to Know When It’s Time to Get Help │ Root Talks 20:11

2M ago20:11

20:11

If you’ve ever found yourself wondering whether you really need a financial advisor, this episode is for you. James and Ari unpack the deeper reasons people seek financial guidance—and why the decision often goes far beyond dollars and cents. Much like seeing a doctor for preventative care, working with the right advisor is about protecting your fu…

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Want to Be a Better Advisor? Learn to Frame Wealth the Right Way 26:30

2M ago26:30

26:30

What if real wealth goes beyond money? In this episode of Root Ready, Harry Sommers joins James for a thoughtful conversation on redefining wealth—not just for clients, but for ourselves as advisors. Together, they explore a more expansive framework of financial planning that considers time, energy, relationships, and purpose. This isn’t about chas…

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5 Signs It’s Time to Retire - Right Now 9:37

2M ago9:37

9:37

At 90 years old, will you remember that final bonus or the time you didn’t spend with the people you love? This powerful question reframes how we think about retirement timing beyond the numbers. Yes, financial readiness matters. But delaying retirement for "just one more cycle" or "just one more raise" often leads to a dangerous pattern—constantly…

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Are You Saving Money in the Right Order? 25:43

2M ago25:43

25:43

We all know we should probably save some more, but when we pass the piggy bank phase and have larger amounts of money, things get a little more complicated than just dropping some coins every once in a while. In this episode of Real Personal Finance, Scott and Nick get into a little detail that most people skip: “where” and “how” matter as much as …

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Watch Me Stress Test a $1 Million Retirement Plan 19:28

3M ago19:28

19:28

A seven-figure portfolio can feel like a green light for retirement—but the numbers don’t always tell the full story. In one case study, a couple with over $1 million saved faced a withdrawal rate close to 14% based on their desired lifestyle. That’s nearly three times higher than what’s typically considered sustainable. This story is a reminder th…

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Why Brokerage Accounts Might Be the Most Underrated Tool in Your Financial Plan 18:35

3M ago18:35

18:35

Retirement accounts like 401(k)s and IRAs often get all the attention, but there’s another tool that can play a powerful role in your long-term strategy: the humble brokerage account. Unlike retirement accounts with age restrictions and penalties, brokerage accounts offer flexibility. You can access funds at any time, for any purpose without early …

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How to Master the Skills That Usually Only Come With Age 26:00

3M ago26:00

26:00

What makes a truly great financial advisor? It’s not just technical knowledge or years in the industry. In this episode, we explore what clients—especially those approaching retirement—really want: a trusted guide who understands the emotional side of financial planning. Many people ask, “Can younger advisors provide meaningful advice about retirem…

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5 Things Retirees Regret - And What You Still Have Time to Get Right 13:27

3M ago13:27

13:27

After working with hundreds of people navigating retirement, we’ve seen a clear pattern: the biggest regrets aren’t about money. They’re about meaning. Too often, people retire from something—but never toward something. They solve the financial side without planning for the life side. And that leads to some common regrets: No clear purpose after wo…

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Stop Worrying About Running Out of Money: Here's What You Need to Do 14:41

3M ago14:41

14:41

The biggest question I hear from people planning for retirement is this: Am I going to run out of money before I run out of life? But here’s the thing, no matter how much you’ve saved, that fear doesn’t automatically go away. In this video, I walk through what the data actually says about your chances of running out of money, where the 4% rule come…

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Politics and Planning: What’s the Right Balance for Advisors? 17:15

3M ago17:15

17:15

In this episode, we’re taking a surprising cue from Hamilton to explore a common challenge for advisors: how to handle political conversations with clients. Should you speak up like Hamilton or hold back like Burr? There’s no one-size-fits-all answer—but the key is staying grounded in your role as a guide, not a commentator. When clients bring up p…

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This Is What Financial Planning Really Changes 18:25

3M ago18:25

18:25

What does it really mean to change someone’s life through financial advice? While we’re not saving lives like doctors, the impact we have on our clients’ futures can be just as meaningful. Often, it’s not about the numbers—it’s about helping someone move forward when fear is holding them back. We’ve seen it firsthand. Like the dentist who had every…

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How Much Do You Need to Retire on $10K a Month? 13:17

3M ago13:17

13:17

If your goal is to spend $10,000 a month in retirement, how much do you really need saved? The answer isn’t as simple—or as overwhelming—as it might seem. In this episode, I break down the key factors that influence your retirement number beyond the common 4% rule. We’ll explore how Social Security can significantly reduce what you need to save, wh…

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From Saver to Spender: How to Ease the Emotional Shift into Retirement 26:09

3M ago26:09

26:09

Retirement is supposed to be the reward after decades of hard work, but for many, the hardest part is learning how to actually spend the money they’ve saved. In this episode, we explore why that transition feels so uncomfortable and how creating a retirement paycheck can help make spending feel safe and sustainable. We talk through the natural phas…

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I've Helped Hundreds of People Retire Comfortably. Here's the Exact 7-Step Framework I Used. 21:38

3M ago21:38

21:38

Retirement planning isn’t about chasing numbers, it’s about building a life with intention. The Sequoia System helps you get clear on what matters most, organize your finances around that vision, and create a plan that supports the freedom, peace of mind, and purpose you’re truly after. We start with your life vision, translate that into a monthly …

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Ready to Retire? Here's How to Tell Your Company │ Root Talks 24:32

4M ago24:32

24:32

In this episode, Ari and James explore the emotional and practical sides of retiring—specifically, how to have the conversation that officially ends your career. Whether you're months away or years out, this discussion tackles the fear, hesitation, and freedom that come with telling your boss you're done. You'll hear real stories from Root Collecti…

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Keys to Nailing Withdrawal Rate Conversation with Clients 23:28

4M ago23:28

23:28

Today’s episode goes beyond the 4% rule to uncover the real concerns behind client questions like, “How much can I safely spend in retirement?” We explore the origins of sustainable withdrawal strategies, from Bengen’s 1994 research to Guyton’s Guardrails, and show how dynamic approaches can ease anxiety and build confidence. Most clients aren’t ov…

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How Much Can We Expect to Spend in Retirement with a $4M Portfolio? 18:11

4M ago18:11

18:11

In this episode, we walk through a retirement planning scenario involving a couple in their early 60s with a $4 million investment portfolio. Their financial plan reveals something surprising: they may not need to wait until 65 to retire. Instead, thoughtful planning opens the door to retiring earlier—without compromising the lifestyle they value. …

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Rethinking Your Retirement Timing 18:19

4M ago18:19

18:19

Why do some people delay retirement when they’re more than ready, while others want out the moment they hit the financial edge? In this episode, we explore the emotional weight behind retirement decisions, from the fear of losing identity to the overlooked value of early, healthy retirement years. You’ll hear how flexible paths like consulting or “…

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Social Security at 62 vs 67 vs 70: When should you start claiming your benefits? 19:14

4M ago19:14

19:14

Deciding when to start your Social Security benefits might be the single most consequential financial decision of your retirement journey. Should you claim early at 62, wait until full retirement age at 67, or delay until 70 to maximize your monthly check? The answer isn't as straightforward as many think. Your Social Security benefit is calculated…

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The Surprising Regrets of Wealthy Retirees | Root Talks 16:05

4M ago16:05

16:05

Retired with millions—but full of regret? In this episode of Root Talks, James and Ari share the real stories no one talks about: wealthy retirees who did everything “right” financially but still feel like they missed out. From sacrificing health and relationships for more savings, to realizing too late that they were planning for someone else’s ve…

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Roth Conversions Done Right: What Great Advisors Know That Software Doesn’t 22:42

4M ago22:42

22:42

In this episode of Root Ready, James shares how advisors should think about Roth conversions—starting with the basics and not just relying on software. Software can help with numbers, but it can’t see the full picture. James explains why Root advisors use software as a tool, not the final answer. He talks through key things to consider before doing…

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We have a $3M Retirement Portfolio. How Much Can We Spend Without Running Out of Money? 15:26

4M ago15:26

15:26

Jeffrey and Cindy came to me with $3 million saved and one big question: How much can we actually spend in retirement? In this video, we walk through a retirement planning scenario—looking at spending goals, taxes, travel, healthcare, and how Social Security might factor in. While the numbers vary, the framework we use applies whether you're workin…

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What’s the Purpose of Your Money? 12:49

4M ago12:49

12:49

What should you do with extra cash when markets feel shaky? In this episode, we break down why your savings rate is the real engine of wealth, and how understanding the purpose behind your money brings clarity to every financial decision. You’ll learn why market downturns can be golden opportunities, but only if your foundation is solid and your ti…

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Root Talks: Spend Your Way to a Happier Retirement: 5 Pillars of Better Spending 19:01

5M ago19:01

19:01

Many great savers hesitate to spend once they retire—unsure how to shift gears after years of discipline. In this episode, we talk through what it looks like to use money with intention, not just someday, but now. Prompted by a thoughtful note from a Root Collective member, we share stories—personal and client-based—about the small upgrades that ma…

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A Guide for Navigating Client Conversations When Markets Are Crazy 30:55

5M ago30:55

30:55

When market volatility strikes, emotions often run high. Clients nearing retirement may feel especially vulnerable, and traditional conversations around long-term investing can sometimes miss the mark. In this episode, James Conole, CFP®, shares a powerful framework for navigating emotional client conversations during turbulent markets. Drawing ins…

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The Most Powerful Tax-Free Retirement Tool: Start Leveraging Your HSA Now 16:59

5M ago16:59

16:59

Health Savings Accounts (HSAs) don’t get much attention—but they should. With triple tax advantages (tax-free contributions, growth, and qualified withdrawals), HSAs offer a level of flexibility that’s hard to beat. I break down how to use an HSA not just for healthcare today, but as a long-term planning tool. That includes how to qualify, contribu…