Best James Conole, CFP® Podcasts (2025)

1
This Is Why Financially Ready People Struggle to Retire 11:51

9h 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…

1
Am I Behind? Rethinking Retirement Catch-Up Strategies 30:02

5d 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…

1
What Should You Do With Your 401k When You Retire? 16:25

7d 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 …

1
DIY vs. Financial Advisor: How to Know When It’s Time to Get Help │ Root Talks 20:11

12d 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…

1
Want to Be a Better Advisor? Learn to Frame Wealth the Right Way 26:30

13d 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…

1
5 Signs It’s Time to Retire - Right Now 9:37

14d 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…

1
Are You Saving Money in the Right Order? 25:43

19d 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 …

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

21d 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…

1
Why Brokerage Accounts Might Be the Most Underrated Tool in Your Financial Plan 18:35

26d 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 …

1
How to Master the Skills That Usually Only Come With Age 26:00

27d 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…

1
5 Things Retirees Regret - And What You Still Have Time to Get Right 13:27

28d 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…

1
Stop Worrying About Running Out of Money: Here's What You Need to Do 14:41

1M 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…

1
Politics and Planning: What’s the Right Balance for Advisors? 17:15

1M 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…

1
This Is What Financial Planning Really Changes 18:25

1M 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…

1
How Much Do You Need to Retire on $10K a Month? 13:17

1M 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…

1
From Saver to Spender: How to Ease the Emotional Shift into Retirement 26:09

2M 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…

1
I've Helped Hundreds of People Retire Comfortably. Here's the Exact 7-Step Framework I Used. 21:38

2M 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 …

1
Ready to Retire? Here's How to Tell Your Company │ Root Talks 24:32

2M 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…

1
Keys to Nailing Withdrawal Rate Conversation with Clients 23:28

2M 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…

1
How Much Can We Expect to Spend in Retirement with a $4M Portfolio? 18:11

2M 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. …

1
Rethinking Your Retirement Timing 18:19

2M 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 “…

1
Social Security at 62 vs 67 vs 70: When should you start claiming your benefits? 19:14

2M 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…

1
The Surprising Regrets of Wealthy Retirees | Root Talks 16:05

2M 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…

1
Roth Conversions Done Right: What Great Advisors Know That Software Doesn’t 22:42

2M 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…

1
We have a $3M Retirement Portfolio. How Much Can We Spend Without Running Out of Money? 15:26

2M 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…

1
What’s the Purpose of Your Money? 12:49

3M 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…

1
Root Talks: Spend Your Way to a Happier Retirement: 5 Pillars of Better Spending 19:01

3M 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…

1
A Guide for Navigating Client Conversations When Markets Are Crazy 30:55

3M 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…

1
The Most Powerful Tax-Free Retirement Tool: Start Leveraging Your HSA Now 16:59

3M 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…

1
Liberation Day, Trade Wars, and Your Portfolio: What Investors Need to Know 24:00

3M ago24:00

24:00

Is market volatility really all about tariffs? In the wake of the unexpectedly aggressive “Liberation Day,” headlines would have you believe so. But the bigger culprit isn’t trade policy—it’s uncertainty. While U.S. markets have taken a noticeable hit, international developed markets are down only about 1.3% as of this recording. So what’s really g…

1
When is the Best Time to Realize Gains in my Investment Account? 17:47

3M ago17:47

17:47

If you’re sitting on large investment gains in a brokerage account and wondering whether it’s worth taking the tax hit, this episode is for you. I walk through a clear framework I use with clients to help them decide when—and if—it makes sense to realize those gains. I also explain several strategies that can potentially reduce or even eliminate th…

1
Root Talks: How Does the Advisory Team Structure Work at Root? 24:42

3M ago24:42

24:42

What actually goes into creating a world-class client experience at Root? We're walking through the structure behind Root's advisory team—and how we ensure every client gets consistent, thoughtful guidance no matter who they’re working with. We break down the different advisor roles, from Client Service Associate to Senior Financial Advisor, and ex…

1
Become a Highly Effective Advisor: Time Management & Productivity Tools 22:50

3M ago22:50

22:50

Struggling to get meaningful work done despite your technical expertise and people skills? You're not alone. Every financial advisor knows the frustration of ending a busy day feeling like nothing important was accomplished. The culprit? It's not your ability – it's how you're managing your time and attention in a world designed to fragment both. I…

1
How Much Do I Need to Retire? (3 Simple Steps to Determine the Right Amount) 17:31

3M ago17:31

17:31

Wondering if you can retire at 60 with $2 million? In this episode, I walk you through a simple, 3-step process to figure out exactly how much you need in your portfolio to retire comfortably—and confidently. Whether you've already run the numbers or you're just starting to think about retirement, this is a great way to gut-check your plan. We'll t…

1
The Art of Knowing When to Save or Spend 20:51

3M ago20:51

20:51

Balancing today’s lifestyle with tomorrow’s goals isn’t easy, but it’s doable. In this episode, we answer a listener's question about 401(k) contribution limits and employer matching, which opens up a broader conversation about financial flexibility and smart savings strategies. We break down 2025 contribution limits, including catch-up provisions …

1
Maximize Your Retirement Tax Savings: How to Maximize Tax-Saving for Each Account 19:06

4M ago19:06

19:06

Want to pay less in taxes during retirement? You actually have more control over your tax rate than you might think. James breaks down how different investment accounts—like brokerage accounts, 401(k)s, Roth IRAs, HSAs, and inherited accounts—are taxed and how smart withdrawal strategies can help you minimize taxes over time. He also explains key c…

1
Root Talks: How to Get Past the Fear of Retiring Even When You Have Enough 22:02

4M ago22:02

22:02

Many professionals find that retiring isn’t just about having enough money—it’s about feeling ready to leave behind the structure, identity, and comfort of a career. In this Root Financial podcast episode, James and Ari explore the emotional hurdles of retiring from a high-paying, high-stress job, even when financially prepared. They highlight the …

1
How to Create Meaningful Conversations When Presenting Portfolio Performance to Clients 27:59

4M ago27:59

27:59

We explore how advisors can effectively present portfolio performance to clients, especially during periods when their investments underperform relative to major market indices like the S&P 500. Through practical examples and a structured approach, we demonstrate how to transform potentially difficult conversations into relationship-strengthening o…

1
The Hidden Flaw in Monte Carlo Analysis That's Ruining Retirement Plans 24:32

4M ago24:32

24:32

Many retirees focus on achieving a high Monte Carlo “probability of success” in retirement—but is chasing a 99% success rate always the best move? In this episode, James highlights a real-life story of a man forced to delay retirement after a divorce dropped his probability of success from 99% to 70%. James explores why this single number shouldn't…

1
Try Before You Buy: How to Test-Drive Big Life Transitions 20:19

4M ago20:19

20:19

Major financial transitions don't have to be binary choices – testing your assumptions before making big moves can prevent costly mistakes and regrets. In this episode, Nick and Scott talk about test-driving potential life transitions to help guide your decisions. • Looking at buying a home? Try setting aside the difference between rent and project…

1
Why many retirees REGRET relying on Social Security Income 13:20

4M ago13:20

13:20

Relying too much on Social Security? You’re not alone—over 40% of retirees count on it for at least half their income. But that safety net has some major gaps. In this video, I break down four key reasons why Social Security isn’t enough—and what you can do to secure a more stable retirement. Questions answered: 1. Why is it a mistake to rely too h…

1
Root Talks: What Role Does "Fun" Play in an Advisory Relationship? 15:50

4M ago15:50

15:50

How do you keep things fun when markets—or life—get tough? We're breaking down why “fun” isn’t just about ping pong tables and perks—it’s about being prepared, building trust, and maintaining strong relationships before challenges arise. James shares a personal story from the early Covid days, highlighting how mindset and self-care helped him show …

1
Your Role as an Advisor Is Not What You Think It Is 12:36

4M ago12:36

12:36

A simple question from my dad years ago completely transformed my approach to financial advising: "What is your role as an advisor to your clients?" After several incorrect guesses, his answer stunned me with its clarity and wisdom - "Your role is to help organize your clients' thinking." This perspective shifted everything. While many of us excel …

1
Defining the Six Core Standards of Financial Advisor Excellence 25:53

4M ago25:53

25:53

What separates truly exceptional financial advisors from the merely adequate ones? It's not credentials, years of experience, or even what firm they've worked for – it's something more fundamental. In this foundational episode of the Root Ready podcast, we define the six core standards that constitute excellence in financial advising. Drawing from …

1
Root Ready Intro Episode: A Podcast for Growth-Minded Financial Advisors 12:44

4M ago12:44

12:44

What does it truly mean to be an exceptional financial advisor in today's world? The answer goes far beyond technical designations or sales ability. The Root Ready podcast tackles a critical gap in advisor development. While the industry often laments talent shortages, the real issue lies in how we're preparing advisors to excel. James Conole, foun…

1
9 Things To STOP DOING After 60 16:19

4M ago16:19

16:19

If you're over 60, it's time to stop certain habits that may be holding you back from fully enjoying your retirement. In this video, I’ll share key lessons learned from working with retirees, including how small shifts can lead to a more meaningful and financially secure future. From when to stop saving, how to spend wisely, prioritizing health, an…

1
Taking Control of Your Financial Future: Planning, Investing & Risk Management 24:21

4M ago24:21

24:21

In the face of the uncertainty of life, it’s difficult knowing that many things are out of your control. Focusing on your financial well-being can often feel daunting, especially with the unpredictability of markets. In this episode, we discuss aspects of your financial journey that you can control, like… - The importance of having a structured fin…

1
Your Roth IRA Could be Locked For 5 Years. Here's Why 12:28

4M ago12:28

12:28

Roth IRAs are a great way to build tax-free retirement income—but the withdrawal rules can be tricky. In this video, I’ll break down the five-year rules, how contributions, conversions, and growth are treated, and smart strategies to avoid unnecessary taxes. Understanding these rules can help you make the most of your Roth IRA and keep more of your…

1
Root Talks: How Do Smart Retirees Handle Big One-Time Expenses? 18:58

5M ago18:58

18:58

Root Collective member Gary asks how to fund a $40K home remodel before retiring—should he use a taxable brokerage account, tax-deferred 401(k), Roth IRA, or cash? Ari and I break down how to handle big one-off expenses into a three-part framework: Portfolio Sustainability – Can your investments handle both recurring and one-time expenses? Investme…

1
The Best Retirement Spending Stories I've Heard This Year 11:29

5M ago11:29

11:29

Are You Spending Your Money on What Truly Matters? A few weeks ago, I challenged you to do the most important thing you can with your money this year—not Roth conversions, not optimizing Social Security, but something far more impactful: aligning your spending with what truly brings you joy. I asked you to write down one thing you've always wanted …

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James Conole, CFP® Podcasts

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