Best James Conole Podcasts (2025)

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It’s Open Enrollment Season: How to Avoid Leaving Money on the Table 24:16

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18h ago24:16

24:16

A lot of people are under-utilizing their corporate benefits, unintentionally leaving money on the table. Open enrollment is a great opportunity to review your company’s benefits plan to ensure that you’re taking full advantage of everything they offer. In this episode, we walk through some of the most common areas you can optimize your benefits, s…

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Ep 461: Helping Clients Live Intentionally And Generously With Charitable Giving Events (That Also Drive New Growth) with Zac Larson 1:29:59

3d ago1:29:59

1:29:59

Crafting a charitable giving strategy isn't just about tax efficiency—it's a way for clients to define the deeper purpose of their wealth. When advisors center generosity in both planning conversations and firm culture, they can strengthen relationships and attract values-driven clients. This episode explores how integrating charitable intent into …

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3 Steps to Build a Retirement Paycheck That Lasts 19:17

3d ago19:17

19:17

Early retirement income can feel complicated, but a steady paycheck from savings starts with a simple framework. This episode reframes withdrawal decisions, explains why a fixed 4 percent rule can be too conservative in some cases, and shows when a 5 percent starting point may fit with the right allocation and ongoing adjustments. A million dollar …

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Your Tax Planning Window Won’t Last Forever | Top 3 Strategies to Prioritize 21:28

6d ago21:28

21:28

Retiring early isn’t just about having enough money, it’s about using the right tax moves in the right years. This conversation between James and Ari maps the three biggest levers for early retirees: Roth conversions, ACA health insurance subsidies, and 0% long-term capital gains. A real-world case study shows how account mix and spending levels ca…

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Will Low Returns Ruin Your Retirement? (How to Interpret Goldman Sachs 3% Forecast) | Root Talks 16:17

8d ago16:17

16:17

What if the next 10 years bring just 3% returns from the S&P 500? In this episode, we turn that forecast into a real-world retirement plan—not panic. You’ll learn how to stress test your portfolio, build flexibility into your spending, and design a withdrawal strategy that can survive tough markets. Listen as James and Ari break down: Sequence-of-r…

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Stop Ending the Day Exhausted: A Playbook for Peak Performance 17:45

9d ago17:45

17:45

Ever finish a day full of meetings or creative work and feel wiped out, even when you love what you do? James did too, until one image changed how he looked at energy forever. After seeing a scan of a “brain on meetings,” he realized the problem wasn’t the work itself, it was the lack of recovery between high-focus efforts. That insight led him to …

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Ep 460: Establishing The Operational Systems It Takes To Truly Serve Ultra-HNW Clients Effectively with Stephanie Hughes 1:29:59

11d ago1:29:59

1:29:59

While many financial advisory firms seek to move 'upmarket' and serve high-net-worth and ultra-high-net-worth clients, these clients typically require (and often demand) a different level of service—and can benefit from a more integrated experience across legal, tax, and financial domains. For these firms, creating efficient operational systems is …

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3 Investments That Should Never Go In Your Retirement Portfolio 12:08

10d ago12:08

12:08

Think your retirement’s safer with a little gold, a favorite stock, and a home full of equity? Time for a reality check. In this episode, we put three “sacred” retirement assets to the test and show how they can quietly derail the one outcome that really matters: a steady paycheck for life. You’ll learn how to define your retirement portfolio’s rea…

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We're 62 with $2M: Retire Now or Wait? 13:27

14d ago13:27

13:27

The real question isn’t “Can we retire?”, it’s “On how much, and when do the big costs fade so our savings can breathe?” In this episode, James walks through one couples' retirement plan to show how timing, travel, and housing choices can turn a shaky forecast into a confident glidepath. He highlights the income canyon most people miss (the stretch…

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What Business Owners Need to Know About the OBBBA 16:38

16d ago16:38

16:38

The One Big Beautiful Bill Act has some pretty great enhancements for business owners, but you have to know what you’re looking for in order to get them. Whether it’s the extension of Qualified Business Income, the 100% Bonus Depreciation, or Enhanced Qualified Small Business Stock, the bill has something for businesses of any size. In this episode…

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Ep 459: Working More Collaboratively With Clients' CPAs For Better Tax Planning (And Cross-Referral) Outcomes with Steven Jarvis 1:30:00

18d ago1:30:00

1:30:00

Tax planning strategies can fall flat if financial advisors and CPAs aren't working together. Miscommunication, timing issues, and a lack of context can create friction—or worse, lead to missed opportunities or costly mistakes. Steven Jarvis is the CEO of Retirement Tax Services, a tax education and preparation firm that partners with financial adv…

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10 Ways Retirement Has Completely Changed in 30 Years 11:32

18d ago11:32

11:32

Forget the gold watch and glide path to the couch. Retirement has been rewritten. In this episode, James walks through the 10 biggest shifts redefining life after work—and how to replace outdated rules with a plan that’s practical, human, and built for how people actually live today. From the mindset shift away from Depression-era scarcity to using…

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$10M+ Net Worth Case Study: What to Do First 16:48

21d ago16:48

16:48

What if the real financial risk isn’t running out of money, but running out of time to use it well? In this episode, listen as James and Ari unpack a $14 million case study with concentrated inherited stock, sizable retirement accounts, and big questions about spending, portfolio risk, taxes, and legacy. See how a single allocation decision can swi…

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Ep 458: Overcoming Perfectionism Burnout While Still Serving Clients Well With A Standard Of "Calm Excellence" with Lisa Brown 1:30:00

25d ago1:30:00

1:30:00

Given the high stakes involved (and the desire to provide high-quality service) when working with clients, it can be tempting for financial advisors to lean into perfectionist tendencies. However, doing so can sometimes lead to overwork and potentially burnout, particularly as a firm grows over time. Lisa Brown is the President of Greenwood Gearhar…

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The 3 Worst Retirement Mistakes I See All the Time 12:25

25d ago12:25

12:25

By James Conole, CFP®

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The BEST Retirement Advice (From 909 Real Retirees) 11:36

28d ago11:36

11:36

What if the riskiest move isn’t retiring too early, but waiting so long your best years pass by? This episode unpacks the real regrets of 909 retirees and the practical steps they wish they’d taken sooner. Design purpose. Spend on what matters. Do it while health and energy are on your side. Beat the “one more year” trap. Working longer can look sa…

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The Cliché Advice You Should Finally Pay Attention To 19:47

30d ago19:47

19:47

We’ve all heard the clichés: focus on what you can control, embrace the pain not the suffering, fight for what you want. Easy to dismiss, right? But the truth is, those sayings stick around for a reason. They hold the kind of wisdom that can change how you approach life, work, and even setbacks. What often gets missed is that clichés aren’t about p…

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How to Quickly Communicate the Real Value of Your Advice 25:05

1M ago25:05

25:05

Advisors often stumble when they try to prove their worth by listing services. Tax planning, investments, estate documents... it can feel like noise to a prospect who just hears “another $27,000 a year.” What really moves the needle is helping clients connect their unspoken fears and goals to the value you deliver. The truth is, the skills that got…

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Ep 457: Making Financial Planning Less Scary For New Clients By Focusing First On What Brings Them Joy with Larry Sprung 1:30:00

1M ago1:30:00

1:30:00

While many financial advisors begin with dollars and data, today's guest believes the path to long-term client relationships starts with one powerful question: What brings you joy? By focusing on leading with purpose and values, he has grown a $200M firm and attracted clients who align with his philosophy. Larry Sprung is the founder of Mitlin Fina…

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5 Signs You Should Fire Your Financial Advisor 12:59

1M ago12:59

12:59

Most people stay with the wrong financial advisor far too long: out of loyalty, inertia, or fear of starting over. But the cost of sticking with the wrong person can be measured in dollars, stress, and lost years you can’t get back. 5 Signs You Should Fire Your Financial Advisor 1. They always say “ask your CPA” instead of doing proactive tax plann…

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Advice from Retirees: What They Wish They Knew in Their 50s 18:39

1M ago18:39

18:39

Ever wish your 80-year-old self could give you a nudge today? After years working with clients in their 70s and 80s, three lessons rise to the top: treat wealth as money, time, and health, know your financial independence number, and prioritize what money can’t buy while you still can. In your 50s–60s, many people hit a rare “sweet spot” where fina…

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Ep 456: Expanding From $75M Solo To $260M Multi-Advisor Team By Creating A Company Blueprint Of How Clients Will Be Served with Hilary Hendershott 1:29:59

1M ago1:29:59

1:29:59

Scaling a solo advisory firm into a thriving team-based business takes more than strong systems—it takes a shared sense of purpose and values that guide every decision. This episode explores how one advisor used a living "Blueprint" to align her team, empower her staff, and create a consistent, values-driven client experience. Hilary Hendershott is…

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Roth vs. Traditional IRA – Which One Really Saves You More? 12:32

1M ago12:32

12:32

Is a Roth IRA really better than a traditional IRA? The truth is... it depends on your tax situation. In this video, you’ll learn why your current tax bracket versus your retirement tax bracket should drive your decision, not blanket advice. Most retirees pay less in taxes later in life, which creates opportunities for smart strategies like tax arb…

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You Could Spend WAY More Than the 4% Rule Suggests (Says the Man Who Created It) 21:25

1M ago21:25

21:25

Financial planning’s most famous guideline just got an upgrade. In this exclusive interview, James speaks with Bill Bengen—the MIT-trained engineer turned financial advisor who created the 4% rule—about his updated research and what it means for retirees today. Bengen reveals that diversification alone can raise the safe withdrawal rate to 4.7%, an…

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How to Know You’ve Found the Right Financial Advisor │ Root Talks 18:18

1M ago18:18

18:18

What makes you trust someone with your financial future? In this episode of Root Talks, James and Ari unpack the powerful role of intuition in building lasting relationships with financial advisors, business partners, and even loved ones. They explain how what we call a gut feeling is actually condensed pattern recognition, your brain quietly scann…

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Frame It Right: A Simple Shift That Changes Client Behavior 11:58

1M ago11:58

11:58

Have you ever had a client who was financially ready to retire but just couldn't pull the trigger? They keep working, chasing one more bonus, one more year of 401(k) contributions, watching their financial projections climb higher while their actual life satisfaction stagnates. Listen as James unpacks what makes someone financially ready to retire,…

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Ep 455: Adding Hard-Dollar Value For HNW Executives By Guiding Them In Negotiating For More (Equity) Compensation with Emily Shacklett 1:29:59

2M ago1:29:59

1:29:59

Executive pay packages are complicated—which often leads to these individuals leaving money on the table. From equity negotiations to non-compete clauses, the right financial advisor can help clients fight for what they're worth. In this episode, we dig into how advisors can create real value for their clients during career transitions. Emily Shack…

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What’s the Smartest Investment Mix for Retirees Right Now? 13:42

2M ago13:42

13:42

Navigating market volatility in retirement requires more than the traditional 60/40 portfolio. This episode explores three critical risks every retiree must address to maintain financial security through changing market conditions. The first is sequence of return risk, which can devastate a portfolio if early withdrawals align with a downturn. List…

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The Real Reason Most People Struggle in Retirement (It’s Not Money) 6:55

2M ago6:55

6:55

Retirement planning is often framed as a numbers game where you can get lost in focusing on maximizing your 401(k), minimizing taxes, and chasing investment returns. But financial security alone doesn’t guarantee fulfillment. The bigger challenge many retirees face is psychological, not financial. The transition from decades of work into retirement…

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

2M 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

2M 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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Ep 454: Turning Abstract Behavioral Finance Research Into Practical Tools To Better Client Outcomes with Dr. Daniel Crosby 1:30:00

2M ago1:30:00

1:30:00

Behavioral finance is often viewed as abstract but it can be a powerful, practical tool for helping clients make better decisions and build lives that align with what matters most. This episode explores how applying behavioral insights and positive psychology can deepen client relationships and drive more meaningful planning conversations. Dr. Dani…

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

2M 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

2M 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

2M 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

2M 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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Ep 453: Improving Efficiency By Turning Client Meetings Into Working Sessions So There Is Less Follow-Up To Manage with Becky Walsh 1:29:59

2M ago1:29:59

1:29:59

Delivering financial planning efficiently doesn't have to mean compromising on depth or personalization. This episode explores how a "working session" model can streamline the client experience, reduce prep and follow-up time, and still create space for thoughtful, relationship-driven planning. Becky Walsh is the founder of Oak Maple Finance, an RI…

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

2M 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

2M 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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Ep 452: From $200M To $1.4B In 5 Years By Spending 15% Of Revenue On Marketing (That Still Works) with Gabriel Shahin 1:30:00

2M ago1:30:00

1:30:00

Scaling an advisory firm quickly requires more than just marketing - it demands intentional infrastructure, rapid lead conversion systems, and a team built for volume. This episode explores how investing heavily in digital marketing, building internal efficiencies, and empowering advisors can drive explosive growth without sacrificing client servic…

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

2M 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

2M 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

2M 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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Ep 451: Evolving Your Leadership Style And Hiring Process As The Firm Grows From 1 To 20 Team Members with Maggie Kulyk 1:29:16

2M ago1:29:16

1:29:16

Running a successful advisory firm takes more than great client service - it also means learning how to lead a team and build infrastructure to support growth. This episode explores how developing leadership skills, hiring intentionally, and leaning into personal values can lay the foundation for a thriving, mission-driven business. Maggie Kulyk is…

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

2M 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

3M 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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Ep 450: Adding $80M To Your Practice In 7 Years By Providing Financial Education Through Local Seminars with Ryan Morrissey 1:29:59

3M ago1:29:59

1:29:59

High-net-worth retirees are hungry for clear, actionable retirement education - but often don't know where to find it. This episode explores how hosting local educational seminars can create a consistent pipeline of engaged prospects and drive meaningful business growth for financial advisors. Ryan Morrissey is the founder of Morrissey Wealth Manag…

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

3M 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

3M 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

3M 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…