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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 s…

Many retirees focus …

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 drive such massive decisions. He explains how context—like income sources, spending flexibility, and home equity—matters more than a static success rate. You’ll learn why 100% isn’t always ideal, and how to build a retirement plan…

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…

Relying too much on …

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 heavily on Social Security for retirement income?2. What are some strategies to supplement Social Security income in retirement?Submit your request to join James:On the Ready For Retirement podcast: Apply HereOn a Retirement Makeover episode: …

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 m…

How do you keep thin…

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 up for clients.The takeaway? A great advisor isn’t just there for the good times—they’re prepared to guide you through the tough ones, too.Submit your request to join James:On the Ready For Retirement podcast: Apply HereOn a R…

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 retire…

If you're over …

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, and letting go of worries that no longer serve you, these insights will help you make the most of your retirement years.📌 Watch now to discover how to live with more freedom, joy, and financial confidence!Questions answered:1. How can I m…

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…

Roth IRAs are a grea…

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 Money tax-free. Let’s dive in!Questions answered?1. When can you withdraw money from a Roth IRA without paying taxes or penalties?2. How do the two different five-year rules for Roth IRAs affect withdrawals?Questions answered?1. When can you wi…

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 …

Root Collective memb…

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?Investment Allocation – Ensure your assets are positioned to avoid selling at a loss.Tax Optimization – Withdraw strategically to minimize lifetime taxes.The key? Plan ahead, align financial decisions with long-term goals, and make the most of your reti…

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 Secur…

Are You Spending You…

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 to do or buy but haven't, set a date to make it happen, and identify where the funds would come from.In today’s episode, I’m sharing some of the incredible responses I received—stories of Travel, family experiences, and meaningful pu…

One of the biggest ironies in retirement is that the people who save and invest the most often struggle the most with actually spending their money in retirement. In this video, I’ll walk you throug…

One of the biggest i…

One of the biggest ironies in retirement is that the people who save and invest the most often struggle the most with actually spending their money in retirement. In this video, I’ll walk you through a simple framework to make spending easier—without guilt or second-guessing.I’ll share a compelling client story, a personal experience, and actionable steps you can take to shift your mindset and enjoy the retirement you’ve worked so hard for. If you’ve ever hesitated to spend on things you value, even when you can afford to, this is for you.We’ll cover:Why our money habits from the p…

You’ve worked hard, built wealth, and reached financial security… so why is it still so hard to spend? In this episode, we dive into the unexpected challenge of shifting from a saver’s mindset t…

You’ve worked hard…

You’ve worked hard, built wealth, and reached financial security… so why is it still so hard to spend? In this episode, we dive into the unexpected challenge of shifting from a saver’s mindset to actually enjoying your money.From a millionaire couple hesitating over a $5 bag of M&Ms to a husband upset about a bottle of Fiji water—this is more common than you think! Behavioral Finance reveals why past money habits stick with us, even when we don’t need them anymore.We’ll break down how to retrain your mindset, align spending with what truly matters, and ensure your wealth enhanc…

Retirement isn’t just about the numbers—it’s about time, health, and the life you want to live. Too many people delay retirement, chasing "one more bonus" or "one more year" without considering …

Retirement isn’t j…

Retirement isn’t just about the numbers—it’s about time, health, and the life you want to live. Too many people delay retirement, chasing "one more bonus" or "one more year" without considering the bigger picture.In this video, we’ll walk through five key questions that can help you decide. If you answered yes to any of these, retirement might be closer than you think! Watch now to gain Clarity on your next steps.Questions answered?1. How do you know if it's the right time to retire?2. What are the risks of delaying retirement for financial reasons?Submit your request to join Jame…

In this episode, we're talking about the importance of a strategic withdrawal plan in retirement to keep taxes in check and set you up for long-term financial stability. Ari and I break down why …

In this episode, we&…

In this episode, we're talking about the importance of a strategic withdrawal plan in retirement to keep taxes in check and set you up for long-term financial stability. Ari and I break down why a simple 50/50 split between traditional and Roth accounts isn't enough—you need to plan based on your tax situation and future needs. Using a listener's example, we walk you through how to think about tax brackets, required minimum distributions (RMDs), and when it might make sense to convert funds to a Roth IRA.We also discuss the role of asset location—putting riskier investments …

In this episode, we're talking about the importance of a strategic withdrawal plan in retirement to keep taxes in check and set you up for long-term financial stability. Ari and I break down why …

In this episode, we&…

In this episode, we're talking about the importance of a strategic withdrawal plan in retirement to keep taxes in check and set you up for long-term financial stability. Ari and I break down why a simple 50/50 split between traditional and Roth accounts isn't enough—you need to plan based on your tax situation and future needs. Using a listener's example, we walk you through how to think about tax brackets, required minimum distributions (RMDs), and when it might make sense to convert funds to a Roth IRA.We also discuss the role of asset location—putting riskier investments …

James challenges the idea that financial security comes from always having more—more savings, more income, more investments. Studies show that no matter how much people have, they often feel like th…

James challenges the…

James challenges the idea that financial security comes from always having more—more savings, more income, more investments. Studies show that no matter how much people have, they often feel like they need twice as much to feel secure. That mindset can make fulfillment feel just out of reach.Instead, James asks: What’s one thing you could do or buy to make this year special? He shares stories like a couple who used an unexpected windfall to buy a boat—not as an investment, but to create years of unforgettable memories.The takeaway? Money isn’t the goal—it’s the tool that helps you …

Vanguard’s Advisor Alpha study shows that working with an advisor can boost net returns by around 3% annually through smart Investing, tax planning, and behavioral Coaching. But the real value? It�…

Vanguard’s Advisor…

Vanguard’s Advisor Alpha study shows that working with an advisor can boost net returns by around 3% annually through smart investing, tax planning, and behavioral coaching. But the real value? It’s not just about numbers.Ari and James break down how advisors help clients stay level-headed, avoid costly mistakes, and feel more confident about their future. Research even shows investors with $1.2M+ report greater financial happiness with an advisor by their side.Not everyone needs one, but knowing when professional support can make a real difference? That’s the key.Submit your request to …

For nearly 50 years after Social Security's inception in 1935, benefits were not subject to federal income taxes. That changed in 1983 when Congress introduced taxation on benefits for higher-inc…

For nearly 50 years …

For nearly 50 years after Social Security's inception in 1935, benefits were not subject to federal income taxes. That changed in 1983 when Congress introduced taxation on benefits for higher-income retirees, using a "provisional income" threshold of $25,000 for individuals and $32,000 for couples. However, these thresholds were never adjusted for inflation, leading to a significant increase in the number of retirees paying taxes on their benefits—now nearly 50%. President Trump has proposed eliminating federal taxation on Social Security, a move that could benefit retirees financially…

Join the new Root Collective HERE!Retirement isn’t just about having enough money—it’s about making the most of it. That’s why we’re launching a new retirement community designed to go beyon…

Join the new Root Co…

Join the new Root Collective HERE!Retirement isn’t just about having enough money—it’s about making the most of it. That’s why we’re launching a new retirement community designed to go beyond financial planning. Sure, we’ll cover investing, tax strategies, and Estate planning, but we’re also creating a space to talk about the things that make retirement fulfilling—connection, travel, health, and purpose.Inside, you’ll be able to engage with like-minded peers, get expert insights, and explore ideas to shape the next chapter of your life. We’ll have guest speakers, live event…

To maximize your Social Security benefits in retirement, it’s essential to understand five key limits and thresholds:✅ Earnings Limit: If you start Social Security before full retirement age, bene…

To maximize your Soc…

To maximize your Social Security benefits in retirement, it’s essential to understand five key limits and thresholds:✅ Earnings Limit: If you start Social Security before full retirement age, benefits may be reduced if your wages exceed the annual or monthly earnings limit. Only income earned after starting benefits counts.✅ Social Security Wage Base: This is the maximum amount of earnings subject to Social Security taxes each year. It impacts both how much you pay into the system and the benefits you may receive.✅ Maximum Benefit: Your benefit amount is based on factors like your life…

Root Financial is redefining what it means to serve clients by putting team culture front and center. In this episode, James and Ari dive into the firm’s bold move to hire a Head of Culture—an unc…

Root Financial is re…

Root Financial is redefining what it means to serve clients by putting team culture front and center. In this episode, James and Ari dive into the firm’s bold move to hire a Head of Culture—an uncommon role in financial advising—dedicated to supporting the growth and well-being of their advisors. Why? Because when advisors thrive, clients get the personalized attention they deserve.At Root, we’re intentional about avoiding the usual industry traps, like overloading advisors with massive client lists or sales quotas that can compromise service. Instead, we focus on sustainable growth, a…