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 tw...
Mar 11, 2025•12 min•Ep. 274
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. Th...
Mar 06, 2025•19 min•Ep. 273
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 o...
Mar 04, 2025•11 min•Ep. 272
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,...
Feb 25, 2025•18 min•Ep. 271
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 r...
Feb 20, 2025•24 min•Ep. 270
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...
Feb 18, 2025•10 min•Ep. 269
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 con...
Feb 13, 2025•25 min•Ep. 268
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 o...
Feb 11, 2025•12 min•Ep. 267
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 know...
Feb 06, 2025•33 min•Ep. 266
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 h...
Feb 04, 2025•13 min•Ep. 265
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 i...
Jan 30, 2025•16 min•Ep. 264
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 bene...
Jan 28, 2025•18 min•Ep. 263
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 ...
Jan 23, 2025•26 min•Ep. 262
The Social Security Fairness Act, signed into law on January 5 by former President Joe Biden, repeals the Windfall Elimination Provision (WEP) and Government Pension Offset (GPO), which previously reduced Social Security benefits for individuals with non-covered pensions, such as teachers, firefighters, and postal workers. This change significantly increases benefits for affected individuals, in some cases by over $1,000 per month, and applies retroactively to the end of 2023. While the law addr...
Jan 21, 2025•11 min•Ep. 261
In this behind-the-scenes episode, James and Ari explore what sets Root apart in the financial advising industry. Moving beyond traditional roles like stock pickers and planners, they emphasize Root’s mission as “protectors” of clients’ most cherished goals, helping them achieve a life of purpose and fulfillment. They discuss how Root’s culture prioritizes personalized care and intentional growth, from hiring advisors who embody Root's ethos to reinvesting in services like tax planning and ...
Jan 16, 2025•28 min•Ep. 260
Direct indexing, an advanced investment strategy, allows investors to own individual stocks within an index instead of a mutual fund or ETF, offering greater control and flexibility. This approach is particularly valuable for tax-loss harvesting, where selling underperforming stocks and reinvesting can offset gains and reduce taxes without losing market exposure. Ideal for high tax brackets, concentrated stock positions, or charitable giving, direct indexing can boost returns by 0.5%-1.85% annua...
Jan 14, 2025•24 min•Ep. 259
James and Ari provide a behind-the-scenes look at Root Financial, shifting from typical financial strategies to how their team operates. They discuss Root’s intentional approach to maintaining consistency in financial advising through rigorous hiring practices and its structured training program, "Root University." James emphasizes the importance of aligning advisors with the firm's ethos to ensure clients receive a consistent and personalized experience. The hiring process focuse...
Jan 09, 2025•25 min•Ep. 258
Many individuals are hesitant to retire, even when financially prepared, due to uncertainty and a lack of clear planning. This episode provides a practical guide to making retirement a reality, focusing on three key steps: Assess Your Current Financial Health Envision Your Ideal Retirement Connect Financial Readiness to Goals By addressing these steps, you can retire confidently, balancing future preparation with enjoying today. Questions answered? 1. How can I determine if I am financially read...
Jan 07, 2025•18 min•Ep. 257
In this episode of Root Talks, James and Ari dive into the reality that retirement planning can be tricky, with the fear of running out of money and the regret of underspending often at odds. The key is finding balance—spending wisely while enjoying life. Tools like projections, guardrails, and trade-off scenarios help bring clarity. The “rule of 72” shows how compound interest can grow savings significantly over time, helping build lasting wealth. On the flip side, too much frugality can lead t...
Jan 02, 2025•23 min•Ep. 256
LJ and Kelly share their inspiring journey of embracing a retirement lifestyle before fully retiring. Motivated by Kelly’s experiences as a physical therapist, witnessing many patients unable to enjoy retirement due to health issues, the couple prioritized travel and adventure. In 2021, they embarked on a year-long U.S. road trip, staying in Airbnbs for months at a time, visiting friends and family, and exploring cities deeply. They emphasize meticulous planning for finances, healthcare, and log...
Dec 31, 2024•38 min•Ep. 255
James and Ari discuss diversification and the nuances of managing investments. A client plans to split his funds across multiple institutions, like Schwab and Vanguard, believing it will improve diversification, but true diversification isn’t about holding accounts at different places but ensuring varied asset allocation. Using examples, James and Ari highlight risks such as single stock and sector concentration, explaining that owning the same stock or sector across institutions offers no added...
Dec 26, 2024•23 min•Ep. 254
Retirement is an exciting milestone, but it often comes with common fears. With proper planning, these concerns can be addressed to ensure a fulfilling and secure new chapter. Here are five major retirement fears and strategies to overcome them: Fear of Outliving Savings Optimize your Social Security strategy (e.g., delay benefits for higher payouts or collect earlier to reduce portfolio withdrawals). Save adequately by identifying your retirement goals and creating a tailored savings plan. Cond...
Dec 24, 2024•17 min•Ep. 253
Many middle-aged adults nearing retirement face anxiety over uncontrollable factors like Social Security cuts, lower investment returns, and increasing tax rates. Ari and James discuss how fear of these uncertainties can cause “analysis paralysis,” leading some to delay retirement unnecessarily. Instead of fixating on what cannot be controlled—like Congress or market behavior—they recommend proactive financial planning and modeling worst-case scenarios. For example, if Social Security were cut b...
Dec 19, 2024•25 min•Ep. 252
Are you mistaking a Monte Carlo analysis for real financial planning? I'll explain why this common tool, often used by financial advisors, is not a substitute for a true financial plan. A Monte Carlo analysis provides probabilities of success based on investment outcomes, but it doesn’t offer actionable steps, strategies, or a clear path to achieving your goals. I’ll break down the benefits and limitations of Monte Carlo simulations and show you what real financial planning should deliver: ...
Dec 17, 2024•20 min•Ep. 251
Here’s the thing: retirement isn’t just about hitting a magic number—it’s about understanding what you actually want out of your life once work is no longer in the picture. In their chat, Ari and James dive deep into this question, starting with a listener’s email: “I’ve got $7.8 million, no debt, and I’m 57—can I retire?” Sounds simple, right? Not quite. The duo walks through their Sequoia system, a framework designed to help people figure out whether they’re ready to retire and, more important...
Dec 12, 2024•31 min•Ep. 250
James breaks down five common retirement mistakes and how to avoid them for a secure and fulfilling future: Spending Wrong: Overspending risks running out of money; underspending misses out on life. Bad Timing: Retiring too early strains finances, while retiring too late sacrifices experiences. Ignoring Risks: Overlooking inflation or focusing only on market volatility hurts long-term stability. Over Helping Kids: Excessive financial support can jeopardize retirement security. No Strategy: A lac...
Dec 10, 2024•17 min•Ep. 249
In their new podcast, Root Talks, James and Ari open up about the story behind Root—their financial advisory firm—and how it grew from humble beginnings into a nationwide company with hundreds of clients, a 30-member team, and nearly $1 billion in managed assets. James shares how the unexpected twist of being forced out of a stable financial advisor role led him to reevaluate everything. That introspection sparked the vision for Root, a firm built around purpose-driven financial planning. For hi...
Dec 05, 2024•31 min•Ep. 248
Chris was burned out. Despite enjoying aspects of his work, the relentless grind of long hours and aggressive saving left him exhausted and longing for retirement. His goal was to save as much as possible, retire in a few years, and finally spend time with his wife, travel, and enjoy life. However, James, founder of Root Financial, offered surprising advice: stop saving for retirement. After analyzing Chris’s portfolio, James discovered that the growth of Chris’s investments was outpacing his ne...
Dec 03, 2024•15 min•Ep. 247
Roth conversions are almost a buzzword today, with many people jumping into them like they’re a guaranteed fix for tax worries—much like rushing into surgery hoping it will solve all your problems. But just like surgery, Roth conversions require careful consideration, and they’re not always the right solution. Before deciding to convert, it’s essential to understand why not to do it. Here are some key reasons to skip—or at least pause—on Roth conversions: - Lower Future Tax Bracket: If you antic...
Nov 28, 2024•30 min•Ep. 246
Meet Sarah—a retiree with a multi-million-dollar portfolio, no mortgage, and all her income needs covered by Social Security. Yet, she hesitates to furnish her newly expanded home, fearing it would “waste” money. In this episode, James unpacks Sarah’s story to explore why so many of us struggle to spend, even when we're financially secure. James explores concepts like: - The Purpose of Money: Money is a tool, not an end goal—it’s meant to be exchanged for experiences and joy. - Diminishing ...
Nov 26, 2024•21 min•Ep. 245
