Ready For Retirement

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 the taxes you might owe, including how to take advantage of the 0% long-term capital gains tax bracket, gifting appreciated assets, and tax-loss har...

Transcribed - Published: 22 April 2025

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 explain how our “farm system” approach helps us grow top-tier advisors from the ground up. It’s not just about years of experience—it’s about shared...

Transcribed - Published: 17 April 2025

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 talk about how to calculate your real retirement expenses (hint: it’s probably not your current salary), factor in income like Social Security or a...

Transcribed - Published: 15 April 2025

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 concepts like the 0% capital gains bracket, step-up in basis, and Social Security taxation. Learn how to make tax-smart moves with your retirement i...

Transcribed - Published: 8 April 2025

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 value of aligning retirement with your future self’s goals and priorities, not just your current fears. Submit your request to join Jam...

Transcribed - Published: 3 April 2025

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 succes...

Transcribed - Published: 1 April 2025

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 you...

Transcribed - Published: 25 March 2025

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. Subm...

Transcribed - Published: 20 March 2025

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 ho...

Transcribed - Published: 18 March 2025

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 t...

Transcribed - Published: 11 March 2025

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.T...

Transcribed - Published: 6 March 2025

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...

Transcribed - Published: 4 March 2025

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 va...

Transcribed - Published: 25 February 2025

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...

Transcribed - Published: 20 February 2025

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....

Transcribed - Published: 18 February 2025

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 t...

Transcribed - Published: 13 February 2025

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 yea...

Transcribed - Published: 11 February 2025

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...

Transcribed - Published: 6 February 2025

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 pr...

Transcribed - Published: 4 February 2025

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 expl...

Transcribed - Published: 30 January 2025

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...

Transcribed - Published: 28 January 2025

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 cli...

Transcribed - Published: 23 January 2025

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 ...

Transcribed - Published: 21 January 2025

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 es...

Transcribed - Published: 16 January 2025

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% an...

Transcribed - Published: 14 January 2025

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 focuses on cultura...

Transcribed - Published: 9 January 2025

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 HealthEnvision Your Ideal RetirementConnect Financial Readiness to GoalsBy addressing these steps, you can retire confidently, balancing future preparation with enjoying today. Questions answered? 1. How can I determine if I am financially r...

Transcribed - Published: 7 January 2025

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 l...

Transcribed - Published: 2 January 2025

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...

Transcribed - Published: 31 December 2024

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 ad...

Transcribed - Published: 26 December 2024

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 p...

Transcribed - Published: 24 December 2024

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 cu...

Transcribed - Published: 19 December 2024

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: c...

Transcribed - Published: 17 December 2024

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 impor...

Transcribed - Published: 12 December 2024

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 lack...

Transcribed - Published: 10 December 2024

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. Fo...

Transcribed - Published: 5 December 2024

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 hi...

Transcribed - Published: 3 December 2024

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 ...

Transcribed - Published: 28 November 2024

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 M...

Transcribed - Published: 26 November 2024

Are you delaying retirement, working for "just one more year" to feel ready? In this episode, Ari and James dive into goalpost planning—the tendency to postpone retirement over financial or emotional uncertainties. Learn how to prioritize life goals over arbitrary benchmarks, like saving $1M or following a generic 60/40 portfolio strategy. 🎙️ Highlights from the conversation: The emotional challenges of leaving work and finding purpose in retirementWhy cash flow matters more than hitting a s...

Transcribed - Published: 21 November 2024

In today’s episode of Ready for Retirement episode James covers when to adjust your portfolio as retirement nears—a crucial step for balancing growth and security. If adjustments happen too late, market downturns could delay your plans; if too early, you might miss out on potential growth. The focus is on reallocating stocks to more stable investments like bonds as you approach the time you’ll need to start drawing from your portfolio. Historical data shows that while the stock market grows ...

Transcribed - Published: 19 November 2024

Meet Ari Taublieb 👋 If you didn’t already know, Ari and I work together at Root Financial, and we thought it was finally time to launch a podcast series together. In our very first episode, we dive into a topic that many people shy away from: talking to your parents about money. Whether it’s discussing their estate plans, long-term care, or the tough conversations around wealth, these talks can feel awkward—but they’re absolutely essential. In this episode, we break down: ▪️ Our personal st...

Transcribed - Published: 14 November 2024

Roth IRAs offer great tax-free income benefits, but to make the most of them in retirement, here are seven things you need to know: Contribution Limits: In 2024, you can contribute up to $7,000 annually ($8,000 if 50+), across both Roth and traditional IRAs.Access to Contributions: You can withdraw your contributions at any time, tax-free and penalty-free. Only earnings are subject to penalties if withdrawn early.The Five-Year Rule: To withdraw earnings tax-free, the Roth IRA must be held f...

Transcribed - Published: 12 November 2024

Have you thought about what moving to a new state might mean for your retirement budget and lifestyle? In this Ready for Retirement episode, the focus is on preparing for an out-of-state retirement. James outlines three essential considerations for retirees planning a move: 1. Housing Costs and Expenses: From property values and local property taxes to potential capital gains from selling a current home. 2. Overall Cost of Living: Everything from groceries to utilities varies widely between ...

Transcribed - Published: 5 November 2024

Many dream of retiring early, but you would be surprised to learn that many people who retire early regret doing so. James reveals five things that lead people to regret early retirement and provides practical tips to avoid these pitfalls. He explains why many individuals who retire before 65 struggle due to a lack of planning, overly conservative investment strategies, and failure to envision life beyond work. He highlights the importance of aligning financial plans with personal goals, mai...

Transcribed - Published: 29 October 2024

James sits down with someone who’s financially set to retire—mortgage paid off, kids through college, and investments in place—but he’s still grappling with one big question: what’s next? Instead of focusing solely on financial strategies or retirement planning, James gives him some unexpected advice: start journaling. This led to a deeper conversation about finding purpose beyond optimizing your portfolio. What would your life look like without constraints? What actually matters most to you...

Transcribed - Published: 22 October 2024

For many, Social Security makes up a large portion of their retirement income, so it’s important to know how to maximize your Social Security benefit. James explains how Social Security works, diving into some important foundational aspects. He then explains four key strategies for maximizing benefits: 1. Work for 35 years to avoid zero-income years in the calculation. 2. Delay benefits, if possible, until age 70, increasing payments by 8% annually after full retirement age. 3. Leverage spou...

Transcribed - Published: 15 October 2024

ames responds to a question from Chris regarding restricted stock units (RSUs) and how to avoid costly mistakes when managing them. He explores whether it’s wise to hold onto company stock or diversify for a safer financial future. He breaks down how RSUs work, from vesting schedules to the tax implications of receiving stock as part of your compensation package. He also explains the critical considerations you should make when deciding whether to hold or sell vested shares and how this decis...

Transcribed - Published: 8 October 2024

Patrick and Mary will soon both be retired. They are curious about what their withdrawal strategy should be as they balance various retirement accounts, including a pension, IRAs, and a brokerage account. They've been using tax gain harvesting to minimize taxes and plan to eliminate gains by 2024. A key question is whether to withdraw from their IRAs or brokerage account first, considering their state’s tax exclusion. James explains that by managing withdrawals and Roth conversions strategica...

Transcribed - Published: 1 October 2024

Ben has been a saver his entire life, which helped position him for an early retirement at the age of 53. Yet, he faces a big challenge. Having maintained his modest lifestyle, Ben’s comfortable portfolio has continued to grow and has nearly doubled in value. James and Ben discuss the challenges of making mindset shifts and the proactive steps Ben has taken to encourage himself to spend more. Questions answered: How did Ben decide to retire when he was in his peak earning years? What are t...

Transcribed - Published: 24 September 2024