Shows
Ready For RetirementMaximize Your Retirement Tax Savings: How to Maximize Tax-Saving for Each AccountWant 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 income so you can keep more of what you’ve saved.Questions answered:1. How can I reduce the am...2025-04-0819 minReady For RetirementRoot Talks: How to Get Past the Fear of Retiring Even When You Have EnoughMany 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 James:On the Ready For Retirement podcast: Apply HereOn a Retirement Makeover episode: Apply Here Timest...2025-04-0322 minReady For RetirementThe Hidden Flaw in Monte Carlo Analysis That's Ruining Retirement PlansMany 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 that supports a meaningful life, not just a per...2025-04-0124 minReady For RetirementRoot Talks: What Role Does "Fun" Play in an Advisory Relationship?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 Retire...2025-03-2015 minReady For RetirementRoot Talks: How to Overcome the Scarcity Mindset and Start Spending in RetirementYou’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 spendi...2025-02-2023 minReady For RetirementRoot Talks: How Should I Split Retirement Withdrawals Between Pretax and Roth Accounts?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 inve...2025-02-1324 minReady For RetirementThe Most Important Thing You Can Do For Your Financial PlanJames 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...2025-02-1111 minReady For RetirementRoot Talks: What Does Vanguard Say About Financial Advisors?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 reques...2025-02-0632 minReady For RetirementRoot Talks: How Do We Approach Team Building?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, aligning our goals wi...2025-01-2325 minReady For RetirementRoot Talks: What's the Difference Between Root Financial and Other Advisory Firms?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 estate planning to enhance client experiences.James and Ari also address how Root balances expansion with maintaining high service quality, ensuring each client feels uniq...2025-01-1627 minReady For RetirementRoot Talks: Behind the Scenes at Root Financial: How We Approach Team BuildingJames 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 cultural fit, technical skills, and a shared philosophy of integrating financial planning with life goals.Ari highlights the collaborative and values-driven workplace culture, sharing anecdotes about the thorough training pr...2025-01-0924 minReady For RetirementHere's How to Avoid a Retirement Filled with Anxiety or RegretIn 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 to regrets, like missing out on travel or neglecting health. Intentional spending, aligned with your v...2025-01-0223 minReady For RetirementHow Many Investment Firms Should I Split my Money Between?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 diversification.They emphasize the importance of understanding risks—like single stock, sector, and asset allocation risks—before trying to diversify. While protections like SIPC keep m...2024-12-2622 minReady For RetirementWhat If Social Security is Cut? Here's What it Means for Your RetirementMany 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 by 50%, retirees could rely on portfolio withdrawals or adjust spending. They emphasize flexible strategies, such as delaying benefits, working part-time, or reducing expenses to balance income needs.Ultimately, successf...2024-12-1925 minReady For RetirementHere's What Your Retirement Strategy Should Look Like with an $8M PortfolioHere’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 importantly, how to do it right. It starts with defining y...2024-12-1230 minReady For RetirementTop 5 Most Avoidable Retirement MistakesJames 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 of planning for taxes, investments, and withdrawals leads to inefficiency.Plan wisely to balance financial security with an enjoyable, purposeful retirement.Questions answered:1...2024-12-1017 minReady For RetirementRoot Financial's Backstory: How and Why the Company Was FoundedIn 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 him, it’s always been about using money as a tool to create meaningful lives—not just about bu...2024-12-0531 minReady For RetirementUnconventional Retirement Strategy: How to Save Less AND Retire with MoreChris 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 new contributions. Continuing to save aggressively was unnecessary and came at the cost of his health, rela...2024-12-0314 minReady For RetirementThis is the Biggest Way People Waste Money in RetirementMeet 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 Marginal Utility of Wealth: More money doesn’t alwa...2024-11-2621 minReady For RetirementThe Downside of Working "Just One More Year"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 specific savings numberReal-life example: a mid-50s teacher couple weighing part-time work, pensions, and travelThe truth about 60/40 portfolios and inflation-proof investingSubmit your re...2024-11-2124 minReady For RetirementHow Soon Before Retirement Should You Adjust Your Portfolio?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 over the long term, short-term volatility can be risky close to retirement. Timing this transi...2024-11-1927 minReady For RetirementHere's How To Discuss Money Effectively With Your ParentsMeet 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 stories and insights on how to approach these conversations▪️ Tips for...2024-11-1420 minReady For Retirement3 Steps to Prepare for an Out-of-State RetirementHave 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 regions. It’s also wise to consider personal lifestyle goals—like travel or access to nature—as these can impact ongoing expens...2024-11-0517 minReady For Retirement5 Things People Regret About Early RetirementMany 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, maintaining a balanced portfolio to outpace inflation, and considering part-time work as a transitional phase. He also encourages listeners to “pr...2024-10-2921 minReady For RetirementThis Is the Single Most Important Thing You Can Do to Prepare for RetirementJames 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? And how can you ensure your future is filled with meaning, not just money?It’s not just abo...2024-10-2221 min