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Ready For Retirement is the podcast dedicated to helping you learn the tips and strategies that will help you achieve your retirement goals. When it comes to retirement planning, it can quickly become overwhelming and easy to not take action. I designed this podcast because I want you to have the knowledge and confidence to create your secure retirement. My ultimate goal for all of my clients (and listeners) is to create peace of mind and that starts with having a strategy. I want you to spend more time thinking about what matters most to you in retirement. I post weekly episodes to keep you up-to-date on all the best tips and strategies to create a retirement that excites you. Everything from investing tips, tax planning, withdrawal strategies, insurance planning, Social Security, and that's just the start! Let's help you maximize your return on life. We use your money and the strategies I share in this podcast to do just that!
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Retired with millions—but full of regret? In this episode of Root Talks, James and Ari share the real stories no one talks about: wealthy retirees who did everything “right” financially but still feel like they missed out. From sacrificing health and relationships for more savings, to realizing too late that they were planning for someone else’s version of success, these lessons are emotional, practical, and essential. What you’ll learn: Common regrets wealthy retirees confess after leaving...
Jeffrey and Cindy came to me with $3 million saved and one big question: How much can we actually spend in retirement? In this video, we walk through a retirement planning scenario—looking at spending goals, taxes, travel, healthcare, and how Social Security might factor in. While the numbers vary, the framework we use applies whether you're working with $300,000 or $30 million. We explore how to think about sustainable withdrawal rates, portfolio flexibility, and trade-offs between spending ...
Many great savers hesitate to spend once they retire—unsure how to shift gears after years of discipline. In this episode, we talk through what it looks like to use money with intention, not just someday, but now. Prompted by a thoughtful note from a Root Collective member, we share stories—personal and client-based—about the small upgrades that matter: better experiences, more time, stronger health, and generosity that deepens relationships. We also walk through five areas where spending o...
Health Savings Accounts (HSAs) don’t get much attention—but they should. With triple tax advantages (tax-free contributions, growth, and qualified withdrawals), HSAs offer a level of flexibility that’s hard to beat. I break down how to use an HSA not just for healthcare today, but as a long-term planning tool. That includes how to qualify, contribute, invest the funds, and take strategic withdrawals. I also explain why it’s worth tracking medical expenses—even if you don’t reimburse yoursel...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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....
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...
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