Ready For Retirement

Thinking about retiring early and worried it might hurt your Social Security benefits? Good news: it probably won’t. A common myth is that you have to work into your 60s to get the most out of Social Security. In reality, benefits are based on your 35 highest-earning years—not the age you stop working. This episode breaks down how benefits are calculated, what “bend points” are, and why even part-time income in semi-retirement can make a difference. There’s also an important distinction betwe...

Transcribed - Published: 12 August 2025

Money conversations fall short when only one spouse is at the table. It’s easy to treat financial planning like another household task to divide and conquer, but unlike errands, your financial plan is the blueprint for your shared future. What we’ve seen time and again is that the person sleeping next to you often holds the key to your blind spots. They know what stresses you out, what brings you joy, and what dreams you’ve stopped saying out loud. That’s why the best financial plans aren’t j...

Transcribed - Published: 7 August 2025

Forget the myth that you need a million dollars to retire. What really matters is creating sustainable cash flow—not hitting a magic number. Retirement success comes down to three things: your expenses, guaranteed income (like Social Security or pensions), and the gap your savings need to fill. For some, that gap is smaller than expected. Real examples—like a couple living comfortably on $300K in investments—show it’s possible. Small lifestyle changes, like cutting $1,000 in monthly expenses,...

Transcribed - Published: 5 August 2025

Can a children’s poem change how you think about retirement? In this episode, we unpack the hidden wisdom in Shel Silverstein’s “Smart” and how it reflects a common retirement planning mistake: trading time and well-being for wealth you may no longer need. We explore why it’s hard to step away from accumulation mode—even after reaching financial independence—and how this mindset can cost you more than it earns. The real risk isn’t running out of money. It’s not recognizing when you have enoug...

Transcribed - Published: 29 July 2025

The hardest part of retirement isn’t always financial, it’s psychological. For many, stepping away from work isn’t a light switch, but a dimmer that adjusts over time. This episode of Root Talks unpacks what makes the retirement decision so complex, especially for high-achieving professionals whose identity is tied to their careers. Through a real-life case study, the conversation explores how severance offers can become powerful “test drives” for retirement, offering space to reimagine life ...

Transcribed - Published: 24 July 2025

Even with a strong financial plan in place, many professionals find themselves hesitating at the retirement decision—stuck in the cycle of “just one more year.” The numbers say it’s possible, yet the fear of leaving behind a paycheck, a title, or a sense of purpose keeps them working long past the point of “enough.” This episode reframes retirement readiness through the lens of the five dimensions of wealth: financial, time, physical, social, and mental. Financial wealth is just one piece. Ti...

Transcribed - Published: 22 July 2025

If you’ve ever found yourself wondering whether you really need a financial advisor, this episode is for you. James and Ari unpack the deeper reasons people seek financial guidance—and why the decision often goes far beyond dollars and cents. Much like seeing a doctor for preventative care, working with the right advisor is about protecting your future, reducing stress, and reclaiming your most precious resource: time. From saving 20+ hours a month of DIY management to gaining peace of mind, ...

Transcribed - Published: 10 July 2025

At 90 years old, will you remember that final bonus or the time you didn’t spend with the people you love? This powerful question reframes how we think about retirement timing beyond the numbers. Yes, financial readiness matters. But delaying retirement for "just one more cycle" or "just one more raise" often leads to a dangerous pattern—constantly moving the goalpost while trading away your most vibrant, healthy years. In this episode, we explore the critical difference between lifespan and ...

Transcribed - Published: 8 July 2025

A seven-figure portfolio can feel like a green light for retirement—but the numbers don’t always tell the full story. In one case study, a couple with over $1 million saved faced a withdrawal rate close to 14% based on their desired lifestyle. That’s nearly three times higher than what’s typically considered sustainable. This story is a reminder that retirement success isn’t just about hitting a number, it’s about how your money is structured to support your life. A solid plan makes the diffe...

Transcribed - Published: 1 July 2025

Retirement accounts like 401(k)s and IRAs often get all the attention, but there’s another tool that can play a powerful role in your long-term strategy: the humble brokerage account. Unlike retirement accounts with age restrictions and penalties, brokerage accounts offer flexibility. You can access funds at any time, for any purpose without early withdrawal penalties. That kind of control can be incredibly valuable, especially if your goals include retiring early, helping family, or funding ...

Transcribed - Published: 26 June 2025

After working with hundreds of people navigating retirement, we’ve seen a clear pattern: the biggest regrets aren’t about money. They’re about meaning. Too often, people retire from something—but never toward something. They solve the financial side without planning for the life side. And that leads to some common regrets: No clear purpose after work: Retirement without direction quickly turns from freedom to restlessness.Neglecting health too long: Wellness is what fuels the retirement you’v...

Transcribed - Published: 24 June 2025

The biggest question I hear from people planning for retirement is this: Am I going to run out of money before I run out of life? But here’s the thing, no matter how much you’ve saved, that fear doesn’t automatically go away. In this video, I walk through what the data actually says about your chances of running out of money, where the 4% rule comes from, and why many people end up being far too conservative with their spending. I’ll also share a more flexible way to approach withdrawals so ...

Transcribed - Published: 17 June 2025

What does it really mean to change someone’s life through financial advice? While we’re not saving lives like doctors, the impact we have on our clients’ futures can be just as meaningful. Often, it’s not about the numbers—it’s about helping someone move forward when fear is holding them back. We’ve seen it firsthand. Like the dentist who had every detail in place to open her own practice but couldn’t take the final step. What helped wasn’t another spreadsheet—it was a mindset shift. Or the c...

Transcribed - Published: 12 June 2025

If your goal is to spend $10,000 a month in retirement, how much do you really need saved? The answer isn’t as simple—or as overwhelming—as it might seem. In this episode, I break down the key factors that influence your retirement number beyond the common 4% rule. We’ll explore how Social Security can significantly reduce what you need to save, why account types like Roth vs. traditional IRAs make a major difference, and how your withdrawal strategy and retirement age can shift the numbers ...

Transcribed - Published: 10 June 2025

Retirement planning isn’t about chasing numbers, it’s about building a life with intention. The Sequoia System helps you get clear on what matters most, organize your finances around that vision, and create a plan that supports the freedom, peace of mind, and purpose you’re truly after. We start with your life vision, translate that into a monthly income goal, and map out your cash flow using a mix of reliable income sources and portfolio withdrawals. Then we align your investments with thos...

Transcribed - Published: 3 June 2025

In this episode, Ari and James explore the emotional and practical sides of retiring—specifically, how to have the conversation that officially ends your career. Whether you're months away or years out, this discussion tackles the fear, hesitation, and freedom that come with telling your boss you're done. You'll hear real stories from Root Collective members who’ve taken the leap, insights on counteroffers, and a powerful reframe: every “yes” to more work is a “no” to your time, your family,...

Transcribed - Published: 29 May 2025

In this episode, we walk through a retirement planning scenario involving a couple in their early 60s with a $4 million investment portfolio. Their financial plan reveals something surprising: they may not need to wait until 65 to retire. Instead, thoughtful planning opens the door to retiring earlier—without compromising the lifestyle they value. What we cover: • A breakdown of how a $4 million portfolio can support early retirement • Income sources, spending needs, and sustainable withdrawa...

Transcribed - Published: 27 May 2025

Deciding when to start your Social Security benefits might be the single most consequential financial decision of your retirement journey. Should you claim early at 62, wait until full retirement age at 67, or delay until 70 to maximize your monthly check? The answer isn't as straightforward as many think. Your Social Security benefit is calculated using your 35 highest-earning years, adjusted for inflation. This forms your Primary Insurance Amount (PIA) – what you're entitled to at full ret...

Transcribed - Published: 20 May 2025

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...

Transcribed - Published: 15 May 2025

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 ...

Transcribed - Published: 13 May 2025

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...

Transcribed - Published: 1 May 2025

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...

Transcribed - Published: 29 April 2025

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