Ready For Retirement

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.
• Neglect...

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.

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 helpe...

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 ...

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...

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, ...

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 retir...

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 form...

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.

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 withdra...

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 de...

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 explai...

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 c...

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 adviso...

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 (hin...

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 taxa...

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 y...

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, spen...

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 s...