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 today and planning for tomorrow.

This isn’t just about getting by—it’s about using what you’ve saved to live intentionally. And just as important, it’s about avoiding the regret of leaving money (and meaningful experiences) unused.

If you're thinking about how to align your spending with your values in retirement, this conversation is for you.

Questions we explore:

1. How can I estimate a sustainable spending level in retirement?
2. How do I balance enjoying life now with preserving assets for the future?

Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here

Timestamps:
0:00 - Jeffrey and Cindy's plan
3:24 - Understand cash flows
5:45 - Projected portfolio withdrawals
7:22 - Probability of success
9:26 - Monitor your withdrawal rate
11:12 - Key takeaway
13:26 - Wrap-up

Create Your Custom Strategy ⬇️

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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 often brings clarity and connection: experiences, time, giving, health, and environment.


Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here

Advisory services are offered through Root Financial Partners, LLC, an SEC-registered investment adviser. This content is intended for general informational purposes only and should not be construed as personalized investment, tax, or legal advice. Advisory relationships are established only through a signed agreement. Any examples discussed are hypothetical and for illustrative purposes. If client experiences are referenced, no compensation was provided and their experience may not be representative of others. Root Financial does not provide tax or legal advice. Tax planning topics are discussed in the context of comprehensive financial planning and should not be relied upon as a substitute for professional advice. All investments involve risk, including possible loss of principal. Past performance is not indicative of future results. Watching or listening to this content does not create an advisory relationship. Comments shared publicly are unsolicited and do not reflect the views or experience of all clients. They are not verified and should not be construed as testimonials or endorsements.

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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 yourself right away—to create future options for tax-free income.

What you'll learn:
1. How an HSA can help reduce your lifetime tax burden and fit into a broader retirement strategy
2. Ways to maximize the tax benefits beyond just paying current medical bills

Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here

Timestamps:
0:00 - How HSAs work
1:12 - Eligibility and contribution limits
3:19 - HSA details and nuances
4:36 - Timing flexibility
8:11 - Case study -- John
9:31 - Leveraging tax benefits
10:50 - Qualified medical expense
11:51 - Use HSA to the fullest extent
14:19 - HSAs in the grand scheme of things

Create Your Custom Strategy ⬇️

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Join the new Root Collective HERE!

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 harvesting. Whether you're approaching retirement or just looking to be more intentional with your investments, these tools can help you make more informed decisions.

Toward the end, I also point to a related video where I explain how a separately managed account may benefit high-income investors with significant brokerage assets.

Questions answered:
1. When does it make sense to realize investment gains in a taxable brokerage account—and when should you hold off?

2. What strategies can help reduce or eliminate the taxes owed on long-term capital gains?

Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here

Timestamps:
0:00 - When not to sell
2:40 - Understand risks on both sides
5:54 - Tax strategies
8:55 - Gifting stocks to charities
11:14 - Gifting to family
12:44 - Understanding step-up in basis
14:18 - Capital losses offset capital gains
15:11 - Wrap-up

Create Your Custom Strategy ⬇️

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Join the new Root Collective HERE!

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 values, rigorous training, and a culture of mentorship.

If you’re considering working with Root—or just curious about what makes us different—this behind-the-scenes conversation will give you a look at how we build a team designed to support you and your goals at every step.

Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here

Timestamps:
0:00 - Selling product vs service
2:58 - Four roles supporting clients
5:36 - Project management
8:16 - Root's growth plan
11:00 - A farm system
12:33 - Requirements to be a Root advisor
15:09 - Freedom within guardrails
19:03 - Why this matters
21:31 - Wrap-up

Create Your Custom Strategy ⬇️

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Join the new Root Collective HERE!

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 pension, and then figure out what size portfolio you actually need to fill the gap. I’ll also cover some key nuances that can make or break your plan—like uneven income, taxes, and what happens if one spouse passes away.

If you’re looking to make smart decisions about retirement, this episode is for you.

Questions answered:
1. How do I figure out how much I really need to retire, based on my actual expenses—not just my current income?

2. How can I tell if my $2 million retirement portfolio will be enough to support my lifestyle at age 60?

Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here

Timestamps:
0:00 - Determine retirement expenses
3:54 - Retirement taxes will be lower
5:12 - 2 ways to determine expenses
7:17 - Determine nonportfolio income sources
8:38 - Determine portfolio withdrawal rate
11:06 - Consider uneven income sources and expenses
12:54 - Consider taxes in retirement
14:00 - When a spouse dies
15:22 - Wrap-up

Create Your Custom Strategy ⬇️

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Join the new Root Collective HERE!

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 income so you can keep more of what you’ve saved.

Questions answered:
1. How can I reduce the amount of taxes I pay in retirement?

2. How are different retirement accounts—like 401(k)s, Roth IRAs, brokerage accounts, and HSAs—taxed when I withdraw money?

Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here

Timestamps:
0:00 - Brokerage accounts
4:29 - Standard 401(k)
6:27 - Health savings account
9:54 - HSAs after age 65
11:00 - Inheritance
13:01 - Inherited IRA account
15:33 - Social Security
17:00 - Wrap-up

Create Your Custom Strategy ⬇️

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Join the new Root Collective HERE!

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 James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here

Timestamps:
0:00 - A comment from the Collective
3:03 - A first-day-of-school analogy
4:25 - What would my future self do?
6:47 - Helpful feedback
8:32 - Make sure you're ready financially
10:20 - A life you don't retire from
13:18 - The opportunity cost
16:39 - More words of wisdom
18:44 - Making the decision is the scary part

Create Your Custom Strategy ⬇️

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Join the new Root Collective HERE!