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 ⬇️

Get Started Here.

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 ⬇️

Get Started Here.

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 ⬇️

Get Started Here.

Join the new Root Collective HERE!