When is the Best Time to Realize Gains in my Investment Account?

Ready For Retirement

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30:55

A secret field that summons lightning. A massive spiral that disappears into a salt lake. A celestial observatory carved into a volcano. Meet the wild—and sometimes explosive—world of land art, where artists craft masterpieces with dynamite and bulldozers. In our Season 2 premiere, guest Dylan Thuras, cofounder of Atlas Obscura, takes us off road and into the minds of the artists who literally reshaped parts of the Southwest. These works aren’t meant to be easy to reach—or to explain—but they just might change how you see the world. Land art you’ll visit in this episode: - Double Negative and City by Michael Heizer (Garden Valley, Nevada) - Spiral Jetty by Robert Smithson (Great Salt Lake, Utah) - Sun Tunnels by Nancy Holt (Great Basin Desert, Utah) - Lightning Field by Walter De Maria (Catron County, New Mexico) - Roden Crater by James Turrell (Painted Desert, Arizona) Via Podcast is a production of AAA Mountain West Group.…

21 days ago 17:47

MP3•Episode home

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 ⬇️

Chapters

1. Investment Gains Tax Framework (00:00:00)

2. When to Hold vs When to Sell (00:03:05)

3. Utilizing 0% Tax Brackets (00:06:10)

4. Charitable Giving and Family Gifting (00:09:35)

5. Step-Up in Basis and Tax Loss Harvesting (00:12:57)

6. Final Tips and Resources (00:16:20)

285 episodes

#Trading #Business #Podcasting Education #James Conole, CFP® #James Conole #Retirement Planning #Investing #Tax Planning #Investment Planning #Retirement #Dividend Investing #Stock #Bond #Cash

When is the Best Time to Realize Gains in my Investment Account?

Ready For Retirement

43 subscribers

published 21 days ago

MP3•Episode home

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

Create Your Custom Strategy ⬇️

Get Started Here.
Join the new Root Collective HERE!

Chapters

1. Investment Gains Tax Framework (00:00:00)

2. When to Hold vs When to Sell (00:03:05)

3. Utilizing 0% Tax Brackets (00:06:10)

4. Charitable Giving and Family Gifting (00:09:35)

5. Step-Up in Basis and Tax Loss Harvesting (00:12:57)

6. Final Tips and Resources (00:16:20)

285 episodes

#Trading #Business #Podcasting Education #James Conole, CFP® #James Conole #Retirement Planning #Investing #Tax Planning #Investment Planning #Retirement #Dividend Investing #Stock #Bond #Cash

All episodes

Ready For Retirement

1
Root Talks: Spend Your Way to a Happier Retirement: 5 Pillars of Better Spending 19:01

12 days ago19:01

19:01

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. Create Your Custom Strategy ⬇️ Get Started Here. Join the new Root Collective HERE!…

Ready For Retirement

1
The Most Powerful Tax-Free Retirement Tool: Start Leveraging Your HSA Now 16:59

14 days ago16:59

16:59

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 ⬇️ Get Started Here. Join the new Root Collective HERE!…

Ready For Retirement

1
When is the Best Time to Realize Gains in my Investment Account? 17:47

21 days ago17:47

17:47

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!…

Ready For Retirement

1
Root Talks: How Does the Advisory Team Structure Work at Root? 24:42

26 days ago24:42

24:42

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!…

Ready For Retirement

1
How Much Do I Need to Retire? (3 Simple Steps to Determine the Right Amount) 17:31

28 days ago17:31

17:31

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!…

Ready For Retirement

1
Maximize Your Retirement Tax Savings: How to Maximize Tax-Saving for Each Account 19:06

5 weeks ago19:06

19:06

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 ⬇️ Get Started Here. Join the new Root Collective HERE!…

Ready For Retirement

1
Root Talks: How to Get Past the Fear of Retiring Even When You Have Enough 22:02

6 weeks ago22:02

22:02

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 ⬇️ Get Started Here. Join the new Root Collective HERE!…

Ready For Retirement

1
The Hidden Flaw in Monte Carlo Analysis That's Ruining Retirement Plans 24:32

6 weeks ago24:32

24:32

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 success rate. You’ll learn why 100% isn’t always ideal, and how to build a retirement plan that supports a meaningful life, not just a perfect score. Questions answered? 1. Should I delay retirement if my Monte Carlo probability of success drops? 2. Is a 100% probability of success the best goal for my retirement plan? Submit your request to join James: On the Ready For Retirement podcast: Apply Here On a Retirement Makeover episode: Apply Here Timestamps: 0:00 - An encounter at the gym 2:37 - What is Monte Carlo analysis? 4:18 - Consider severity of failure 6:19 - Consider other assets, like property 7:35 - Is a 100% probability score really success? 10:55 - Monitor and course correct 14:13 - Margin 15:07 - No universal number 16:13 - Assumptions about spending 18:27 - Retirement spending smile 20:57 - Context matters Create Your Custom Strategy ⬇️ Get Started Here. Join the new Root Collective HERE!…

Ready For Retirement

1
Why many retirees REGRET relying on Social Security Income 13:20

7 weeks ago13:20

13:20

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 your request to join James: On the Ready For Retirement podcast: Apply Here On a Retirement Makeover episode: Apply Here Timestamps: 0:00 - One-off expenses 1:34 - Inflation & CPIW 4:21 - Tax on provisional income 7:33 - Peace of mind 8:33 - Maximize your benefit 9:22 - Supplement SS 10:24 - Leverage your home Create Your Custom Strategy ⬇️ Get Started Here. Join the new Root Collective HERE!…

Ready For Retirement

1
Root Talks: What Role Does "Fun" Play in an Advisory Relationship? 15:50

8 weeks ago15:50

15:50

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. Submit your request to join James: On the Ready For Retirement podcast: Apply Here On a Retirement Makeover episode: Apply Here Timestamps: 0:00 - About Root Collective 0:56 - Making a serious topic fun 2:07 - A lesson from Covid 5:06 - "Fun" is being prepared 8:04 - Emotional downtimes require a team 11:27 - On building trust 13:33 - Wrap-up Create Your Custom Strategy ⬇️ Get Started Here. Join the new Root Collective HERE!…

Ready For Retirement

1
9 Things To STOP DOING After 60 16:19

8 weeks ago16:19

16:19

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 how to live with more freedom, joy, and financial confidence! Questions answered: 1. How can I make the most of my retirement years financially and emotionally? 2. What habits should I stop after 60 to live a healthier, happier, and more fulfilling life? Submit your request to join James: On the Ready For Retirement podcast: Apply Here On a Retirement Makeover episode: Apply Here Timestamps: 0:00 - 1 - Saving 2:24 - 2 - Spending when it's not fun 3:38 - 3 - Trading time for money 4:52 - 4 - Putting off experiences 6:27 - 5 - Neglecting your health 8:15 - 6 - Caring what others think 9:17 - 7 - Watching dome-and-gloom news 11:16 - 8 - Neglecting your financial plan 13:00 - 9 - Making decisions as if you'll live forever Create Your Custom Strategy ⬇️ Get Started Here. Join the new Root Collective HERE!…

Ready For Retirement

1
Your Roth IRA Could be Locked For 5 Years. Here's Why 12:28

9 weeks ago12:28

12:28

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 the two different five-year rules for Roth IRAs affect withdrawals? Questions answered? 1. When can you withdraw money from a Roth IRA without paying taxes or penalties? 2. How do the two different five-year rules for Roth IRAs affect withdrawals? Submit your request to join James: On the Ready For Retirement podcast: Apply Here On a Retirement Makeover episode: Apply Here Timestamps: 0:00 - The 5-year rule 1:09 - Contributions 3:39 - Conversions 5:36 - Growth 6:51 - An example 8:55 - Conversions before 59.5 years 10:23 - Summary Create Your Custom Strategy ⬇️ Get Started Here. Join the new Root Collective HERE!…

Ready For Retirement

1
Root Talks: How Do Smart Retirees Handle Big One-Time Expenses? 18:58

10 weeks ago18:58

18:58

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. The key? Plan ahead, align financial decisions with long-term goals, and make the most of your retirement funds. Submit your request to join James: On the Ready For Retirement podcast: Apply Here On a Retirement Makeover episode: Apply Here Timestamps: 0:00 - Gary R's question 2:52 - Can your retirement support it? 4:43 - How should investments be allocated? 6:28 - Have a tax strategy 8:54 - A caution; a reminder about sleep 12:03 - Intentionally set aside 14:23 - Mental hang-ups and biases 16:37 - The Collective Community Create Your Custom Strategy ⬇️ Get Started Here. Join the new Root Collective HERE!…

Ready For Retirement

1
The Best Retirement Spending Stories I've Heard This Year 11:29

10 weeks ago11:29

11:29

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 incredible responses I received—stories of travel, family experiences, and meaningful purchases that turned dreams into reality. These stories serve as a reminder: financial planning isn’t just about growing wealth; it’s about using it to create a life you love. If you haven’t already, take that step. Don’t wait for "someday." Let’s make sure we’re spending in a way that truly reflects what we value most. Questions answered: 1. Why is it important to align your spending with what you truly value? 2. How can you take action to ensure your money is being spent in a way that brings you joy? Submit your request to join James: On the Ready For Retirement podcast: Apply Here On a Retirement Makeover episode: Apply Here Timestamps: 0:00 - Reviewing the challenge 1:42 - Ice fishing and family trips 2:46 - Urgency 4:19 - Diving the Red Sea, family cruise 5:35 - Pets and optimizing travel plans 7:28 - Uncertainty and urgency 8:53 - Values, purpose, and happiness Create Your Custom Strategy ⬇️ Get Started Here. Join the new Root Collective HERE!…

Ready For Retirement

1
One Simple Tip to Make Spending Easy in Retirement 17:52

11 weeks ago17:52