Category: Podcast

Ep. 18 – How a Roth Conversion Strategy Could Save Our Client Over $427k in Taxes Throughout Retirement

Roth conversions are definitely gaining lots of popularity, especially with the Tax Cuts and Jobs Act of 2017 expiring in 2026. Because of this, I have noticed consumers believe they should automatically start converting their IRAs and 401ks to Roth accounts!

First and foremost, you have to run the numbers. For every scenario that is a “home run” like the one I’ll discuss today, there is a scenario where it does not make sense. Or, perhaps the time isn’t right (yet).

Make sure to check out this latest episode to hear the first of our three-part series from our recent educational workshop, “How to Reduce Taxes in Retirement.”


Ep 17. – The Consequences of Extended Care in Retirement

Nobody wants to think of themselves as getting old or frail. In fact, many retirees in their 60s, 70s, and even 80s are still traveling the world. The risk of extended care will never impact them. But if you need extended care, what are the consequences to your loved ones? They are not just financial but physical and emotional.

We are honored to have Harley Gordon join us on this episode, “The Consequences of Extended Care in Retirement.”

Harley is a founding member of the National Academy of Elder Law Attorneys (NAELA), and the founding principal of the CLTC, or Certification in Long-Term Care designation. He’s recognized as one of the top 10 most influential people in the Long-term Care Industry.

We hope you enjoy this episode and hope you learn something that makes an impact.

Ep. 16 – How to plan for Required Minimum Distributions (RMDs)

It’s natural for us to think about how to GET to retirement, but not about how retirement will actually work.

The same is true for saving into a 401k or 403b plan.  Most think about how to invest their 401k and maximize growth.  However, what about the distribution process?  And more importantly, what is the tax impact of those distributions?

Taxes are our clients’ #1 expense during retirement, and RMDs play a big part in tax planning.  Naturally, I am a big advocate of having an RMD plan.

We will dive into how Required Minimum Distributions (RMDs) work and how to plan for them strategically.  Thanks for tuning in!


Ep. 15 – 2023 Market Outlook

2023 Market Outlook

2022 was a tough year for both stocks and bonds.  In fact, it was perhaps the worst year for a 60/40 portfolio, period.  For retirees and pre-retirees, this makes income planning very difficult!  How do you combat record inflation when both stocks and bonds are falling?  Additionally, the risk in stocks is likely not over as the fed continues its rate hike strategy, and a recession is likely.  

The good news is, there are opportunities for retirement investors!  Tune in to hear more about our key opportunities for 2023.

-Yield is back in fixed income

-The value vs. growth story

-International stocks time to shine?

-Bucketing strategy!

Ep. 13 – Planning for Healthcare Costs in Retirement – Medicare Considerations

(transcription) - Planning for Healthcare Costs in Retirement - Medicare Considerations (featuring Ari Parker, Lead Medicare Advisor @ Chapter)

Kevin Lao (KL):

Hello everyone, and welcome to the planning for retirement podcast, where we help educate people on how retirement works. I’m Kevin Lao, your host. I’m also the lead financial planner at imagine financial security. Imagine financial security is an independent financial planning and investment firm based in Florida.

However, this information is for educational purposes only and should not be used as investment legal or tax advice.

This is episode number 13, called planning for healthcare costs in retirement. Hope you enjoy the show. And if you like what you hear, leave us a five star review and make sure to subscribe or follow and stay up to date on all of our latest episodes.

I’m very excited today to be joined by Ari Parker. Ari is the head Medicare advisor of Chapter, and is one of the country’s leading Medicare experts. He’s helped thousands of Americans sign up for Medicare, breaking it down into simple bite size pieces. I like that simple.  His work has been featured in Forbes, CNBC, CBS money, watch market watch Huffington post, and many other publications.

He’s a graduate of Stanford law school. He trains and leads Chapter’s team of 30 plus licensed Medicare advisors and lives in Phoenix with his wife and two dogs. His book is coming out in September.
“It’s not that complicated” is the title of the book, the three Medicare decisions to protect your health and money.

Their website is ask and Ari’s email is [email protected] Ari. Thank you so much for joining today. Appreciate it.

Ari Parker (AP):

Pleasure to be with you, Kevin.


So I am excited to have you on mainly because my firm, obviously being in Florida, I specialize in retirement planning and oftentimes healthcare and Medicare questions come about.

And I’ve been doing this for 14 years now and I still feel like Medicare confuses me. How do you feel about that?


Absolutely. It can be very confusing. People aren’t sure which enrollment deadlines apply to them, whether they need to sign up for it or not.

This is why I wrote a book on it. And it’s something that our team helps people with every day.


Love it. Love it. Well, for this episode I reached out to you earlier this week.  I like to do episodes based on real life questions that I field from my clients.  This one, I’m gonna call them Jack and Diane.  Jack is 66. Diane is 57. Okay. Their daughter just had twins. I can relate, I’ve been there.

We had twins a couple of years ago, understandably so it takes a village to raise twins. So now they want to sell their house here in Northeast Florida and move closer to their daughter. Um, so instead of Jack working a few more years and getting Diane closer to that age, 65, that magical age, 65 of Medicare eligibility, and also his age 70, which would be the full social security benefit.

They’re wondering, Hey, you know what if Jack retired tomorrow and they moved closer to their daughter to be near their twins?  Now the decisions are what do they do with healthcare, right? I mean, we’ve got Diane who’s eight years away from turning 65 and being Medicare eligible.

And then we’ve got the decision for Jack and he needs to then enter into this world of complexity of Medicare, which hopefully you can break that down. So what I thought we would do is maybe start with the Medicare decisions, and then we can transition into Diane’s decisions around healthcare pre-Medicare.  So why don’t we just start with the basics of Medicare?

Let’s pretend I’m Jack, what would you say to me?

Basics of Medicare


I’d like to summarize.  Jack is 66 years old and has retired. Diane is 57 years old, but isn’t working.




It is very likely that Jack should enroll in Medicare.  Jack by virtue of having retired from a large group employer, which is defined as 20 employees or more has a special enrollment period to start Medicare, that enrollment period lasts eight months.

Jack probably doesn’t want a gap in his coverage. So it’s important to do it sooner than later. You don’t wanna wait until the end of the eight month period. You don’t wanna miss that period either because then you’re in a whole world of pain.


You get slapped with penalties, right?


Yes. I’m happy to get into the penalties, but it is very likely that Jack should enroll in Medicare. It’s a five minute process. He can do it online through his portal. And then yep. Happy to get into what Medicare covers.


It’s very easy to enroll in Medicare. But you hear all of these questions like, okay, what you do with original Medicare versus Medicare advantage? I think I read a trend recently that the number of people buying Medicare advantage plans has been going up by roughly 34% per year which is substantial.

So it’s gaining traction. Why don’t we talk about the differences between traditional Medicare versus the Medicare advantage route?

Medicare Original vs. Medicare Advantage


Original Medicare has two parts, part a is hospital insurance, which covers you when you’re inpatient. It also covers hospice care, skilled nursing facilities. It means you’re inpatient.

Part B is outpatient coverage. It’s visits to the doctor to specialists, ambulance services, durable medical equipment, even outpatient surgery, all covered under Medicare part B. For Jack because he’s paid federal income taxes for at least 10 years. Part a hospital is premium free. There’s a charge for part B.

However, that charge will be $170 and 10 cents per month for 2022 and might go up for next year. We don’t know yet those numbers will be released in the fall.  But there’s a charge for part B and most Americans pay $170 and 10 cents. Mm-hmm what Jack will get in return is 80% of his medical services covered.

He’ll owe the other 20% out of pocket with no cap. My mom just had a knee replacement, $40,000 procedure. Original Medicare picked up $32,000. If she hadn’t had any additional coverage, she would’ve owed eight, $8,000 out of pocket, plus all the pre-op post-op physical therapy.  Which is why you would then think about that.


They call this medigap coverage, right? The supplemental coverage, correct?


Exactly. There’s only two types of additional coverage (or Medicare advantage. Medigap sits on top of original Medicare and covers the 20% remainder. Here, we’re talking about plan letters like plan F plan G, or plan N.

Those are the three most common types. And what those do is preserve the flexibility of original Medicare. There’s no PPO or HMO restriction. You can see any doctor who accepts, accepts Medicare nationwide. If you live in St. Augustine, but wanna see a doctor in Houston, it’s no problem. You can go and see that doctor as long as they accept original Medicare.

So it’s really flexible for someone who likes to travel or has a second home outside Florida, for example.  Also importantly, the Mayo clinic accepts Medigap, which is a very important consideration for people who live in Florida.

On the other hand, you have Medicare advantage.

Medicare advantage is managed care. These are also known as all in one plans or part C.  William Shatner talks about it on television, Jimmy Walker, they’re advertised heavily and they’re going be advertised even more heavily as the fall approaches. Now, what people like about these plans is it comes with additional benefits like prescription drug, coverage, vision, dental, hearing, transportation benefits.

What people like less about it is that it’s managed care and here there’s prior authorization that’s there’s restrictions. And so it, it’s just important to understand the trade offs involved in the decision between Medigap and Medicare advantage.


So the advantage, just to clarify for the listeners, the advantage would be replacing the original Medicare route.

Plus that supplement, and there’s some advantages to that in terms of additional benefits. I’ve also heard some advantages in terms of simplicity. But there also could be some disadvantages, that managed care piece that you mentioned.

So with Medicare advantage, you might actually have to go see a primary doctor before going to get a major procedure done or getting an MRI done or knee replacement, things like that. Is that what you’re saying?


Exactly. What people really like about Medigap is the flexibility. You can see any doctor nationwide who accepts Medicare.

You don’t have to ask for permission, you don’t need a referral. It also has coverage outside of the United States. In fact, I had a client who was vacationing in Paris and suffered a heart attack. They had Medigap plan G and their plan G has 80% coverage abroad for the first 60 days.

You’re outside the United States. Now the great news, it was a $35,000 hospital bill from the heart attack, but he recouped 80% of the cost because he had coverage. And so it’s a big decision to make, and it really depends on your lifestyle factors, which is something you can be useful to discuss with an independent advisor.

There’s no charge to work with one now.  And the industry is set up that way. It’s great. You get the same price, whether you work with an independent advisor, as you would, if you call the carrier.


I went through the same situation being pre-Medicare and launching my own business.   I had to go out and buy my own insurance.

It was nice to work with someone who’s an expert.  My premiums are the same, but I can get someone to give me advice on those little things that I would’ve never thought about.


And you have a dedicated point of contact it’s not as if you call the carrier you wait for customer service to answer, and then you get a different customer service representative every time.

No one likes that experience.  Instead, when you work with an independent advisor like chapter, we’re an example of one, then you get a dedicated contact and that is your person who will help you troubleshoot any issues that come.

Medicare decisions if you travel or are a snowbird


You mentioned an interesting point about travel.  It seems like if I’m working with someone or you’re someone who is big into traveling, whether it’s domestically or, or overseas, or perhaps you’re a snowbird.  Maybe you live six months minus a day in Maine or New York or New Jersey, and then the other six months plus a day in Florida.

You might have a little bit more flexibility in the networks with the original Medicare, right?   Rather then going with the Medicare advantage coverage there’s is that correct?


There’s no network restriction with original Medicare.  So if you wanna preserve the flexibility of original Medicare, then you ought to strongly consider a Medigap plan.

If you’re comfortable with managed care restrictions and you’re not planning to travel too far away from your home. Then a Medicare advantage plan might work really well.


Now Medigap has a higher premium than Medicare advantage plans, right?


Cost depend on where you live, they can cost anywhere from $90 to about $185.

And if you live in New York, it’s a lot more expensive than that.  But in Florida’s around 175 to $185 per. Medicare advantage plans on the other hand have a very low premium, in fact, many plans have a $0 premium, but there are trade offs.


And the trade offs from what I understand, it’s more like your traditional health insurance with the deductibles and copays and things like that.

So if you’re, if you’re going to the doctor a lot that original Medicare, even though the premiums are higher, that actually might be more advantageous because you’re saving money on a much lower deductible. Right?  I think the deductible is $300 per year or something like that?


You, you got it.

The, the deductible is exceptionally low. The deductible for original Medicare is $233 for 2022.


Is that per individual or per couple? It’s probably per individual, right?


There’s no Medicare family plan. It’s individual.

Many advantage plans have a $0 deductible, but as you mentioned, it’s pay as you go insurance similar to work provided coverage. For example, if you go see a specialist you’re going to owe a copay and your doctor needs to be in network. If your doctor’s out of network, then you might have co-insurance or the visit might not be covered at all.


Okay. So if you’re like my wife that loves to just go to doctors and do a lot of things, you might wanna go with original Medicare. Right?  You’re not going to have those copays and things out of pocket along the way, like you would with advantage.


That’s exactly the type of conversation we’d have with someone in a 15 minute introductory call, we would talk through how often they go to the doctor or the types of doctors they see, because it goes doctor by doctor.  And Kevin, it’s even as granular as choosing a doctor based on the location where they practice.

One location might be in network with a plan. But the other location that the doctor practices out of might be out of network.


So that’s an important thing.  You can almost back into it, like if you have doctors that you’re a big fan of, and you’re making this healthcare decision, see if they are in network obviously.

I think with original Medicare, I think I heard this stat that 98% of, of practices actually allow for original Medicare, right? Whereas advantage the percentage is much lower. So, if you’re gonna go that route with the lower premium and things like that, you might just wanna make sure that the doctors that you really are in network, right?

Medicare Open Enrollment Planning Opportunities


Exactly people who don’t go to the doctor very often tend to be quite happy with a Medicare advantage plan. As long as the doctors that they do see are in network with the plan. Now here’s the rub. This changes every single year. The plans themselves change, the doctors you see change, the care that you need changes, and your prescriptions change too.

And a lot of the reason people like Medicare advantage is because it’s all in one. Many of the plans include prescription drug coverage as well. So it’s really important to shop all your options every year. The time to do that is coming up. That window is October 15th to December 7th, October 15th is when you can shop all options available to you for 2023.


That’s for advantage, original or both?  Do they both have the same open enrollment?


The, the saying is if, if you go Medigap, you typically marry your Medigap and date your drug plan.  You wanna review your prescription drug plan every single year, because there are savings to capture here.  Now it’s good to review your Medigap plan every few years, but really it’s set it and forget it.

Keep paying your premiums. You know exactly what you’re paying for. You’re paying for it to cover the other 20% that Medicare otherwise wouldn’t. On the advantage side, it’s really important to review your options and the time to do that is in the fall. So you should, if you go the Medigap route, you should review your prescription drug coverage.

Every fall. If you go the Medicare advantage route, you should review your coverage every fall. If you’re on original Medicare and didn’t get Medigap or Medicare advantage when you first signed up, then the fall is also an opportunity for you to choose a Medicare advantage plan or to change or adjust your prescription drug plan.


Interesting.  So that actually brings up another question I had. At one point, I heard that if you start with a certain type of insurance and then later decide to change that, potentially you might have some medical underwriting or some sort of health questionnaire.   And if something changed with your health, that might impact your insurance.

Am I misremembering that?


You’re bringing up something that’s really important, which is that in the state of Florida, you have a one time open enrollment opportunity, a one time golden ticket to get a Medigap plan with no underwriting. That is no question about your health history.

If you miss that window, unless a Medigap protection applies, you have to answer questions about your health history, and people get dinged all the time.  Let’s say they’re on three medications for high blood pressure, for example. A carrier is going to look really closely at that.  Same thing with type two diabetes, or an issue with your back or your kidneys or your liver, your heart.   Those are all things a carrier would want to know about.

If you miss your open enrollment period, which is the six months after you start Medicare part B.  And it’s good to act early here. It’s actually good to do it even before your Medicare begins, because you want to secure that one time opportunity to get a Medigap plan without answering questions about your health history.


So this is, this is within six months of starting B, right?  And the trigger of starting B is turning age 65, or if you’re still working, you can delay that decision for B and just do it when you retire. If you have employer healthcare coverage, right?

So it might even be like age 68 or 67. Like in this case, Jack would be 66, right?


That’s right.  There are three ways to start. The first is by way of turning 65.  The second is by way of a special enrollment period. And here that would be Jack. Jack is coming off work provided coverage. His employer is 20 employees or more.  Jack has a special enrollment period to sign up for Medicare. The third way is through the general enrollment period, which is January 1st to March 31st, but the general enrollment period is really only if you made a mistake, it means that you should have signed up for Medicare already and you waited too long.

Now, if you have a disability or if you have end stage renal failure, for example, then you get Medicare. But that those are special circumstances. And if that applies to you, happy to be a resource here, you can reach out to me by email [email protected]

Special Enrollment for Medicare and Medical Underwriting


So this is super important, that special enrollment period without medical underwriting.  I think some people, especially clients that I’ve talked to in the past, they say “Hey, you know what, Kevin, I’m healthy now.  I’m not going to the doctor very much. I can get away with an advantage plan. Maybe keep my premiums low.”

But then later on, if they decide to switch to original because maybe their health changes, maybe there’s a recent diagnosis that’s not favorable.

That’s a problem. You’re making a bet. Yeah. That your good health will continue.  And so, what would happen? I mean let’s say Jack hypothetically started with advantage and then later on wanted to switch to original and something did change with his health.

Could they just exclude him or would his premiums be higher? Or how would that work?


There’s no underwriting for a Medicare advantage plan.

For context, what Kevin is talking about here is if Jack wanted to go from a Medicare advantage plan to a Medigap.  And Jack’s health history declines.  In 46 states, Jack unfortunately would have to answer questions about his health history. Now, hopefully his health hasn’t declined that much and a carrier would still accept him.

The carriers ask different questions about your health history, and it varies state by state. And so interesting here, we had to build a database to sort through all the complexity.  It would be worth exploring whether Jack qualifies for a Medigap protection, because if he’s moving for example, and let’s say he moves to Maine, Maine is a guaranteed issue state.

What that means is that Jack can get a Medigap plan. 


But that’s why talking to someone like you is helpful because you’ve got to know the rules.


Exactly. I mean, the rules are changing. The rules vary by state.


Could one spouse start with original and the other spouse choose advantage? I mean, they’re sort of independent of one another, right?


Yeah. We see this all the time, especially with couples in Florida where there’s a lot of competition, Florida has a very rich Medicare advantage market.

There’s a lot, especially south Florida, has a lot of competition across carriers. And it’s growing in north Florida too, but that just goes to show you that it’s important to shop all your options every year because the options are changing.

Usually they make the same decision. If one is on a Medigap plan, they both go Medigap. If one, doesn’t go to the doctor at all, then they might do great on a Medicare advantage plan while the spouse might go to the doctor a lot and instead would prefer to be on Medigap, it’s individual coverage.


Yeah. I could see that being my wife and I, when we’re Medicare eligible, my wife is gonna go original. I might go advantage, but we’ll see what happens at that point.


I see that with my spouse too. 

Avoid penalties!


Now you mentioned the special enrollment. I wanted to bring this up. I was reading something recently about.

If you’re 65 and you’re still working.  You don’t have to enroll in Medicare, right. As long as your company has 20 or more employees. Right?  But if your company has fewer than 20, you have to enroll. Is that right?


Yes. You must. In order to avoid penalty.


What’s the thought, what’s the thinking there?

What’s the rationale around, requiring that 20.


The rationale is that for small employers and small employer is defined as 19 or fewer employees, then Medicare is supposed to be your primary insurance.

You can remain on the company plan, but the company plan pays secondary to Medicare. So in effect, what that means is if you work for a small employer, 19 or fewer employees, then what will happen is your work provided insurer can start denying claims for the ones that Medicare should have covered as primary insurer.

So Medicare as primary insurer is supposed to pick up 80% of the coverage. If you didn’t start Medicare, then there’s no one on the hook for the 80%.   The small group employer insurance could deny claims.


I’ve had a few people over the years that turned 65 and they say, “Hey, I don’t need to worry about enrolling in Medicare” because that’s maybe what they’ve read or heard from a friend.  But I’ve had a few of those people work for small businesses and they must enroll.

Otherwise you get hit with some penalties when you do go to enroll later on.


Yes, you get hit with penalties and it’s also dangerous because then your insurance can deny claims where Medicare should have been paying as primary.  And of course, since you haven’t started Medicare, you have no one to cover those primary obligations.

What are the total costs for original Medicare vs. Medicare Advantage?


So before we transition to what to do with Diane’s coverage, all in premiums if you went original Medicare Par A plus Part B plus Part D and the Medigap coverage, what’s a price range?


First, we have to start with what they owe for Medicare part B. Do Jack and Dianne earn less than $182,000.



Medicare part B premium with no IRMAA, which is income related monthly adjustment amount. So let’s assume a standard premium. Okay. The standard premium for part B is $170 and 10 cents.

And it’s non-negotiable unless you qualify for Medicaid, which is for the low income. So regardless of whether they go Medigap or Medicare advantage, they owe the $170.10.

Now if Jack starts taking social security, the $170 and 10 cents per month will be deducted from his social security.

If he hasn’t started, then he’ll be invoiced on a quarterly basis.

In terms of Medigap, if Jack lives in Florida will range anywhere from 120 to $185, depending on whether he chooses plan N or plan G.  Then Jack would need a standalone prescription drug plan unless he has prescription coverage, at least as good as what Medicare provides. And there are separate late enrollment penalties here.

So it’s really important to not miss the enrollment period to sign up for a drug. Drug plans typically costs anywhere from 10 to $25 per month, depending on the prescriptions one takes. So Jack’s cost picture if he goes Medigap is $170 and 10 cents, plus 120 to $185 per month for Medigap plus 10 to $25 for the standalone prescription drug plan.


So like $310ish to 370ish. Per month. All in for original Medicare and then out of pocket after that.  The only Medicare related expense Jack would see would be the $233 charge for the annual deductible.

How does your income affect Medicare premiums?

You brought up a good point about the 170 or less of adjusted gross income.  I’m sorry, 182,000 or less. Your part B premium, for those of you that don’t know, this is based on your income, your adjusted gross income.

And so there is a, a premium range. Okay. So, um, hypothetically, if you were the next premium band up, which is 182,000 to 228,000, your part B premium goes up by about $700 per year. For single filers that premium band would be 91,000 to 114,000, your premiums go up by about $700 per year.

The next band up for singles 114 to 142. And then for married filing joint, it’s 228 to 284. And the premiums are basically double than what they were on that first band. So this is a big part for me as the numbers guy, I like to help try to mitigate as much as possible my client’s taxable income in retirement. There are several ways to do it, but, income tax free withdrawals are the primary way.  And so those are Roth distributions, distributions from things like health savings accounts or life insurance, even non-qualified annuities, reverse mortgages could be another option or real estate income.

So by reducing taxable income in retirement, you could also in essence, reduce what you pay in Medicare premiums, which could also help alleviate that pressure on drawing your assets down too quickly during those retirement years. But thanks for breaking down the premiums for original.

What about advantage?

You hear the premiums are much lower, but what are some ballpark ranges of what you can expect for premiums?


Sure. Jack would owe $170.10 for Medicare part B. And then there are advantage plans as low as $0 premium. These plans would also likely come with prescription drug coverage wrapped in.

We would need to make sure that Jack’s prescriptions are covered affordably. What matters here is the name of the medication. Whether Jack can tolerate a generic or has to go brand name.  The dosage and the pharmacy that Jack likes to go to each of these factors influence price. And so it’s actually a really complicated equation.

What’s also important is making sure that the additional benefits appeal to Jack and that they meet his lifestyle needs, but there are great $0 Medicare advantage plans that would be available if Jack decides to go that route. And here Jack would need to, in exchange for that $0 premium, accept the network restriction.


Got it. So researching those doctors, looking at the prescriptions that he may or may not be taking and backing into the decision that way. But it sounds like your premium could be 50% less, right?


Yes. It would be 50% less. There are some things to consider. First there’s co-pays when you go to the doctor. Costs if Jack sees specialists.  The bill’s going to rack up if he sees those specialists more than once per month. So if he goes to see a specialist twice per month, then the copays will start to add up.

Also importantly, Jack needs to make sure that if one of the doctors is out of network, let’s say Jack would need to accept the consequences, which is that the carrier could deny coverage in that case. Or there might be onerous co-insurance requirements.


Okay. And that’s something I assume you can run some numbers, right?

Some hypotheticals based on how much they’re going to see certain specialists or how many times they anticipate going to see the doctor, and prescriptions. And then you can do a cost benefit analysis.


It’s important to shop. It’s important for Jack to shop all his options every year because the plans change.


So let’s talk about Diane a little bit.  So she’s got eight years until she gets to 65. So we’ve got some time, what are her options?

One thing we talked about was Cobra for her.  I mean, could she get on Cobra to continue on the group plan or does she just have to go straight to the private market, which would be the exchange?


Diane can Cobra for up to 36 months as a result of Jack’s retirement.

So that’s an option for her. That’s one option. Another option would be to look at the affordable care act exchange. There are generous federal subsidies right now, depending on Jack and Diane’s earnings. Diane might qualify for some of the subsidies and could find a lower cost plan that might be more comprehensive then Jack’s former employers work provided CORBA.


Okay, so she can use Cobra. He cannot use Cobra because Medicare needs to take over as the primary. So he’s gotta go Medicare.

She has the option of whether it be Cobra or individual insurance through the exchange,   I think those subsidies just got extended through 2025.  Yes, the subsidies were extended under the inflation reduction act, which passed Congress last month.  And it’s cool because, you know, on the, um, and I did these calculators too, when I was doing my own coverage for my family.

You could go in there and type in a hypothetical income that you think you’re gonna earn for the year. And they’ll actually quote you what those subsidies might be per month.  And so that’s another benefit of having a tax free income in retirement, right? Because if, if you retire before 65 or before your Medicare eligible and you lose group health insurance.  If you can keep your income or your taxable income low enough, you can potentially qualify for a lot of subsidies and keep those premiums down until you turn 65. Right?


That’s right.

We’re Medicare experts. Only Medicare.  But yeah, so for Diane, she’s got those two options. She could Cobra, she can look at the exchange.  Compare the two and see which one’s more comprehensive and which is more cost effective as well.


Well, this is great, Ari. I don’t know if there’s anything else we missed that you think the listeners should know about?  I think you, you covered a lot of good stuff but any final thoughts.


Yeah. The fall is coming fast which means only one thing, annual enrollment period. It’s time. If you’re Medicare eligible to shop all of your options. Unfortunately over 70% of people won’t do it, but there’s huge cost savings to capture here. It’s helpful.

If you use an independent advisor to assess all your options, chapter is an example of one, and you can visit us at our website at


That’s awesome. I mean, I think that’s a huge benefit. And, and I, as you know, the reason I met you, I have several clients that use chapter and that know you personally and love the service.  And you can kind of take over that responsibility because you know, when they think of fall, they’re not thinking of Medicare open enrollment, they’re thinking of, traveling to the mountains to see the foliage.  Or kick off for their favorite football team. They’re thinking of spending time with their grandchildren.

Well thank you so much a for joining and helping clarify this complex topic and making it simple.  I’m also excited to check out your book in September.

It’s not that complicated, so I love the title. If you guys have questions directly and want to reach out to Ari, his email is [email protected]  Thank you everybody for tuning into today’s episode, I heard hope you learn something valuable and we appreciate all of you and hope that you follow us and give us a subscribe and make sure you continue to tune in.

Until next time, this is Kevin Lao signing off.

Episode 12: Should I pay off my mortgage early?

(transcription) Should I pay off my mortgage early?

Kevin Lao 0:17
Hello, everyone, and welcome to the planning for retirement podcast where we help educate people on how retirement works. I’m Kevin Lao your host, I’m also the lead financial planner at Imagine financial security. Imagine financial security is an independent financial planning and investment management firm based in Florida. However, this information is for educational purposes only and should not be used as investment, legal or tax advice. This is episode number 12. Should I pay off my mortgage early? I hope you enjoy the show. And if you like what you hear, leave us five stars, it really helps and make sure to subscribe or follow to stay up to date on all of our latest episodes.

So this is such an important question and one I get all the time for not just folks that are approaching retirement, but younger folks that just took out their first mortgage and they’re trying to figure out, you know, should they pay it off in 30 years?

Should they pay it off early? And this particular question was was fielded because my client was speaking to a work colleague that’s several years of senior to her. And they recommended that she take $500 a month and apply it towards principle every month, and that would essentially pay down the mortgage after 20 years instead of 30. I mean, that sounds great on paper, I mean, after 20 years, you have no mortgage and free cash flow that you can do whatever you want with. You can invest all of that free cash flow at that point in time. But what is the opportunity cost to not investing that $500 a month, let’s say in a side fund? And so that’s really what we’re going to be addressing today. And really, the concept of paying down your mortgage early or not, comes down to three things. Number one is your personal risk tolerance. And number two is your ability to generate a certain rate of return in that side fund. And then number three is liquidity concerns. Okay, so we’re gonna address all three of these. So the first thing to talk about is risk tolerance. The first challenge of investing that into a side fund versus paying down the mortgage early is that the side fund is generally not going to be a guaranteed rate of return. Even if you look at CDs, or Treasury rates,. Yes, certainly interest rates have come up a little bit, but where are you going to get a four and a half percent, or even a 5% guaranteed rate of return? Nowhere, it doesn’t exist at this point in time. And so paying down the mortgage, just for the simple fact that it’s a guaranteed rate of return of four and a half percent. And that might be aligned with your risk tolerance. In this case, maybe you do pay down that mortgage, over 20 years, because four and a half percent is a pretty damn good rate of return on guaranteed money. Okay? Now, let’s say we take that out of the equation, we understand that the money in the side fund is not going to have a guaranteed rate of return of four and a half or 5%. But let’s say you’re okay with that. You say, Hey, I understand diversification, I understand how investing in stocks work or mutual funds or ETFs. And I am confident I can get a five or six or even 7% rate of return in the side fund over time. What happens to that side fund over 20 years or 30 years or 40 years? Okay, and so that’s what I did for her I crunched the numbers, I just pulled up Excel and I literally just took the the mortgage calculator amortization schedule from And I plugged everything into Excel. And we calculated after 20 years that mortgage would be fully paid off if she applied that $500 of additional additional principal every single month for that 20 years. Okay, then I ran the second scenario. So let’s call a client a, let’s call client a the one that pays the mortgage down in 20 years, okay, and let’s call client b be the one who pays the mortgage off over 30 years, which is the scheduled amortization. And they invest that $500 a month into let’s call it a side fund. And I ran three different scenarios, let’s say you earn 5% or 6% or 7%, what is the difference over the duration of your life expectancy. So the first thing we found out is that after 20 years, client a has paid off the mortgage but client B has enough in their side fund to pay off the remaining principal if they wanted to, assuming a 5% return! And so this goes back into what I mentioned earlier about liquidity. Your house is not technically liquid. Sure you can tap into it via a cash out refinance which would then reset a new amortization schedule or you could do a HELOC, but that’s also debt against your property. And so it’s not technically a liquid asset whereas the side fund if you set it up properly, it is 100% liquid, you can tap into it at any point in time. Now, of course, if you’re investing that money into a 401 k or a 403 B plan, there’s penalties if you tap it before 59 and a half, but you might not really care about that. On your balance sheet, you have enough saved and invested assuming a 5% rate of return, that equals the remaining principal on your mortgage. In my opinion, client B is winning here, because they have money on their balance sheet that’s 100% liquid. And if they felt like it, they could pay off the mortgage just like client a did. Now, after 20 years, what happens to client A is they have 100% of that principal and interest payment to invest in the side fund. So now they begin their side fund after 20 years as opposed to on day one. So then I tracked after 20 years, what happens to the side fund of client B versus the new side fund of client A. Assuming a 5% rate of return, assuming we stay disciplined, and we’re investing those payments every single month. For client B, it’s that $500 per month of excess principal that they weren’t applying against the mortgage. And now for client A, it’s roughly $31,000 per year that they’re now applying to the side fund. Well, after another 10 years, once the mortgage is fully paid off for client B, client B still has 10% more (just over $40,000) in their side fund, then client A. So if you look at it mathematically a 5% rate of return for someone that’s reasonably aggressive, maybe a balanced investor, they mathematically have more money in their side fund, then did client A even after client a paid off the mortgage, and then reinvested all of those payments into that side fund. Now, what happens when you do 6%, or even 7%? Well, now the multiples go up even higher, instead of having 40,000 more, client B has over $200,000 more in that side fund than client a assuming a 7% rate of return. And if you look at the s&p 500, historically speaking, just over nine and a half percent annually over the course of the last 30 years. I mean, who knows a lot of people think returns are going to be lower over the next decade or two, no one has a crystal ball on this. But I think 7% is a reasonable return for someone who’s fairly aggressive. And so again, it goes back to the first point of risk tolerance. Are you comfortable with taking on some more risk? And are you comfortable with understanding that comparing this to paying down your mortgage is not apples to apples. Paying off your mortgage is a guaranteed rate of return of whatever the interest rate is. Whereas if you invest in the side fund, you might get six, you might get five, you might get seven, but you might not. Maybe we go through a period of time over the next 10 or 20 years, like the lost decade of 2000 to 2010. No one has a crystal ball on this. But if you understand that, you know what your appetite for risk is, and you apply that principle to paying off the mortgage or not, it’ll help make a decision that is best for you. Now, how you invest that side fund, there’s also many factors there. Are you disciplined with the investments? Are you investing in a very well diversified portfolio? Or are you trying to hit homeruns by investing in let’s say, digital assets, or, one or two concentrated positions or stocks that you really, really think you like. Because if those don’t pan out, that negates the entire purpose, because the likelihood of you earning that 7% over the course of the 20 or 30 years, is lower than if you’re well diversified, well disciplined, and well positioned to capture the market returns, as opposed to swinging for the fences. And the last thing is liquidity. All along the way, as you’re investing into that side fund, that money is liquid on your balance sheet, if you had an emergency pop up, let’s say it’s a major medical expense or you lost your job, you could tap into that side fund, whereas during emergencies, you might not be able to tap into the home equity. Maybe you lost your job. How are you going to take out the HELOC or do a cash out refinance? No bank is going to give you a loan. Or what if you have a major medical bill? It might take 30 to 60 days to underwrite your home equity line of credit or do the cash out refinance. So having that side fund that is liquid right away on day one is a huge benefit to that client B who is investing into the side fund versus paying off their mortgage sooner. Personally if you want to know I am client b. I like to leverage the bank’s money, I like to stretch out the debt as long as possible just given how low interest rates ar. The first home I purchased in 2016 had a three and a half percent rate. This home that we just purchased has a 3% mortgage, so I’m confident I can get a five, six or 7%. And that’s a much higher multiple than comparing it to what my interest rate is on my mortgage. But I understand the risk there on the side fund, I understand it’s not guaranteed. And I also understand that I have much more liquidity in that side fund than I do in my home. Now, as interest rates continue to go up the argument to paying off that mortgage early pendulum is beginning to swing in that favor, especially if rates go up to maybe 6%. Then, your appetite for risk needs to be fairly high to to accommodate that higher return in that side fund.

Now, with all of that being said, I talk to clients all the time that are approaching retirement, and they’ve had this goal of being debt free in retirement for many, many years! 15, 20 or even 30 years! Using math to convince them to invest more on their balance sheet versus paying down the mortgage by the time they retire is completely irrelevant to them. Because the qualitative factor of owing nothing to anybody is that much more important than how much they have on their balance sheet. So if that is you, pay off that mortgage by the time you retire, get aggressive, figure out that amortization schedule that lines up with your anticipated retirement date. And don’t feel badly about losing out on those opportunity costs. Because the psychological benefit and that peace of mind you’re going to have by checking that box off of being debt free in retirement is that much more meaningful for you.

Thanks, everybody, for tuning into this episode of the planning for retirement podcast. I hope you learned something valuable. We really appreciate your support and following our podcast journey. If you have any feedback on the show, or even if you have questions that you want answered on the show, send me an email at [email protected] Just write in the subject line “podcast” and who knows, maybe your question will be answered on the next episode. Until next time, this is Kevin Lao signing off.

Episode 11: What is tax planning vs. tax preparation?

What is tax planning vs tax preparation?

What is Tax Planning vs. Tax Prepartion


Kevin Geddings 0:21
Six minutes now after 11 o’clock, we’re live from St. Augustine, we hope that you’re having a good day so far. Kevin Lao joins me here live in the studio. And of course, he is an expert when it comes to financial planning and the like, Kevin, how are you doing?

Kevin Lao 0:36
I’m doing well, Kevin, thank you for having me. As always, yes,

Kevin Geddings 0:39
Imagine financial security, just imagine it if you can. I know a lot of our listeners are a little nervous these days, you know, they made the really bad mistake of looking at their January 30. Second quarter, you know, IRA statements that rolled in in the second week of July, you should never have opened those,

Kevin Lao 0:57
you know, a lot of clients, and people are telling me that they’ve been throwing their statements in the fire pit. So maybe that’s a good solution.

Kevin Geddings 1:03
Kevin has been doing this work for a long, long time. And he’s based right here in Northeast Florida. He’s worked with people from all over the country. And we’re going to talk today about tax planning versus tax preparation. And I know what you’re thinking, hey, it’s July, what? Why are we talking about taxes? You don’t do that until the end of the year or April? But no, there’s a reason why you would want to talk about tax planning now, right, Kevin?

Kevin Lao 1:25
Yeah, this is, first of all, please don’t take this as tax advice. Everyone has their own unique situation. But you know, there’s two different schools of thought you have tax preparation, and you have tax planning. And, a lot of people think tax preparation is tax planning. What that means is, in March or April, you gather your 1099s and your W2s and you throw them at your accountant last minute and make them work to death until they file your returns and figure out how much you owe. Or if you have a refund. And there’sonly a few things that you can actually do to impact your tax liability at that point in time. Whereas tax planning is proactive, where you’re not even just looking at the current year in terms of your tax projections and opportunities to reduce your taxable income now, but you’re looking years into the future, to look for opportunities to mitigate your tax exposure, particularly in your retirement years.

Kevin Geddings 2:17
Yeah, there are specific things you can do. And it’s amazing, so many people don’t do these things. I know, you may be thinking, well, you know, the government or somebody can give you some advice or guidance is really on you, or it’s on us individually to figure out a way to minimize, you know, our tax risk.

Kevin Lao 2:35
And it’s a boring topic, I was telling one of my neighbors, I was like, Hey, I’m gonna jump on the radio and talk about tax planning. He’s like, that sounds exciting. It’s not exciting for most people. And so that’s one of the main reasons they hire a firm, it’s not just for investment management, but it’s for this tax planning concept. And one of the basic things that pretty much everyone can do that’s contributing to, let’s say, a 401 K plan or an IRA, and they’re still in the accumulation phase, as to whether, weigh the pros and cons of whether or not you’re doing a traditional 401K or an IRA contribution versus a Roth 401 k or IRA contribution. And the basic concept of it is, do you think taxes are going to be higher or lower for you in the future? If you think taxes are going to be higher for you in the future, whether it’s because your income is going to be higher in the future, or you think potentially the government’s going to raise taxes in the future. Remember, at the end of 2025, the tax cuts and Jobs Act is sunsetting. So tax brackets, in general, unless they change, things are going to go up for most people. So if you’re in the camp, Hey, you think tax rates are probably going up over time, you may want to consider doing a heavier dosage of Roth contributions, whether it be in a Roth IRA or Roth 401 K. And you know, you’ve got to be careful with this. Because once you enroll in a 401 K plan with your company, the default for 99% of companies out there is in the traditional 401 K plan. And so you need to look and see your options. Can you do a Roth 401 K contribution or 403 B contribution or Roth TSP, if you work for, you know, military or government. And so this is a an easy sort of analysis to figure out, those Roth versus traditional contributions for retirement.

Kevin Geddings 4:07
Hey, if you’re just hopping in the vehicle, that’s the voice of Kevin Lao. And of course, he is the principal at imagine financial security that’s located right here in Northeast Florida. And they work with individuals just like you and me, and he will help you get to a better place in terms of your retirement. We’re all worried, Kevin, about running out of retirement savings, you know, outliving our retirement, but you help people with that all the time.

Kevin Lao 4:31
Yeah, I mean, that’s, that’s the number one concern, they don’t want to be a burden on their loved ones. You know, and a big a big part of that is health care. And, Fidelity does a study every year. Right now, a 65 year old couple is expected to spend $300,000 on health care costs alone during retirement, and that’s not even including long term care costs. That’s a totally different issue. One of the things that I’m a big proponent of, if you have five or 10, or even more years of working, is whether or not you can qualify for a Health Savings Account better known as an HSA. I wrote a blog post about this on my website, I believe this is the most tax efficient vehicle you can utilize to save for retirement. It is a triple tax benefit, tax deductible contributions, tax free Growth and Tax Free distributions, as long as those distributions are used for healthcare related expenses. Now, the trick is, don’t get super aggressive spending those HSA contributions during your working years. Do the best you can to pay out of pocket for a lot of those healthcare costs. Because what you can do is you can turn around and invest that HSA take advantage of the market being down invest that HSA to let that grow for the next 15-20 years of tax free growth. So you can actually pay for those health care costs that Fidelity mentioned in retirement.

Kevin Geddings 5:48
So you can actually take HSA funds and invest those in the market. Yeah,

Kevin Lao 5:52
Most of the time, once you hit $1,000 in savings. There are limits, once you’ve contributed more than $1,000, then you can start to invest the surplus, so you have to keep a certain amount of cash, and then you can invest a certain amount. For me, I invest every dollar that I can in the HSA and I do my best to never touch the HSA. You can touch it before 59 and a half for health care related expenses. So, if you have an emergency medical event that happens, by all means you need to consider this as an option. But if you can let those continue grow tax free, it’s the most efficient vehicle you can utilize to save for retirement because it can be also used to pay for those long term care costs that I mentioned, it could also be used to pay for long term care insurance premiums tax free. So there’s a lot of benefits that you can utilize with the HSA, once you get to retirement.

Kevin Geddings 6:34
Wow. And there’s no cap in terms of how big that HSA account can become?

Kevin Lao 6:39
There is no cap on how big it can become, there is a cap on how much you can contribute. So for 2022 for if you’re single $3,650 If you’re married filing jointly $7,300 per year in annual contributions. So think about that. $7,300, over a 10 year period, you just contributed $73,000 into a tax free health care plan that hopefully you’ve invested wisely. And hopefully that doubles a couple of times over the next 20 years. And all of a sudden now you have 210 $220,000 in an HSA.

Kevin Geddings 7:10
These health savings accounts, Kevin Lao. I mean, sometimes you’ll see little ads at your bank, are there other ways? I mean, how would you recommend setting up these accounts and can they be set up through an investment account approach? Or how does that normally work?

Kevin Lao 7:26
Ya know, there are a lot of different carriers The first qualification to use an HSA is you have to have a high deductible health plan. If you don’t have a high deductible health plan, you can’t qualify for an HSA. And there’s some rules around that. So, just do a Google search and say, Hey, do I qualify for an HSA? But if you’re with an employer, a lot of times, they’ll say, hey, this type of health program, you can utilize an HSA, this one, you cannot. For military service, or government, if you’re on TRICARE, those cannot qualify as high deductible health care plans. So you cannot use an HSA if you’re military tricare. But if you’re civilian, and you’re working for an employer that has different healthcare options, go to them and say, hey, which which of these offers a high deductible plan with an HSA and which of them are kind of your traditional health care programs. And they usually partner wit a broker to set up the actual HSA account.

Kevin Geddings 8:17
moving funds into an HSA a health savings account, that’s just part one aspect of tax planning that Kevin Lao can help you with, once again tax planning is taking advantage of all the legal vehicles that are out there that will reduce your tax exposure, right?

Kevin Lao 8:33
Absolutely. Yes, I mean, a big one right now, we were talking a lot about this off air, with the markets down, we’re officially in a bear market since last time I was on the show. Which is basically measured by a 20% drop from a previous high. So many people out there might have some losses, some embedded losses in their investment accounts. And a lot of times, like we talked about, people are kind of throwing away their statements, they’re burying their head in the sand, but these losses can be utilized to offset potential capital gains or income in the future. And so the strategy is better known as tax loss harvesting, it has to be done inside of a taxable account, it cannot be done in an IRA, whether it be a Roth or even a 401K plan, it has to be in a non qualified account. But if you recognize the loss, meaning you sell that investment at a loss, now you actually have a Realized loss. And so let’s say you sold an investment at a loss for $50,000, that loss can be utilized to offset capital gains, whether it be this year or in future years, or reduce your taxable income, up to $3,000 per tax year. And the best part is, there’s no limitations on how many years you can carry that forward. So if you’re recognizing a lot of these losses, while the markets down, you can sell these investments at a loss, and we’ll talk about reinvesting that in a second and utilize those losses for many, many years to come. Now, the key is to avoid the wash sale rule. And so what that means is you cannot sell an investment and then turn around within 30 days and buy the same investment, or a substantially identical investment. Okay? So if you buy an individual stock, it’s pretty simple. You can’t sell Apple and buy Apple in the next 30 days. Otherwise, it’s a wash sale rule, it’s the same investment. But let’s say you have a mutual fund, like fidelity s&p 500 fun if you sell that, and bought, let’s say, the Vanguard s&p 500 fund, that might be a substantially identical investment. So you’ve got to be careful with that wash sale rule. The rule is within 30 days, you can’t turn around and buy an identical or the same security within 30 days otherwise, the tax loss harvest doesn’t work.

Kevin Geddings 10:36
Hey, we’re talking about tax planning versus just tax prep. And obviously Kevin Lao knows his stuff. Imagine financial security that’s imagine financial security located right here in Northeast Florida, you can always reach him at cleverly enough, or call the office number 904-323-2069 That number again, 904-323-2069. We’re gonna put all of Kevin’s information up on our social media platforms as well at WSOS radio on Facebook and Instagram. We’ll be right back.

Kevin Geddings 12:10
The Beatles here on 103.9. We had to play tax man because while we’re talking about tax planning versus tax preparation with Kevin Lao, he, of course is the principal at Imagine financial security, imagine financial security located right here in our part of the world. And he helps individuals, with all sorts of financial issues mostly focused on trying to get you ready for retirement. That could be retirement for you in the next 10 or 15 years. Or maybe you’re one of these, you know, super successful 20 Somethings that wants to retire like Kevin at age 40.

Kevin Lao 12:39
I wish. Having three kids under three, I think I’ve got a little ways to go. But yeah, that’s a good point. Early retirees is definitely a hot topic and it’s not necessarily retiring, and then not doing anything. It’s retiring from your day job, and then at 45 or 50, doing a passion project and having that financial independence to do so. So I think we talk a lot about the FIRE movement, financial independence to retire early. So it’s gaining a lot of traction.

Kevin Geddings 13:09
If you know somebody who’s in that situation, or you’re in that situation, I would encourage you to reach out to Kevin. Today though, we’re talking about tax planning, some various aspects of it. In the last segment, we talked about health savings accounts and how they can be a very interesting vehicle that can be more than you think. The way I was thinking of it before Kevin stopped by today, which is, well just a pool of money that you set aside tax free, and then you spend it down on your eyeglasses and things like that. But it can actually be a much more creative vehicle than that. So he has a great blog posts at his website, that you can read about his thinking on health savings accounts. We were talking about, obviously, tax loss harvesting, with a lot of investments that have taken a hit here in 2022. There’s some benefits there. Let’s talk about one of the old school things even baby boomers out there, we’ve been told all of our lives, hey, you make a charitable contribution, give some money to the Salvation Army and you get to write that off your taxes.

Kevin Lao 14:03
Absolutely. This is probably one of the one of the topics that is that is misunderstood by just about everybody. They think they’re donating to charity, and they’re getting a tax deduction for it. But studies have shown that nine out of 10 taxpayers since the tax cuts and Jobs Act Act went into effect in 2017. Nine out of 10 taxpayers are taking the standard deduction. So it doesn’t matter what you’re doing with charitable donations. It’s technically not making a difference from a tax standpoint, because the standard deduction was multiplied by two with that legislation, which is, set the roll off at the end of 2025. But for now, most people are not itemizing deductions, and therefore those charitable donations don’t matter. Except for $600 for a couple and then $300 For a single if you’re if you’re doing the standard deduction and you’re doing charitable donations, you can take $300 If you’re a single filer and $600, if you’re married and actually reduce your taxable income, but everything above that is not dedutible if you’re taking the standard deduction.

Kevin Geddings 14:59
So I would imagine people that worked with you. And some of our listeners have some significant retirement savings. If they want to make charitable contributions, you can give them some advice, right?

Kevin Lao 15:08
Yes, one of the big ones, one of my favorite strategies is called a QCD, or qualified charitable distribution. Okay, so this is for individuals that are over 70 and 1/2 that have Ira plans, they can donate up to 100,000 dollars per year from their IRA to a charity. And this works extremely well, when you turn 72, and you’re taking required minimum distributions. The amount you have to take out per the IRS rules based on your life expectancy table. So if you’re taking out, let’s say, $50,000, because the IRS makes you, and normally you give, let’s say, $10,000, to charity, okay, well, you can take $10,000 from that required minimum distribution and donate it straight to charity. And that is never included in your ordinary income. Okay, so it’s better than a tax deduction. So don’t even worry if you’re itemizing, or taking a standard deduction that is not included in your ordinary income. So now, it looks like your distribution was only $40,000, not $50,000. So for folks that have, let’s say, Social Security income coming in, or they have maybe a pension from the military, or government, maybe they don’t need all of the required minimum distributions, and they’re sitting there complaining, oh, the IRS, they make me take out all this money. And if they’re charitably inclined, or maybe they just want to reduce their taxable income, they can start to do those QCDs each and every year and have a QCD plan is what I like to call it. Especially if it’s going to reduce your tax bracket. And that’s another thing, we can get into all day long, but tax brackets also impact what you pay for Medicare premiums, and QCDs work extremely well coincided with both of those two topics.

Kevin Geddings 16:41
It just strikes me, Kevin, there’s so many folks that don’t know this stuff, because the government doesn’t say, Hey, here’s a little pamphlet where we’re gonna explain how we’re going to nail you on taxes, you really have to go out there and search and find on your own.

Kevin Lao 16:54
Yes, all this information is online. That’s like the nice thing about the internet, you can do Google searches all day long, and read about QCDs and required minimum distributions or charitable donations. I think the value that my clients find, in working with someone like my firm, or other financial planners out there is that we can get that information that you can find yourself and apply it to what is relevant to your situation, and maximize those rules in your favor based on your circumstances and your financial situation.

Kevin Geddings 17:27
Well, what you do with people is you work with them in a tailored way, right? Because it sounds cliche, but the reality is, we are all different. Even if you have the same amount of money, you have half a million or a million in assets, or 2 million, or what have you, how you want to utilize those funds in retirement is greatly different from person to person.

Kevin Lao 17:45
That’s why that’s one of the reasons why we named our firm what it is, I like to have people imagine what financial security means to them, it means different things to different people. You know, one other thing real quick if we have time to talk about is the donor advised fund which is also the acronym d A F, donor advised fund. And so if you’re not 72, if you’re not taking those required minimum distributions yet, what you can do is you can make these contributions to a donor advised fund, which think of it as like your own personal charity. So if you’re charitably inclined and you typically make, let’s say five, or six, or even 10,000 dollars per year to a certain charity, but you’re not getting a tax deduction for it because you’re taking the standard deduction. It doesn’t really matter how much you donate to charity, you’re already getting that standard deduction, what you can do is we call it bunching, bunching those contributions. So in one year, make a larger donation into this DAF, this is still your account. But the nice thing is, let’s say you put in $50,000, which might be five years worth of donations, now you can deduct those contributions, because it’s above that standard deduction. And then what you can do with that DAF is completely up to you from there. It has to be used for charitable donations going forward. So you can’t donate it to, you know, little Johnny’s college fund, or pay yourself a salary, it has to be a legitimate 501 C3 organization. And you can start to make donations from that donor advised fund on a tax free basis. And the cool thing is similar to the HSA, like we talked about, you can also invest that donor advised fund in a diversified pool of funds. So you can set that account up with fidelity or Schwab or Vanguard or whatever it might be. Get that invested according to a plan that works for you and your risk tolerance. And you can actually potentially have more money to give to charity over time. And it’s also kind of a multigenerational tool. I see clients utilize it teaching their kids to be charitably minded, those types of things. And again, you can actually take the deduction for those contributions because of the bunching rule.

Kevin Geddings 19:43
And that’s the voice of Kevin Lao. If you just hopped in the vehicle, and we’re taking a little break from the music we’re gonna get back to the songs are here in just a second. And we’re talking about tax planning versus tax preparation, what can be done to minimize your tax risk, regardless of the income that you have or whatever your assets are? Kevin works with individuals on the He’s issues and on investment issues overall to make sure that you have the retirement that you always wanted. So we’ll be right back. Talk to me about Medicare planning.

Kevin Lao 20:17
Yeah. So Medicare planning is an interesting one. When you turn 65, you’re going to enroll in Medicare, and you’ve been paying into the system for your entire career. Your employer takes out a certain percentage of your paycheck to pay into the Medicare system, what a lot of people don’t realize is that your premium for Part B is dependent on your modified adjusted gross income. Okay, and so based on that modified adjusted gross income, you might pay what’s called an Irma penalty, okay. And so, if you look at if you look at different things, like your Social Security, or a pension that you might have, or perhaps it’s required minimum distributions, once you add all that up, you need to see, hey, is your premium going to be higher for Medicare, and that also coincides with those Roth conversions to potentially pay a little bit more tax now to not only save in tax your tax brackets going forward, but also to reduce what you might pay for your Medicare premiums? Once you’re 65 or older.

Kevin Geddings 21:15
if you have any questions about tax planning, or just investing in general and getting ready for a secure retirement, you can get in touch with Kevin Lao by going to the website. That’s So Kevin Lao, we see all these ads on television all the time for life insurance, that you can be 70 years old, and be a diabetic with one of your arms falling off, and you can still get a term life insurance, you know, but you help people with these issues, right, figuring out whether life insurance is a good investment or not?

Kevin Lao 21:47
I know a little bit too much about life insurance and long term care insurance. But it’s a topic that’s super important. And I think it’s one that’s often misunderstood by by the consumer. But the basic idea around life insurance in retirement is, if you have a goal to leave a legacy to your children, or a charity, or maybe you have an estate tax issue, life insurance could be one of the most efficient tools you can utilize to pass on to the next generation, because it’s income tax free to those beneficiaries. Whereas if you think about your 401 K, or an IRA plan, those are going to be taxed to your beneficiaries, assuming those traditional contributions are tax deferred contributions. And, think about the secure Act, which is another piece of legislation that passed at the end of 2019. It’s made the rules on on passing those 401 ks and IRAs to the next generation, extremely tax inefficient. So, if your kids are working at Google, or some big tech company or Amazon, they’re making way more money than you ever made, you need to think about that, what is their tax situation going to be if they inherited your IRA tomorrow? So life insurance can be a good solution to offset some of those tax liabilities upon the inheritance of those 401Ks and IRAs. And again, it’s it’s one of those things, the earlier you do the life insurance planning, the more cost effective it can be. And so I work with my clients in terms of shopping carriers with them, looking at all of the different landscapes, all these different contracts, and help them understand what they currently have and what they might potentially need. Because these contracts are extremely complicated. I think the insurance companies, they like to make things complicated, but that’s one thing I can help my clients is like looking at their current life insurance, looking at their current long term care, does it make sense to refresh and upgrade based on what the markets doing now, and based on what their long term goals might be?

Kevin Geddings 23:41
Yeah, well, it’s a great vehicle. There’s all these different vehicles that are out there, whether it’s health savings accounts that we were talking about earlier, you know, obviously taken advantage of some of the investment losses that many of us have experienced, since the beginning of 2022, charitable donations, how those can be structured with donor advised funds, all that stuff. I know if it all sounds like a foreign language to you, that’s okay. Because it’s not a foreign language to Kevin. That’s what he does all day long, and he actually enjoys it. It’s fun. You can tell. I enjoy getting to spend time with Kevin on the radio because not everybody loves what they do. But he actually loves what he does.

Kevin Lao 24:18
I you know it’s fun. I mean, helping people plan for retirement. It’s an exciting time in people’s lives. But it’s also very unnerving, because there’s a lot of uncertainty, a lot of unknowns. The media likes to play on fear. So people read things and they say, hey, does this apply to me? Does this not apply to me? So I think I think my clients really appreciate an objective third party that’s not affiliated with the media, telling them what what is relevant for them and what they need to be concerned about.

Kevin Geddings 24:43
I highly recommend working with Kevin once again, That’s The phone number 904-323-2069. As promised, here’s the phone number 904-323-2069. You’ll get a sense of Kevin In his bio, his thinking on a variety of financial issues, if you check out the website, that’s where you may want to start. Kevin LAO. Thank you very much for coming by. We learned a lot.


Episode 10 – Six Reasons to Take Advantage of Roth Conversions

Are you approaching retirement with the bulk of your next egg in tax deferred 401ks or IRAs? With so much uncertainty on where tax rates might head in the future, you might be wondering, “Should I take advantage of Roth conversions?” They are not for everybody, but in the right situation you could end up saving thousands, or even hundreds of thousands of dollars, in taxes during your lifetime. Additionally, your heirs will also benefit from a more tax efficient inheritance. I hope you enjoy this episode, which includes my interview with Kevin Geddings at WSOS 103.9 in St. Augustine!

Episode 9: The 5 Most Common Estate Planning Mistakes

Kevin Lao  00:00

[music] hey, everybody and welcome to the Planning for Retirement Podcast where we help people plan for retirement. My name is Kevin Lao and I’m your host. Just a quick disclaimer, I have my own registered investment advisory firm. It’s Imagined Financial Security. We’re registered here in Florida. But this information is for educational purposes only and should not be used as investment, legal or, tax advice.


If you do have questions about how to work with my firm, you can go to my website at So, today’s episode nine, the 5 Most Common Estate Planning Mistakes, I’ve seen a lot of them over the years, being in the business and I’ve been thinking about doing this episode for a long time, because Estate Planning is a conversation I have with just about everybody, and it’s not a fun conversation because we’re talking about death, disability in capacity.


So, no one wants to address Estate Planning and it’s no surprise that only 1/3 of American adults have an Estate Plan in place. But one thing I always hear from any client is, that they don’t want to be a burden on their loved ones. I’ve put together this episode, and hopefully you find this helpful. These are easy to address, easy to fix. But I always recommend talking to a licensed attorney that can actually help you create and execute your documents properly.


So, the first most common mistake is probably, obvious for most and that’s simply not having an Estate Plan.

So, if you’re one of the 2/3 of adult Americans, you’re obviously in the majority, and you may not have an Estate Plan, that’s ok. It’s very easy to set up your basic will, your basic power of attorney, which is someone that can make financial decisions, if you’re incapacitated, a living will which is essentially, if you are in a vegetative state.


Who’s going to make that decision? What are your wishes in that situation or, a power of attorney for health care, which is someone that can also make healthcare decisions on your behalf, if you’re unable to? Those are the primary documents that most Estate Plans will incorporate. You may need a trust, you may not need a trust and that’s again, up for a licensed attorney, someone that can review your situation and give you some advice on that.


Many people think that if their situation is fairly simple, they may not need a trust and that’s may be true. But you might need a trust for variety of reasons, which we’ll cover here in a minute. So, number one, simply getting an Estate Plan done is, really the first battle.

We get into mistake number two, which is not properly executing those Estate Planning documents.

Again, I’m guilty of this too, my wife and I, we did our first Estate Plan before we had children. So, it was all about who’s going to receive our assets, if something happened to both of us? Who’s going to take care of our dogs? At the time, we had three dogs in our household.


So, there were there was some complexity but not a lot. Since then we had three children and we finally updated our state plan about a year ago. It felt pretty good, frankly, to get it done. To make sure everything was directed to our beneficiaries, making sure that we had guardianship for our kids. If something were to happen to both of us.



We had someone named that would take care of our kids and also to manage the assets for them. But not properly executing your documents is, super common because it takes a little bit of heavy lifting. If you set up a will or, set up a trust, you are going to have to go in and look at all of your accounts whether you have 401K’s, IRAs, life insurance, annuities, bank accounts, investment accounts, and you might need to make some changes on those beneficiary designations.


So, there are two types of assets in this world, assets that can pass outside of the probate process by having a beneficiary, and then assets that will pass through probate if proper beneficiaries are designated or, if there are no investment beneficiary designation, eligibility. So, let’s start with accounts that can be passed outside of probate.


Most commonly those would be retirement accounts like a 401K, 403B, life insurance contracts, annuity contracts, even assets that are not held inside of retirement accounts like, joint bank accounts or, individual bank accounts or, joint or, individually held investment brokerage accounts. All of those have the option to name a primary beneficiary and most of the time a secondary or, contingent beneficiary. And then for bank accounts the alternative, the name for it is a TOD or, a POD, which is transfer on death or, payable on death.


So, once you’ve reviewed all of your accounts and you have an Estate Plan in place, most of the time your attorney will tell you, hey, here’s who you should name as primary based on your wishes. Here’s who you should name as the contingent beneficiary based on your wishes and you have to do that for every single account that you have. Again, this is up to you, your attorney is not going to do this for you. You’ve got to contact those institutions, get those beneficiary designations updated.


I’ve seen scenarios where clients have been divorced for 20 years, and their ex-wife or, ex-husband is still the primary beneficiary on their 401k. Especially, if you’ve moved around from company to company, a bunch of different retirement accounts or, you have several life insurance policies, one with work, one outside of work, one that your grandmother took out for you when you were a baby, look at all those beneficiary designations. Make sure they are up to date and then make sure you have a contingent beneficiary if that option is available.


Now, the second part to this mistake of, not properly executing is, if you have a trust, making sure that the assets that should be held in trust are titled to the trust. So again, some heavy lifting involved, especially, if you’re moving a property inside of a living trust or, an investment brokerage account inside of a living trust. If you’re naming a trust as a primary or, contingent beneficiary of those accounts that we just talked about, all of that needs to be done by the individual client.



Again, if paperwork might be involved, you might need to get on the phone with customer service and jump through some hoops. But it’s worth it in the end, because your documents aren’t really going to do anything unless you have the proper beneficiary designations and the assets are titled with the right ownership.


So again, those are all scenarios that you can easily review, take a look at, making sure that they’re all up to date, and review them once every year, two years, three years. I mean, if your situation isn’t really changing a lot, you may not need to review them every year. But definitely every couple of years, every three years, you probably want to review those beneficiary designations and make sure that they’re titled properly.


Third most common mistake is thinking a living trust or, a trust in general, is just for ultra-high net worth people.

I hear this all the time, hey, Kevin, I don’t need a trust. I don’t have over 11 and a half million dollars, which is the current exemption for estate tax purposes. Maybe they have $5 million or, $6 million and they might have other concerns in terms of inheritance for their children or, grandchildren or, they might be concerned about divorce of the one of their kids and assets being split to that son-in-law or, daughter-in-law that they’re not a huge fan of to begin with.


Maybe there’s a creditor protection concern or, spendthrift concerns are a child with special needs that may need care for the rest of their life. Therefore a trust could make a lot of sense in solving those issues in terms of inheriting assets outright. So, all of those reasons are reasons to own a trust, whether it be a living trust or, an irrevocable trust or, a testamentary trust or, if you have minor children that’s another one.


My wife and I, we have three kids that are under 18. If something were to happen to both of us, we have guardianship named and we also have a trust that would be set up to be managed for our boys, until they are of age and that is designated inside of the trust.


So, think of a trust as essentially another entity that will help you execute your wishes and manage the assets properly for your beneficiaries, if there are concerns about them inheriting assets outright or, if you just want to make sure that those assets stay in the family and aren’t subject to divorce proceedings or, creditor protection concerns those types of things.


Another reason I have a trust is, to simply avoid probate. Probate is expensive. It can cost anywhere from two to 3% of your estate. So, if you have an estate that’s $2 million, I mean, that could easily cost you a 30, 40 $50,000 to go through the probate process, and setting up a trust might cost you three or $4,000.



So, this is a big reason why a lot of people will go through the process to setting up a living trust, even if there aren’t a lot of the concerns that I just mentioned. They love their son-in-law or, daughter-in-law or, their kids are totally able to manage a large inheritance. They may still want to set up a trust. So it’s passed outside of the probate process to avoid the cost of probate and also the public record of probate. It keeps that privacy involved.


The assets may still stay in trust for a lot of those concerns that we just talked about. But that beneficiary their son or, daughter or, whoever that beneficiary is, can still access the assets for whatever purpose that they want to access those funds for, if they’re able to manage it themselves. You also have the ability to set up a corporate trustee.


This is an area that I see is, definitely becoming more common where, maybe there’s several children involved, and one of them is just completely off the rails. Not able to manage assets. There’s a lot of concern, if there was a big windfall of a million or, $2 million that’s passed on to one of the children, they may want to have a trust set up for that beneficiary, and not have that person as the trustee into, in terms of making the financial decisions, when you’re no longer here.


So, you may want to consider a corporate trustee, which is a trust company or, a bank or, financial institution, can serve as a corporate trustee, to ensure the wishes of the trust are executed on that beneficiary’s behalf if you have concerns of the management of those assets.


Special needs trusts and other things as well, having a corporate trustee. I see a lot of times will fit in those situations, because the siblings of that special needs child may not be available. Maybe they’re, a neurosurgeon or, they’re deployed overseas, and they’re just not available to make those financial decisions for their brother or, sister. So a corporate trustee can also be put in place, in lieu of an individual, if you have a trust setup.


There’re a lot of benefits of trust. I’m talking a lot about trust, because I’m a big fan of them, just for the simplicity of the execution of your wishes, and all of the benefits of trust provides, whether it’s a living trust or, a testamentary trust. Again, consult your attorney, see if that makes sense in your financial plan and if it does, make sure that it’s properly executed on the back end.


All right, number four, is leaving tax inefficient assets to beneficiaries.

So, what does that mean? There are certain assets that when they’re passed on to the next generation, are going to be heavily taxed, and then there are some assets that are not going to be taxed at all that are super tax efficient to leave to beneficiaries.


The big one I’ll highlight here is, for traditional 401k is, traditional IRAs that used to have the benefit of what’s called a stretch IRA, when they’re inherited by a non-spousal beneficiary, like a son or, daughter or, a grandchild. Those are no longer available for most beneficiaries. Ok, there are some exceptions to the rule.



I did a Podcast on this recently, maybe episode three or two. It’s called the Tax Trap of Traditional 401Ks and IRAs. So, look at that, I talked more about this in detail but generally speaking, there could be a scenario where, you have several accounts and certain accounts you may want to designate for retirement income, and spend those down during your lifetime.


Then there are other assets that you may want to protect and preserve, to leave those, to the next generation, given the tax efficiency of those, how those assets are passed on? A lot of that’s going to be dependent on your tax situation in retirement, if you’re in a high tax bracket or, low tax bracket, where you think taxes might go in the future? And then also, what tax bracket is your beneficiary in?


Are they in a really high tax bracket or, a really low tax bracket? And that will drive a lot of those decisions that you’re going to want to make as you approach retirement, and then go through retirement, in terms of spending on your assets.


Number five, last but not least is, just simply not informing key decision makers with important information.

I mentioned earlier, not being a burden on loved ones is important to just about, everyone I talked to. What I find is, that sometimes, you’ll get an Estate Plan done, and you may not tell your brother-in-law that they’re the executor or, you may just mentioned in passing, hey, something happened. Would you be able to manage the trust or, manage the financial affairs?


But they really don’t understand or, know what that means, what’s involved? And I’ve seen a lot of scenarios where a big mess is left to a family member, to clean up and take care of it. So, I think, being transparent with the key decision makers, that are going to help execute your estate, whether it’s a trust or, being the executor of your will, I believe is super important, and then making getting things organized in a way that’s easy for those individuals to execute on.


So, if you have tons of accounts all over the place, does that make sense? Do you want to simplify your balance sheet a little bit? I create a two page document for all of my clients just to simply say, hey, here’s a list of our assets. Here’s a list of our liabilities. Here’s a list of insurance. Where are those accounts held? Who’s a point of contact that you can reach out to? Here’s even a phone number that you can call, and giving that out to my clients powers of attorney or, executors or, trustees.



I find that as super valuable just to make sure that process is easy for those individuals that are going to execute on your plan. Hope you found this helpful. That’s it for today. Be sure to subscribe if you like what you heard, that way you can stay up to date on new episodes. Again, I always love to hear from you if you have any questions about your personal situation that you want to talk about. You can just visit my website at and schedule a call with me.