Ep 237: Ask the Professor: Legal Tax Hacks Your CPA Isn’t Talking About

This is going to be a great episode.

Welcome to episode number 237 of the weekly Wealth Podcast.

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Alright, here we go.

Welcome to the Weekly Wealth Podcast.

I am certified financial planner David Chudick.

This podcast and my wealth management practice are both designed to help the mass affluent to live better lives by how they handle their money.

We talk about financial strategies, prosperous mindsets, and simply how to build true wealth.

So come on and let's enjoy this journey together.

Every once in a while, my colleague and friend Justin Chastain comes on and we dive deeply into a topic.

Today we're talking talking about taxes, which I know none of us enjoy paying, but.

Hey, Justin, how are you?

And tell me again, why do we call this the Ask the Professor segment of the Weekly wealth podcast?

David, again, it's always good to be here.

I'm doing well.

I always say, hey, you know, if the best part of waking up is Folgers in your cup, you're not grateful enough.

Best part of waking up is knowing you're alive.

So it's listening to the weekly Wealth Podcast.

Absolutely.

I was just going to put that plug in there.

But you know, ultimately why people call me the professor, it is, I pay people a lot of money to call me that.

But then secondly, education is in my heart and I teach for Dalton Education twice a week, certifying financial planners all over the United States.

So education is definitely in my heart and it's part of my practice.

And how when we're talking through planning, it's not so much just telling somebody what to do, it's giving them the education and the tools and then giving them the right solution so that money is not the ultimate thing that they're worried about.

They're going and maximizing their best life possible.

Money is just the tool to give us good lives.

I mean, nothing more, nothing less.

If you take all the problems you've ever had and then if you take the ones out that maybe a little bit of money wouldn't have taken away.

I mean, life's normally pretty good.

You know, we gotta eliminate or reduce money problems to the extent that we can.

Now you're my go to guy if I ever need details.

I don't wanna tell my age, but I passed the CFP exam in 2006, so that'll be 20 years ago and lots changed since then.

You know, some rules, some tax laws and things change.

So if there's ever a refresher that I eat, I'm going to the guy who's teaching candidates that are studying.

So I appreciate, appreciate our relationship, but today we're going to talk about taxes.

Now let's go ahead and say, well, this isn't tax advice.

Make sure you're talking to your cpa, your advisor.

This is really educational and this is generic in nature.

So again, before you implement any of these strategies, make sure you are working with your own advisors.

But we have five areas of taxes.

We're going to spend a few minutes on each one and hopefully give you some good 30,000 foot level stuff.

So let's jump into Social Security, give us like the Cliff Notes version of how Social Security benefits are taxed and maybe some ways to reduce taxes on your benefits.

So a lot of people don't realize this, but regardless, if you are under full retirement age, which is going to be different for most, but generally speaking, for most people listening this podcast, it's going to be around 67.

If you are still working, your Social Security income benefits after full retirement age are not going to be reduced, but they do have potential to be taxed.

And you'll be luckily and surprised to know that the indexes that the IRS has set out for our income taxes around Social Security benefits are not indexed for inflation.

They've been the same since 1984.

So again, a little as being an 80s baby.

I appreciate the 80s, but it would be nice to have things indexed for inflation around taxation.

So you're saying that the government is doing something that makes no sense.

Well, now you know again, as Uncle Sam, he's always there at the party that's asking for gifts and handouts.

But you know, that is very unusual, David, now that you bring it up, typically the government is very logical and rational and they don't make things more complicated than it needs to be.

So yes, that is very surprising around that.

But if you are earning over a certain threshold, your Social Security tax benefits could be taxed at either 0, 50% or 85% of that benefit.

Now, if you're a high income earner, that percentage of what you're drawing from Social Security we will probably more than likely gladly say, hey, we'll have this 85% tax of Social Security benefit because what you're earning in income definitely offsets any ability for income streams that you're going to need moving forward.

So that's the good thing.

But in your planning, you do need to be aware of where your income is.

Also working with a CPA to make sure we understand what income tax brackets that you're in and also leveraging that so that we're not caught by surprise when Social Security is taxed.

And hopefully at that point, if you're earning that kind of money, it's not going to be detrimental to any cash flow issues that you would have in retirement, but it is something that you need to be aware of.

So I know a lot of CPAs and a lot of tax preparers, people in the tax industry.

I love them all, or almost all of them, but almost none of them do proactive tax planning.

Most of them say, hey, Justin, you know, it's April 10th of 2026.

Here's what you owe for 20.

Almost none of them say, hey, Justin, you know, we're in October of 2025.

The year's not over yet.

But let's talk about some things that we can still do by 1231 to reduce your tax burden.

And that typically is going to fall either on you, the individual, or you and your financial advisor to look at proactive tax planning.

Now, for me, there have been some times in my life where I've had like a big tax bill, but I planned for it and it stunk, but I knew it was coming and I got it as low as I could.

But what really hurts is when you get that tax bill that you're not expect and you don't have the cash put aside for.

That's why proactive tax planning with Justin or with David or with your financial advisor is super, super important.

All right, so let's look at retirement accounts and withdrawals, traditional IRAs, Roth IRAs.

You can watch TikTok and learn about Roth IRAs.

And they're the new thing.

Tell me a little bit about how traditional IRAs are taxed.

Tell me how Roth IRAs are taxed.

And then let's also talk about what the heck are RMDs.

And I don't know why the IRS has to put abbreviations on everything, but hey, that's another question.

Well, and again, I think it goes back again.

Why abbreviate it makes it more complicated.

I think we're catching on to a theme here, David.

Maybe just a little bit, but.

But it's a great question.

And I think a lot of clients, regardless of their economic, social situation, they really don't understand the tax ramifications of an ira, Roth ira, or what we call even a brokerage or something that is taxable.

So we as financial planners like to walk through with our clients the importance of having a tax deferred account, an IRA tax free, a Roth IRA and taxable accounts.

And I'll kind of leverage the difference in your IRA, traditional IRA, we call these qualified plans.

Your 401k is very similar if you have put pre tax money into this.

So how these work is you make contributions pre tax.

So that means there's not been any tax taken out of that.

The account grows tax deferred.

But upon distribution, when you have to start taking required minimum distributions, that's what that RMD stands for, you will be taxed at ordinary income levels.

Now depending, and a lot of people, if you're not working in retirement, your, your ordinary income tax bracket could be lower than in your working years.

But we work primarily with high net worth clients and business owners.

And you know when they want to retire, David, ultimately when they get put in that coffin right now, that doesn't mean their grind is the same, but they still want to be doing something.

So they're going to have earned income of some capability.

Well, if they have to take RMDs and they're still earning a significant amount of income.

We've now been taxed at a higher rate upon this distribution than we needed to henceforth while Roth could come into play.

So Roth came in to our existence in 1999 and it was based off of Senator Roth.

That's how it got its name.

But it works just the opposite, a little bit.

We call these non qualified contributions.

So you pay tax on the income you contribute, it grows tax deferred.

And then upon disbursement, when you need this money at 59 and a half, there is no tax involved in it.

So even now for planners, what we are doing when we are looking at tax planning, we're looking out forward and saying okay, does it make sense if you have this 401k rollover or IRA money to do, maybe some Roth conversions?

Because we eliminate the required minimum distribution and we can pull that money out tax free.

The only thing we have to do in that current year of conversion is pay ordinary income on the amount that was qualified, the IRA or 401k portion.

So we're leveraging constant tax brackets because tax brackets affect your growth inside of these earnings more so than even taking on higher risk.

We have to be really aware of that.

And then lastly the importance of having a taxable account because there's some really unique and Cool things that we can do.

And we're not going to use these often, but we'll put some growth or capital appreciation accounts inside taxable accounts because we'll get taxed at capital gains rates there.

Same thing with dividends.

If the dividends are qualified, hey, we're going to be taxed at long term capital gain rates.

Why do we like that?

They're lower than ordinary income tax bracket rates.

And we as planners with the CPA that's doing the tax filing and as we're doing the tax planning, we can look at something called tax loss harvesting, which I mean, again, the downside to that is we took a loss, but we can offset some of our capital gains and ordinary income taxes based on this tax loss.

Harvesting or harvesting.

And then we can also do something called tax gain harvesting as well, where we're playing into those capital gain rates.

So as planners, we are constantly not looking at just your rate of return in Social Security.

Our biggest thing is what are we doing to mitigate the tax obligation in retirement?

Because we know that's going to eat into your wealth more so than any rate of return that we're going to have to go and get to take on a higher risk to get there.

Let's talk a little bit about something that I think a lot of people don't understand, and that's the concept of marginal tax rates.

If your taxable income is over $394,601, your next dollar gets taxed at 32%.

So you make a dollar.

The federal government gets 32% of it.

So yes, you are in a 32% tax bracket.

But the dollars from 206,000 to 394,000 only got taxed at 24%.

And then the dollars from 96,000 to 206,000 got taxed at 22%.

But then the dollars from 23,000 and change to 96, they got taxed at 2012 percent, which is much, much, much lower.

So how do marginal tax rates kind of come in into the planning process?

What are some things that you and I might help our clients with with regards to tax bracket management?

And that's a great question.

And to define marginal tax bracket, it's really just the last dollar that you earned.

What rate was that taxed at?

What we're constantly doing as planners, and again, you summed it up beautifully.

When we're looking 20, 30 years down the road, we are constantly looking to say, okay, we understand.

If we took this IRA rollover and did a Roth conversion we know that there is going to be income taxed and it could put somebody over that threshold to go from a 24% tax bracket to somewhere in the 30%.

Well, that might not be the best solution for that.

Whereas your cpa, which is still very vital to your overall financial planning team, board members, as we like to call them, they're looking at the here and now on how to file that correctly.

Not so much what we're going to be doing in the next 10 to 15 years.

So what we want to do is saying, okay, what can we do to do these Roth conversions in a tax efficient method where we're not putting you over that threshold?

And then also keep that money in a much lower overall tax effective bracket?

Because that's really what we're trying to do.

So if you ever hear anything tax effective bracket, what we're looking at, that effective rate is, okay, yeah, we know that our marginal income could be as high as 32%.

But with the strategies that we're implementing, how are we lowering that overall tax obligation?

That's what we're trying to do is, is to lower that overall effective rate so that we, we're not going from one margin to the other.

That is going to harm that client.

There's other strategies as well.

Just from your overall contributions with IRAs and retirement accounts.

A lot of our clients, especially ones that have some excess left over, there's things that we can do even with charitable giving, a lot of people don't understand, but you can do qualified charitable donations.

Right.

So that we're not also creating either any estate or gift taxation which comes into play as well.

Sometimes people overlook that.

And yes, there are some higher limits for those right now.

But especially when you're getting into the business owner, entrepreneur, or families that are high achieving, that could easily cost them money not just in the here and now, but what they plan on leaving in their overall estate.

Yep.

So here are two fun facts for you.

A married filing jointly family that has a $250,000 taxable income.

Now if we look at the tax tables, that would be in the 24% tax bracket, marginal tax bracket, but because some of the income was taxed at much lower rates, because we're in a progressive tax bracket system, that $250,000 family has an effective tax rate of 18.3%.

So they don't pay 32% of their money to taxes, they'll pay 24% of the next dollar.

Now, let's say you go to someone much higher, $800,000, income, they are in the 37% tax bracket.

So the next dollar would be taxed at 37%.

But their effective tax rate or the average rate they've been taxed on all of their money is, and I put air quotes only 27.5%.

So that's right at 10% lower than their, than their marginal rate.

So I think one thing, a lot of people, and I'm talking, you know, wealthy people as well, do not understand tax brackets and how they work.

And you know, David, bringing up these great examples, but I would say that one of the things that gets lost in every conversation with a lot of clients, and I'm sure that, that you have this in conversation too, and you and I talk about it a good bit, but say you were casually at a party and somebody just says, hey, what's going on?

Unique in your field?

Or what, what, what's the market doing?

You know what I tell people as a financial planner, and especially dealing with high net worth clients and business owners, I would say that rates of return are probably one of the least things that we talk the most about.

Not because it's not important, but, but David, don't you think, and would you not agree that until we understand the tax situation and the overall financial plan for a particular family or business owner, we can't really just start talking about investments because we need to know how those investments and rates of return fit into the overall plan.

Absolutely.

When I meet someone and you know, you kind of go through small talk, hey, what do you do for a living?

I'm a financial advisor.

Well, hey, should I buy Nvidia?

Should I buy crypto?

You know what, what should I buy?

And the real true answer is those answers.

Number one, I don't know what your specific situation should allow you to do, but number two, that is a part of your financial plan.

It's just a part.

You know, there are times when maybe even selling off some stuff and realizing a huge gain may not be the greatest thing in the world.

So managing tax scenarios is really important.

So let's say that I have some stock of XYZ Company.

Doesn't matter what company it is.

And maybe I bought it 10 years ago at $10 a share and now it is, let's say $500 a share or $200 a share, there's a big gain.

And if I sell off that right now, what would that mean for me, tax wise?

Let's say I had 10 shares that I bought for $10 a share and now I still have 10 shares and it's worth $200 a share each, so that's $2,000.

What are some tax consequences if I sold it all at once?

You sold it all at once, depending on, and again depending on the account.

But if it's in a brokerage account and you had it out there, you're going to pay capital gains tax on that increase.

So what that means is.

And capital gains rates are different than ordinary income, but if you are looking at it generally speaking, you're either going to be in a 0, 15 or 20% capital gains bracket.

So you're going to pay at least a portion of that now again, and it's going to be based.

Capital gains rates are going to be based upon your marginal tax bracket as well.

That's how it's leveraged.

But you're going to either have to take it out of that, those earnings that you actually sold that stock for, or the cash is going to have to come from somewhere because you will pay that taxation in the year that you sold that stock.

And I know we've done a previous podcast on NUA and net unrealized appreciation and what you can do from employer owned stock, which you get some benefits from capital gains rates, but in a traditional brokerage account, that is going to be the benefit that it's not going to be taxed as high.

But the good portion to that is if you've earned over and above your cost basis of that particular stock, you're in a gain position and that's ultimately what you would want to be.

On the flip side of that, if you lost money, you could do something called tax loss harvesting.

So in the example where we gained money, here's two, two tricks that you may, may or may not work into your scenario.

Number one, we're recording this late in 2025, let's say that stock, we just decided we don't want to hold that stock anymore.

We don't believe it's a good holding.

We could sell part of it this year and then wait until January 1st and sell part of it next year and we could spread the gain over two years for tax purposes.

So that's something, you know, and that's something that our team, even if we're managing money, would potentially make a decision like that.

The other thing is we could give that stock.

Now we don't cash the stock out and give the cash to a charity, but we could give that stock to a charity and then we're not realizing the gain and we're getting a charitable deduction and most bigger 501 organizations will have a brokerage account and they are able to accept gifts of stock.

So going back to that scenario of when people ask financial advisors, what should I do?

Where should I invest?

There are so many tricks, so many different strategies that don't really have to do with should you buy Nvidia, should you buy Crypto, should you buy Apple, should you buy it has to do with other things that help you to manage, in this case, your tax liability.

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Estate Planning Implications so I think all of us would be in a really good position if we had to worry about estate taxes.

That means you've done well and we can argue until the sun goes down if you know, the ultra high net worth should have to pay or if the estate should have to pay taxes or not.

Nobody called me and asked me what I thought the law should be.

So the law is what it is.

But let's talk about some legacy and estate planning planning tools and thought processes.

David, you bring up a good point.

Now they did call me, but I told them that as a good politician I was not present that day.

So my vote did not go anywhere.

But you are right and I think that there's probably that, that gray area rule.

But what a lot of people in our industry as they're talking through what I have noticed and even the clients that I want to work with, yes, they're high achievers and that means different things to people.

But generally they're good people, right?

They either want to create generational wealth for somebody bigger than themselves, their family, but they also have purposes and organizations that are bigger than themselves.

So legacy and charitable planning is something that they talk quite a bit about.

And there are something called qualified charitable distribution.

So you can make a direct contribution to your university or alumni, a check directly to them.

Even if, and I've seen this with particular clients, maybe they have Somebody in their immediate family that they want to pay a hospital bill for.

Well, you don't want to go and cut a check to that family, and then the family cut a check to the hospital.

That person wants to cut a check directly to the hospital.

That's called a qualified charitable donation.

You're giving it from your pocket, from your estate to the organization.

And if you have accounts that have required minimum distributions, and I have several accounts, accounts and clients that do this, they will utilize their RMDs and give a portion to that RMD every year to that direct organization.

So we literally cut a check from their brokerage account or not, or from their ira, but from the actual account that they have money with.

And it goes directly to a university, a hospital system, cancer research, anything that's important to them.

So doing these things can also do a lot of things.

It can reduce the estate in a healthy way.

But then also you're not paying excess taxes on gifting because it's a qualified charitable distribution.

So leveraging those different strategies and creating goodwill can also create a positive externality on the backside where we're actually giving to organizations that are bigger than ourselves.

And that's one way that you can actually utilize the gift in a state and taxation regulations that are very complicated and use it to your advantage to create some goodwill.

So you just talked about some, some strategies that can help an individual to, to, to give while they're alive in many cases.

Now here's another potential fun fact.

Let's say Justin is my client.

And let's say Justin, 76 years old.

And let's say Justin's fairly healthy and he has a big pension and he has a bunch of rental properties that are paying his monthly expenses.

But he also has a $3 million IRA.

And he doesn't need to take that money except for the government is saying through his RMDs, he has to take money.

Well, if Justin can qualify, he can take that money out every month or once a year.

He could buy a big old life insurance policy.

Now again, he has to be healthy enough.

And then let's say his RMD monies that he has to take out, he uses that to pay for life insurance.

And now that might buy another million or $2 million of death benefit that could either go to his grandkids or a foundation or me or his church or anything else.

So that's a way to leverage your RMDs to create some generational wealth.

So again, financial advisors have strategies way beyond, hey, should I buy this stock?

Or that st and we can talk to our clients and know based on what they're telling us is important to them, we can suggest strategies.

Now, if that same hypothetical Justin client was telling me, you know what, I want to die with $0, I've given everybody around me a good life and I'm cool with spending all my money and enjoying life as much as I can, I would say, hey, that's awesome, congratulations.

And we're not going to buy any more life insurance for you because that does not fit the goal that you are telling me that you have.

Let's talk a little bit about any other tricks for business owners to potentially use to lower their taxable income.

Okay, so one for me is any business expense.

If you can find a, I'm sorry, a personal expense, if you can find a legitimate way to tie that to business, then oftentimes you can get a write off or a tax deduction that'll lower your business profit and that'll eventually lower your either your pass through earnings or the corporation's earnings.

But we can often find a business purpose for personal expenses or somewhat personal expenses.

What you got on the business owner side?

You know, David, and I think this is a great topic to bring up.

I would say this as well.

And you know, I spent a lot of my career, you know, working around business strategy and even exit strategy for business owners.

And one of the things I say is, you know, the biggest asset on any business owner's balance sheet is their people.

So investing in things like employee benefits, right.

Whether it's through insurances or 401k and retirement plans.

Why?

Because that gives you an opportunity.

And I, and I say this, create goodwill first and foremost.

That's your foundation.

Because culturally the biggest wealth opportunity for a business owner is how much cash and wealth is being generated in that business.

As planners and as exit strategy planners or planners, we want to make sure that we are strategically and effectively withdrawing that wealth in a tax efficient manner out of that business when they're ready to sell.

But the number one way to try to do that is create a culture with employee benefits that shows that on the balance sheet and the financial statements and the tax returns.

Because the first thing that most people when they go to sell a business, that another business owner is going to ask them when you leave, what is in place to retain your best employees.

And there are tax efficient strategies utilizing employee benefits to do just that.

Are you a longtime listener of the weekly wealth podcast?

If you've learned anything and if you've enjoyed the Podcast, will you do me a favor?

Will you tell a few of your friends, your families, your colleagues, or your co workers about the show?

As I always say, I believe that how we handle our money should positively impact our lives and the lives of those around us.

And I hope that this podcast can be a small piece of that puzzle for all of our listeners.

And ultimately, many business owners are just decent people that want to see their team do well.

So, yeah, invest in benefits for your team and ultimately, like any other investment, over the long term, it will more than likely pay off.

Yeah, there's some costs upfront and it may hurt a little bit to write that matching contribution check every month, but it hurts more when your good people leave you for another company that's offering some big benefits.

So we, Justin, you and I, we both enjoy working with business owners.

Business owners have a lot of financial decisions to make and they wear a lot of hats.

And as a business owner, you have to be the plumber, you have to be the book, you have to be the attorney, the accountant, and you have to know your trade.

And then you also have to make financial decisions.

So if you're a business owner, don't go it alone.

Make sure that you're working with some with your competent advisor team.

So, well, if anybody's listening here and they're like, you know what?

David's awesome, but I like when he has the Ask to Professor episode.

And I'd like to speak with Justin.

I have some financial questions.

How might they reach you?

So I have business cards which mean I'm legit, but then I also have an email address, and that's justinarallelfinancial.com and that's one of the best ways to reach out to me.

And you'll set up a zoom or an in person zoom.

In person.

Do you charge $1,000 an hour?

2,000.

What do you charge?

Nothing that monetarily that you have to give up.

Just a short conversation to see where you are and ultimately where you want to be.

And David, you know, in these discovery meetings that we do, the reason we don't charge, we're really just seeing if we can provide value for the client and vice versa as much for us to see.

Hey, and if it's not a good fit, I'll send a recommendation of other advisors and financial planners that we know that might best suit that client.

It's nothing stringent where once you set this up, you're going to owe me anything.

At that point, we're just seeing if there's enough value for us to start a relationship.

Absolutely.

I know.

I've spoken with prospective clients and the first conversation we talk a little bit about details and I've told people, I mean, there's really nothing I can do.

Why don't let's accelerate debt payment, let's dump as much money as you can towards debts and then let's touch base in a year because right now that's the biggest issue.

That was the facts, that was the truth.

So there certainly didn't need to pay me for that advice because that's just where they were at that point.

And then hopefully they dig out and maybe there are some other issues, issues to solve in the future.

So if you'd love to speak with justin, go to justinarallelfinancial.com justin works remotely with clients, but also out of our downtown Greenville, South Carolina office.

And also, as always, my email is davidarallelfinancial.com so we appreciate that you've listened to this podcast today and I always like Justin's input on the details of some financial topics.

I talk a lot about mind mindset and then when we want to get into the nitty gritty, I bring Justin the professor on.

So let's close out the show.

Justin, give us one tip that anybody can implement that can help them.

Somewhere on the tax front, I would.

Say just start small and learn quickly.

And the best way to do that, if you have or if you're looking for a financial planner, ask them, is tax planning a part of your overall business strategy?

And again, I tell people, especially as complicated as the tax structure is becoming, you need a good CPA and you need a good financial planner that is doing tax planning.

They're two different things, but they're not things that one or the other could be removed from.

They need to work together and just ask your planner, hey, do you work with CPAs to do tax planning?

I think that's going to be critical for people that are looking to retirement moving forward.

And it's not just about returns.

Put tax planning as part of something.

You're asking your financial advisor if they're doing and if not, see if there's other ones out there that could help you with that.

Absolutely.

I'm actually working with two clients right now and we're helping them to get state tax credits through affordable housing funds.

So they're saving 15 or 16% on their south Carolina state income tax by getting involved with the fund.

That's a 30,000 foot level description, but that's just a way that we're helping clients.

That's not something that I make money off of.

I'm not selling a product.

That's just I'm helping my clients to save money with a tax strategy.

So.

All right, everybody.

Well, we appreciate that you're listening to the show.

Make sure you're telling your friends, your family, your colleagues and your co workers.

Make sure that you are subscribing on the platform platform that you listen and just help us to spread the word.

As I say every week, I believe that how we handle our money should positively impact our lives and lives of those around us.

And I hope that this podcast and our social media content can be a small piece of that puzzle in your life.

Thanks, Justin.

Thank you, David.

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However, Parallel Financial does not warrant its accuracy or completeness.

These materials are provided for informational purposes only and should not be used for or construed as an offer to sell or a solicitation of an offer to buy any security.

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So here's your bonus content for this episode.

Just like I interviewed my friend and my colleague Justin Chastain for this episode, we are collaborating.

We are helping each other.

So look where you can form some partnerships in your life.

Maybe if you're a business owner, you can partner with other businesses in similar industries and recur, refer clients back and forth.

And maybe if you're not a business owner, you can just partner with one of your friends, one of your families, one of your colleagues, or your co workers to support them along their financial journey of building and maintaining wealth.

All right, everybody, have a great weekend.

Thanks.