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Is a Roth Conversion Right for You?

IRAs, or individual retirement arrangements, are a popular way to save for retirement, and with good reason: IRAs have numerous benefits. You may already be familiar with some of the different types of IRAs, including traditional IRAs and Roth IRAs. But you might not know it’s possible for people who typically don’t qualify for a Roth IRA to convert a traditional IRA into a Roth IRA. Depending on the details, this process is known as a “Roth conversion” or a “backdoor Roth IRA,” and in this post, we’ll walk you through two common scenarios where they’re likely to be beneficial.

IRA basics

First, let’s review a few basics about IRAs. IRAs are retirement accounts you open for yourself, unlike 401(k) plans which are offered through your employer. Roth and traditional IRAs have lower contribution limits than 401(k)s and they tend to have more flexibility around investment options. Here are some highlights at a glance:

Traditional IRAs: In general, depending on your income and whether you have a 401(k) plan at work, you get a tax deduction in the year you contribute to a traditional IRA and then pay taxes on withdrawals.
Roth IRAs: You don’t get a tax deduction when you contribute to a Roth IRA, but withdrawals after age 59 ½ are tax-free. You can’t contribute directly to a Roth IRA if you earned $161,000 and over as a single filer or $240,000 and over as a married joint filer in 2024, and those numbers rise to $165,000 and $246,000 respectively in 2025.

The tax advantages of both account types can be significant, but the tax-free growth and withdrawals you get with a Roth IRA can be especially powerful. Not everyone is eligible to contribute to a Roth IRA directly, so that’s where Roth conversions come in. A Roth conversion is when you move money from a traditional IRA to a Roth IRA. You might owe taxes in the year of the conversion, depending on whether you have any pre-tax funds in your account, but then your withdrawals from your Roth IRA after age 59 ½ are tax-free.

Let’s look at two instances where a Roth conversion is likely to be beneficial.

Scenario 1: One-off Roth conversion in a low-earning year

Let’s say you know you’re in an unusually low-earning year. Maybe you’re going to grad school or you’re taking time off to travel. You have an existing traditional IRA with some pre-tax funds in it (either because you rolled over a 401(k) from a previous employer or you contributed to one directly), and since you’re in a lower-than-usual tax bracket, now could be a good time to pay taxes on the conversion and then benefit from the tax-free growth and withdrawals you get with a Roth IRA in the future.

Let’s look at an example of how this might work. Assume your ordinary income tax rate will be 20% this year instead of the 40% it would be in a typical year. You have $10,000 (pre-tax) in a traditional IRA, and you’re wondering if you should execute a Roth conversion. If you were to leave the money in a traditional IRA for 30 years, assuming a 6% return compounded annually, it would be worth $34,460.95 after paying a 40% tax upon withdrawal. However if you converted the account to a Roth IRA, you’d pay $2,000 in taxes now (that’s your 20% current income tax rate multiplied by the value of the account), but the value of the remaining $8,000 compounded at 6% annually over the next 30 years would be worth $45,947.93 after taxes, because you wouldn’t owe any additional taxes upon withdrawal as long as you were at least 59 ½ years old. In other words, converting your traditional IRA in a low-earning year has the potential to give your retirement savings a big boost.

Scenario 2: Backdoor Roth to save more for retirement

Let’s assume you earn too much to contribute directly to a Roth IRA and you aren’t eligible to deduct contributions to a traditional IRA (either because your income is too high or because you have a 401(k) plan at work), but you still want to save some additional money for retirement. Assuming you don’t have any pre-tax money in a traditional IRA and don’t anticipate needing the funds within five years, you’re likely to benefit from a type of Roth conversion known as a “backdoor Roth.”

Again, let us explain with an example. If you fit the description above, you can either invest by opening a taxable investment account or making a non-deductible contribution to a traditional IRA. If you invest $7,000 in a taxable investment account at a 6% return compounded annually over 30 years, ignoring the taxes you’d have to pay on dividends and the gains associated with account rebalancing, your account would be worth $40,204.44 at retirement, but you’d still owe capital gains taxes when you sell to withdraw. If your capital gains tax rate in retirement were 15% then that account would only be worth $35,223.77 after taxes. However if you contributed $7,000 (after-tax) to a traditional IRA (this is the contribution limit for 2024 and 2025 if you are under 50) instead and converted to a Roth IRA, your account would be worth $40,204.44 at withdrawal because you would owe no taxes on the sales (again, assuming you were at least 59 ½ at the time).

When a Roth conversion isn’t right for you

If you’re still unsure, here are two signs that a Roth conversion probably isn’t right for you:

You plan to retire within five years. You have to wait at least five years to withdraw earnings from a Roth IRA with no penalty, even if you are 59 ½ years old (the typical age at which you can start taking withdrawals with no penalties).
You don’t have enough cash on hand to pay taxes on the conversion. These taxes could be significant if you have a lot of pre-tax money in a traditional IRA. You can estimate them by multiplying the amount of pre-tax money in your traditional IRA by whatever you expect your marginal tax rate to be.

Automation makes it easy

Typically, the Roth conversion process involves a bunch of paperwork. But at Itrust, we’ve automated the process so you can convert an Itrust SEP or traditional IRA to a Roth IRA with just a few taps on your phone. Automated Roth conversions are just one of the many tax-minimization features we offer you at no additional cost, including:

Tax-Loss Harvesting, both at the ETF level and the individual stock level
Tax-minimized withdrawals
Tax-minimized brokerage transfer
Tax-sensitive rebalancing

At Itrust, we want to help you build long-term wealth so you can meet your financial goals (like retirement!) with confidence. We hope the information in this post helps you make an informed decision about Roth conversions. For even more help planning for retirement, check out our IRA calculator.

How Can I Minimize Taxes When I Invest?

Taxes often signal good news for investors: they’re usually a sign you’re making money. At the same time, taxes can also eat into your returns and reduce the amount of earnings that you get to keep. Fortunately, there’s a lot you can do as an investor to lower your tax bill and invest more tax-efficiently. In this post, we’ll explain seven ways you can minimize the taxes you’ll owe on your investments.

1. Invest in index-based ETFs

Index-based ETFs are exchange-traded funds that let you track a broad market index with one investment. They are inherently tax-efficient because they pass on very few earnings (or “taxable gains”) to investors who own the ETF, even when the value of the ETF is increasing—which, of course, you hope it will over the long run.

How do index-based ETFs manage this? One, there’s not much change in the companies included in an index from year to year—typically, there’s only about 5-20% turnover each year, depending on the index in question. As a result, the ETF manager doesn’t have to sell stock that’s at a gain very often in order to remove it from the ETF’s holdings. And two, ETF issuers can reduce the gains they have to pass along to investors by intelligently realizing investment losses on the individual investments that make up the index.

2. Invest for the long term

Long-term investing isn’t just a smart way to take advantage of compounding—it’s also more tax-efficient than short-term investing. That’s because your investments are taxed at a much lower rate if you hold them for at least a year and a day, meaning you get to keep more of what you earn. To get this lower tax rate, you need to hold your investments long enough so that your gains will be treated as long-term capital gains, not short-term capital gains.

Long-term capital gains are taxed at a maximum rate of 20% at the federal level. By contrast, short-term capital gains are taxed at the same rates as ordinary income (like your paycheck). The top tax rate at the federal level for short-term capital gains is 37% in 2022.

3. Optimize your asset allocation for taxable and tax-advantaged accounts

You should factor in the rate at which your investments will be taxed when you select an asset allocation. The fancy name for this is “asset location,” but it really just means choosing the right investment mix for each type of account you have. For example, if you have a Roth IRA, any withdrawals after age 59 ½ that follow IRS rules should be tax-free. Because of this, you might consider holding more investments with less favorable tax treatment in that account than you would in a taxable account.

Asset location can be complicated to figure out on your own, which is why you might prefer to let a service like Itrust do it for you. Itrust uses what’s known as “differentiated asset location” in choosing the right mix for your taxable and tax-advantaged accounts. Our software evaluates the way each asset class is taxed, its risk and return profile, and how it balances out other asset classes to pick the mix that’s right for your account and situation.

4. Rebalance with dividends

Rebalancing your portfolio means buying and selling investments to keep your mix of investments (or “asset allocation”) from drifting too far away from what you want it to be. In other words, you sell some of the investments that have done well and you buy more of the investments that have performed less well. Rebalancing is important because it ensures your portfolio stays at (or near) your intended level of risk and expected return.

Let’s say you had a portfolio with 60% stocks and 40% bonds, and stocks performed extremely well and bonds did not. Over time, your asset allocation might drift to 70% stocks and 30% bonds. To rebalance your portfolio and get back to your target allocation, you would need to sell some stocks and buy some bonds.

Of course, selling your winners usually means realizing some taxable gains. Fortunately, dividends can help with this. If you hold investments that pay dividends (for investments offered at Itrust, this information is readily available if you search here), you can use those dividends to rebalance your portfolio by buying investments you need more of. This should reduce the number of investments you need to sell to rebalance your portfolio, and reduce your tax bill as a result. When you invest with Itrust, we automatically rebalance your portfolio with dividends.

5. Harvest your losses

Tax-loss harvesting is a strategy that has historically been used by sophisticated, wealthy investors with high-end financial advisors to lower their tax bills. The concept is simple: when an investment declines in value below its purchase price, you sell it, “harvest” the loss, and then buy a similar investment that keeps your portfolio at the right level of risk and expected return. Come tax time, you can use the losses you’ve harvested to effectively cancel out other capital gains so you don’t owe taxes on them. No gains? No problem. You can use your harvested losses to offset up to $3,000 of ordinary income (like your salary) each year and carry the rest of the losses forward to a future year.

As you might imagine, tax-loss harvesting can become very time-consuming if you’re doing it manually. Itrust’s Tax-Loss Harvesting service automates this process with the ETFs in your portfolio at no extra cost, and because software doesn’t get bored, it can look for losses every day the market is open and find more opportunities to harvest them than a human checking a few times a year is likely to. In 2021, our Tax-Loss Harvesting service generated average estimated tax savings worth between 4-9x our annual 0.25% advisory fee for clients who started using the service in a Classic or Socially Responsible portfolio last year.

Direct indexing

If you’re really serious about maximizing your harvested losses, you can use a strategy known as direct indexing. Direct indexing involves holding the individual stocks that make up a given index (rather than an ETF that tracks the index) and conducting tax-loss harvesting with those individual stocks. Individual stocks tend to be more volatile than indexes, so it’s easy to imagine a situation where a broad index might be up but a few individual stocks are down. As a result, you’ll generally get more opportunities to harvest losses with direct indexing than you would with ETF-level tax-loss harvesting. At Itrust, we offer our Direct Indexing service in all taxable Investment Accounts of at least $100,000 at no extra cost.

6. Incorporate your existing investments when you transfer between accounts

Selling investments that have increased in value generates a taxable gain—and that means you’ll probably owe the IRS money. So if you’re moving investments from one platform or institution to another, you can minimize your taxes by incorporating existing investments into your new portfolio whenever possible (instead of selling and realizing a gain, moving your money, then buying the same investments all over again). At Itrust, our software automatically incorporates your existing investments whenever it can.

7. Keep taxes in mind when you make withdrawals

If you make a withdrawal from your investment account, you will typically need to sell some investments. To minimize the taxes you’ll owe, don’t just sell investments at random. Instead, consider selling investments that have lost value first—this won’t generate any taxes—followed by investments with relatively small gains, or gains that qualify for long-term capital gains treatment. This can help you minimize the taxes you’ll owe as a result of the withdrawal. When you withdraw from an Investment Account at Itrust, our software automatically sells investments to keep you close to your desired asset allocation—and within each asset class, we sell investments tax-efficiently.

Bonus tip: use a robo-advisor to improve your after-tax returns

If you have a lot of time on your hands, it’s possible to implement most of the tips in this article by yourself. But it probably won’t be fun. When you invest with Itrust, we automate all of this for you to help maximize your after-tax returns with no extra effort or extra cost on your part. The following services are all included in Itrust 0.25% annual advisory fee:

Expert-built portfolios of index-based ETFs
Different asset allocations for taxable and tax-advantaged accounts
Tax-sensitive rebalancing with dividends
Tax-loss harvesting
Direct indexing (for accounts of $100,000 or more)
Tax-minimized brokerage transfers
Tax-minimized withdrawals

At Itrust, we’re focused on maximizing your after-tax returns: we believe that’s a big part of what sets us apart from other robo-advisors. At the end of the day, we want to see our clients (you!) successfully build secure and rewarding financial futures. Helping you keep more of what you earn is just one way we try to get you there a little faster.

Ask: Should I Pay Off My Mortgage Early or Invest?

Welcome to our Ask series, where we tackle your questions about personal finance and investing. Want to see your question answered here? Reach out to us on social media and we’ll try to address it in a future column.

If I have extra cash, should I use it to pay off my mortgage early or invest?

If you have cash to spare and are currently paying a mortgage on your home, you might wonder if you should use that extra cash to pay off your mortgage early (also known as prepaying your mortgage) or use it to add to your investments, like an Automated Investing Account at Itrust, instead. There’s no one-size-fits-all answer, but in this post, we’ll provide a framework for thinking about the decision.

At Itrust, we believe investing is key to building long-term wealth, but there can also be benefits to paying off your mortgage sooner. For the purposes of this post, we’ll assume you have a 30-year fixed-rate mortgage. Here are some factors to consider as you decide between paying off your mortgage early and investing.

**Make sure you really have extra cash**

Cash plays an important role in our financial lives. It’s true that having too much cash can work against your long-term financial health, but it’s important not to overcorrect: Having insufficient cash can be very stressful. Before you decide to pay off your mortgage early or invest, it pays to make sure you really have extra cash. As a rule of thumb, we think it makes sense to hold enough cash to cover the following:

A good emergency fund, with three to six months’ worth of expenses
Any significant known expenses within the next year. This could include things like an upcoming vacation, your wedding, or a large home repair. (An exception: You could also consider keeping money for large near-term expenses in an investment account with very little risk to your principal, like Itrust’s Automated Bond Ladder.)
Your regular monthly expenses that you cover out of each paycheck, like groceries and childcare

If you don’t have enough cash to cover these items without dipping into your savings, consider holding off on either putting more cash in the market or paying off your mortgage early.

Pay off your highest interest debt first

Once you’ve confirmed you do have extra cash, you should take stock of all of your debt—not just your mortgage. Some debt is far more expensive than other debt. You can tell how expensive your debt is by looking at the interest rate you’re paying on it: Debt with a higher interest rate is more expensive to you. Because of this, it usually makes sense to pay off your highest interest debt first.

Let’s imagine you have $10,000 in credit card debt and the APR (annual percentage rate) on that debt is 24.62% consistent with the national average as of June 5, 2024. Let’s also imagine you have a 30-year fixed-rate mortgage with an interest rate of 7.40%, consistent with the national average as of June 21, 2024. If you received a $10,000 bonus at work, it would make sense to pay off your credit card debt first because that debt has a significantly higher interest rate than your mortgage, and it’s probably much higher than your expected returns from investing, too.

Take a closer look at your mortgage interest rate

If you’ve already handled your high-interest debt, then it makes sense to compare the interest rate on your mortgage to your expected returns from investing. Your expected returns can be difficult to predict, but you can use tools like Itrust’s historical performance page to make a more informed guess. When you pay off debt with a known interest rate, you’re essentially getting a known rate of return on your money because you know exactly how much you’ll save in interest. Let’s say the interest rate on your mortgage is 2% (lucky you!) and your long-term expected return from investing is 5%. You could make the case for investing your extra cash, because your interest savings from paying off your loan are likely to be lower than your investment returns, even after taxes. Keep in mind, however, that “expected returns” are just that—expected, not guaranteed.

On the other hand, if your mortgage interest rate is 7% and your expected return from investing is still 5%, you might want to take the opposite approach and pre-pay your mortgage. That’s because the amount you would save in interest is higher than what you’d expect to earn on that money if you invested it.

But what about the mortgage interest tax deduction? If you itemize your tax deductions, you can deduct the interest paid on up to $750,000 of mortgage debt for homes purchased after December 16, 2017 on your tax return. This means if you prepay your mortgage, you could lose some or all of this deduction. In general, we don’t think this should be the driving force behind your decision, but it is important to be aware of the tax implications of mortgage prepayment. Here’s a very simplified example to help you think this through: If you have a mortgage interest rate of 7%, you qualify to deduct your interest, and your tax rate is 30%, then the after-tax rate on your mortgage would be 4.9% (or 7% x (1 – 30%)). Just remember that in order to get an apples-to-apples comparison, you’ll want to compare this after-tax interest rate to your expected after-tax investment return, which can be even more difficult to accurately predict than pre-tax returns.

Prepayment, recasting, or refinancing? Consider your options

Paying off debt like a mortgage early can be psychologically rewarding, but prepayment isn’t your only option. Some people incorrectly assume that prepaying their mortgage will automatically lower their monthly payments going forward, but this generally isn’t the case. However, there are alternatives to prepayment that do have the potential to lower your monthly payments. Here’s a quick overview of various options and how they compare:

Mortgage prepayment: Paying extra money towards the principal (or loan amount) of your mortgage. Prepayment allows you to pay off your mortgage faster and save money on interest, but doesn’t change the amount of your monthly payments. Occasionally, you may pay a prepayment penalty for paying your mortgage off early (more on that below).
Mortgage recasting: Paying extra money towards the principal of your mortgage, and then recalculating your monthly payments. Recasting lowers your monthly payments and saves you money on interest, but you won’t pay off your mortgage any earlier. You may also need to pay a fee of a few hundred dollars to recast.
Mortgage refinancing: Taking out a new mortgage, usually at a lower interest rate, with the goal of lowering your monthly payments and the total amount you’ll pay in interest. Refinancing can change the date you’ll pay off your mortgage in either direction, depending on the terms of the new loan. Refinancing can come with significant fees—potentially two to five percent of the new loan amount.

Consider your amortization schedule

Most of the time (assuming you have relatively standard loan terms, and not a less common arrangement like an interest-only mortgage or a balloon mortgage), your mortgage payment includes a mix of principal and interest—and over time, that mix changes. Mortgage payments are mostly interest when you first take one out, and they gradually include more principal as more time goes by and you build more equity in your home.

If your mortgage payments still include a lot of interest, there’s likely more benefit to prepaying, recasting, or refinancing. On the other hand, if you’re paying mostly principal, there’s less benefit to prepaying, recasting, or refinancing and you are more likely to be better off investing your extra cash instead.

Check your mortgage’s prepayment terms

Prepayment penalties, or fees for paying off your mortgage early, aren’t very common. But if you’re considering prepaying your mortgage, you should make sure that your lender won’t penalize you for it.

Why would lenders do this? When you prepay your loan principal, you are ultimately reducing the amount of interest you’ll pay your lender. Prepayment penalties are a way for lenders to recoup some of that lost interest, and these penalties vary in both amount and structure—you could owe a flat fee or a percentage of the loan balance, for example. Read the details of your mortgage carefully and don’t be afraid to ask your lender to clarify if you’re unsure about your prepayment terms. If your mortgage does include a prepayment penalty, make sure you are cognizant of this cost—it could tip the scales towards investing instead.

Key takeaways

To recap, here’s what we suggest keeping in mind as you consider the tradeoffs involved in prepaying your mortgage or investing.

Before you pay off your mortgage early or invest, make sure you actually have enough cash on hand.
Take stock of all of your debt and consider paying off your highest interest debt first.
Compare the interest rate on your mortgage to your expected return from investing.
Prepayment isn’t your only option. Look into recasting and refinancing if your goal is to lower your monthly payments.
You’re more likely to benefit from mortgage prepayment if you took out your mortgage relatively recently and your payments still contain a lot of interest.
Don’t forget to check your mortgage’s prepayment terms.

If you ultimately decide it makes sense to invest your savings instead of prepaying your mortgage, we suggest investing in a globally diversified portfolio of low-cost index funds like Itrust’s Classic portfolio. We’ll help you maximize your risk-adjusted returns and minimize your taxes while our software handles all of the busy work like trading and rebalancing for you.

We hope this helps!

Our Thoughts on Investing in Cryptocurrency

Note: As of March 21, 2024, Itrust uses the iShares Bitcoin Trust (IBIT) to represent the Bitcoin asset class instead of the Grayscale Bitcoin Trust (GBTC). As of September 9, 2024, Itrust uses the iShares Ethereum Trust (ETHA) to represent the Ethereum asset class instead of the Grayscale Ethereum Trust (ETHE). Read more here.

Earlier this summer, we began supporting cryptocurrency exposure in Itrust portfolios. We’re very excited about this, and we’re proud to offer clients so many choices in building their ideal portfolio. We also take seriously our role as a fiduciary, and we want to offer some guidance to anyone who is considering investing in cryptocurrency — either at Itrust or elsewhere.

One of the most important things to understand about cryptocurrency as an investment is that it’s highly volatile — this means it can either gain or lose a significant amount of value in a short period of time. For example, Bitcoin, the largest digital currency by market capitalization, has a price history marked by large rallies and crashes, and in the last 12 months it has traded as high as $64,863.10 and as low as $9,916.49. On May 19, over the course of a single day, Bitcoin’s value fell 30%. It’s true that many people have profited handsomely from investing in digital currencies, but it’s not for the faint of heart.

Because of this volatility, we consider investments in cryptocurrency risky. This includes the Grayscale statutory trusts GBTC and ETHE, which we offer on our platform. These trusts allow investors to get exposure to cryptocurrency without owning coins directly, but introduce another variable: potential tracking error which can cause the price of a share of the trust to differ from the value of the underlying asset.

We don’t say all of this to scare you away from investing in cryptocurrency. We’re proponents of financial innovation and believers in the power of software — and as a result, we’re excited about digital currencies. We know many of our clients are equally excited, so we want to give you a framework for thinking about these investments. Our advice is this: if you’re going to invest in cryptocurrency, we think you should have an investment thesis.

An investment thesis is a logical argument for why an investment will increase in value over time. Often, an investment thesis will evaluate an investment’s cash flow, but that isn’t possible in the case of cryptocurrency. Instead, a successful investment thesis for cryptocurrency should draw on research and analysis of its characteristics and future economic events. For example, Fidelity’s investment thesis for Bitcoin references the asset’s fixed supply and a number of factors that could drive an increase in Bitcoin demand including deglobalization and the transfer of wealth to millennials. Whether or not you agree with these specific reasons for investing in cryptocurrency, this is the kind of logic we encourage you to use.

Unfortunately, some of the most common reasons for wanting to invest in cryptocurrency don’t make great investment theses. Many people want to invest in cryptocurrency because it has performed well in the past — but this doesn’t necessarily mean it will continue to do so in the future. Some people might also feel pressure to invest in cryptocurrency because it seems like everyone else is doing it, but FOMO doesn’t make a good investment thesis, either.

We’re delighted to be the first investing service to allow clients to get exposure to cryptocurrency in a diversified and automated portfolio with features like tax-sensitive rebalancing and our industry-leading Tax-Loss Harvesting. We hope this advice helps you navigate the question of how to invest in cryptocurrency so you can confidently build wealth on your own terms.