Roth Conversions: When You Should Convert Your IRA or 401(k) to Roth?

Roth conversions are popular in 2020. Many Americans are taking advantage of low account values (asset values are low from stocks to real estate) and are converting Traditional dollars and assets to Roth. Others are seeing themselves in lower tax brackets than usual and see it as an opportune time to convert to Roth and pay taxes at a lower tax bracket. If you have a traditional IRA or 401(k), then that money grows tax-deferred, BUT you pay tax on the money as it is drawn out at retirement. And that’s a big BUT. On the other hand, you get zero tax deduction on Roth IRA and Roth 401(k) contributions but they grow and come out tax-free at retirement. What’s better? Well, in the end the Roth account is a much better deal as you’re pulling out what you put in AND the growth of the account after years of investing and saving. That’s likely a larger amount than what you put in so you’d typically be better paying tax on what you put in (or convert) rather than paying tax on the the larger sum that you will take out later. The trade-off of course, is you’re playing the long game. You’re skipping a tax deduction or paying tax now to convert in return for tax-free growth and tax-free distributions at retirement. The Roth seems to be the better deal. Yet, most Americans have been sucked into traditional IRAs and 401(k)s because we get a tax deduction when we put the money in a traditional account, saving us money on taxes now.

For more on the differences between Roth IRA and Roth 401(k), take a look at the video from my Partner Mark J. Kohler:


The good news is that you can convert your traditional IRA to a Roth IRA, or your traditional 401(k) to a Roth 401(k). The price to make that conversion is including the amount you convert to Roth as taxable income for the year in which you make the conversion. So, if I convert $100K from my traditional IRA to a Roth IRA in 2020, I will take that $100K as income on my 2020 tax return, then pay any federal and state taxes on that income depending on my 2020 tax bracket. Many retirement account owners want to move their traditional funds to Roth, but don’t like the idea of paying additional taxes to do so. It can be a big tax hit when you do your taxes. I get it. Nobody likes paying more taxes now, even if it clearly saves you more as your account grows and the entire growth comes out tax-free.

Chunking Conversions

One way to soften the tax blow of the Roth conversion is to chunk the amount you want to convert over two or more years. For example, if you are at the end of the year in November 2018 and you want to convert $100K to Roth, you may decide to convert $50K by December 31, 2020  to have that taxed in the current year and then convert the remaining $50k on January 1, 2021 to have that amount taxed in 2021. This way, you don’t have as much of an income swing and it spreads the tax due over the two years. You could also do $33K each year to spread it out of 3 years.

The following are three cut-and-dry situations of when you should definitely convert your traditional IRA or 401(k) funds to Roth:

1. Up-Side Investment Opportunity – I’ve had numerous clients over the years convert their traditional funds to Roth before investing their account into a certain investment. They’ve done this because they’ve had a tremendous investment opportunity arise where they expect significant returns. They’d rather pay the tax on the smaller investment amounts now, so that the returns will go back into their Roth IRA or 401(k), where it can grow to an unlimited amount and come out tax-free. These clients have invested in real estate deals, start-ups, pre-IPOs, and other potentially lucrative investments. So, if you have an investment that you really believe in and will likely result in significant returns, then you’re far better off paying a little tax on the amount being invested before the account grows and returns a large profit. That way, the profit goes back into the Roth and the money becomes tax-free.

2. Low-Income Year – Another situation where you should covert traditional funds to Roth is when you have a low-income tax-year. Since the pain of the conversion is that you have to pay tax on the amount that you convert, you should convert when you are in a lower tax bracket to lessen the blow. For example, if you are married and have $75K of taxable income for the year and you decide to convert $50K to Roth, you will pay federal tax on that converted amount at a rate of 15% which would result in $7,500 in federal taxes. Keep in mind that you also pay state tax on the amount that you convert (if your state has state income tax), and most states have stepped brackets where you pay tax at a lower rate when you have lower income. If you instead converted when you were in a high-income year, let’s say $250K of income, then you’d pay federal tax on a $50K conversion at a rate of 33% which would result in federal taxes of $16,500. That’s more than twice the taxes due when you are in a lower-income year. Now, you may not have taxable income fluctuations. But, for those who are self-employed, change jobs and have a loss of income, or have investment losses where taxable income is lower than normal for a year, you should think about converting your retirement funds to Roth. You may not have a more affordable time to make the Roth conversion.

3.Potential Need for a Distribution After Five Years – One of the perks of Roth accounts is that you can take out the funds that are contributed or converted after five years without paying tax or the early withdrawal penalty (even if you aren’t 59 1/2). For Roth conversions, the amount you convert can be distributed from the Roth account five years after the tax year in which you converted. The five-year clock starts to tick on January 1st of the tax year in which you convert, regardless of when you convert within the year. So, if you converted your traditional IRA to a Roth IRA in November 2020, then you could take a distribution of the amounts converted without paying tax or penalty on January 2nd, 2025. If you try to access funds in your traditional IRA or 401(k) before you are 59 1/2, then you will pay tax and a 10% early withdrawal penalty even if the amounts you distribute are only the contributions you put in, not the investment gains. Clearly, the Roth account is much more accessible in the event you need personal funds. Keep in mind, you don’t get this perk immediately: You have to wait 5 years from the tax year in which you converted before you can take out the converted amount tax and penalty free.

One final thought to consider when converting to a Roth is that there are no do-overs. You used to be able to do what was called a Roth re-characterization where you could undo a Roth conversion but the ability to undo a Roth conversion was eliminated in 2018 forward. As a result, make sure you’re committed before you convert as there are no mulligans, do-overs, or re-characterizations anymore. Also, if you want the conversion to fall onto your current year tax return, then make sure you convert those sums by December 31.

Mat has been at the forefront of the self-directed IRA industry since 2006. He is the CEO of Directed IRA & Directed Trust Company where they handle all types of self-directed accounts (IRAs, Roth IRAs, HSAs, Coverdell ESA, Solo Ks, and Custodial Accounts) which are typically invested into real estate, private company/private equity, IRA/LLCs, notes, precious metals, and cryptocurrency. Mat is also a partner at KKOS Lawyers and serves clients nationwide from its Phoenix, AZ office.

He is published regularly on retirement, tax, and business topics, and is a VIP Contributor at Mat is the best-selling author of the most widely used book in the self-directed IRA industry, The Self-Directed IRA Handbook: An Authoritative Guide for Self-Directed Retirement Plan Investors and Their Advisors.

3 Year-End IRA Tips

vgsgn1482893180It’s the end of the year and many IRA investors are stressing about what they need to do by December 31, 2016. Here’s what you need to know for your IRA as it relates to year-end.

1. 2016 Contribution Deadline. First, the good news. You don’t have to make your 2016 contributions by year-end. You have until April 18, 2017 to make your traditional IRA, Roth IRA, or SEP IRA contributions for 2016. Check out the “IRS Year-End Reminders for IRAs” here for more details.

2. Roth Conversions. If you are planning to convert traditional IRA dollars to Roth for 2016, then you must make that conversion by December 31, 2016. If you convert in 2016 (by 12/31/16), then the amount you convert will get reported on your 2016 tax return. For those that have a down year or that simply want to start down the path of moving funds from traditional (tax-deferred funds) to Roth (tax-free), you’ve got to jump on this now. Your IRA custodian will typically have a Roth Conversion form that you complete and return to them. If you are converting cash, then the process is pretty simple as the value of the conversion is the cash amount. If you have a self-directed asset such as real estate or an LLC interest, you will need an appraisal or valuation of that asset in order to convert it to Roth. And lastly, if you’re on the fence about doing a Roth conversion because you’re worried about how much it will cause you in taxes, the IRS allows you to un-do the Roth conversion later in 2017, your funds go back to traditional funds, and you don’t have to pay the tax. This is one of the few things the IRS let’s you un-wind. Check out my prior article on Roth re-characterizations here.

3. The Over 70 1/2 Club. For those over 70 1/2 with traditional IRAs, you are required to take required minimum distributions (“RMD”) from your account each year. The deadline for 2016 RMDs is December 31, 2016. There is a 50% excise tax penalty for failure to take RMDs. In other words, if you don’t distribute the money to yourself from your IRA in time, the IRS will just take half of it to penalize you. Those with Roth IRAs need not worry as Roth IRAs are exempt from RMD. I’ve explained the facts and fiction on RMDs in a prior article you can find here.

So, if you’ve got a Roth conversion or RMD to take for 2016, you better get your “IRA” in gear. If you’re wondering about IRA contributions, don’t worry, you’ve got until April 18, 2017 to make them.

Prohibited Transaction Case Lesson: The Substance of the Transaction Matters

prohibited-transactioncase-studyA prohibited transaction case from 2015 taught an important lesson for self-directed IRA investors. That lesson is that the substance of the actual transaction matters and that you cannot avoid a prohibited transaction by creating entities or other artificial structures that create no business purpose. Summa Holdings, Inc., et al, v. Commissioner, T.C. Memo 2015-119 (2015)

In Summa, two brothers invested a minimal amount of funds from their Roth IRAs into a new corporation called JCH. JCH then established and owned 100% of another new company called JCE. This new company, JCE, then in turn contracted with and received income from a company owned and majority controlled by the Roth IRA owners’ father. Clearly, any transaction between the brother’s Roth IRAs and their father would be a prohibited transaction. The prohibited transaction rules restrict your IRA from transacting with a disqualified person and the list of disqualified persons includes the father of and IRA or Roth IRA owner. IRC 4975 (e)(2)(F).

The Tax Court, in Summa, had to determine if the transactions between companies the Roth IRAs owned and companies in which the Roth IRA owner’s father owned and controlled were a prohibited transaction. The Tax Court relied on what is known as the “Substance Over Form Doctrine” to find a prohibited transactions for the Roth IRAs receipt of income. The Substance Over Form doctrine provides that the substance and not the form of a transaction determines its tax consequences. So, despite all of the companies, three in total, that separated the brother’s Roth IRAs from their father there is still a prohibited transaction as the overall substance of the Roth IRAs transactions was to unfairly shift income and assets to the tax-free Roth IRA accounts.

In fact, the Roth IRA owners stipulated with the IRS  that the sole reason for their Roth IRAs investment into the companies and for the transactions was to accumulate income and assets tax-free. They conceded that there was no other business or investment purpose for the transactions. Consequently, the Tax Court rightly found a prohibited transaction and disqualified the Roth IRAs.

While careful planning and structuring is critical in your self-directed IRA transactions, no structure can overcome the lack of a legitimate investment or business interest for an IRAs investments. When investing your IRA into a deal, make sure your IRAs isn’t receiving any favorable treatment or benefit from a disqualified person (e.g. from the Roth IRA owner’s father). If your IRA is getting some favorable treatment or allocation of income or assets from a disqualified person, as was the case in Summa, you too could have a prohibited transaction.



Who are Self Directed IRA Investors? An Essay

I was recently interviewed and asked, “what has caused so many investors to self-direct their retirement plan?” As many people know, self-directed retirement plan investors use their self-directed IRA and 401(k)s to invest into real estate, private companies, precious metals and other “non-wall street” investments. I’ve worked with thousands of self-directed IRA and 401(k) investors and as I reflected on the question, I realized that there are three primary categories of self-directed investors.


These investors like to invest in what they know. They avoid mutual funds and the stock market because they have a competitive advantage over other investors and usually have a special expertise over other investors. Because they have a special expertise, they often expect to make significant returns and therefore will frequently use Roth IRA or 401(k) accounts for their investments. Let me offer a few examples from actual un-named clients of mine that all resulted in 7 figure returns.

  • Software Engineer. Software Engineer who used Roth IRA funds along with some other technology savvy investors and funded an LLC. This LLC then engaged and paid some un-related developers to develop new programming that the Roth IRA investors knew would have value. The LLC owned by the Roth IRAs then in turn negotiated a royalty agreement with an unrelated company who wanted the technology to be used in a specific software program that it would sell commercially. The LLC receives royalties on the use/sales of the product. The income goes back to the Roth IRAs tax free.
  • Real Estate Developer. Real estate developers and investors personally develop millions of dollars of real estate a year and decides to use his Roth IRA to fund a specific real estate investment. Real estate developer converted a couple hundred thousand dollars of traditional IRA funds to Roth IRA funds so that he could acquire a specific piece of real estate that was to be held and later sold. The developer knows the land would have significant value over the next few years as a result of zoning law changes and planned development from neighboring property. The Roth IRA paid for some paper development zoning changes upon acquisition and then held the property as an investment for a few years. The property later increased nearly 10 times in value as neighboring development took off.
  • Bio-Tech Start-Up Entrepreneur. An experienced bio-tech investor had an opportunity to invest at early stages in a patent that was going to be the basis for a new bio-tech start-up. The investor used Roth IRA funds and funded additional research costs in exchange for an interest in the patent that was being developed by un-related researchers for commercial purposes. The patent was the basis of value for a start-up venture and the Roth IRA received a significant share of the company in exchange for the patent interest.

This group would also include former Republican Party Nominee, Mitt Romney, and famous Venture Capitalist, Peter Theil, whose large self-directed IRAs have been reported on extensively.

Keep in mind, the rules for these investments are complex and careful planning must be taken to avoid prohibited transactions, as well as unrelated business income tax (UBIT). However, when properly executed with the right investment, this group can sock away significant returns in tax-free Roth accounts. There’s no better deal in the tax code than this!


This is the largest group of self directed IRA investors. These investors have seen stagnant performance, losses, or ridiculous fees eat away at their retirement account.  They are generally tired of the ups and downs of the stock market and want stable investments they can actually understand. This group usually invests in real estate, in its various forms, because it can offer more stable returns and because the investor can actually understand the investment (something they can’t do from a 100 page mutual fund prospectus). Here are a couple of actual client examples.

  • Retired Corporate Manager Becomes a Real Estate Investor. A retired real estate investor client of mine rolled over former employer 401(k) funds to a traditional self-directed IRA. This investor is in their early 60’s and uses the income from her retirement account to live on. She invested her traditional IRA into a modest 3 bd 2 bth single family rental. The property has no debt and the cash-flow goes back into her IRA. She routinely takes distributions of the cash-flow to supplement her retirement income. Since this is a traditional IRA she is taxed on the distributions (as she would with any traditional IRA) but she is not reducing the actual investment value of the IRA as she only distributes the cash-flow. This client has had an increase in confidence as the rental income has proven to be consistent over time and she still knows that her IRA owns the property so she doesn’t feel like she’s depleting her retirement account when she takes distributions of the cash-flow. Frankly, I’ve talked to hundreds if not thousands of clients in a scenario similar to this.
  • Real Estate Broker Loans Solo 401(k) Funds to Other Investors. This real estate broker uses his self-directed 401(k) to loan money to real estate investors buying investment properties. Some people refer to use these loans as hard money loans or as trust deed loans. The 401(k) will loan funds to other real estate investors in situations where banks are typically un-willing to lend. The real estate broker lends to properties in markets that he knows and receives a first or second place deed of trust (mortgage) securing his loan. The typical loan terms are 10% annual interest with 2 points. This self-directed investor knows real estate and has been able to receive annual returns far in excess of the stock market.


These investors value hard assets over paper assets. They are generally disillusioned by the stock market and feel that price to earnings ratios of publically traded companies have sky-rocketed without regard to company performance. They tend to believe that stock prices have nothing to do with actual value but instead are propped up by the Wall Street money machine. They’ve usually had retirement accounts for years and have seen their account go through the dot-com bubble and the financial crisis. They have little faith in paper assets and desire to move to a self-directed account at a time when they believe the market is going to collapse. Most of these investors will invest in precious metals or real estate.

  • Retired Corporate 401(k). A retired corporate employee rolls over a portion of his prior employer’s 401(k) to a self-directed IRA and buys actual precious metals that are stored at a depository for his IRA. The precious metals are not an ETF or a fund but are actual, physical, gold bullion that meets the retirement plan rules for ownership by an IRA. Common precious metals would be gold or silver bullion as well as specifically approved American Eagle coins.
  • Working Corporate Employee with Prior Employer 401(k). A 50 year old corporate employee uses her present employer retirement plan for standard mutual fund investments based on risk factors and tolerances for investors her age. Her current employer’s plan cannot be self-directed but she rolls over a prior employer’s 401(k) to a self-directed IRA and uses that self-directed IRA to invest in real estate investments with other like-minded investors. The investors use their self directed IRAs and each invest into the newly created IRA/LLC (and LLC owned by IRAs). The LLC then uses the combined funds to purchase a multi-family property. In the end, her IRA owns a 20% interest in an LLC that owns an apartment building.

There are many other characteristics of self-directed investors and even more examples of these groups in the industry. However, the three groups above seem to capture 90% of the growing self-directed retirement plan market. Additionally, many investors have cross over and identify in two or all three of these groups. Because self-directed IRAs and 401(k)s give investors options for greater control and because they provide better access to investment opportunities, we will only continue to see growth in the self-directed retirement plan market.

By: Mat Sorensen, Attorney and best-selling Author of The Self Directed IRA Handbook

Mat has been at the forefront of the self-directed IRA industry since 2006. He is the CEO of Directed IRA & Directed Trust Company where they handle all types of self-directed accounts (IRAs, Roth IRAs, HSAs, Coverdell ESA, Solo Ks, and Custodial Accounts) which are typically invested into real estate, private company/private equity, IRA/LLCs, notes, precious metals, and cryptocurrency. Mat is also a partner at KKOS Lawyers and serves clients nationwide from its Phoenix, AZ office.

He is published regularly on retirement, tax, and business topics, as well as a VIP Contributor at Mat is the best-selling author of the most widely used book in the self-directed IRA industry, The Self-Directed IRA Handbook: An Authoritative Guide for Self-Directed Retirement Plan Investors and Their Advisors.


In a recent Private Letter Ruling (PLR 201423043), the IRS stated that a deceased person’s Roth IRA may be inherited by the Roth IRA owner’s surviving spouse through their Trust when the surviving spouse was the sole beneficiary and had sole control of the Trust upon the passing of her husband.

As many retirement account owners already know, listing your Revocable Living Trust as the beneficiary of your retirement account can be tricky as the Trust needs to meet certain requirements in order to receive rolled-over funds from the surviving spouse.

For example, Under Reg. § 1.408-8, Q&A 5, a surviving spouse of an IRA owner may elect to treat the spouse’s entire interest as a beneficiary in an individual’s IRA as the spouse’s own IRA, but only if the spouse is the sole beneficiary of the IRA and has an unlimited right to withdraw amounts from the IRA.

The IRS has stated that, “If a trust is named as beneficiary of the IRA, this requirement is not satisfied even if the spouse is the sole beneficiary of the trust.” Under the PLR though, the IRS stated that when the surviving spouse is the sole trustee of a trust and has the sole authority and discretion under the trust to pay the IRA proceeds to herself/himself, then the spouse may rollover the deceased spouses Roth IRA to the surviving spouses Roth IRA as long as the rollover occurs within 60 days of the distribution from the deceased person’s IRA.

The rules regarding spousal rollovers can be tricky and you should consult with your attorney before listing your trust as the beneficiary of your IRA. As a result, I have the following three tips to follow when listing beneficiaries on your retirement accounts.

  1. When In Doubt, List Your Spouse Directly, Don’t List Your Trust – If you aren’t sure about whether your Trust qualifies as a beneficiary for your retirement account, then list your spouse directly as the beneficiary.
  2. If You List Your Trust  Instead of Your Spouse, Make Sure Your Trust Qualifies- Have an attorney review your Trust to make sure that it meets the requirements above (that your spouse will have sole control and authority under the trust to distribute the IRA to himself/herself) so that your spouse can rollover the retirement account in the most tax advantageous manner possible. For example, a spouse can rollover their deceased spouse’s account into their own account as was shown in the PLR above. That’s a great tax benefit as you can keep the funds in a retirement account and outside of taxation longer. However, if the Trust doesn’t meet the proper requirements then the trust receives the retirement account and it cannot be directly rolled into the retirement account of the surviving spouse and must instead be distributed.
  3. Consider a Separate IRA Trust for IRA’s Over $1M- If you have an IRA over $1M, you may benefit by having a special IRA trust as the beneficiary of your IRA. It depends on your goals and tax planning, but is worth considering.

Bottom line, the rules here are very tricky so consult with your estate planning attorney on the best way to list your heirs as beneficiaries on your retirement accounts.

By: Mat Sorensen, Attorney and Author of The Self Directed IRA Handbook