Does Flipping Make Sense for Your Self-Directed IRA?


A lot of investors learn about the potential of investing in real estate with a self-directed IRA, and immediately gravitate toward property flipping. There’s good reason for this, as a well-executed flip can be a very profitable venture and a great way to grow your retirement savings.
However, flipping in a self-directed IRA is complex. A thorough evaluation of the concept is required before running off to the next foreclosure auction with your newly established Checkbook IRA.
Flipping properties in an IRA is not as simple as finding a good deal on a distressed property, fixing it up, and selling it at a profit. The tax-sheltered nature of a self-directed IRA or Solo 401(k) comes with certain restrictions per IRS rules. These restrictions can be quite noticeable when trying to flip houses.
Once you understand the different paradigm in which an IRA or 401(k) operates, you can approach the opportunity of flipping strategically, and choose an approach that suits your goals while remaining in compliance with IRS guidelines.
Rule #1 – Hands Off
With a self-directed IRA, you have tremendous flexibility to invest in a wide variety of opportunities. You also have close control over what your IRA invests in, and the administration of the account.
However, what you always need to keep in mind is that IRS rules require all your IRA’s activities to be conducted exclusively for the benefit of your IRA. You can’t personally benefit from the IRA, nor may you provide benefit to the IRA via the provision of goods or services.
When it comes to investing in real estate flipping, this means you need to take a big step back from the actual flipping and act more like a fund manager.
Your services have value. If you gift those services to the IRA, it’s like making non-documented contributions to your IRA. IRS rules prohibit this, and a violation of those rules can be catastrophic to your IRA.
You can act in an oversight and administrative role. Identifying opportunities and negotiating purchases, coming up with a rehab plan, hiring vendors to do the work, and dealing with the expense and income transactions along the way are all acceptable.
You shouldn’t perform work on the property personally, as this would be a clear violation of IRS rules. You should also avoid becoming the delivery person for your contractors by making frequent runs to the hardware store. Any permits should be acquired by your hired contractors, and not by you.
For many investors who have experience in the contracting trades, these restrictions can be a deal killer. Making the jump from contractor to “investment manager” is not for everyone, but it is a requirement when your IRA is the investor.
Rule #2 – Unrelated Business Taxable Income
When your IRA invests in a stock and then sells the stock later for a profit, that transaction is fully tax sheltered. So the same concept applies when your IRA sells a property at profit, right? Not exactly.
An IRA or other tax-exempt entity receives tax-favored status when it receives income from passive sources. When a tax-exempt entity engages in a trade or business on a regular or repeated basis, however, then taxation on Unrelated Business Taxable Income (UBTI) applies.
This tax is designed to protect tax-paying businesses from unfair competition. When a tax-exempt entity generates UBTI, the resulting tax paid is referred to as Unrelated Business Income Tax (UBIT).
Holding a stock and selling it at some point in the future is a passive investment that’s fully tax sheltered. But buying houses, fixing them up, and then selling them isn’t considered passive — this is a real estate development activity.
As such, if your IRA flips houses on a regular or repeated basis, it will generate UBTI. The trust tax rates for UBTI ratchet up to 37% pretty quickly, and can put a real dent in the profitability of a flip transaction.
So what is “regular or repeated”? The answer is: “It depends, and the IRS gets to make the determination based on the facts and circumstances of a particular situation.”
The IRS rules are not so specific as to outline what frequency of property flips over what time-period will cross this threshold. Rather, the IRS has the flexibility to determine if a particular activity is substantially similar to commercial enterprises in the same field. If so, then your IRA’s flipping transactions may be exposed to UBIT.
What this means is that an occasional flip transaction, especially if mixed into an IRA portfolio that is also producing passive income, will likely not be considered a trade or business regularly engaged in. If all your IRA does is flip, and you’re also actively flipping homes outside your IRA, the threshold for UBTI exposure might be lower.
What makes the concept of UBTI even more challenging is that it’s your responsibility as the taxpayer to make the determination as to whether your IRA has tax liability and file accordingly. If you guess wrong and get audited, then there will be additional penalties for the failure to file and back taxes the IRA should have paid. It’s in the best interest of your IRA to take a conservative approach to the frequency of flip transactions.
Weighing the Options
With these IRS rules in mind, you need to take a look at your intended flipping strategy and determine if it’s realistic. For many investors just starting to evaluate a self-directed IRA, this can mean a significant adjustment in expectations.
I can’t tell you how many times in the last dozen years we’ve had an initial conversation with an investor who anticipates being the contractor for their IRA that will flip 3-5 houses per year – all tax free. That would be great, but it’s not possible within the IRS guidelines.
There are several approaches to flipping that work within the rules that apply to retirement plans. Determining which is best for you depends on your expertise, amount of capital available, and how involved you wish to be.
Limited Flipping
The simplest approach to flipping is based on limited frequency and limited engagement.
For many investors just wanting to diversify their portfolio and who see an opportunity to flip in a specific market, this is a viable strategy. A few different transaction structures fit into this methodology:
- Your IRA can provide 100% of the capital for acquisition and rehab, and you can act in a limited role as the project manager by choosing vendors and materials, and ensuring the project is run according to scope and timeline. At the time of sale, all profits will return to the IRA.
- Your IRA can partner with a contractor, with the IRA providing some or all of the capital. The contractor may only provide their services, or they may bring a mix of capital and services. The profits of the deal can then be split accordingly between the IRA and the contractor.
Hybrid Flips
If your IRA has significant capital and there is real opportunity for profit with flips in your market, then an alternate approach we call a hybrid-flip may be an option that allows you to turn more deals.
Buying and fixing up a house is not what characterizes a real estate transaction as a flip. Immediately selling that fixed up property is what makes it a flip, and therefore a trade or business activity.
If your IRA fixes up a property and then holds that property as a passive rental for at least a year, then the future sale isn’t considered a flip, but rather just the disposal of a passively held asset — kind of like that stock mentioned earlier.
The profit potential of a flip comes from purchasing at a discount and adding value. If you can be patient about capturing that added value with a deferred sale, then the gain can be fully tax-sheltered within the IRA. The IRA may also benefit from the rental income over the holding period.
Taking a long time to rehab and sell the property will not achieve this goal. There has to be a rental usage for at least 12 months to make the property a passively held asset.
Many of our investors will directly flip one or two properties per year, then utilize the hybrid flip model to do more deals on the passive side of the ledger.
Being the Bank
Your IRA doesn’t necessarily need to be the flipper to generate solid income in a market where flip opportunities are available. Another great approach is to step back and have your IRA act as a private lender to other investors who are flipping houses.
This strategy is especially appealing for investors who may not have a lot of time or expertise with house flipping. The IRA can hold a mortgage secured by a property being flipped. The interest income received on the mortgage is passive income that isn’t classified as UBTI.
Volume Flipping with a UBIT Blocker
With the passage of the Tax Cuts and Jobs Act of 2017, another approach to flipping became viable. This strategy involves the use of a UBIT blocker corporation.
While this method doesn’t eliminate taxation on high frequency flipping, it reduces the tax rates significantly so it can make sense to flip inside the IRA.
An IRA with UBIT exposure will pay up to 37% tax based on federal trust tax rates. With the TJCA, the corporate tax rate was reduced from 35% to 21%. By investing the IRA into a taxable corporation that engages in flipping, the IRA can reduce the tax rate on flip profits from the 37% trust rate to the 21% corporate rate.
The flips take place in the corporation and the corporation then pays tax at 21%. After-tax profits can then either be retained in the corporation and deployed into additional flips, or issued as non-taxed dividends to the IRA shareholder.
The UBIT blocker doesn’t change the rules related to self-dealing. All activities of the IRA-owned corporation must be conducted at arms’ length, just as in any other IRA scenario.
This strategy only makes sense for those investors with the capacity to fund multiple flips per year. The cost of establishing and maintaining the corporation and filing corporate tax returns won’t be justifiable for a smaller portfolio.
Retirement Funded Development Corporation
The above strategies apply to a self-directed IRA or Solo 401(k) and fit within the arms’ length requirements of such plans. There’s an entirely different route that allows you to use existing retirement savings to capitalize your own business and invest in yourself — without taxes or penalties.
With a Business Funding IRA, you can create your own retirement funded real estate development company and be personally involved in flipping houses. You can even draw a salary.
If you have experience in house flipping and want to be directly involved with flip projects, this Business Funding IRA — sometimes called a Rollover as Business Startup — can be a path to creating your own business and striking out on your own.
This alternative structure involves forming a sub-chapter C corporation as your active business. The corporation establishes a 401(k) retirement plan that you can then rollover existing IRA or 401(k) savings into.
The retirement plan then purchases shares of the parent corporation via an employee stock option purchase (ESOP). The retirement plan is now a shareholder of your business that you can use for real estate development.
While there are no taxes or penalties for using this self-funding method, the business itself will operate as a normal taxable entity. So there is a trade-off of access to capital at the expense of tax-sheltering of income.
However, if your business is profitable, you can still achieve sheltering benefit by issuing dividends to shareholders — which will be tax-deferred to the retirement plan, and by making new contributions to the plan.
As with the UBIT blocker, this more complex plan strategy is only beneficial if you have sufficient retirement capital to fund a business that can execute multiple transactions per year.
Which Path is Right for Your IRA?
We hope this brief overview has helped you gain a better understanding of how flipping houses fits within the special rules that apply to tax-sheltered retirement plans, and the different approaches that can be used to engage in flipping opportunities.
If you would like to learn more about how to best deploy your IRA into flipping, please feel free to contact us. One of our expert advisors will help you better understand your options.
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Quick answers to common questions
We’ll take you through a simple, step by step process designed to put your investment future into your own hands…immediately. Everything is handled on a turn-key basis. You take 100% control of your Retirement funds legally and without a taxable distribution.
YES! In 1974, Congress passed the Employee Retirement Income Security Act (ERISA) making IRA, 401(k) and other retirement plans possible. Only two types of investments are excluded under ERISA and IRS Codes: Life Insurance Contracts and Collectibles (art, jewelry, etc.). Everything else is fair game. IRS CodeSec. 401 IRC 408(a) (3)
It’s actually pretty simple. Early on, regulators let the securities industry take the lead in educating the public about retirement accounts. Naturally, brokers and banks promoted stocks, bonds, and mutual funds—giving the impression that those were the only allowed investments. That was never true... and still isn’t. You can probably guess why they kept the rest under wraps.
It is possible to use funds from most types of retirement accounts:
- Traditional IRA
- Roth IRA
- SEP IRA
- SIMPLE IRA
- Keogh
- 401(k)
- 403(b)
- Profit Sharing Plans
- Qualified Annuities
- Money Purchase Plans
- and many more.
It must be noted that most employer sponsored plans such as a 401(k) will not allow you to roll youraccount into a new Self-Directed IRA plan while you are still employed. However, some employers will allow you to roll a portion of your funds. The only way to be completely sure whether your funds are eligible for a rollover is by contacting your current 401(k) provider.
A Solo 401(k) requires a sponsoring employer in the format of an owner-only business. If you have a for-profit business activity – whether as your main income or as a side venture – and have no full-time employees other than potentially your spouse, your business may qualify. The business may be a sole-proprietorship, LLC, corporation or other entity type.
A self-directed retirement plan is a type of IRA or 401(k) that gives you greater control over how your retirement funds are invested. Unlike traditional accounts held at banks or brokerage firms that limit you to stocks, bonds, and mutual funds, self-directed plans allow you to invest in a wide range of alternative assets including real estate, private businesses, precious metals, cryptocurrency, and more.
These plans still follow the same IRS rules and maintain the same tax-deferred or tax-free benefits as conventional retirement accounts. The difference is simply in how and where you choose to invest.
No. Moving to a self-directed IRA or Solo 401(k) does not trigger any taxes, as long as your funds are eligible for rollover.
Self-directed retirement plans maintain the same tax-advantaged status as traditional plans offered by banks or brokerage firms. The key difference is flexibility—our plans are designed to give you greater control and allow for a wider range of alternative investments beyond stocks, bonds, and mutual funds.
A prohibited transaction is any action between your retirement plan and a disqualified person that violates IRS rules and can lead to serious tax consequences. Under IRS Code 4975(c)(1), prohibited transactions include:
- Selling or leasing property between your plan and a disqualified person Example: Your IRA cannot purchase a property you already own.
- Lending money or extending credit between the plan and a disqualified person Example: You cannot personally guarantee a loan your IRA uses to buy real estate.
- Providing goods or services between your plan and a disqualified person Example: You can’t use your personal furniture to furnish a rental property owned by your IRA.
- Using plan income or assets for the benefit of a disqualified person Example: Your IRA cannot buy a vacation home that you or your family use.
- Self-dealing by a fiduciary (using plan assets for their own benefit) Example: Your CPA shouldn't loan your IRA money if they’re advising the plan.
- Receiving personal benefit from a deal involving your IRA's assets Example: You can’t pay yourself from profits your IRA earns on a rental.
If a transaction doesn’t clearly fall within the allowed guidelines, the IRS or Department of Labor may review the situation to determine if it qualifies as a prohibited transaction.
Disqualified persons are individuals or entities that are prohibited from engaging in certain transactions with your IRA or 401(k). Doing so could trigger a prohibited transaction, which may result in taxes and penalties.
Here’s who is considered a disqualified person:
- You (the account holder)
- Your spouse
- Your parents, grandparents, and other ancestors
- Your children, grandchildren, and their spouses
- Any advisor or fiduciary to the plan
- Any business or entity owned 50% or more by you or another disqualified person, or where you have decision-making authority
These rules exist to prevent self-dealing and ensure your retirement plan remains in compliance with IRS regulations.
(Reference: IRC 4975)
Understanding and following these rules can be tricky, but it’s very doable. The best way to stay compliant is to work with professionals who specialize in self-directed retirement plans. They can help you navigate IRS guidelines and avoid prohibited transactions.
If an IRA holder is found to have engaged in a prohibited transaction with IRA funds, it will result in a distribution of the IRA. The taxes and penalties are severe and are applicable to all of the IRA’s assets on the first day of the year in which the prohibited transaction occurred.
Yes. While self-directed retirement plans allow for a wide range of investments, there are a few important restrictions.
You cannot invest in collectibles or life insurance contracts, and you must avoid prohibited transactions—activities that benefit you personally rather than the retirement plan. These include things like buying or selling property to yourself or family members, using plan assets for personal gain, or self-dealing in any way.
Violating these rules could cause your entire IRA to lose its tax-advantaged status. To protect your account, it’s essential to work with professionals who understand IRS regulations and can help you stay compliant.
This is a common misconception. In many cases, professionals may simply be unfamiliar with self-directed retirement plans, as they fall outside their usual scope of work. CPAs and tax preparers are trained to file taxes, not necessarily to advise on alternative retirement strategies. Financial advisors and brokers often work for firms that focus on traditional investments like stocks and mutual funds—and may not benefit from or support alternative options like real estate or private lending.
Self-directed retirement investing is legal under IRS rules—but like any specialized area, it requires working with professionals who understand how it works.
The IRS has rules in place to make sure your IRA is used only for the exclusive benefit of the retirement account—not for personal gain or to help family members. These rules can get complicated because there are many ways a conflict of interest can occur, even unintentionally.
For example, if your IRA buys a house and rents it to your mother, you might be reluctant to evict her if she stops paying rent. That emotional connection creates a conflict between what’s best for your IRA and your personal relationships, something the IRS aims to prevent.
These rules help ensure your retirement account stays compliant and protected. (See IRC 408)
Yes. Most tax-deferred retirement accounts—such as Traditional IRAs, old 401(k)s, 403(b)s, and TSPs—can be rolled over into a self-directed IRA or Solo 401(k), depending on your eligibility. Roth IRAs cannot be rolled into these accounts.
You can contribute directly from earned income, subject to annual IRS contribution limits. The method and amount depend on the type of plan you have (e.g., Solo 401(k) vs. IRA).
To take a distribution, you'll request funds through your custodian or plan administrator. Distributions may be taxable depending on your account type and age. Early withdrawals may be subject to penalties.
For 2025, the Solo 401(k) max contribution limit is $81,250 if age 60-63, $77,500 if age 50-59 or 69+, and $70,000 if under 50. Traditional and Roth IRAs have a limit of $7,000 ($8,000 if age 50+). Limits are subject to IRS adjustments.
Yes. IRA contributions are typically due by your personal tax filing deadline (e.g., April 15). Solo 401(k) contributions follow your business tax filing deadline, including extensions.
IRS reporting requirements vary depending on the type of self-directed retirement plan you have. Here’s a quick breakdown of what you need to know
Please note: Our team can help you understand what’s required for your specific account, but we don’t provide tax or legal advice. We always recommend working with a qualified tax professional to ensure full IRS compliance.
Self-Directed IRA (Traditional or Roth)
- Form 5498 – Filed by your custodian each year to report contributions, rollovers, and the fair market value (FMV) of your account.
- Form 1099-R – Issued if you take a distribution or move funds out of your IRA.
- Annual Valuation – You'll need to provide updated FMV for any alternative assets held in the account, such as real estate or private placements.
Solo 401(k)
- Form 5500-EZ – Required if your plan assets exceed $250,000 as of year-end. Must be filed annually by the plan participant.
- Form 1099-R – Required if you take a distribution or roll funds out of the plan.
- Contribution Tracking – Keep records of employee and employer contributions. These are not filed with the IRS but may be needed for tax reporting or audits.
SEP IRA
- Form 5498 – Filed by your custodian to report contributions and FMV.
- Form 1099-R – Filed by your custodian. Issued for any distributions.
- Employer Contributions – Must be reported on your business tax return (and on employee W-2s, if applicable).
Health Savings Account (HSA)
- Form 5498-SA – Filed by your HSA custodian to report contributions.
- Form 1099-SA – Filed by your HAS custodian. Issued for any distributions.
- Form 8889 – Must be included with your personal tax return to report contributions, distributions, and how funds were used.




