8 Clever Tax Strategies to Get the Most of Your IRA

Despite their limitations, individual retirement accounts (IRAs) are incredibly powerful. And you can do all kinds of creative tricks with them to build a huge nest egg, tax-free. 

Try these “alternative” IRA strategies to get the most out of these tax-advantaged retirement accounts and potentially retire with nothing but tax-free income. 

1. A Roth SDIRA With Secured Debt Investments

Debt investments can offer predictable monthly interest payments that you can live on. Unfortunately, the IRS taxes interest at the regular income tax rate. Don’t expect any baked-in tax advantages like you get with real estate syndications or rental properties. 

This past month, our co-investing club invested in a secured note paying 16% interest. The note is secured with first-position liens against a portfolio of single-family properties. Collectively, our members invested $569,000. 

For most of us, that means paying a full tax rate on that juicy interest income. But if you invested using a self-directed Roth IRA, those interest payments would pile into your IRA account tax-free. You can keep reinvesting that money for an ever-larger tax-free portfolio. When you retire, you pay no taxes on the withdrawals, either. 

2. A Roth SDIRA With High-Yield Equity Investments

The same principle applies to real estate equity investments that pay a high distribution yield or cash-on-cash return. 

For example, last year, we invested in a land-flipping fund that pays 16% in distributions. That part is fun. 

But again, the IRS taxes distributions at the regular income tax rate. Not so much fun.

Once again, if you invest through a Roth SDIRA, those distributions will just keep compounding your account balance—tax-free. 

3. A Roth SDIRA With Syndications Targeting “Infinite Returns”

A typical value-add real estate syndication works like a giant property flip: The operator buys a run-down multifamily property (or other large property), renovates it and raises rents over a couple of years, and then they sell for a tidy profit. 

Some operators take a different tack. They approach it more like the BRRRR strategy: After renovating the property and raising rents, they refinance based on the new higher value. Upon refinancing, they pay passive investors like you and me some or all of our original capital back—but we keep our ownership interest. 

And we keep collecting cash flow, even though we may no longer have any money tied up in the property. That means we can reinvest the same capital again and again and again, creating a cycle of “infinite returns.” 

If you invest through a Roth SDIRA, there’s theoretically no limit on the returns you can earn on your initial contributions. 

4. A Roth SDIRA With Flip Profit Splits

“Brian, if you run a full-time house-flipping business, you can’t invest your SDIRA dollars in your own business!” 

True enough. But what if you go in on some house flips as a silent partner in someone else’s business? 

Last year, we partnered with a house-flipping company on a series of flips. The company is flipping as many houses as they can with our money over an 18-month period, then returning our capital along with our share of the profits. 

The partnership structure itself builds in a compounding effect. Our partner company can flip larger or more properties as they sell partnered houses, and our share of the profits gets reinvested in more deals. 

At the end, we get a payout with a chunk of long-term capital gains. That itself saves us money on taxes: Instead of being taxed for short-term gains on each flip, we only receive our portion of profits after 18 months. 

But imagine if you invested through a Roth SDIRA. You get all the compounding from that fast turnover and that high velocity of money. And you don’t pay a dime in taxes. 

5. Combine a “Normal” IRA With Tax-Advantaged Real Estate Investments

My investment portfolio includes roughly 50% stocks and 50% passive real estate investments. 

If I’m going to own both stocks and real estate anyway, why not hold the stocks in a simple brokerage IRA while owning the real estate investments “taxably”? 

Granted, not all real estate investments come with built-in tax advantages. I’ve outlined a few, such as secured debt investments, that don’t come with any. 

But real estate syndications and some funds and private partnerships come with outstanding tax benefits. You can take advantage of accelerated depreciation through cost segregation studies (and possibly bonus depreciation if that gets extended). 

So, you show a loss on paper on your tax return, even as you collect distributions in the real world. 

And when the property sells, you face the big bad wolves of long-term capital gains taxes and depreciation recapture? Just reinvest the money in a new syndication or fund using the “lazy 1031 exchange” strategy. 

Easy-peasy.

6. Open a Solo 401(k)

If you’re self-employed—and that includes real estate investors—you can open a solo 401(k). 

“Why would I bother opening a solo 401(k)?” Because the contribution limit is a whopping $70,000 in 2025. If you’re over 50, that rises to $77,500. 

And yes, you can open a Roth solo 401(k), not just a traditional one. 

You can also roll over funds from your solo 401(k) to your self-directed IRA. It opens a world of possibilities for your real estate (and other alternative) investments. 

7. Invest Through an HSA for a Secondary Retirement Account

Health savings accounts (HSAs) offer the best tax benefits of any account. They combine the perks of traditional and Roth accounts: You can deduct the initial contribution, the investments compound tax-free in the account, and you pay no taxes on withdrawals. 

“Yeah, but only if I use the withdrawal to pay for health-related expenses, right?”

Sure—which is a broad category, and you’ll have no shortage of health-related expenses in retirement. Have no doubt about that.

All this means you can use your HSA as a secondary retirement account. You get a write-off today, and you get tax-free withdrawals later. 

As an added benefit, if you reach financial independence and retire early, you can start withdrawing money from your HSA at any age. You don’t have to wait for 59 1/2. 

8. Income Too High? Do a Backdoor Roth Conversion

If you earn more than $150,000 as a single filer or $236,000 as a married couple in 2025, you can no longer make a full contribution to a Roth IRA. Above $165,000, you can’t make any contribution at all. 

Fortunately, Uncle Sam left a back door open for clever investors. Instead of contributing to your Roth IRA, contribute to a traditional IRA. You can’t write off the contribution—but you can roll it over to a Roth IRA. 

And from there, the money compounds tax-free just like your other Roth IRA funds, and you pay no taxes on withdrawals in retirement. See why it’s called a backdoor Roth contribution? 

Final Thoughts

If you want to win the game of money, you need to know the rules. And nowhere is that clearer than tax strategy. 

I pay very little in income taxes. Part of that is because I live and invest from overseas and take advantage of the foreign-earned income exclusion, but I also get enormous tax benefits on the hands-off real estate investments I make. 

In fact, these tax benefits wipe out all the taxes I’d otherwise owe on my stock and other investments as well. And I’ve steadily been converting my traditional IRA funds to my Roth IRA—paying no taxes—so I can live tax-free in retirement.