Self-Directed IRA & Solo 401(k) Live Q&A With John Bowens (September 2026)

“Can my IRA buy a rental with a mortgage? Can it buy from my brother? What happens to it when I die? Real questions about self-directed IRAs and Solo 401(k)s.”

This self-directed IRA Q&A is our September 2026 live session: 90 minutes with guest John Bowens, Director & Head of Education and Investor Success at Equity Trust Company and author of Wealth Beyond Wall Street, and Laura Dohanes, CPA. Together they answered real questions from business owners and investors about self-directed IRAs and Solo 401(k)s. Watch the full session below, then jump to any individual answer.

Quick answer: This is the full September 2026 self-directed IRA and Solo 401(k) Q&A. Use the list below to jump to your question, from what a true self-directed IRA is and what it can’t hold, to prohibited transactions, UDFI and the Solo 401(k) fix, flips and UBIT, leaving IRA real estate to your kids, Roth conversions and what the IRS sees on Form 5498.

Every question, with its own deep-dive

Each question has its own full write-up with the details, examples and FAQs. The articles roll out on Tuesdays, Thursdays and Saturdays through November 17, 2026, and each one appears here as soon as it’s published:

The questions answered in the session:

1. Is my brokerage IRA really “self-directed”? What changes when I move to a true self-directed IRA?
2. What can a self-directed IRA hold, and what are prohibited transactions?
3. Rapid fire: can my IRA buy from my parents, fix up its rental, or lend to my company?
4. Buying a rental with a mortgage in my IRA: the UDFI tax and the Solo 401(k) fix
5. Custodian, TPA, attorney, CPA: who does what, and will anyone stop a bad move?
6. What happens if I break a rule (IRA vs Solo 401(k)), and what if I already did?
7. How does real estate in my IRA pass to my kids when I die?
8. What does a self-directed IRA cost, how long does it take, and is it worth it under $1 million?
9. Can my IRA buy a business? (And why ChatGPT gets it wrong)
10. Should I buy an annuity inside my IRA or Roth?
11. Can I partner with my own IRA on a flip or rental?
12. If I do all my flips in my Roth IRA, are they tax-free?
13. Can I buy a rental with my IRA and write it off against my income?
14. Is the IRS watching self-directed IRAs? What Form 5498 reports
15. Converting IRA real estate to Roth without leaving my kids a tax bomb

Also answered live: does the custodian sign subscription documents?

One question is answered only in the full session. When your IRA invests in a private placement, does the custodian have to sign the subscription agreement? John’s answer: no. Custodians would rather not, because it’s extra work for everyone. The problem is that many sponsors don’t understand self-directed IRAs. A good custodian can give you a drafted letter authorizing you to sign on behalf of your IRA; if not, some custodians will sign once you’ve read, approved and signed the document yourself.

The short version of each answer

Want the one-line takeaways before you dive in?

• A true self-directed IRA: a brokerage “self-directed” IRA is their menu; a true self-directed IRA can hold real estate, private equity, notes, metals and crypto. Move money by trustee-to-trustee transfer.
• What it can’t hold: no collectibles, life insurance or S-Corp stock, and no deals with disqualified persons (you, your spouse, ancestors, descendants and descendants’ spouses).
• Rapid-fire rules: parents no, brother maybe, desk work only, no personal use, non-recourse loans only, and every dollar through the account.
• Leveraged rentals (UDFI): leverage in an IRA creates UDFI tax, even in a Roth; a self-directed Solo 401(k) generally avoids it.
• Who does what: the custodian holds title and stops blatant violations, but compliance is always yours, so build a team.
• Breaking a rule: one prohibited transaction can disqualify a whole IRA; in a Solo 401(k) it’s generally a 15% excise tax per year, and 100% if it’s never corrected.
• When you die: IRAs pass by beneficiary form; heirs don’t have to sell, most have 10 years, and there’s no step-up: the appraised value comes out taxed (traditional) or tax-free (Roth) and becomes their basis.
• Cost and timing: transfers take 5–8 business days, rollovers about three weeks; fees run roughly 0.5%–0.75% a year; you don’t need $1 million.
• Buying a business: not a business you’ll run (that’s a ROBS), but a small passive stake in a startup (not an S-Corp) can work.
• Annuities in an IRA: you can, but it’s a wrapper inside a wrapper with surrender charges, so ask what it adds.
• Partnering with your IRA: strictly pro rata from day one, don’t rely on the IRA to fund your share, and desk work only.
• Flips in a Roth: not if the IRA runs a business: UBIT can reach 37%. John’s rule of thumb is that more than two flips in one to two years raises the risk.
• Writing off the IRA’s rental: no, because the IRA owns the rental and keeps its deductions; contributions are capped, transfers aren’t.
• Is the IRS watching?: custodians report your IRA’s value every year; ask whether a deal would hold up, and document it first.
• Roth conversions: conversions are taxed at fair market value; convert in slices through a Solo 401(k) and leave heirs tax-free money.

Why we hosted a self-directed IRA Q&A with a custodian

Laura’s firm usually sees self-directed IRAs and Solo 401(k)s at the messy end: multiple entities, multiple states, and something that broke. This session was about getting ahead of that, with someone who sits on the custodian side every day. John has educated more than 100,000 investors on self-directed accounts, and his recurring theme matched Laura’s: these are among the most powerful tax tools available, and the rules exist to protect them.

Three things to take with you. First, these accounts are tools, so know what you’re trying to achieve before you choose one. Second, compliance is always yours: you direct the account, and the penalties land on you, not the custodian. Third, figure out which piece you’re missing (a custodian question, a strategy or tax question, or a legal one) and bring in the right person before the deal, not after.

Official IRS reference: IRS — Individual Retirement Arrangements (IRAs)

Key takeaways

• A 90-minute self-directed IRA and Solo 401(k) Q&A with John Bowens of Equity Trust Company.
• Fifteen questions have their own in-depth article; one more is answered in the full video.
• Topics: what SDIRAs can hold, prohibited transactions, UDFI, UBIT, inheritance, Roth conversions, Form 5498.
• Compliance on a self-directed account is always the owner’s responsibility.
• The Q&A runs monthly; only newsletter members get the invite.

Self-directed IRA and Solo 401(k) FAQs

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These answers come from our monthly open Q&A. Only newsletter members get the invite (real tax strategy for business owners, twice a week, no fluff).

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Guest: John Bowens, Director & Head of Education and Investor Success at Equity Trust Company, appeared as a guest. Custodians, including Equity Trust Company, do not provide tax, legal or investment advice.

Disclaimer: This article is for educational purposes only and is not tax, legal, or financial advice. Every situation is different. Talk to a qualified professional about your specific facts before making any decisions.