This document discusses issues to consider with self-directed IRAs, including: 1) Self-directed IRAs allow investors to choose their own investments beyond the trustee's options, but there are legal and practical issues to be aware of. 2) Transactions can involve prohibited self-dealing if they involve the IRA owner, family members, or IRA service providers. 3) Prohibitions aim to maintain the IRA's tax-exempt status and prevent conflicts of interest, such as holding non-bank custodians, commingling assets, or borrowing against the IRA. Practitioners will discuss these issues.

1. DRAFT January 4, 2010
Issues to Consider with Self Directed IRAs
The 2006 tax legislation afforded new distribution options for plan participants and beneficiaries
of qualified retirement plans. Such result makes it desirable to do a rollover to an IRA. There
continues to be interest in self‐directed IRAs (that is, an IRA owner choosing his/her investment
options, beyond that of the IRA trustee’s or custodian’s investment options). However, there are
practical and legal issues that the IRA owner must be aware of before making self‐directed
investment decisions. This panel of practitioners and government officials will discuss these
practical and legal issues.
Self‐directed IRAs can be further divided into (1) traditional brokerage IRAs, where the owner
may invest principally in registered investments, and (2) non‐traditional custody‐only IRAs,
investing principally in non‐registered or "alternative" investments. For purposes of this
discussion, we focus on the latter as a fast‐growing area that is subject to a great deal of
confusion.
I. Background / Framework
A. Code section 408 sets out certain requirements for tax qualification
1. Certain activities that can result in loss of tax exemption under
section 408 are commonly included under the broad umbrella of
"prohibited transactions" (and we do so here), but they are more
accurately characterized as qualification conditions (see below)
2. These "tax prohibitions" are solely under the jurisdiction of the
IRS
B. In general, rollover IRAs are not subject to Title I of ERISA
C. IRAs are subject to the prohibited transaction rules of Code section 4975
1. The Department of Labor has jurisdiction over interpretation and
issuance of exemptions
2. The IRS has jurisdiction over enforcement and imposition of the
excise tax
3. The penalty for engaging in a prohibited transaction with your own
IRA is tax disqualification of the entire IRA
Query – can you reduce the risk by isolating a questionable
investment in a separate IRA?

2. Note – recent bankruptcy court ruling that engaging in a
prohibited transaction also results in loss of bankruptcy
exemption1
4. The penalty imposed on anyone other than the IRA owner for
engaging in a prohibited transaction with an IRA is a 15% initial
excise tax on the "amount involved", plus an additional 100%
under some circumstances if not timely "corrected"
Note – "correction" and "amount involved" are determined
pursuant to pre-ERISA regulations relating to foundations,
and are not easily applied in some cases, particularly to
"self-dealing" types of transactions
II. Code section 4975 Prohibited Transactions
A. Generally. Code section 4975(c)(1) prohibits any direct or indirect:
1. Sale or exchange, or leasing, or property between an IRA and any
"disqualified person" with respect to the IRA.
2. Lending of money or other extension of credit between an IRA and
any disqualified person.
3. Furnishing of goods, services or facilities between an IRA and any
disqualified person.
4. Transfer of IRA assets to, or use of IRA assets by or for the benefit
of, any disqualified person.
5. Act by a fiduciary that involves the fiduciary "dealing" with the
assets of an IRA in his own interest or for his own account (self-
dealing).
Note – definition of "interest" can be quite broad
6. Receipt of any consideration by a fiduciary from any other party
dealing with the IRA (kickbacks).
Note – the Code contains no fiduciary "conflict of interest"
analog to ERISA section 406(b)(2) (though this is not
typically relevant in the case of a self-directed IRA).
B. Disqualified person. As relevant to a self-directed rollover IRA, the term
"disqualified person" generally includes:
1. Any fiduciary
2. Any service provider to the IRA (adviser, broker, accountant, etc.)
3. Any family member of a fiduciary or service provider
1
In re: Willis, No. 07-11010 (Bankr. D. Fla. Aug. 6, 2009).
2

3. Note - "family member" is defined as a spouse, ancestor,
lineal descendent or spouse of a lineal descendant (but not a
sibling)
4. Any corporation, partnership, trust or estate owned 50% or more
by a fiduciary or a service provider
Note – ownership by the IRA itself does not cause an entity
to be a disqualified person
C. Fiduciary. In the case of a self-directed IRA, the term "fiduciary"
generally includes:
1. The IRA owner
2. A person hired by the IRA owner to exercise investment discretion
over the account
3. A person providing non-discretionary investment advice to the
IRA owner (a) on a "regular basis," (b) pursuant to an agreement
or understanding (including course of dealing), (c) if the person
receives any form of compensation (direct or indirect), (d) if the
owner relies on the advice as a (not the) primary basis for making a
decision, and (e) the advice is "personalized."
Note – brokers and financial planners often argue (rightly
or wrongly) that they are not fiduciaries to IRAs because
their advice is not "personalized," particularly where the
IRA is part of a larger portfolio.
Note – many IRA service providers are unaware that
providing non-discretionary advice and obtaining client
consent does not relieve them of fiduciary responsibility.
D. Plan assets. DOL regulations provide that when a benefit plan including
an IRA makes an equity investment in an entity, the underlying assets of the
entity are treated as plan assets (subject to the prohibited transaction rules) on a
look-through basis unless an exception applies. The principal exceptions are:
1. Publicly offered securities.
2. De minimis holdings. Less than 25% equity ownership by benefit
plan investors.
3. Operating companies. Investments in companies that develop or
market goods and services other than the investment of capital, plus
certain “hybrid” entities known as “venture capital operating companies”
(VCOC) and “real estate operating companies” (REOC).
E. Indirect transactions. DOL Interpretive Bulletin (IB) 75-2, 29 C.F.R.
section 2509.75-2, provides that notwithstanding the fact that an entity does not
hold plan assets, if an investment in an entity is made with the expectation or
understanding that the entity will engage in a transaction that would be prohibited
if made directly, then such indirect transaction will also be prohibited. Similarly,
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4. if the plan by itself can cause the entity to engage in a transaction, then the
transaction will be treated as if the plan were a party to the transaction. See
discussion of Adv. Op. No. 2006-01A, below, for an example.
Note – this rule is commonly overlooked.
F. Exemptions. The prohibited transaction rules are subject to a number of
statutory exemptions, and the Department of Labor has authority to issue
administrative exemptions, which it does on a "class" basis (available to
anyone meeting the conditions) and on an individual basis (available only
to the named parties). "Key" exemptions of note to owners of self-
directed IRAs include:
1. "Reasonable services." Code section 4975(d)(2). Permits the
IRA to pay third-party service provider fees.
Note – this exemption does not cover self-dealing.
2. Bank deposits. Code section 4975(d)(4). Permits a bank to place
IRA assets in its own deposit accounts - commonly used to for
sweep services in the self-directed context.
3. Benefits distributions. Code section 4975(d)(9). Eliminates any
"technical" violation where IRA assets are distributed to the
accountholder.
Query – does this cover "in-kind" distributions or only
cash? (Retirement home example.)
4. Reasonable compensation. Code section 4975(d)(10). This
includes reimbursement of permissible out-of-pocket expenses.
Note – this exemption does not cover self-dealing.
5. "Conflicted" investment advice. Code section 4975(d)(17).
Permits a non-discretionary adviser or its affiliate to receive third-
party compensation (e.g., commissions) under certain conditions.
6. Transactions with service providers. Code section 4975(d)(20).
Permits the IRA owner to cause the IRA to enter into purchases
and sales, loans, leases, etc. with service providers who are not
acting as fiduciaries.
7. "Basic" securities transactions. Class PTE 75-1. Covers certain
day-to-day securities activities involving broker-dealers.
8. "Proprietary" mutual funds. Class PTE 77-4. Permits a
fiduciary to invest client assets in its affiliated mutual funds.
9. Interest-free loans. Class PTE 80-26. Permits the IRA owner or
other disqualified person to lend money temporarily to the IRA for
ordinary operating expenses and "incidental" purposes. The loan
must be unsecured.
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5. 10. Brokerage commissions. PTE 86-128. Permits a fiduciary with
respect to an IRA to direct trades to itself or an affiliate and receive
commissions. Commonly used in self-directed accounts held at
brokerage firms.
Note – DOL has taken the position that mutual fund "12b-1
fees" are not commissions for this purpose.
11. American Eagle coins. PTE 91-55. Provides a limited exemption
from the prohibition on investing in metals and collectibles.
12. The "toaster exemption." PTE 93-1. Permits a financial
institution to give small "gifts" to an IRA owner for opening an
account (generally not to exceed $20 in value).
13. Bank services. PTE 93-33. Permits a bank to provide certain free
or reduced-cost services (e.g., free checking, brokerage discounts,
etc.) to an IRA owner or family member on account of maintaining
an IRA.
14. Relationship brokerage. PTE 97-1. Provides similar relief for
IRAs maintained with a brokerage firm.
III. Common Self-Directed IRA Transaction Issues/Red Flags
A. Transactions involving the IRA owner (loss of tax exemption).
1. Investing in employer's business or employer-sponsored fund.
2. Using IRA assets to start a business.
• DOL Adv. Op. 2001-10A (fiduciary causing a plan to pay it
fees)
• IB 75-2 (investing in an non-plan assets entity with the
expectation of a fee)
• Application of IRS Michael Julianelle "ROBS" memo by
analogy.
3. Receiving compensation from an IRA-owned business.
4. Coinvesting with disqualified persons.
• DOL Adv. Op. 2001-10A (investing in limited partnership)2
5. Structuring distributions for estate planning purposes.
• DOL Adv. Op. 2009-02A (distribution to trust paying fees to
son)
6. Transactions involving family members of the owner.
• DOL Adv. Op. 2006-09A (loan to son-in-law's business)
2
Compare with DOL coinvesting discussions in various insurance company exemptions, e.g., Equitable
Life Assurance, 55 Fed. Reg. 33874, n.2 (1990).
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6. 7. Direct or indirect transactions "using" IRA assets to benefit
anyone with whom the IRA owner has a personal relationship.
• DOL Adv. Op. 2006-01A (leasing of property to IRA owner's
business)
8. "Householding" of IRA and non-IRA accounts.
9. "Checkbook LLC."
10. Personal use real estate (vacation/retirement home).
B. Transactions involving IRA service providers (excise tax penalty).
1. Recommending a rollover into an IRA.
• DOL Adv. Op. 2005-23A
• Securities law implications (FINRA actions, class action suits)
2. Recommending a proprietary/affiliated investment.
• DOL Adv. Op. 2005-10A (dollar-for-dollar fee offset)
• Various exemptions available (see above)
• Hedge funds
3. Receiving a fee for recommending an investment.
• PTE 86-128 (securities sales commission paid by the IRA)
• ROBS memo (promotional fee)
4. "Cross-collateralizing" brokerage accounts.
• DOL Adv. Op. 2009-03A
4. Broker free credit.
• PTE 2006-01
IV. Additional "Prohibitions" Relating to Tax Qualification under Code section
408
As noted above, the following "prohibitions" relate to tax qualification under
Code section 408, and are conditions to maintaining the tax-exempt status of the
IRA:
A. Prohibition on holding custody of assets other than by a bank or other
IRS-approved custodian – contrast with qualified plans which may have
individual trustees
Query – how far "down the line" does this requirement
travel? (Bernie Madoff example)
Query – does the "checkbook LLC" violate this
requirement?
B. Prohibition against investing in insurance contracts
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7. C. Prohibition on commingling except in common trust fund or common
investment fund
1. Common trust fund = IRC 584 common trust fund
2. Common investment fund = Rev. Rul. 81-100 group trust3
Query – what is "commingling"?
D. Prohibition against borrowing (also a 4975 prohibited transaction)
E. Prohibition against pledging account as security for a loan (also a 4975
prohibited transaction)
Query – does this apply to a pledge "internal" to the IRA?
Note – brokerage agreements commonly include pledges
(see discussion of Adv. Op. 2009-03A, above)
Note – few banks will lend to an IRA to acquire real estate
without a personal pledge
F. The following are not strictly "prohibited," but are red flags that can result
in serious penalties or disqualification:
1. "Deemed" contributions in excess of the annual limit.
• "Sweat equity" – problem of distinguishing between managing
the IRA and managing an IRA asset
• Bonus payment for opening new account
2. Under- or over-valuation of assets
• Effect on RMDs
• Potential prohibited transaction issues, see ROBS memo.
3
See, Treas. Reg. § 1.408-2(b)(5)(ii) defining "common investment fund." See also, IRS Notice
2004-50 (Jul. 23, 2004), Q&A 66, re: HSAs under Code section 223 (which appears to have the definitions
reversed).
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