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Self-Directed IRAs and Alternative Investments: Prohibited Transactions, RMDs, Valuation Issues, and Correcting Errors

Recording of a 110-minute CPE webinar with Q&A

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Conducted on Wednesday, July 30, 2025

Recorded event now available

or call 1-800-926-7926

This webinar will detail self-directed IRA (SDIRA) requirements, including allowable investments, required minimum distributions, valuation issues, and prohibited transactions. Our panel of federal tax experts will review relevant court cases and PLRs and offer advice for correcting past IRA errors.

Description

Most taxpayers purchase stocks, bonds, and mutual funds in their retirement accounts. Taxpayers often use SDIRAs to buy alternative investments, including cryptocurrency, land, hedge funds, or racehorses. SDIRAs are subject to the same rules under Sections 408 and 408A as other IRAs; however, complying with these rules is usually more difficult for SDIRAs. Finding a custodian, valuing the assets at year-end, and making required minimum distributions can all be problematic.

Many people, when asked, assume a SDIRA is something that they already have with their bank or brokerage firm, and don’t realize they could be doing more with their tax advantaged accounts (IRAs, 401(k)s, SIMPLEs, SEP-IRAs, Health Savings Accounts, etc.). Standard tax advantaged accounts are usually opened with a bank or brokerage, where the account owner has limited investment options offered by banks/brokerage firms such as mutual funds, exchange-traded funds (ETFs), and similar security like investments. By contrast, an SDIRA is opened at a custodial company that offers a wider array of alternative investments such precious metals, real estate, crypto assets, promissory notes, private companies and more.

Since SDIRAs are often funded with larger and more complex investments, they are targets for IRS scrutiny. Numerous court cases and PLRs detail prohibited transactions, including self-dealing that can negate the IRA subjecting the taxpayer to taxes and penalties on the entire investment. Individuals and tax practitioners need to understand how to contribute to SDIRAs without running afoul of these guidelines.

Listen as our panel of retirement plan experts explains how to benefit from alternative IRA investments while meeting current compliance requirements.

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Outline

  1. SDIRAs: introduction
  2. Alternative investments
    1. Cryptocurrency
    2. Coins
    3. Land
    4. Rental Real Estate
    5. Promissory Notes
    6. Private Companies
    7. Venture Capital/Startups
    8. Others, with the exception of life insurance, collectibles, and S Corporations
  3. Valuation issues
  4. Prohibited transactions
  5. Required minimum distributions
  6. Correcting IRA errors
  7. Court cases and PLRs
  8. Best practices

Benefits

The panel will review these and other critical issues:

  • What types of investments cannot be contributed to an IRA?
  • What valuation methods are used to correctly determine the year-end values of alternative investments in IRAs?
  • Caveats and considerations of holding real estate in an SDIRA
  • Maintaining necessary liquidity in an SDIRA
  • What transactions are prohibited for IRAs and SDIRAs?

Faculty

Gibson, Daniel
Daniel Gibson, CPA, MST

Partner
Eisner Advisory Group

Mr. Gibson is a Tax Partner, with over 40 years of experience in public accounting, with 35 of those years with...  |  Read More

Sorensen, Mat
Mat Sorensen

CEO
Directed IRA by Directed Trust Company

Mr. Sorensen serves as CEO of Directed Trust Company, a self-directed IRA custodian with over 20K accounts and...  |  Read More

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