What value is taxed when a business interest converts to a Roth IRA?
The interest's fair market value on the conversion date, which becomes the taxable distribution amount reported on Form 8606. The IRS applies the willing-buyer, willing-seller standard through Revenue Ruling 59-60's eight factors; investment value, strategic value, and book value are not accepted for the conversion.
Will a custodian accept internal financials or a 409A report for the conversion?
Generally no. Custodians and IRS examiners expect an independent appraisal prepared specifically for the conversion, supported by the cap table, financial statements, records of recent financings or secondary sales, and any transfer restrictions on the exact interest the IRA holds. Company-prepared documents lack the required independence.
Can valuation discounts reduce the taxable amount of an IRA conversion?
Yes, when supportable. Discounts for lack of marketability and lack of control are accepted if grounded in empirical data and the interest's actual restrictions, but unsupported or aggressive discounts are a leading audit target, and an undervalued conversion is underreported income with penalty and interest exposure.
Is the custodian's annual FMV update enough to support a conversion?
No. Annual reporting for alternative assets tolerates lighter evidence, but a Roth conversion is a taxable event and carries higher documentation expectations: typically a full appraisal tied to the conversion date under the Revenue Ruling 59-60 framework, not a carried-forward annual estimate.