A Model for Reporting Gambling Sessions: Shollenberger v. Commissioner

Note: I am not a lawyer, nor should the following be perceived as legal advice.

If you choose to use Etheroll, I would recommend keeping good records. That said, there is precedence for the right to assess the entire casual session as a single event, rather than as an exhaustive series of wins (income) or losses (deductions).

Quote from the United States Tax Court Ruling: "The better view is that a casual gambler, such as the taxpayer who plays the slot machines, recognizes a wagering gain or loss at the time she redeems her tokens. We think that the fluctuating wins and losses left in play are not accessions to wealth until the taxpayer redeems her tokens and can definitively calculate the amount above or below basis (the wager) realized."

I would recommend reading the entire case, which sheds light on the long arm of the IRS, and strangely enough, the common sense approach of the tax Court.

Commentary: http://www.taxabletalk.com/2009/12/28/a-loss-for-the-taxpayer-but-a-win-for-gamblers/

Direct Link: http://ustaxcourt.gov/InOpHistoric/SHOLLENBERGER.TCM.WPD.pdf

At your peril.

Edit: Thank you u/known_and_unknown for clarifications; my post was attempting to make it easier to use Etheroll the platform, not invest in DICE the asset. However, the rabbit hole runs deeper (in the US, it always runs deeper). If we want to speak about the company, all should be aware that a quarterly distribution of Ether is taxable at the current market value as a property dividend. Here's the catch: if you think holding this Ether for more than a year will ease into long-term capital gains, that is incorrect. You need to account for the entirety of that income in the tax year. What traditional companies have that these new enterprises lack are tons of tricks to stop the bleeding; deferments, withholdings, restricted stock (gives the employees the right to receive shares as a gift), etc. It would be interesting to see Etheroll reformulated as an ESOP.