If it's a ROBS, and you invest using already-taxed Roth IRA/401k funds as a rollover into a Roth 401k, you actually don't care about the basis. You just want to characterize it as capital appreciation on an asset acquired in the Roth.
My understanding is ROBS, aside from being hated by the IRS if they step even slightly out of compliance with 401k regulations, are basically close to magic. $50k to set it up, invest $50k in a company to give it $50k capitalization, and sell the company later for $10b; zero tax owed.
With the SBJA2010, you have a similar deal; as long as the capital gain is due to the sale of a qualifying asset, you owe no capital gains, and it doesn't fuck you for AMT either.
I'm going to have to say that I'm not familiar with ROBs, since I never came across it. But, its definitely peaked my interest. From the preliminary reading I've done on it, it's a very aggressive tax planning vehicle and highly despised by the IRS. Which means it probably is as amazing as you say it is.
Allow me some time to read up on the case law in regards to this topic and I'll email you directly if you don't mind. This is something that would definitely be more than a 30 second answer and I'd definitely be interest in discussing it merits and shortcomings with you. Thank you for bringing it to my attention! No matter how many years I deal with taxes there's definitely going to be a lot that I need to learn lol.
If it's a ROBS, and you invest using already-taxed Roth IRA/401k funds as a rollover into a Roth 401k, you actually don't care about the basis. You just want to characterize it as capital appreciation on an asset acquired in the Roth.
My understanding is ROBS, aside from being hated by the IRS if they step even slightly out of compliance with 401k regulations, are basically close to magic. $50k to set it up, invest $50k in a company to give it $50k capitalization, and sell the company later for $10b; zero tax owed.
With the SBJA2010, you have a similar deal; as long as the capital gain is due to the sale of a qualifying asset, you owe no capital gains, and it doesn't fuck you for AMT either.