Thanks for the article MDM interesting. Good point on ROTH I think this may work. One of the special situations im thinking about is a mutual bank conversion, so it is arms length
The most recent one I did was CLBK which was offered at $10 in the IPO (it isnt really an IPO which is why the opportunity exists), and they allowed me to put in $550k. Due to the math of how they work, it gained 63% on the day. I was able to sell all my mutual funds in my ROTH and put all of my IRA into the offer via the broker, (fidelity will do it ameritrade wont as i discovered)
It got me thinking about some of the others i have done for example Investors bank in their second step allowed up to $2.6million to be invested at $10, and Beneficial allowed $1.5M , so hence the question if I didnt have enough in my IRA, could i follow the strategy of overstuffing from my regular account. Anyhow I have accounts at 512 mutual banks and insurance companies all over the US, which I view as a call option on the eventual mutual conversion of the embedded equity, these will eventually all convert. It would be wonderful if I can get these gains to be capital gains free.
thanks again.