Ask HN: Tax lawyer referal for founder stock questions
Context: I am a serial entrepreneur embarking on my next startup, and this time I intend to capitalize the company by buying my restricted shares at a nominal fee with funds from my Roth IRA. I believe this to be legal and not fall under the self-dealing / disqualified person rules because all of the founders, including me, are minority shareholders, we are not related, and my Roth IRA custodian is buying the shares directly from the company.
If Forbes reporting is to be believed, Max Levchin did this trick to shelter founding shares of Slide and Yelp, and Peter Thiel did similar things with Paypal and Facebook. However the lawyer at my IRA custodian (who is used to setting these things up for holding real estate and gold bullion, not founding shares of a private company) doesn't want to touch the deal even though he can't, when pressed, point to a reason why this wouldn't be allowed.
So I ask this community, who is in a unique position to worry about and take these sorts of things seriously, is there any tax lawyer in silicon valley who is likely to know the rules regarding self dealing and IRA accounts and be willing to make an opinion on this? Or generally a tax lawyer who knows how startups work and is willing to investigate?
EDIT: Repost because apparently accounts created through Tor have their submissions hidden.