Note there's significant limits on stock held in a Roth. Last I looked at it, you can't own more than 10% of the company, and you can't be an operating officer:
26 U.S. Code ยง 4975(2):
(H)an officer, director (or an individual having powers or responsibilities similar to those of officers or directors), a 10 percent or more shareholder, or a highly compensated employee (earning 10 percent or more of the yearly wages of an employer) of a person described in subparagraph (C), (D), (E), or (G)
The propublica article says Thiel put shares of his own company in his IRA. If true, that's not something you can do anyone.
26 U.S. Code ยง 4975(2):
(H)an officer, director (or an individual having powers or responsibilities similar to those of officers or directors), a 10 percent or more shareholder, or a highly compensated employee (earning 10 percent or more of the yearly wages of an employer) of a person described in subparagraph (C), (D), (E), or (G)
The propublica article says Thiel put shares of his own company in his IRA. If true, that's not something you can do anyone.