Try this one

Or, simply google "Peter Thiel IRA."

It's really a beautiful scheme, and completely legal.  Thiel used his Roth IRA to buy shares in Paypal when it was a startup.  Now the value has grown into the billions, and he can sell them and owe no tax.

Well that is good for him, but clearly an outlier, and I think he should keep every dime of it and never be threatened with paying taxes on a Roth IRA because that is sort of the agreement when you set it up.

Sure, but I still don't understand your statement,  "Anyone with that net worth isn't dumb enough to keep their assets in an IRA."  Why would you say that?  

The problem I see is getting large assets into an IRA, due to the contribution limits.  But if you can get large assets into an IRA, or grow small assets to large size in an IRA, particularly a Roth IRA, I don't see why one wouldn't want to do that.  Why did you say that?  

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Well that is good for him, but clearly an outlier, and I think he should keep every dime of it and never be threatened with paying taxes on a Roth IRA because that is sort of the agreement when you set it up.

Sure, but I still don't understand your statement,  "Anyone with that net worth isn't dumb enough to keep their assets in an IRA."  Why would you say that?  

The problem I see is getting large assets into an IRA, due to the contribution limits.  But if you can get large assets into an IRA, or grow small assets to large size in an IRA, particularly a Roth IRA, I don't see why one wouldn't want to do that.  Why did you say that?  

I am just saying for the vast majority of investors,  it is very  uncommon to be able to accumulate a massive balance in an IRA and particularly a Roth without getting lucky with stocks and being smart enough to use the conversion process to their financial advantage. 

Maybe dumb was harsh, but I was just implying most people with wealth like that don't have the majority of that wealth in IRAs.

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There's caps on what you can put in, those people took significant risks to build that value and they were either really smart or got really lucky.  Good for them, keep the government hands out of it.

Edit: Also, if it's a traditional IRA and was tax free going in, it'll be taxed coming out at some point.  We can't be double and triple taxing everything.

It wouldn't be a double tax. If it's a traditional IRA with hundreds of millions in it, the money would roll into a regular account and get taxed once.
Also, don't be naive, they didn't take risks. They got special deals from their friends. They made a shell corporation just to filter income through it and make it look like capital gains. It's the kind of trick that becomes very easy to do with today's tax code, when you have tens of millions of dollars.  Do you want to buy into a shell corporation like that? Sorry! They are not traded publicly. Since there is only one buyer, the price can be low going in, and since there's only one seller they can conspire to make the price high going out.

I misunderstood your initial statement regarding converting to a regular account.  Yes it technically wouldn't be a double tax of those gains at that point in time; however, it would be taxed upon conversion to a regular account and then future gains would also be subject to taxes, so in theory you are looking at some form of double taxation that the current vehicles were designed to protect you against, i.e. only being taxed once upon withdrawal.

And I disagree, they did take risks.  Those businesses they invest can fail.  Anyone with a significant amount of money invested into 1 (or few investments) is taking a risk.  Sure, it's less risky for them since they're rich, but it's still significant risk.

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Sure, but I still don't understand your statement,  "Anyone with that net worth isn't dumb enough to keep their assets in an IRA."  Why would you say that?  

The problem I see is getting large assets into an IRA, due to the contribution limits.  But if you can get large assets into an IRA, or grow small assets to large size in an IRA, particularly a Roth IRA, I don't see why one wouldn't want to do that.  Why did you say that?  

I am just saying for the vast majority of investors,  it is very  uncommon to be able to accumulate a massive balance in an IRA and particularly a Roth without getting lucky with stocks and being smart enough to use the conversion process to their financial advantage. 

Maybe dumb was harsh, but I was just implying most people with wealth like that don't have the majority of that wealth in IRAs.

We agree that it is very rare.  I just think it should be taxable when it happens.

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My fellow southpaw Mark Brunell will probably always be my favorite Jaguar.

I am just saying for the vast majority of investors,  it is very  uncommon to be able to accumulate a massive balance in an IRA and particularly a Roth without getting lucky with stocks and being smart enough to use the conversion process to their financial advantage. 

Maybe dumb was harsh, but I was just implying most people with wealth like that don't have the majority of that wealth in IRAs.

We agree that it is very rare.  I just think it should be taxable when it happens.

So you want to change the rules when someone overly benefits from them?

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We agree that it is very rare.  I just think it should be taxable when it happens.

So you want to change the rules when someone overly benefits from them?

Punishing success is the core tenant of the left.

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“An empty vessel makes the loudest sound, so they that have the least wit are the greatest babblers.”. - Plato

Enable success to at the sake of their own voice is a core tenant of the right.

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Enable success to at the sake of their own voice is a core tenant of the right.

Come again?

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“An empty vessel makes the loudest sound, so they that have the least wit are the greatest babblers.”. - Plato

That was supposed to say enabling. Dumb auto correct.

The right defends corporations while they become the enforcement arm of the left. At some point, Republicans need to wake up and stop supporting these multi billionaires.

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That was supposed to say enabling. Dumb auto correct.

The right defends corporations while they become the enforcement arm of the left. At some point, Republicans need to wake up and stop supporting these multi billionaires.

Bingo.

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My fellow southpaw Mark Brunell will probably always be my favorite Jaguar.