Sweet! In that case, would you mind transferring to me - for free - all of your wealth in appreciate assets?
- Albaby

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Sure, provided we had an ironclad agreement that you would give my shares back to me anytime I asked.

And one more thing, just for my peace of mind, while you hold my assets for eventual return to me, you will make regular filings with the Feds and comply with all SEC and FINRA regulations and oversight. In a very real way, the Albaby Wealth Holding Company would function a lot like my Vanguard Account.

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Are you telling me that in that scenario those shares have no value until you actually pay the taxes? - albaby

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Good Point. No doubt there is "value" to possessing something that can be converted to cash when you need to buy something. This is just really semantics, so whatever you call it, it revolves around established terminology of realized vs unrealized gains and their relation to taxable income.