If you’re paying taxes, you’re winning.

If you're paying taxes you should change your accountant

Yes, if you're paying taxes you should engage a wealth management team that knows about collaterialized loans.

If you are making more than enough to pay a significant amount of tax, but get away with paying a derisory amount or even nothing, then you are really winning!

Yep, although the qualified small business stock exemption comes in handy if/when that happens. You get to exempt a percentage of the gain of the sale of your stock, and if you roll over the gain into other QSBS (by investing in startups, for example), you can defer the non-exempted portion.

Or just be like Peter Thiel and do all your angel investing through your Roth IRA...

https://www.propublica.org/article/lord-of-the-roths-how-tec...

He bought gambling stock with his retirement fund, struck gold, and now has 5bn untaxed in a US account?

He bought 1.7 million founders' shares of Paypal (then Confinity, which he cofounded and was CEO of at the time) for under $2000. These are terms you would never offer to an investor, that you'd never offer to an employee.

For comparison, the SEC filing for Paypal's IPO has Thiel Capital investing a bridge loan of $100k in 1998 which was then converted into 500 thousand shares (100x higher valuation than his individual "purchase" the following month).

https://www.sec.gov/Archives/edgar/data/1103415/000091205702...

From the ProPublica article, re: why this was problematic:

> Thiel’s unusual stock purchase risked running afoul of rules designed to prevent IRAs from becoming illegal tax shelters. Investors aren’t allowed to buy assets for less than their true value through an IRA. The practice is sometimes known as “stuffing” because it gets around the strict limits imposed by Congress on how much money can be put in a Roth.

So which loophole let him get away with it?

Longstanding underfunding of the IRS, if I had to guess? It's much more expensive and time-consuming to go after wealthy tax cheats than, say, people incorrectly claiming the earned income tax credit. The ProPublica article states that Thiel was indeed audited in 2011, but the audit was eventually closed with no known outcome.

Yeah, more or less

IRS takes less than 50%.

A lot of this confusion is people talking past eachother. For most people the level of governmental entity taxing them isn't the concern, its the amount of tax the government in general demands in particular contrasted with the level of service provided.

Add up the IRS cut, state and local, gas tax, sales tax, fees to use services already paid for with taxes and are basically required for life in the US (road tolls, document fees, vehicle registration fees, public transit fares, etc), costs for compliance with laws like hiring someone to help you file taxes or taking a day off work to renew your driver's license, higher costs for goods and services due to monopolies granted by government (drug patents where the same drug costs a quarter of what it does in the US everywhere else the world, higher than otherwise internet fees paid to entities like Comcast who are granted monopolies, hospitals that are expensive due to monopolies granted by certificates of need, etc), inflation caused by money printing to pay for foreign wars without broad popular support, housing that is more expensive due to policies that benefit homeonwers at the expense of those without assets etc, etc.

Its way more than half of your productivity that is taken, if you are productive and earn wages. Those earning capital gains are hit about half as hard, another happy little accident that benefits primarily the wealthy and powerful to add to my list above.

Oh and the best part, after paying those taxes for decades once you get sick, all of the sudden, the government and the medical industrial complex doesn't have the money to help you. You get to live in a cardboard box under a overpass.

You're making a comment about people "talking past each other" and yet you're talking about gas tax and sales tax in relation to business acquisitions and venture capital payouts.

Well, I for one could live with that... :)

Oh, the humanity! A founder in that situation is going to just get > 500million, not the full billion! How would they be able to afford food?

Also, aren't taxes on things like stocks, equity, etc far lesser than personal income taxes anyway?