How To Be a Rich Politician Without Looking Like a Dick

Congratulations! You’re a rich guy–the cultural elite–and you’d like to run for office. You’d like to show other Americans how to pull themselves up by their bootstraps (as long as those bootstraps include an inheritance and legacy admissions to Andover and Harvard). Yet there are some people out there who’ll still fault you for following all the rules of a rigged game and coming out on top (even though you started on top).

Those people are the reason you must maintain constant vigilance against financial decisions that paint you as a patrician prick, or a born lucky silver-spooned goober. Remember Romney’s offshore accounts? Financial gaffe central! Or what about Nancy Pelosi’s husband, who profited from a Visa IPO during the fight for credit card legislation?

Mistakes happen, and when you’re a rich guy, you want to stay that way. That’s not a crime! So, while you may never convince all the plebes that you’re a street-walking cheetah with a heart of napalm, you can still do your best to look like a man of the people, all while cashing in on the perfectly legal loopholes that the oligarchs included in our complex regulatory system. Here’s how!

1. Taxes are not just for the little people.

You don’t always have to pay your taxes. This guy didn’t and he still won an election. And you don’t have to pay that much in taxes. But if you’re paying taxes, keep it simple. For every three tax benefits a rich guy gets, turn down one. You’ll smell like a rose, and then you can point to your opponent and say, “Hey! He took all three! What an asshole, am I right?”

2. Keep your investment portfolio simple.

Or, at the very least, keep the one that you would release to the public simple. The one where you’re heavily invested in the Eastern European sex trade should probably stay out of the public eye, unless people suddenly approve of sex slavery. Because then you should definitely cash in on that.

3. Remember the complexities of a Senate confirmation.

Do you travel a lot? Have your secretary keep notes. Do you have a few seemingly unethical expense accounts? Have your secretary photoshop them (or erase them altogether). Is there a hush-hush felony in your past? Unfortunately, if all the people involved haven’t been involved in strange accidents, this might be the one thing that disqualifies you. Or not!

4. Think of the questions you’d hate to be asked, and then make sure you ask them of your opponent before they’re asked of you.

If you can’t find the dirt on your opponent before he finds it on you, well, you’re probably not clever or rich enough to be a politician. So just wait until one of your Harvard buddies climbs the ladder and accept an ambassadorship. Preferably to one of the Eastern European countries! That way you can better oversee your investments.

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