Am I a Chump for Paying My Taxes?

If you combine all of the projects that I’ve started with and without John over the last ten years…Crash Course, SciShow, DFTBA.com, VidCon, as well as a few other miscellaneous things, we have about 50 full time employees now. These companies are successful, I make money and the companies make money.

And when, at the end of the year, there’s more money than there was the year before, whether that money is in my pocket or in the businesses accounts, we pay taxes on that money. Employment taxes, sales taxes, investment taxes, federal and state income taxes and more!

This does not bother me.

What does bother me is that there are a few things that make it easier to not pay taxes and they are things that are not available to small business owners like myself. In order to take advantage of tax loopholes it really helps if:

  1. You’ve been rich for a really long time.
  2. You own lots of real estate.
  3. Your income is massive enough that you can have entire departments of people devoted to lowering your tax bill and still come out on top.
  4. You make your money from investments rather than work.

I want paying taxes to feel like the accomplishment of a civic duty. As the economy grows, as I employ more people, make more money…the income of my country should increase as well. I want to feel good about paying taxes.

But knowing that there are people like Donald Trump out there who have made billions of dollars but likely not paid a dollar in federal income taxes for decades pisses me off.

It makes some small little part of me feel like a chump for paying all this money when if I was “smart” I would have figured a way around it. And that hurts (even though I know it’s irrational, of course) because it changes how I think about paying my taxes from a performance of a civic duty that strengthens this country and benefits my fellow citizens into some kind of game that I, clearly, am losing.

Having been advised by my accountants and lawyers, having had them tell me the extent to which I could go to avoid this tax or hide that asset, I can tell you that this is not a simple thing. There have been several times when a lawyer has advised me to do something and I didn’t do it because, while it would have saved me money, it seemed to clearly violate the spirit, if not the letter, of America’s tax laws.

There’s a spectrum of what you can do and what you should do from “Pay every cent you can” all the way to outright fraud. Every CEO gets to decide for themselves where they want to be on it. But there are some who clearly see this as a system that exists to be beaten. I have met lots of people who see the world that way. “Sure, someone has to pay for veteran’s benefits and aircraft carriers and NASA,” they say, “but if I can get out of it, that’s just the game!”

Now, I don’t go out of my way to pay more taxes than I owe, but I honestly do believe in this country and that I have a contract with it. It must be very seductive to imagine that the government violated the contract first…that it’s all broken and disgusting and even anti-American. That must make it easy to feel morally superior while living a luxurious life and never paying taxes.

I can’t pretend that that’s a choice for me though, because I can’t say that this country is great, that its programs deserve to be funded, and simultaneously see it as a system made to be beaten.

So am I a chump? Maybe. But I’d honestly rather be an idealistic chump who believes in this country than an angry cynic with a few hundred thousand more dollars in the bank.