1099 credit card games


I used to be big into the credit card points games. I loved flying first class and staying in luxury hotels for free or almost free (still do in fact, I just slowed down during COVID and adding a kid to the mix).

I started doing this before I went 1099, but as a 1099, you have a big advantage.

  1. You can sign up for business credit cards with large sign up bonuses since you have a business and
  2. You will regularly make large estimated tax payments each quarter

The first is beneficial because you have access to much higher number of credit cards with sign up bonuses. For example, in addition to the personal Capital One Venture X card, you can sign up for the Venture X Business Card.

Capital One Venture X Business Card (not an affiliate link)

The second is because you can easily hit large minimum spend requirements in one shot.

If you have to make $10,000 payments to the IRS each quarter, you can get one or two bonuses per quarter.

If you have two credit cards that each require $5,000 in spend to get 75,000 points, you can charge the taxes to your credit for a 2% fee and not have to think about it again.

150,000 points at a minimum is worth $1,500, so paying $200 in fees (which you can deduct as a business expense) is worth it to get the points faster.

If you're into saving money on hotels or traveling in style, going 1099 can accelerate your ability to do.


If you're interested in learning how to get your first solo 1099 federal sub-contract, check out my book:

Going 1099: How to become a solo federal sub-contractor and gain control of your working life, earn more money and unlock more free time

I'm Dale, the author of Going 1099

Going 1099 is a book that teaches you how to become a solo federal sub-contractor and gain control of your working life, earn more money and unlock more free time. I wrote it because quite a few people have asked me how they can become a 1099. I figured it was best to write a single book that I can send them and that I can share with others who are interested. This newsletter goes out Monday - Friday and covers topics that will help you succeed in starting and maintaining successful 1099 career.

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