Get sign up bonuses by paying taxes

As a 1099, you will have to pay estimated taxes each quarter to the IRS.

It's not fun sending thousands of dollars to the IRS but you can make it more fun by earning large credit card sign up bonuses.

When I was heavily into the credit card/travel hacking game, I would

• Sign up for a credit card (or three) with attractive sign up bonuses (e.g. earn 100,000 miles after $5,000 in spending)
• Pay my estimated taxes with the new credit card for a 2% fee. A payment of $5,000 would trigger a ~$250 fee
• Get my points bonus
• Use the points to take luxurious vacation (worth far more than $250)
• Expense the credit card fee and get a small tax deduction ($250 X tax rate reducing it by 25% or so)

If you're into travel hacking but work as a W2, you have to manage your spending on different cards to hit the bonus which can become a pain in the butt. As a 1099, you can often get the sign up bonus in one shot, reducing mental overhead.

If you're interested in highly discounted luxury travel, I recommend paying your taxes with a credit card to get the sign up bonus. The rewards vastly exceed the fee if you do it right.

Want the full playbook? Check out Going 1099.