Blog, Side Hustle

Side Hustle: How to make $2,000 in 60 days with Discover and Apple Pay

EDIT: This strategy no longer works as of 11/5/15.

For the first time in a very long time I read a points/miles headline that even I didn’t believe.

I’m still convinced that SOMETHING has to give here. This can’t be. It’s just too good to be true. 

But for the time being I think this is going to work, and I want to share this opportunity with you while it is still around.

I promised to deliver ideas for side hustles and today we are going to start in a big way.

Let’s get rolling.

Last week Discover made a bold move by announcing a new partnership with Apple Pay that features a very lucrative promotion. Here’s an excerpt from their press release.

From September 16, to the end of the year, cardmembers who pay with their Discover card using Apple Pay will automatically earn an extra 10% Cashback Bonus on up to $10,000 of in-store purchases. Discover it Miles, Miles and Escape cardmembers will earn an extra 10 miles per dollar on up to $10,000 of in-store purchases.

Yes, you read that right. 10% cash back on any purchase made with a Discover card using Apple Pay, up to $10,000 in purchases between 9/16 and the end of the year.

Even to the average consumer this is a huge opportunity to save money, but it’s even more lucrative for those of us who are currently “spending” tens of thousands of dollars by manufacturing spend with the Target Prepaid Redcard.

More on that in a second.

But first, a quick note on how to make this promotion even more lucrative.

Discover is also currently running a promotion that gives new cardholders double cash back for the entire first year.

Discover It

Which means that the 10% cashback bonus effectively becomes a 20% cashback bonus for anyone eligible for the double cashback.

Making your potential earnings a whopping $2,000, tax free. $1,000 now, $1,000 paid in one year.

Before we get started we need to take a look at tools that you will need.

  1. A Discover Credit Card
  2. An  Apple iPhone 6
  3. A Target Prepaid Redcard
  4. A store that has Apple Pay, sells Visa Gift Cards, and accepts credit cards for said Visa Gift Cards

1. A Discover Credit Card

I am typically not a fan of Discover’s card products but for 20% cash back I will happily make an exception.

So if you don’t have a Discover card currently, you should absolutely get one right now.

The best option to go with for this side hustle is the Discover It.

Discover Card

Discover It is a pretty basic cashback card that offers 5% back on bonus categories and 1% on all other purchases.  It does not have an annual fee so you can hang on to it forever.

Here’s a link to sign up and receive a $50 bonus (Full disclosure: I also earn a $50 bonus when you use this link). The public offer does not include any sort of bonus.

If you already have a Discover card then you’re going to need to get a second one to earn the double cash promotion. This is only possible if you have had your current Discover card for a year.

2. An Apple iPhone 6

This cashback promotion requires that you use Apple Pay, which is only usable with the hardware built in to the iPhone 6 and iPhone 6 plus.

The only way an iPhone 5 user can use Apple Pay is with the Apple Watch. Earlier iPhone models won’t work at all.

There is no way around this so if you have been thinking about upgrading to an iPhone 6 now would be a good time to do so.

I wouldn’t recommend paying a huge upgrade fee just to take advantage of this promotion but you’re welcome to do as you please.

There is also a chance that you might be able to use a friend’s iPhone 6 to pull this off but we won’t be able to confirm this for a couple more weeks.

3. A Target Prepaid Redcard

You don’t need a Target Prepaid Redcard to get the 20% cashback but you will probably need one if you want to hit the full $10,000 cashback spending limit (unless you organically spend $10,000 in 3 months).

I have written about this product a number of times already so I will keep this brief.

The Target Prepaid Redcard is pretty much a glorified Target gift card. You can load money on it, spend that money at Target, and get discounts and other perks for using it.

It’s most important feature (for my purposes) is that it allows you to pay bills with any money loaded on the card, including your own credit card bills. More on that in a second.

Note that this is NOT the Target Credit and it is NOT the Target Debit card. Please do not email me asking whether you need the debit or credit version.

The Target Prepaid Redcard is a completely separate product and is only available at a few select Target locations. If you don’t live near one of these Target locations you can buy a Prepaid Redcard online (check eBay) from entrepreneurially minded folks who do live near a participating location.

Once you are able to get one it will work at any Target location in the country.

4. A store that has Apple Pay, sells Visa Gift Cards, and accepts credit cards for said Visa Gift Cards

Finding a store that works will require some trial and error but this list is a good place to start.

Personally I think Walgreens or Rite Aid are going to be our best options. Don’t forget that Walgreens has a $500 daily limit for gift card purchases.


Once you have all the tools the mechanics are really quite simple.

Here’s the step-by-step overview.

  1. Buy a Visa Gift Card with your Discover Credit Card, using Apple Pay to checkout
  2. Take that Visa Gift Card to Target and load the balance to your Target Prepaid Redcard
  3. Bill pay the balance back to your Discover card
  4. Repeat as often as needed to reach the $10,000 maximum

Bonus Step: Repeat this entire process for your spouse and any friends/family who trust you to handle it for them.

Each person represents a potential $2,000 profit so it can add up quickly.

That’s it! As always, email me with questions. (bryce[at]getfreeflights[dot]com or contact me here)

And tell your friends! Everyone loves earning free money.


Happy Side Hustling,


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