Re-dipping my toes into reselling

One of my earliest experiments with reselling came in 2012 when the British Airways shopping portal offered 36 points per dollar for first time users shopping at Nordstrom.  I knew I wanted to take advantage of the deal, but there was very little that I wanted to buy from Nordstrom.  Instead, I spent slightly over $4,000 on GPS watches and Beats headphones.  Thanks to the amazing 36 points per dollar deal, I earned more than 150,000 points.  I then shipped the watches and headphones to Amazon to be sold via their Fulfillment by Amazon program (slightly out of date details about Fulfillment by Amazon can be found here).


Since shipping and selling fees were involved, I expected to lose a bit of money from the transaction, but I thought it was still well worth it.  I thought of the loss as the price for buying miles cheaply.  As it turned out, Amazon somehow sold more watches than I gave them, so I actually made money on the deal (see: How Amazon paid me to collect miles).  After that experience, I bought and sold merchandise almost every time I encountered a fantastic portal opportunity.  For example, when the Southwest portal offered 15 points per dollar for shopping at, I bought enough tablet computers to earn 110,000 points and a Southwest Companion Pass (see:  Sears 15X: Shopping for 110,000 points).  Again, I sold the tablets through FBA (Fulfillment by Amazon), but this time I incurred the expected loss.

My buying and selling ramped up to new heights in March 2013 when I managed to earn a million points and miles in one month.  Slightly over half of the million points were from credit card signup bonuses.  Most of the remainder came from creative buying and selling.  The two approaches actually complemented each other in that it was a breeze to meet the minimum spend requirements from my new credit cards: I simply bought more stuff to resell.  For review, please see:

Burned out

My Million Mile Madness challenge was successful, but it wasn’t fun.  Every day of the month was spent searching for new deals to purchase, packing items to send to Amazon, tracking sales, dealing with product returns, and dealing with gift card issues.  For examples of the latter, please see: Million Mile Madness: Bumps in the road.

After completing the challenge, I quit reselling.  There continued to be great opportunities, but I simply wasn’t interested in spending my time dealing with the inevitable issues.  I was burned out and wanted nothing to do with it.

Deep in SYW points thanks to Discover

Discover’s incredible Double Cash Back for 12 months offer for new customers has indirectly lured me back into reselling.  The deal was simply too good to ignore… especially when Discover Deals offered 10% cash back from Sears… and, especially with Discover It offering 5% cash back for department stores ( counts!)… and, especially while the Discover Deals portal paid out for the purchase of gift cards from Sears, the use of gift cards from Sears, and the use of SYW (Shop Your Way) points.

Here’s a summary of how it all stacked:

  • Go through Discover Deals to 10% cash back
  • Buy gift cards and pay with your Discover It card: 5% cash back (thanks to the department store bonus)
  • Go through Discover Deals to 10% cash back
  • Buy items offering 100% back in points and pay with gift cards: 100% back in SYW points (see: Roll gift cards into points for triple rewards)
  • Go through Discover Deals to 10% cash back
  • Buy items you actually want and pay with points: No SYW points earned when using points to pay.

In total, it has been possible to earn 35% cash back which will be doubled to 70% cash back. 

While I have been happily going through the steps described above, I hadn’t planned to do reselling.  My plan was to buy things that I actually wanted and needed.  For example, I recently used SYW points to buy clothes and shoes from Lands End; new glasses and contact lenses for my son from Sears Optical; and some gardening tools from  Only the last type of purchase earned portal points, so the Lands End and Sears Optical purchases will ultimately amount to “only” a 50% rebate.  It’s still an amazing deal no matter how you slice it.

In order to take full advantage of this deal, I’ve been prospectively buying Sears gift cards and using the gift card credit to buy 100% back in SYW points items whenever they’re available.  This has resulted in large amounts of Discover Cash Back, and huge amounts of SYW points.

Re-dipping my toes into reselling

My hand (toe?) was forced when I received an email from Sears’ Shop Your Way telling me that nearly $600 worth of points were about to expire.  Yikes!  I tried, but I couldn’t think of anything that we actually needed that added up to $600.  And, unfortunately, you can’t buy gift cards with SYW points.  So, I went back to my old standby – I bought a few tablet computers for resale.

I found a tablet that Amazon would allow me to sell as new (many brands do not allow this), and that was competitively priced at  After creating my Amazon Seller listing (to ensure that I really could sell it as new), I bought three tablets for about $200 each.  Amazon then inconveniently lowered their price from $199 to $179.  Not only would I have to pay for shipping and seller fees, but I’d have to cover the price gap as well if I wanted my tablets to sell quickly.

I listed the tablets at the same price as Amazon, and the tablets did indeed sell quickly.  On the surface, it appeared that I had suffered a bit of a loss.  Let’s look at the numbers:

  • I paid $587 in SYW points for 3 tablets (The total was $597, but Sears supplied $10 in surprise SYW points)
  • Amazon sent me $484.88 after the tablets were sold (they automatically took out fees, shipping charges, etc.)

That looks like a $102.12 loss, right?  That’s true, but only if you forget about the portal…

Discover Deals reported that I had earned $59.70 in cash back from the purchase of the tablets.  In the long term, that $59.70 will be doubled to $119.40.  Suddenly my loss is looking like a profit!  This is especially encouraging when you consider that I had already earned a total of 25% cash back in the process of acquiring the SYW points and that total will later double to 50%.

Of course, if one or more of the tablets are returned as defective (it happens), the numbers won’t look nearly as good.  As things stand now, though, reselling appears t have been an easy and successful way to convert my SYW points to cash.

Going forward

As I reported recently, Sears has changed their terms & conditions within a number of portals.  They appear to no longer provide portal rewards for the purchase of gift cards or the use of SYW points.  So far, a number of readers have reported that they have continued to earn Discover Cash Back from these types of purchases, but more experimentation will be needed to understand exactly where we stand with this.

It’s also important to note that Discover Deals has dropped the payout for Sears from 10% to 5%.  If history is any guide, though, we will probably see the payout go back up to 10% during holiday season.  In fact, the current 5% rate is scheduled to expire at the end of September, so I expect to see 10% return in early October (Sears may disappear entirely from the portal for a few days first. If so, don’t panic, it will be back).  If the 10% rate returns, and if portal rewards for gift cards and SYW points continue as they have in the past, I’ll continue to buy gift cards and to roll gift cards into SYW points prospectively.

About Greg The Frequent Miler

Greg is the owner, founder, and primary author of the Frequent Miler. He earns millions of points and miles each year, mostly without flying, and dedicates this blog to teaching others how to do the same.

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25 Comments on "Re-dipping my toes into reselling"

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Reselling has become my go to for Manufactured Spending. The big portal points make a huge difference. I’m excited for you to get back into it.


I was under the impression when you sell through FBA, your buyer my not get an exact tablet that you sent in. Basically one will be taken from the shelf at the closet warehouse. So if it comes back as defective how is that treated? Just a risk you take that some jerk didn’t put a broken one in the box?


Make sure you change your settings to NOT co-mingle inventory so that your specific items are what is sold to the customer.


Does anyone know it is possible to ship directly from the store (ie Sears) to Amazon?


Interesting thought. I don’t think this is possible though. I think I recall that the package that gets sent to Amazon must have a special label both inside and outside the box to get categorized.

George Smiley

Don’t do it! ha. It’s profitable, but for me the inevitable headache is too great. And 70% cashback is a lot – granted, but as you point out it’s not possible now and probably isn’t scalable even when it is.


I lost $2000 following this blog’s advice and reselling. Glad you have edged your readers away from it.


Hey, I was thinking on trying it out, why did you lost those 2K?

Phong @

Not sure how this is the blog’g/writer’s fault. Especially an error that big. The guy must have done something majorly wrong (not due to blog) to lose $2000. I could understand $100 or maybe $500, but 2k is just too much.


Thanks! yes, I don’t think blaming others for one’s decisions is a correct path to success anyway. I will test it soon.


Wow… What did you do? Recently entered into reselling and can’t possibly see a loss like that. Not trying to beca jerk, just looking for pitfalls.


What did you do with the $600 worth of 100% SYW items you purchased?


I read the article you linked to. You never posted an update on Amazon clawing back the money they overpaid you. Does that mean you ended up keeping the money?


Hey guys,

Just an update. Got Discover email for correctly tracked CB from Sears for GC purchases.


I feel ridiculous asking this, but I’m buying contacts from Sears Optical online and don’t see a place to enter the gift card, or use SYW points. It just asks for a credit card in billing. I’m signed into SYW. I’m sure I’m missing something obvious. I called Optical and they weren’t sure how to use anything but a credit card (cracked me up oh and, don’t worry, I didn’t give away any secrets. Just asked for general help). Any suggestions are greatly appreciated!


I bought something for $20 from sears with a gift card through Discover deals. A couple of days later, I bought an item for $750 through discover deals and paid with discover card. I didn’t use SYW points or coupons. I am yet to receive cashback emails for both purchases after a week. Anybody got cashback emails from Sears on time recently ?


[…] always a risk of losing money.  For more details about reselling, please see my recent post: Re-dipping my toes into reselling.  Also check out these resell-focused blogs: Tagging Miles, Big […]