The Single Best Way to Rack up Spend & Millions of Miles/Points


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Generate Credit Card Spending Big Rewards

Generate Credit Card Spending Big Rewards

A lot of digital ink has been spilled this year about the loss of spending opportunities and techniques. On a positive note I spend quite a bit less time in Walmart than I used to (although one minute is too much if you ask me), but things are tougher out there. Well, they aren’t as tough for me, because I discovered the true secret to earning a lot of miles/points. Having a lot of spend.

I know that last sentence may seem a little too obvious, but stay with me for a second. We are all trying to generate as much spend as possible. It used to be easier when a lot of techniques were alive, but these days they are not. So where does that spend come from now? Well, for a growing segment of travel hackers it is from starting a business.

The One Key to Generating Miles & Points

Generate Credit Card Spending Big Rewards

Yes, the one best technique of earning a lot of miles/points these days is to start a business. About a year ago I began to get more serious about reselling. It is not my full time job, but I began treating it as a business and focused on growing it. Without going into details, I have earned tons of miles & points over the past year simply from things I purchased and re-sold at a profit.

I’ll share my favorite ways to juice spend and earn big rewards on business spend in another post, but the fact remains that this is the easiest way to rack up huge amounts of spend. I’m not saying it is the only way and for some people other more underground methods are surely easier, but for many people this can and is working.

So what types of businesses am I talking about? Well, there are two hot business types that many miles & points enthusiasts are getting into now.

  • Merchandise Reselling
  • Gift Card Reselling

Whenever you have to purchase something that will make you a profit, then you will generate spend. This is a great thing! Of course there are downsides. As the name would imply, a business is a business. It requires record keeping, organization and time. In the beginning you can multiply the time you think you will spend by 2. Over time though you’ll get faster, better and more organized.

And don’t get caught up in doing what everyone else does. Everyone has unique abilities and skills. Find something that works for you. For example there is a lot of competition these days in the gift card reselling arena, so I suspect things will get tougher there. If you think outside of the box, perhaps you’ll be on to the next thing before everyone else gets there.

Ease Into It

Generate Credit Card Spending Big Rewards

Despite my statements in the previous paragraph, I think perhaps the lowest barrier to entry and the lowest risk endeavor right now is gift card reselling despite its recent popularity. For many, gift card reselling is helping them generate bonus spend in the hundreds of thousands. With that kind of spend comes huge rewards.

Let’s look for example at a sale that Staples had about a month ago. For a couple of weeks they were selling Gap Brands gift cards for 20% off. Many people were able to purchase those cards with a Chase Ink Plus/Cash card and earn 5X Ultimate Rewards points. They then could turn around and sell those cards for a small profit. Even when factoring in the value of time, it was a great deal.

So the big question then is how to get started? Well, the key is taking it slow. Approach your new gift card reselling (or other business) methodically. If you are going to resell gift cards, then which credit cards will you use and how will you track your spend and merchandise? As a new business owner it is also a good idea to approach the exchanges and find out about preferred/bulk relationships. Over time the answers will make themselves clear.


Technology is progressing and with it the easiest methods of spending on credit cards are going away. Banks frown on certain spending techniques and so do gift card issuers. Yes, spending is possible without starting a business, but if you want to rack up huge amounts of spend and millions of points, then this is the single best way.

Am I wrong? What are your thoughts on spend, starting a business and gift card reselling? Please share in the comments!

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  1. Shawn,
    Love your posts!

    You aren’t wrong if you enjoy it and it works for you. Have you figured out your hourly pay for doing this?

    I am fortunate and have a job that is rewarding and pays me very well. Increasingly, I find myself asking the opportunity cost question as banks ratchet down the rewards of playing these games.

    For those immersed in this world to report their hourly income from each activity would quickly allow the rest of us to decide whether to pass or not. 100,000 ultimate rewards points, no question. Making $10 and getting 5000 points, a tougher call for many of us.

  2. Shawn,

    Great post, thanks. Would you consider merchandise reselling enough of an opportunity to give up your day job? I know some people do, but I wonder how you dedicate so much time to other businesses (and the blog) if you’ve also got a day job and a family.

    In any event, I wholeheartedly agree that exploring business opportunities is worth the investment, even if someone chooses not to pursue them.


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