Shep and his dad, who booked an $800 flight to New York for 15,000 points to see the U.S. Open.
Photo: Shep McAllister
Good PointsA weekly Q&A where we ask a guest about their credit card points strategy, and where it's taken them. Want to be featured? Email shep@gizmodomedia.com with the subject line "Good Points."  

Welcome to Good Points, a new weekly Q&A about credit card points, the people who collect them, and where they take us. First up is...myself!

If you know anyone who just won’t shut up about their points strategy (guilty as charged), have them send an email to shep@gizmodomedia.com with the subject line “Good Points” for a chance to be featured. We want to talk to everyone from professional travelers who spend their lives on the road, to people who save all their points on one trip per year, so don’t be shy!


What first got you hooked on collecting points?

I had dabbled a bit in college with one of the Southwest cards, but the real catalyst for me was planning my honeymoon. Flights to Hawaii were really expensive, but I’d heard about this loophole where you could book Delta flights with Korean Air miles, which you could transfer from a Chase Ultimate Reward account. So I signed up for a Sapphire Preferred, got my welcome bonus (it was pretty easy to hit the spending requirement with all the wedding expenses), and that alone covered two roundtrip tickets.

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What are you trying to accomplish by collecting points? Pay for all of your small trips? Splurge on vacations that you wouldn’t otherwise take? Somewhere in between?

I like to think of my points hoard as a kind of travel-specific savings account. When you do the math, I’m getting at least 2% back in travel value on pretty much every dollar I spend (sometimes significantly more), so it’s sort of the modern equivalent of dropping spare change in the vacation jar on the kitchen counter, except it’s automatic, and “free.” I tend to be pretty frugal with my points, and I get needlessly stressed out if my balance drops below a certain threshold, so I try to stretch them as much as I can with clever redemptions, or Chase’s points + cash feature, which basically lets me use a smaller amount of points to get “discounted” airfare.

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What credit cards do you currently hold, and why’d you get them?

Almost all of my spend goes on the Chase Sapphire Reserve, the Chase Freedom, or the Chase Freedom Unlimited, depending on which one will get me the most points on a given purchase. I love that I can pool all three cards’ points in my Sapphire Reserve account to spend on travel, especially since the Freedom cards don’t have an annual fee of their own.

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The big exceptions for me are Amazon and Whole Foods purchases, where I use the Amazon Prime Visa (5% back), and Target purchases, where I have the debit version of the REDCard (5% discount). I also keep a Hyatt Visa open for the annual free night (there’s an annual fee, but it’s still worth it) and automatic Discoverist status, but I don’t actually use it very often.

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What point redemption are you most proud of?

The Hawaii flight I mentioned earlier was the one that got me hooked, and I think I’ll always be chasing that high. But another favorite was actually a booking I made for my dad. I was going to be in New York for work during the U.S. Open, and he wanted to come up and go with me on Labor Day. But the plan came together last minute, and flights from his nearest airport on American Airlines were over $800 roundtrip. Luckily, I saw that British Airways offered award tickets on that very same flight for just 7,500 points each way, so I transfered the necessary Chase points, and got over $.05 per point in value, which to this day I’ve still never topped.

What point redemption are you least proud of?

This is deeply embarrassing, but on a trip to Raleigh to see friends a few years ago, I booked my return flight for the wrong month, and didn’t realize it until I tried to check in that morning. I had to eat the cost of that ticket (it wasn’t too much), and also blow about 30,000 Southwest points to get home. I was glad to have the points to spend, since the flight would have been about $450 out of pocket, but I’m still kicking myself over that one.

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Do you chase status at a specific airline or hotel chain, or do you just shop around for the best deals, locations, and flights?

I proudly consider myself an airline and hotel free agent, but I still have preferences. I fly Southwest when I can, because of how flexible they are with flight changes, and I try to stay at Hyatts when possible, because they have the best award night redemption rates of any major chain (and also because I get a free bottle of water with my Discoverist status from the Hyatt Visa, which makes me feel inordinately important). But these are both pretty soft preferences, and I’ll happily fly or stay with someone else if there’s a better deal available.

What’s the first card you recommend to people who are interested in getting into points, and why?

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I tend to recommend the Chase Sapphire Reserve, but I’ll quickly retreat to the Sapphire Preferred if they balk at the $450 annual fee. Chase just has the best lineup of transfer partners for U.S. travelers, but their travel portal is easy to understand too for anyone who doesn’t want to figure out the transferring aspect of the hobby, which is completely understandable.

What’s one piece of advice you wish you’d known before you got into points collecting?

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Don’t let a major purchase go to waste. If you’re about to buy, like, a new couch or mattress or TV, make sure you’re using the card that will get you the most value back in points, and even consider opening a new one to get a welcome bonus.

How do you keep track of all of your points, bonus categories, free nights, and annual fee dates?

My credit card arsenal is pretty modest compared to a lot of peoples’, so it’s not too tough to remember which cards I should use where. For things like an award night certificate with an expiration date, or a welcome bonus deadline, I’ll usually set a calendar reminder a month or two out from the date to remind myself, which hasn’t failed me yet.

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Let’s finish off with a few rapid fire questions. I give you enough points to take three flights anywhere in the world in economy, or one flight anywhere in the world in first class. What do you choose?

Economy, because I’m a cheapskate at heart.

Top three items on your travel bucket list?

1) Take a shower on a plane (which I realize is incompatible with my previous answer).

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2) Snorkel or dive at the Great Barrier Reef, before it’s gone.

3) Stay at an over-water villa in the Maldives.

Favorite city you’ve ever visited?

It’s cliché, but Barcelona.

Favorite hotel you’ve ever stayed in?

Park Hyatt Paris Vendôme. I had a free night that I could use at any Hyatt in the world. This place cost about $1,000 per night when we went, and I can absolutely see why.

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Favorite airport?

Vegas, purely for the novelty of the slot machines.

Worst airport?

La Guardia is the easy answer, and probably the correct one, but I’ll go with a deeper cut and say London Gatwick. It’s a 30 minute train ride (and not a cheap train, either!) from the city, and it felt like being in a bad mall on Black Friday.

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Airplane drink of choice?

Non-alcoholic: Coke Zero. If we’re talking adult beverages, then always whiskey and ginger ale.

One product you can’t fly without?

A battery pack, if only for peace of mind. I bring along this comically large Anker because it has a USB-C Power Delivery port for my laptop and Nintendo Switch.

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Favorite suitcase?

My lovely coworkers got me an Away carry-on for my wedding, and the hype is justified. It’s a perfect bag.

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Can you sleep on a plane?

No, never, but I keep trying.

Window seat or aisle seat?

Window for a short flight, aisle if I think I’ll need to use the bathroom.