How Adventuring Along's Joe and Ali Olson Earn and Spend Credit Card Points

Photo: Joe and Ali Olson
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 [email protected] with the subject line "Good Points."  

Welcome back to Good Points, a weekly Q&A about credit card points, the people who collect them, and where they take us. This week’s guests are Joe and Ali Olson, who early retired in 2015 to travel the world full time.

They got rid of all their belongings except what fit in a backpack each, and traveled nonstop, only recently settling into a home base for the first time in over three years. Along the way they had two kids, Annabelle (born in Istanbul), and Cassian (born in Amsterdam). The vast majority of their travel over those three years was funded with points, and you can follow along with their adventures at their blog, AdventuringAlong.com

If you know anyone who just won’t shut up about their points strategy, have them send an email to [email protected] 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?

We had been seeing passing mentions about travel hacking for years online, but it sounded like too much effort. Then, in 2014, we went to a financial weekend retreat called Camp Mustache (based around the Mr. Money Mustache blog), and we attended a travel hacking breakout session that blew our minds.

We immediately dove into the blogs, podcasts, etc. and within four months we’d signed up for 23 new credit cards* between the two of us. It was a frantic rush and lots of fun, and it netted us over a million points. We were getting ready to start traveling full-time less than a year later, so we wanted to hit the ground running. It’s saved us so much money over the past few years.

*Our credit scores were in the 760s range, and dipped for a couple months, then went up to the 780s range after about six months. They’re now 800 . Don’t let fear of hurting your credit stop you from travel hacking, if done right it can help!

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?

We were about to quit our jobs to travel, so we basically just wanted to collect as many points as we could to help with the costs of that, which ranged from big flights from the US to Europe and Australia, but also shorter flights between our families’ homes (Seattle and California). There are so many different kinds of points and strategies and airline partners that we’ve been able to use to save us money, no matter what our needs have been at the time.

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

Photo: Joe and Ali Olson

Having signed up for so many cards already, our options have narrowed. There are some cards we can “churn” (cancel and re-apply after a given amount of time to get the signup bonus again), but others that are one bonus per lifetime. That means our most recent cards have been co-branded airline or hotel cards (rather than generic points that work with nearly everything, like Chase or Amex). Our most recent additions were some Southwest cards so we could earn the companion pass, which has been hugely valuable.

What point redemption are you most proud of?

In December 2016, we stayed at a Hilton in Bali which was only 5,000 points a night. On top of that, Hilton was doing a promotion where if you booked through their app and paid with a Visa card, you got 5,000 points back. You needed to pay for something though, so we bought a candy bar for a dollar or two from their mini convenience store and charged it to our room.

Oh, and you’d better believe we booked a night under Ali’s name, then a night under Joe’s, then under Ali’s, etc. So that each was a separate “stay” and eligible for the redemption. We just had to go down to charge something to the room each day.

Five nights in Bali. Total cost: 0 points (technically temporarily 25,000 points, which we had to have available to book those nights, but then they were all refunded back) plus maybe $8 in snack food spending.

What point redemption are you least proud of?

Probably our first redemption, which was for a Lufthansa flight to Europe. We were so new to it, we didn’t realize the high fees that came with that flight. We did use Barclay’s Arrival Plus Cards to pay for those fees, but it wasn’t the best way to spend $300 per person of those credit card bonuses. We realized quickly booking with airlines that don’t have those type of fees for certain routes can be a much more efficient use of those points.

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

We’re all about the best deals. We couldn’t care less about status, really. We just want to get to as many places as we can with our points.

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

Usually, the Sapphire Preferred is the best way to step into the points world. It’s easy to use the Ultimate Rewards portal to book travel while you learn how to transfer points to different airlines. For some people, though, signing up for a couple Southwest cards at the right time can get you a companion pass, which is the best deal in points for people who travel domestically a lot.

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

I wish someone had told me to go online, read a couple of articles, and start as soon as possible. You’re not going to be perfect, but as long as you have a little knowledge and are careful with money and credit cards, there are a lot of great bonuses out there and they don’t last forever.

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

Photo: Joe and Ali Olson

We have a spreadsheet for new card signups (with columns for annual fees, when we have to hit minimum spend amounts by, etc.) AwardWallet is great for tracking points you’ve already accumulated.

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?

First class is a personal “someday” dream for Ali, but in general we can never pass up the economy flights that get us to more places. There’s too much to see and do to waste the points on a first class flight. At this point in our lives, at least. Also, we have kids now (born in Istanbul and Amsterdam) and that would make it hard to really get the first class experience.

Top three items on your travel bucket list?

We both agree on Egypt and Iceland, and Ali picks Slovenia as her third spot while Joe says “South America”. Broad, I know, but we were planning on going to that area of the world when the whole Zika thing hit (at the same time we were working on starting a family), so I’m still disappointed we haven’t been yet. Really, there are so many places out there we want to go.

Favorite city you’ve ever visited?

Prague is one of the most beautiful cities we’ve ever been. Plus, they have TRDLOs, which are delicious sugar pastry things with ice cream that remind us how wonderful the world really is. And you’re a short train ride from a tiny town that includes a crazy bone church. So cool!

Favorite airport?

Any airport with quick moving security, and a Priority Pass lounge.

Worst airport?

LAX. Ugh.

Favorite hotel you’ve ever stayed in?

We stayed at a Sheraton in Port Douglas, Australia. They gave us a suite, and it had a bunch of pools and beach access. They even gave us hotel credits for not getting our room serviced (which we usually avoid anyways), so we got a few treats from the pool bar. It was incredibly relaxing.

Three items you can’t travel without?

- Adventuring Along's Joe and Ali Olson Earn and Spend Credit Card Points', 'B07CXG6C9W');window.ga('unique.send', 'event', 'Commerce', 'theinventory - How Adventuring Along's Joe and Ali Olson Earn and Spend Credit Card Points', 'B07CXG6C9W');" rel="nofollow">Kindle Paperwhite. Hundreds of books available with so little space taken up? Yes, please!

- Adventuring Along's Joe and Ali Olson Earn and Spend Credit Card Points', 'B07H93KK92');window.ga('unique.send', 'event', 'Commerce', 'theinventory - How Adventuring Along's Joe and Ali Olson Earn and Spend Credit Card Points', 'B07H93KK92');" rel="nofollow">Compressible, reusable grocery bags. Great to pull out to grocery shop somewhere, to create an “under seat” snack bag for the plane ride, etc.

- Charles Schwab debit card. Use any ATM in the world, free (literally—they charge you no fees, and they refund you any fees the ATM owner charges). Such a boon for getting cash anywhere.

Suitcase of choice?

When we were traveling ourselves, and even with just the one kid, we managed just a carry on backpack each (Adventuring Along's Joe and Ali Olson Earn and Spend Credit Card Points', 'B06VVJZHB9');window.ga('unique.send', 'event', 'Commerce', 'theinventory - How Adventuring Along's Joe and Ali Olson Earn and Spend Credit Card Points', 'B06VVJZHB9');" rel="nofollow">Osprey Porter 46 for Ali, Adventuring Along's Joe and Ali Olson Earn and Spend Credit Card Points', 'B01M75EIKB');window.ga('unique.send', 'event', 'Commerce', 'theinventory - How Adventuring Along's Joe and Ali Olson Earn and Spend Credit Card Points', 'B01M75EIKB');" rel="nofollow">Pacsafe Venturesafe 45L GII for Joe). We highly recommend this as a way to go for anyone traveling that can manage it. But eventually we added a second kid (and the first got old enough to need more than diapers and some onesies), and backpacks weren’t cutting it. Having to switch to luggage was a sad day, but we found a Kinja Deal on a pair of Amazon Basics brand luggage and have been pretty happy with them.

Airplane drink of choice?

Cran-Apple Juice.

Can you sleep on a plane?

Ali can’t sleep on a plane even if she hasn’t slept in days. Joe can sleep before takeoff.

Window seat or aisle seat?

Joe usually takes the window (to sleep against the side of the plane) and Ali goes for the aisle.

Anything else you want to add related to points?

Make sure you check out the other perks when you sign up for cards. Global Entry reimbursement (which comes with the amazing TSA Precheck) and lounge access are not to be overlooked!


Gizmodo Media Commerce has partnered with The Points Guy Affiliate Network for our coverage of credit products. Gizmodo Media Group and The Points Guy may receive a commission from card issuers.


linkedin facebook pinterest youtube rss twitter instagram facebook-blank rss-blank linkedin-blank pinterest youtube twitter instagram