Don’t forget where you came from – MS edition

EDITORS NOTE: In 2024, I’ve introduced Guest Post Saturdays. Today’s guest post is from the witty, inspiring, and definitely-not-a-giga-chad irieriley.

If you’re like me, you likely didn’t set out in this hobby thinking you’d end up where you did. I was a backpacker when I started back in 2016, dreaming of free economy flights and upgrading from hostels to Hyatt Houses.

I did not think it would lead to hours spent probing fintechs, the rise and fall of the world’s greatest bodybuilding supplement company, and using developer tools to identify offer codes and account masking patterns.

Of course, there’s a lot of steps and shifts in perspective between seeing a TPG ad on TSA bins at LaGuardia and not giving a second thought to 99x Amex AU offers.

MEAB‘s wisdom posts contain a lot of thought provoking questions, but my all time favorite post is this one – concerning perception of dollar value, scaling your spending, and how things change as you go deeper down the rabbit hole. 

To build on Matt’s original premise, I’d posit that the same perception shift occurs with redemption. For the sake of discussion, let’s look at the value of 150k Amex MRs – a sign-up bonus that anyone with a pulse can earn with a personal Platinum card.

• Non redeemer: What are transferable points? I’m just a giga-Chad cashing out my points for Home Depot gift cards.
• Beginning redeemer: Wow, $6k of spend in 3 months is a lot. But 150k points transferred to Delta Skymiles must be enough to get to the moon  roundtrip to Europe in business class apparently, a one way basic economy award to Lubbock.
• Intermediate redeemer: Look at those fools wasting their points on gift cards and transfers to domestic carriers – I got 30cpp by transferring to ANA and booking last minute one way J flights to Japan. 
• Advanced redeemer: Things have come full circle – I have so many points that I will never be able to redeem them all for travel. I’ll book my travel a year out, and I’ll cash out the rest. 150k MRs = $1,650 with a Schwab Plat or ~$1,950 depending on my bargaining skills.

Pictured: A local business owner/giga-Chad on his way to Home Depot to convert the spoils of $7m of Amex spending into a patio furniture set.

Depending on your situation, each viewpoint can make sense. However, I’d imagine most MEAB readers fall into the final segment. 

And in a community that is largely a perfectly aligned Venn diagram with other optimizer communities like FIRE, cash is king, especially when you hit the inflection point where your ability to earn wildly outpaces your ability to burn. 

I was talking to my P2 (and fellow Waldorf Pedregal enthusiast) about how poorly I had strategized earning and redeeming early on, and she provided some much needed perspective on the whole thing when actually looking back at those first redemptions.

Some of our first cards and subsequent redemptions:

• Citi AA Platinum pre-derAAilment – SUB used to fly AA Y to Europe, where we attended music festivals and yacht cruised as backpackers
• Chase Southwest chasing Companion Pass – used to book Y flights to the Caribbean, where we got engaged
• Capital One Venture – I hit the SUB on the engagement ring, and used the cashback to erase the insane VS surcharges on our first J redemption for our honeymoon

Pictured: Mr. and Mrs. irieriley in 2017 enjoying the spoils of their very first award redemption

While the strategy was akin to SideShowBob233 stepping on a rake over and over again, those first few forays into earning and burning provided more to enrich P2 and I’s lives than another $2,000 into VTI ever will. 

I think it’s ok to occasionally zoom out of doing finger math to avoid looking like a kiter or mourning your Paypal burner to remember why you started this hobby in the first place, and it’s very unlikely that you started because you wanted what sometimes feels like a second job. Instead, you wanted a way to take a trip for free, or some extra cash for bills. 

Pictured: MSers determining whether they’re clear to pull back into their hub account

If there’s anything the last 4 years have taught us, it’s that life is short. This is a friendly reminder that points can be used for something besides booking T-355 Qsuites, cashing out or selling – they’re also a tool for engineering unique experiences for you, your friends, and your family. 

Personally, I’m blowing the Chase Sapphire Reserve grocery cash out equivalent of $1,700 of URs to spend 3 nights at a Hyatt SLH 20 miles from my home. A year ago, that would have really pained me. It still does, a bit. But hey, the Hamptons in summer is otherwise too rich for my blood – may as well enjoy it before this particular hotel joins Hilton and becomes 95k 120k 150k HH/nt. And we’re definitely not going because P2 wants to be in the background of Summer House.

And yes, even for those who don’t travel and are firmly #teamcashback. Don’t forget to use your proceeds to treat yourself or a loved one every once in a while. Even if it’s just a boba during a money order run. 

– irieriley

Pictured: In keeping with the Simpsons motif, a fitting desk decoration for a MSer deep in the weeds of earning looking for some perspective