How I redeemed 686,000 points for $54,821 of free travel in 2 months
Why I've stopped leaving money on the table
For those of you I've caught up with recently, I've probably mentioned my growing interest (bordering on obsession) with points & miles and generally getting free stuff. It's a hobby I've flirted with over the past 4-5 years but never really systematically dug into until November of 2021.
Personality-wise, the points & miles hobby suits me: I'm an obsessive optimizer at heart who values experiences over most material goods.
Since November 2021, I've been diving deep into points & miles and have aggressively pursued a strategy to accrue and deploy points rapidly.
In this post, I outline some of the redemptions I've made using points & miles over the past 2 months and what I wish I had known when I was first getting started in the world of points & miles.
Note: there are risks and considerations around your credit score and other parameters that I won't go into here but are very well covered with a simple google search (I'd encourage you to look into this before diving into this hobby).
My most recent 2 months of redemptions:
In the past 2 months, I've successfully deployed 686,000 points (~450,000 of which I've earned in 2022) for $54,821 worth of travel experiences (had I paid cash at the time of booking) for an average redemption value of ~$0.08/point. Here's a snapshot of the types of free experiences I've tee'd up for Katherine and myself (and my parents) over the next year:
Business class flights from New York to Tokyo on Japan Airlines
Business class flights from New York to Paris on Air France
Business class flights from New York to Cairo on Egypt Air
Business class flights from Amman to Detroit on Royal Jordanian
Hotel stays at the Park Hyatt Paris, EDITION Bodrum, and Gran Hotel Miramar
For the longest time, I thought getting this kind of value was reserved for people who dedicate an inordinate amount of time to the hobby and/or have really flexible travel schedules (I do not fall into either camp). Admittedly, the first time I redeemed points, I got $0.01/point of value booking through the AMEX portal. Ouch, and a far cry from $0.08/point of value.
What I wish I’d known when I was first getting started:
Open business cards, then Chase cards, then Citi cards, then AMEX/Barclays/Bank of America Cards. But you can't do it in the opposite order.
Business cards are often not reported to credit bureaus under your name and thus don't count against you when applying to new cards
Chase has strict rules on approving you for a new credit card (called the 5/24 rule). You cannot apply for more than 5 cards in a 24 month period of time. If you're new to this game, start with Chase
Citi also has somewhat strict rules on approving you for a new credit card. It's less formulaic than Chase but if you've opened a lot of cards recently, you're out of luck
American Express, Bank of America, and Barclays seem to care mostly about your credit score and less about how many cards you have open (or have recently opened). Once you've tapped out Chase and Citi, you can open a lot of AMEX cards
Capital One used to be extremely strict but has been recently very lax with their Venture X card from an underwriting perspective. As of the time of this writing, Capital One is likely in the same bucket as AMEX/Barclays/Bank of America
Follow the right content creators across visual & audio. They send a daily/weekly/podcast email to your inbox and help make sure great deals and opportunities don't fall through the cracks. Some of my favorites are as follows:
Doctor of Credit (a bit noisier and a terrible user interface but worth following if you truly want to make sure nothing slips through the cracks. It's too noisy for me and I don't follow it personally)
Twitter
Actually finding award space for the best redemptions is a bit of a pain. The further out you can plan the higher your odds of success (or very last minute depending on the airline). The following are great resources that I use to search for award space:
This is like Google Flights but for points. It's incomplete from a dataset perspective (missing certain airlines like Emirates at the time of this writing) but very comprehensive. Very useful to find award space if you know specific dates and destinations.
You can use the code ALLTHEHACKS (not affiliated with me in any way) for a $1 first month of using the platform
This is like Point.me but has a terrible user interface (but is much more powerful and has support for more airlines). Unless you really want to go deep, I would start with Point.me which has a much friendlier and less frustrating product
Limited to a small number of airlines but is extremely useful for identifying dates that have great award space on non-stop routes
If you decide to sign up for this (it’s my favorite tool of all) you can consider using this referral link
This is for paid hotel awards stays, but if you forward them your confirmation emails, they'll auto-ping you when hotel rates go down
Never open a credit card from google. Always ask a friend/family member for a referral (or use the referral link from one of your favorite content creators in this category). If nobody comes to mind when you're applying to a card, happy to send you my referral link :)
This can often times result in not only the person whose referral link you use getting a bonus, but also you getting a unique deal that you would not be able to access otherwise.
For instance, until 6/8/2022 I have been targeted as an individual for being able to give out AMEX gold referrals where the person referred gets 90,000 points (rather than the standard 60,000 points) and effectively gets the $250 annual fee refunded for the first year.
You don't need to actually hit a ton of spend to accrue a ton of points
For instance the Barclays AAdvantage Aviator Red Card gives you 50,000 (formerly 70,000) bonus American Airlines miles for paying the annual fee ($99) and making a single purchase. A pretty sweet deal considering you can easily use 60,000-70,000 points for a one way long haul international business class flight
Some cards and strategies are for big spenders, but there's great value out there for any budget/lifestyle
Use retention offers to get sign-up level bonus points every year without opening a new card every year
AMEX in particular does a great job of this. I was thinking about cancelling my platinum and gold cards this year but was offered 55,000 and 35,000 points respectively for keeping each of them open (or $550/$350 but I took the points). You can get a retention offer every 13 months but if you accept a retention offer, you can't cancel that card in the 12 months afterwards
If you're planning on cancelling a card, it never hurts to ask the credit card company if there is a retention offer available on your account
You can earn points on your rent payment using Bilt without paying any fees
For folks paying rent, this is a no brainer. Bilt even works if a landlord only accepts checks.
You can pay a consultant to figure out redemptions for you if you don't want to go through the headache of doing this yourself (which, if this hobby does not energize you, can be a frustrating experience early on)
The cost might be $100-200 per person for a round trip business class booking that could save you over $10,000. A pretty good deal, in my view, if you don't want to figure out how to do these redemptions yourself
This means that it's more important to be able to earn than it is to be able to spend effectively
Here's a list of vendors who provide this service
Try figuring out a redemption far enough in the future and then back-solve to the number of points & miles
This is probably the best way to get started in this hobby. Pick an aspirational experience that you're fired up about and then figure out what you need to earn from a points perspective to make it into a reality
Want to fly ANA business to Japan for 2 people round trip from the US? That will be ~80,000 AMEX points per person at best (transferred to ANA). However, ANA releases award availability 355 days in advance and often only 2 seats per flight in business class which get quickly snatched up. Thus, you want to book the moment these seats open up
Want to fly TAP business from JFK to LIS for 2 people one way? That will be 34,000 AMEX, Citi, or Capital One points per person (transferred to Avianca)
Ask for help if you have questions
Most points enthusiasts love helping others out. Big shoutout to Greg Chi for knowing 100x more than I do about all of this stuff and for inspiring me to get started in this hobby and for answering a lot of my questions along the way.
Greg was finding ways to fly free business class to Asia for a weekend while we were at Stanford and helped me book an awesome roundtrip cash ticket from San Francisco - Bangkok - Shanghai - San Francisco my Freshman summer (when I was still broke) for under $10 in addition to taxes and fees (and under $450 total)…
There are some great Facebook groups dedicated to this hobby. I personally like the Frequent Miler and Travel on Points groups.
What I have my eyes on for the rest of 2022:
Business class flights from San Francisco to Naples
Business class flights from Naples to New York
Business class flights from New York to Buenos Aires
Hotel stays at the Conrad Tokyo, Conrad Osaka, Park Hyatt Kyoto, and Park Hyatt Buenos Aires, and a few TBD Amalfi Coast hotels
Bonus - what’s currently in my “wallet” (and Katherine’s, since we operate in two player mode):
AMEX
AMEX Platinum
AMEX Gold - (actually in my wallet everyday)
Delta AMEX Gold
Delta AMEX Platinum
Hilton Aspire AMEX
Chase
Chase Sapphire Preferred Visa
Capital One
Capital One Venture X Visa - (actually in my wallet everyday)
Barclays
American AAdvantage Aviator Red Mastercard
Bank of America
Virgin Atlantic Mastercard
Air France KLM Mastercard