Starting Out in Points and Miles, Step One: Get Organized

Tom, here. Melissa and I have been excited about sharing information about points travel and what we have learned in the last couple of years. One way that we are going to do that is to write a series of posts that we are calling – If We Were Starting Out in Points Today. We are going to approach this “game” as if we were just starting today, 3/22/23, without any travel rewards cards, which is where we were in April of 2021. As we go forward, we will be targeting current available offers at the time of writing each post. Could you do something different? Sure. Is this perfect? No, but I think its a good start. 

So, here’s where I’d start: organization. I know it's kind of boring, but as we have scaled up it has made it manageable to have many accounts. I would find a program that allows you to aggregate and see all of your accounts in close to real time. I’m sure that there are multiple programs that do this but the one that I have experience with is YNAB (You Need a Budget). This is software we have used for budgeting for years. In our new hobby, It has helped us use credit cards, budgeting only the money we have and tracking spending in one place across multiple cards. It has a fee, but it has been worth it to us.  If you want to try in you can sign up for a free one-month trial (https://ynab.com/referral/?ref=6HXYMFtYmmDUa0Yq I appreciate you using my link if you decide to try it).

Once you get your budget organized, I think the best place to start is with a Chase Ultimate Rewards Card that can be transferred to partners. To begin, I would take a look at what cards you already have and determine 5/24 Status of you and your player 2, if you have one. Your player 2 is either a spouse, partner, family member, or friend with whom you plan to earn points. Just look at your credit reports and the dates of anything that is a credit card. You can find this for free on sites like Credit Karma. This is what Melissa and I looked like before we started pursuing travel cards (dates have been adjusted to pretend we are starting now rather than back in 2021).  

Card	Date open	Account owner	Authorized user
PSECU VISA	11/4/2008	Joint	Joint
CITI Costco	5/21/14	Melissa	Tom
Amazon Card	8/15/15	Tom	NA
Home Depot Card	7/11/21	Tom	NA
Gap VISA	11/23/21	Melissa	Tom
Wells fargo Project Loan	7/9/22	Joint	Joint

5/24 Status 

Tom	Fall off date	Melissa	Fall off date
Home Depot Card	7/23	Gap Card	7/23
Gap Card (maybe)	11/23	Wells Fargo Project	7/24
Wells Fargo Project	7/24

So, Tom is 3/24 and Melissa is 2/24 in the Chase computer approval algorithm. Currently, authorized user cards may not count with Chase, but I would have to call the reconsideration line and depending on the agent and what Chase happens to be caring about in underwriting, they may not count the authorized user account. Currently if you are over 5/24 and call in they are excluding AU accounts. Melissa and I ran into this in 2022, but they were not excluding AU accounts and we lost out on bonuses that we had hoped to get. Another thing that I noticed when I looked at our credit reports is that the loan we took out with WF for no fee financing when our AC unit broke was not a loan but a credit card. If I were to finance a new AC today, I’d definitely open a points card with the same no-fee terms and get a bonus.

Tracking data is important, especially when you pay an annual fee for a card (or 7), or when you are pursuing a bonus. It would be really disappointing to miss a bonus deadline by a couple of days or dollars and miss out on your precious points. I have attached a spreadsheet that I use to track data Credit Card Tracking   I track every month when I get a card statement how many points I got,  any extra credits(like with Uber Eats or other extra credits that certain cards come with), any annual fees that came due,  and how much I spend on the card in each month. I want to be able to track the earnings for the year so I can figure out if a card was worth it when the next fee comes around. This is the data from our 2022 points take. 

2022 Points and Cash Back Totals

By tracking what we spend on each card each month I can determine if we could shift spend and meet a new bonus on a new card (some are as high as 15K). By doing this every month when I get a statement, the task does not build up terribly and is not as onerous and overwhelming. The other thing I track is when a card was opened and when the bonus was received. In the long game I want to be able to eventually get the same bonus again, and this info is important to know for eligibility purposes. Now that we have some order, I am ready to go after my first card! 

I would start collecting points with an Ultimate Reward card, and if I didn’t already have a Sapphire Card, I would definitely start there with the Sapphire Preferred. First because it only has a 95-dollar annual fee and his a very high in branch welcome bonus. For a while as we begin playing this game, it will be the only fee I will pay. It gives me the ability to transfer to many partners. Southwest and Hyatt is where I would start living in Pittsburgh. You also could book travel in the Chase portal (like Expedia) for a min of 1.25 cents per point,  and if you decide this is not fun and confusing, you could cash out for 1 cent per point. Another reason to hold this card is if you book airfare with it you get some trip delay insurance, even if you just pay the taxes for a flight. Melissa and I had to stay in Orlando in 2022 for 2 extra nights because our flight was canceled - if we had booked our airfare taxes and fees with the Sapphire card, we could have been reimbursed for our hotel and food for up to $500 per ticket! Lesson learned! You can also get primary car rental insurance with this card and save some money if you rent a car when you travel. Finally,  it is easy to downgrade this card after a year if you do not want to pay a fee. 

I would call a Chase branch to make an appointment (I called the Shadyside Chase on 3/23 and confirmed they have the 90K points after 6K in spend offer) and open the Sapphire Preferred Card. This is where I would start.  This post has gone long, so I’ll pick up next time with strategies for meeting the minimum spends, and why the bonuses really move the needle.  

Mistakes Were Made

Beach sunrise photo for attention inspiration.

Whether you are trying to hack one big trip, or you've jumped into points and miles with full abandon, you'll quickly find that it is a game of rules, details, and a lot of fine print. As Tom and I got more into travel hacking, we found ourselves learning from small mistakes and missteps. While there is no one right or wrong way to do this, there are things that we found out along the way that we wish had known because it may have changed our strategy. Here are some of the highlights? low-lights? of our learning curve - maybe they will help you! 

Not Fully Grasping Chase's "5/24" Rule
To be quite honest, most of the other mistakes we've made below are loosely associated with this concept. Chase has an unwritten rule (that is supported by many data points in the travel-hacker world) that if you have 5 or more new personal credit card openings in the past 24 months, they will not approve you for one of their cards when you apply. As soon as enough time passes and you drop down to 4 in the last 24 months, bingo, approval. They will not tell you on the phone that this is their rule, but they will tell you that there are too many cards associated with your name if you are in this camp. If you are making a spreadsheet or using a travel-hacking organization app, this is an important piece of information to track - card opening dates for any cards you have.  The goal isn't necessarily to always be under 5/24 - but it is important to have a strategy that includes going for what you want in that family of cards first, so you don't wind up in Chase jail like we were. This is a pretty straightforward and simple rule, and I'll go on below to explain why it is very important...

Not Fully Grasping the Power of Chase 
I would say that we sort of understood the above rule when starting out, but what took a little more time and a card denial to really grasp is that Chase Ultimate Rewards (URs) are where it's at (I really wanted to open the World of Hyatt card after visiting friends at their awesome resort when we were stuck in Orlando for a flight delay). URs are really versatile and valuable in the travel hacking world, and beyond that, Chase has other co-branded cards with Hyatt, Southwest, IHG, United, Marriott, and on and on. Is this the only points/miles bank you should focus on? Not necessarily. But if you are new to the travel hacking hobby, it might make sense to pick a couple of places you want to go and then familiarize yourself with what the best points currency would be to take you there. I bet 8 times out of 10 it will involve opening a Chase card. 

Adding Each Other as Authorized Users to Every Card
It made tons of sense to us at first that if Tom opened a card, he should add me as an authorized user and vice versa so that we could both easily use the card and attack the spending requirement of a bonus we were working on. Plus, marriage and togetherness and what's mine is yours and stuff. Turns out, this isn't a great idea for a couple of reasons. The big reason, if you haven't already guessed, is that it will mess up your 5/24. When applying for a new card online, these accounts where you are listed as an authorized user will trigger the computer algorithm and you will likely get denied. You can potentially call for reconsideration, but this may have varying degrees of success depending on the customer service rep you get. This is how we found ourselves quickly at or over 5/24, as we each had double the accounts associated with our names. The good news is, it is easy to remove yourself as an authorized user if you are running into problems, which is what we ended up doing for a couple of cards. Certain cards have made sense for us to keep each other on as authorized users, but we've moved away from signing each other up every time. The second reason making your partner an automatic authorized user on every card might not be a great idea is because it can limit the degree to which you can make this a two-player game... which is the next thing we learned...

Not Leaning into the Two-Player Game
What I mean by this is that there is no reason that Tom and I can't open the same card in the same year in order to double our points. On top of that, usually you can get additional points for making a referral. Right now, for instance, I could theoretically open the Ink Cash card, one of Chase's no annual fee business cards and get 75,000 URs. Either in a few months, or really, tomorrow, I can refer Tom to the same card, and he can also aim for the 75k bonus while I would get an additional 40k for referring him. Then, we'd have 190,000 points to work with which could either go a long way towards a trip or get cashed out for $1900. If you don't have a spouse or partner to do this with, you could potentially try to rope in a friend or family member who you are trip planning with - if you can't link you accounts due to the bank rules (some have very generous point-sharing policies and others don't), you could have player one work on flights and player two work on hotels - lots of possibilities!

Shying Away from Opening Business Cards
But wait, do Tom and I own a business? How would we be able to open one of those cards? Turns out, if you have any minor side-hustle, even selling your old junk on Ebay from time to time, you are eligible for these cards. You apply as a sole proprietor, use your SSN instead of an EIN number, and remain very honest about your projected revenue. What's more, you don't even need to use it only for the business (ever the rule follower, I had to investigate this). This aspect of travel hacking was something I originally had no interest in... but Tom always is one step ahead of me, truly the player one around here. Applying for business cards from time to time has become part of our strategy because they often offer great sign-up bonuses and perks for low or no annual fee, and most of them don't end up working against you on your 5/24 - even business cards you've opened with Chase! Now, if you have an established business, you obviously can use this strategy - making sure to be careful about your accounting. But if you don't have an obvious business - maybe you should consider a garage sale or some dog-walking!

Succumbing to FOMO
Honestly, this is something Tom and I will probably continue to do. We've made a strategic plan based on what works best for us and where we'd like to go... but then, the IHG card comes out with the highest sign-up bonus ever! What's a travel hacker to do? Well, sometimes we think it through and decide it doesn't fit in the plan, and sometimes we decide to go for it. The important thing to remember is that in a few months some other bank will be offering the "highest offer ever," so don't fret too much if something comes up that seems so good but you can't make it work right now. We are trying to take a longer view - a marathon view, if you will - and not let FOMO guide our decision-making. 

Traveling for "Free": The Basics

So how did this happen? How did we go from barely using a credit card at all to opening several new  cards and putting all possible expenses on them?

Lets go back to the beginning, maybe 15 years ago, when Tom was back in school and we were living on one very modest income. Guess what happened? Credit card debt. After really looking at our finances and working really hard to get out of that hole, we vowed to never use credit cards again. Well, that sounds more like something Melissa would vow. In all seriousness, we were nervous about making mistakes with credit cards or getting too comfortable with them because of how quickly the debt can snowball. As we both furthered our careers and had more income available to us, Tom kept trying to get Melissa to use credit cards that gave cash-back, but she kept resisting. 

Finally, one day in 2021, Melissa got really hyper-focused on hacking a trip to Disney World. She has loved bringing her family to the happiest place on earth but has hated the price tag that comes along with that. She listened to podcasts and consulted blogs and websites and kept coming across the idea of loyalty programs and frequent flyer miles. She thought to herself, gee, we don't travel nearly enough to get enough points to be able to do anything as a family of five. But then she read more and realized that these people just open credit cards for the sign up bonuses that they then use for any number of things - flights, hotels, cash back etc. The banks just give these rewards out. While there are other little hacks that can cut the cost of travel, she was amazed to find that this credit card bonus way got the closest to zero money than any other tricks or tips. How could she turn away from the idea of taking a trip for close to zero money? Well, she couldn't and that's why we're here.

Here are our FAQs that aren't actually FAQs but rather questions we are guessing someone might ask:

1. How does this work?
It's very simple, really. If there is a credit card with a good sign-up bonus that one of us is eligible for, we apply for it. Banks typically will lure new customers in by offering something like in the case of the Chase Sapphire Preferred card, 60,000 Ultimate Rewards after you spend $4,000 in three months. We open the card, shift all of our ordinary expenses onto it (hello, grocery bill! For a family of five we could almost hit that spend in 3 months), and then get the reward points. In the case of that particular card, there are multiple airlines and hotel chains that are transfer partners, so we then use those points to book travel and start the process over with a new card. For instance, 60,000 Ultimate Rewards is enough to take our family to this resort in Puerto Rico for 4 nights. We might just have to do that! 

2. Do I have to open a million new credit cards?
Not exactly. What we've found is that the most "bang for your buck," though, is not in focusing on putting all of you spending on one particular card, but on really focusing on sign up bonuses for new cards. Of course you can maximize particular spending categories, like gas or groceries, on cards that will give you certain multipliers - and we do that too - but it doesn't come close to the points generated from new card openings. For example, in 2022 we were able to generate a little over 900,000 award points by opening 7 new cards between us. This included the sign up bonuses plus using certain cards in categories that had good multipliers for things (5x on groceries, 4x on dining etc). Lets say instead of focusing on new card openings we had focused only on the Amex gold card. That is a great card that gives 4x back on dining and groceries. As a very generous budget, lets pretend we could spend $2000 a month in those categories and maybe $2000 a month on the non-elevated categories at 1x back. We would have made 90,000 points on the sign up bonus and about 120,000 points for the year on normal spending, topping out 210,000 points. If I haven't lost you yet, the point is that 900,000+ points is more than 210,000 for the same amount of spending in a household.

3. Wow! Are you in a lot of debt?
Actually, no, we are not. The only way this method of travel hacking works is if you pay off your full balances on all cards every month. With interest rates being sometimes as high as 25%, a one month mistake could potentially cost hundreds of dollars. Without paying off cards in full each month, this hobby quickly becomes profitable only to the bank and not to you. It's important to note here that this form of travel hacking really might not be for everyone. You may need to work on building up your credit first. Or, you may be in a place in life, like we were for many years, where you are operating on a super tight budget, and the temptation of using credit cards for things you can't actually afford is too high. The keys to making credit card points and miles work for you is to pay off your cards each month and to not buy things you typically wouldn't just to meet a minimum spend.

4. Won't you run out of cards and bonuses to get?
This was something Melissa got worried about early on, and so she had a tendency to want to hoard her points and not redeem them. However, each major card-issuing bank has sometimes as many as 10-15, or even more, co-branded and specialty credit cards with unique features and bonuses. Working at a pace of 6-8 credit card openings per year, we haven't even scratched the surface of what's out there, and new cards are always getting introduced. What's more, each bank has its own set of rules, but there are many cards that we could eventually get again. Veterans in this hobby have been doing this for 15-20 years and are still generating way more points than Melissa and Tom may ever see. 

5. Aren't the points hard to redeem - can you actually go anywhere?
So far we've found transferring Chase Ultimate rewards to Hyatt and Southwest extremely easy and instantaneous. In fact, you could focus all of your travel hacking on these programs and travel pretty extensively within the US. We've also had great success with Marriot Bonvoy and have used a travel expense erase feature on our Capital One card. We were able to use these things to do the travel we wanted to do and didn't feel restricted in what we have been able to do. Melissa has a big family trip to France coming up, so we will keep you posted on how that works. 

6. What about your credit score?
This really hasn't been an issue. We tend to see a small dip after a card company has made a credit inquiry when making a new application, but then it goes back up to where it was. Overall, we've both seen our scores get higher since starting this. 

7. Do you pay for cards with annual fees?
Absolutely, if we calculate to perks of the particular card and find that they are worth it to us and come out in the net positive, we do. Typically, the sign up bonus itself will make most cards worth opening for at least a year. When the card anniversary comes around, we again evaluate if it makes sense to pay the fee to keep the card, downgrade to a different no-annual fee card, or cancel altogether once the fee has posted (they will refund it). It is important though, to keep the card open for at least a year and to have a plan for how you will redeem your points if you plan to close it. Without the right kind of card account with a particular bank, you might end up forfeiting your points and rewards.

8. Is this time consuming?
There is definitely a good bit of organization and time that can go into making this work for you, but you may find that its worth it. As we said above, you can get into this a little or a lot, depending on your goals. And, you don't have to write a blog! There are apps out there such as Travel Freely and Award Wallet that will help you keep your information organized and cut down on the amount of time it takes to keep everything straight. Tom is definitely the organizer in our duo, and his system involves keeping our YNAB current and using various excel spreadsheets he made to track everything from card opening dates to bonus deadlines to 5/24 status. If this all sounds too overwhelming, focusing on trying one card that will help you with a hotel stay and one card that might help you with flights is a good way to start. Then, you can assess how hooked you are and how much more you might want to do!

Our Favorite Resources

One of the greatest things we've found as we've gotten into the points and miles hobby is that there is endless information out there on how to maximize earnings and redemptions. People who travel hack seem really willing to share their tips and finds with the whole world - or at least with those who are listening! Tom and I both like to look at several different places for info, but here we've narrowed it down to our top five go-to points and miles resources. See if you notice any differences between our favorite sites (hint - Melissa likes to redeem and Tom likes to earn).

Tom's Top Five:

1. The Frequent Miler 
This is Tom's number one, go-to website, podcast, YouTube channel, newsletter - everything! - in the points and miles world. He particularly likes subscribing to their newsletter where time-sensitive alerts about great deals and offers come as frequently as you decide you want. They cover a wide range of information and are committed to sharing it freely without a lot of ads or solicitation. 

2. Doctor of Credit
Tom has a whole points and miles-adjacent hobby of earning free money from bank account bonuses. Doctor of Credit keeps him up to date on any great bonuses out there, and he particularly likes the forums and comments that give information about people's experiences with certain banks. Doctor of Credit also has plenty of info about credit card sign up bonuses, great shopping portal deals, improving your credit, and really anything bank-related you could think of. 

3. RJ Financial/Run the Bank
Tom likes RJ's YouTube channels for great info on banking in general and of course, leveraging banking incentives and bonuses. RJ takes more of a cash-back approach, but this information helps balance out the travel hacking/points and miles perspective. 

4. Ask Sebby
This is a great all-around resource for all things financial, banking, and points and miles. He has well organized info on the website about all of the major points and miles programs as well as reviews on just about every card you can imagine. He also has a very active YouTube channel if this is your preferred way to get your info. 

5. Geobreeze Travel
Tom likes to listen to Julia's podcast because she interviews a wide range of guests and covers just about every topic in the points and miles world with a particular interest in the intersection of personal finance and award travel. From stacking shopping portal offers to tips on finding the best hotels in a certain country, this podcast is always a fun listen!

Melissa's Top Five:

1. The Frequent Miler
What do you know!? The same number one! Melissa is frequently amazed at how quickly this small team can put together content and most likes to read their trip reports and hotel reviews. She has some interesting new aspirations because of these guys, which include getting offered a free cruise and going on a dirt-cheap vacation in exchange for sitting through a timeshare presentation. We shall see!

2. Katie's Travel Tricks
Melissa stumbled upon Katie in her Instagram reels, where elder millennials find everything worth finding. She loves this site for its easy-to-follow information on travel-hacking for families. Katie's site includes maps of all-inclusive hotels, maps of hotels for large families, and user-friendly guides for booking all kinds of reward travel for your family. 

3. Miles to Memories
Melissa loves listening to this podcast, and she's not even sure why. Maybe it's the soothing intro music? She started listening to it as a cross-over because her Disney travel agent is an editor and contributor. This podcast is the rabbit-hole that piqued her interest in points and miles, and she has continued faithfully listening to it for its fun spin and interesting interviews. 

4. Geobreeze Travel
Melissa also really enjoys the Geobreeze podcast. Julia has a very down-to-earth style, and the people she interviews are at various stages of their own points and miles journeys - from people who are experts in a particular airline reward system to people who are just starting out and have to work around certain scheduling or income restrictions. All very helpful content!

5. Travel On Points
Travel on Points has a really excellent website with solid information about strategy and very useful resources for understanding flexible travel partners and booking international award flights. While their website is great, what Melissa likes best about ToP is their Facebook group. People post questions, trip reports, and other interesting tidbits all day long, and the moderators, many of whom also have non-travel hacking day jobs, respond quickly and keep the group running in one of the most positive Facebook groups out there. 

A Walk Through Our Early Redemptions

We started dabbling in points and miles midway through 2021 and picked up the pace as we got into 2022. We've been collecting and redeeming credit card points for almost 2 years, so I thought it would be fun to walk through all of the flights and hotels we've booked so far. When we first started doing this, I started to worry that we'd run out of bonuses for which we were eligible. I was quite mistaken - there is a whole community of points and miles experts out there who have been doing this for years and still have not run out of cards to open and rewards to earn.

In the beginning, all we really wanted to do was cut down on the cost for five people to fly to Disney. We opened the Chase Southwest Rapid Rewards card for a 40,000-point bonus. Tom understood much more quickly than I did that the Chase Sapphire and Chase Freedom were the next step. Soon we had over 100,000 Ultimate Rewards that could be transferred to Southwest with the potential to keep earning points with 5x on groceries. We quickly had enough points to book our flights to Disney, and more left to book flights to Austin for my cousin's wedding. The addiction began in earnest!

I won't walk through all of the rest of our credit card openings - that would get long and boring - but here is a photo chronicle of what we have redeemed since November of 2021:

Tom and I had a no-kid trip to Austin to attend my cousin's wedding. We booked flights via Southwest for around 40,000 points and saved ourselves $600.

Next up were our five flights to Disney in January of 2022. We used around 95,000 Southwest points after transferring what we needed from Chase and saved around $1500. Photo of my family's favorite Disney landmark.

Up next, in May 2022, was our first trip back to NYC since before the pandemic started. I was meeting my college roommates for a little reunion, so Tom decided to bring the kids and hang out with his brother and partner who live there. We used Marriott Bonvoy points to book three nights at the Courtyard Manhattan/Midtown East. This saved us around $1200. 

Next, for August, 2022, we booked two nights at the Courtyard Marriott Bayfront in Erie, PA, with this view from our room. The cash price at this hotel is always really high, but I always wanted to stay here. Overall, we liked the hotel, but it was super crowded, and the infinity pool looked way cooler on the website than in person. We used 2 free night certificates for this, saving us around $700.

After a couple of days swimming and hanging out on the beaches of Lake Erie, we traveled on to Niagara Falls where we stayed at the Embassy Suites Fallsview. We booked a suite with an amazing view via the Capital One portal (I had a period of obsession with this portal) and used points erase to save about $500 on this trip.

In January of 2023, we took a long weekend in the mountains of West Virginia where we were able to use the points eraser on our Capital One card. That's the smile of a guy who didn't have to pay for his lovely mountain cabin. Savings this weekend totaled around $750.

 

Finally, later in January, we did the silliest thing of all! We went back to Disney and stayed at the Walt Disney World Swan hotel for nearly free, just because we could. We loved this trip because the hotel had great pools, great food, was walking distance to our two favorite parks, and was included in some bougie Disney perks like early entry and late-night extended hours. We also used Chase Ultimate Rewards in combination with Southwest Rapid Rewards to book our flights. Savings here were $1500 for flights and $2800 for the two rooms we booked. 

All told, from November 2021 through January 2022, we were able to book roughly $9550 worth of travel. We've learned a lot along the way and are looking out for even better redemptions in the future. What's even more exciting is we have a nearly free spring break trip to Colorado already booked, and we still have about 500,000 points in different flexible currencies to use for whatever else we decide to do. On top of all of that, we have a plan for the rest of the year to rake in more bonus points and start checking off some bucket list trips - can't wait!

Who We Are

 

Tom and Melissa live in - guess where? - Pittsburgh! They live there with their three kids and needy dog. Tom and Melissa are busy parents who both work in healthcare, so they don't usually have the flexibility to go after a great spur of the moment deal or travel at off-peak times. While they've gotten tons of information from the travel-hacking community at large, they started this blog to try to share information and connect with other people with day jobs, kids, and other responsibilities that make award travel more challenging than many of the influencers make it out to be. They are particularly interested in trying to connect with other Pittsburghers who are already doing this or who want to get started.

When Tom is not finding ways to earn more points and bank account bonuses, he enjoys running or getting out into the woods for a hike. When Melissa isn't looking for ways to redeem Tom's points, she also enjoys those things with a tiny bit of cycling sprinkled in. At the top of Melissa's travel hacking bucket list is to get the family to Hawaii for as little cash cost as possible. Tom really wants to see the Northern Lights from a Scandinavian country. Come along with us and see what we can hack!