One card for every year I’ve been alive: My journey from college student to points pro

Jul 20, 2020

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In many ways, award travel is in my blood. My dad traveled a few nights out of every month for work, diligently racking up United miles and SPG points. This meant that our family was able to travel (almost) for free every time we took a vacation, but in my mind, I always associated those free trips with the time my dad spent on the road for business.

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It never crossed my mind that I could travel like that (and then some) without regular business travel to boost my account balances. The day I realized that wasn’t true, my life changed forever. Here’s the story of how I went from a hopelessly romantic college student to a points pro with more credit cards than years I’ve been alive.

Related reading: Best travel credit cards of June 2020

In This Post

Chasing true love across the country

Points and miles are more fun when you have someone to share them with. Photo by Ethan Steinberg / The Points Guy
Points and miles are more fun when you have someone to share them with. (Photo by Ethan Steinberg/The Points Guy)

My first foray into the world of travel rewards was born out of desperation and a summer love story I didn’t want to end. My girlfriend and I met at camp when we were younger and stayed close friends throughout high school, despite me living in Maryland and her in Florida. We reconnected at a New Year’s party hosted by some camp friends during our senior year of high school and started dating shortly after. The only problem was, I was set to leave for college in Chicago, while she was going to school in D.C.

I started Googling “how to get free flights,” and quickly settled on Southwest Airlines as my go-to for flights between Washington National (DCA) and Chicago Midway (MDW). I took online surveys that paid out a few hundred miles at a time, and between that and the points I earned flying to and from campus over breaks, I was able to scrape together enough miles to see her about once a quarter.

Related reading: Battle of the Airlines: Why I think Southwest Airlines is the best

Southwest's "Maryland One", a Boeing 737 with the Maryland state flag painted onto it, celebrating their stronghold of BWI
A Southwest 737 (in my home state colors no less!) epitomized my early days of travel hacking

I spent that winter break with her in Miami, and one night she sent me an article. It was a profile in Rolling Stone of a prominent travel blogger who’d given up his apartment and decided to live on the road full time. Rolling Stone even sent a reporter to interview him in Cathay Pacific first class en route to Hong Kong, because that was the only way to track him down!

I spent my 21st birthday flying Cathay Pacific first class from LA to Bangkok, enjoying my first legal glass of champagne ???? Photo by Ethan Steinberg / The Points Guy
I spent my 21st birthday flying Cathay Pacific first class from LA to Bangkok, enjoying my first legal glass of champagne. (Photo by Ethan Steinberg/The Points Guy)

Just like that, I was hooked. I spent the rest of that break buried in my phone reading every luxury flight review I could find on the internet. Something had clicked, and I realized that Southwest Rapid Rewards points were just the tip of the iceberg. Barely a year would pass before I got to take my first first-class flight aboard a Lufthansa A380. But something was missing: I didn’t have a credit card yet.

My first credit card

As I continued voraciously devouring every points and miles blog I could find, it became clear to me that credit cards were the key to unlocking all the future trips I was starting to conjure up. But at the ripe age of 19, with no credit history, I assumed I’d have to start from the ground up. There happened to be a Citi branch on my campus, so I walked in one day and applied for their student credit card with a welcome bonus of — wait for it — 2,500 ThankYou Points.

To this day, that’s the biggest mistake I’ve ever made with credit cards and for a few different reasons. First of all, the card earned 1 point per dollar on all purchases. With near-zero expenses, I was never going to earn enough points for any free flights. Second, that application cost me a valuable 5/24 slot with Chase. I was able to get most of the Chase cards I wanted (more on that later), but to this day I still haven’t been able to get approved for the card that tops my wishlist, the Chase Ink Business Preferred® Credit Card.

Getting added as an authorized user on my dad's United card helped boost my credit score right out of the gate. Photo by Isabelle Raphael / The Points Guy
Getting added as an authorized user on my dad’s United card helped boost my credit score right out of the gate. Photo by Isabelle Raphael / The Points Guy

The other reason this was such a huge mistake is that I didn’t need to start with a student card. When I left for college, my dad had added me as an authorized user on his United Explorer Card, instantly lending me 20+ years of on-time payment history. In the blink of an eye, I had a perfect credit history that stretched back since before I was born! Once I realized this, I decided to get serious about my credit card strategy and applied for the Chase Sapphire Preferred® Card. I remember getting the approval notification while I was in lab and nearly dropping my computer in excitement. I was playing in the big leagues now.

With 50,000 bonus points in my pocket, I spent the rest of the summer picking up a few other cards including the Chase Freedom® (No longer open to new applicants) and Chase Freedom Unlimited®, which to this day are still some of my favorite cards in my wallet. I started using my Freedom Unlimited to pay rent each month, and thankfully my apartment manager didn’t charge any additional fees for using a credit card. My roommate even let me pay his half of the rent and Venmoed me the money back instantly, netting me an extra 1,000 or so points per month.

From 0 to 12 cards in a year

I burned through my 5/24 slots faster than I ever would’ve imagined, and turned my attention next to American Express. Having access to different types of points can prove incredibly valuable, as it lets you cherry-pick which ones you use allowing you to get a higher value out of each set.

Related reading: What to do after you reach 5/24

I focused on cards with strong bonuses, low (and preferably waived) annual fees and decent bonus categories. This led me to cards like the SPG Amex (now the Marriott Bonvoy Amex card which has been closed to new applicants) and The Amex EveryDay® Credit Card from American Express.

The information about the Amex EveryDay has been collected independently by TPG. The card details on this page have not been reviewed or approved by the issuer. 

While the branding has changed considerably from the SPG days, I still get a lot of use out of the Marriott Bonvoy Amex, one of the first cards I ever applied for
While the branding has changed considerably from the SPG days, I still get a lot of use out of the Marriott Bonvoy Amex, one of the first cards I ever applied for. (Photo by The Points Guy staff)

While my dad had helped me out of the gate by “lending” me his credit history, I knew it was important for me to build a solid credit score on my own. I tried to focus on cards that either had no annual fee or such valuable rewards that I could keep them open forever, boosting my average age of accounts. It’s hard to predict the future, but I’m happy to report that I still have five of those first 12 cards open and active in my wallet. It can be very easy to get caught up in the thrill of chasing bonus after bonus, but having a long term plan served me well and helped my credit score continue to rise despite all the applications.

With low income and low expenses, it wasn’t always easy to meet all those welcome bonuses. Being able to pay rent on a credit card helped a lot, and I started to badger my friends about picking up the tab every time we went out for dinner or drinks and having them Venmo me back. Thankfully, they were all willing to indulge me even if they didn’t understand exactly what I was doing. I also asked my parents to do the same, paying some of their bills on my credit cards and having them Venmo me back. Having higher expenses, especially from a large business, will let you rack up points faster, but it’s certainly still possible as a broke college student.

Taking a chance on business cards

One of the greatest benefits of starting so young is that I didn’t have as many myths or misconceptions about credit cards to unlearn. Specifically, I had no hesitation about applying for a number of business cards to support my fledgling SAT tutoring business. I found American Express was very willing to issue me a number of business cards early on, including a Marriott Bonvoy Business™ American Express® Card and an American Express® Business Gold Card.

Being able to essentially get two of each card (i.e. an SPG card and an SPG business card, a personal and business Amex Gold, etc.) helped me reach a critical mass of points much faster and made it easier for me to start studying up on the redemption side of things.

A trip to remember

I went from nothing to over 150,000 Chase Ultimate Rewards points in the span of a couple of months, and I was ready to use them. I felt invincible at that point, and after reading so many reviews of luxury flights I wanted to try it out for myself. The perfect opportunity arose when my girlfriend told me she’d been accepted to a study abroad program in India that summer and we started planning for me to visit.

It didn’t take me long to zero in on Lufthansa’s first class as being the absolute best product I could fly with my Chase points. First class from Chicago (ORD) to Delhi (DEL) via Frankfurt (FRA) would’ve run me 140,000 United miles, which I had saved up at this point. I’d done my homework and knew that Lufthansa wouldn’t release first class award space until 15 days before the trip, so I booked a business class ticket on the day I needed to fly so I’d have something to fall back on.

Further Reading: 6 tips for booking Lufthansa first-class awards

(Photo by Ethan Steinberg / The Points Guy)

Sure enough, exactly 15 days out Lufthansa released first class award space on both legs. It would be a 747-8 from Chicago to Frankfurt, a layover at Lufthansa’s stunning first class terminal, and then on to Delhi on the upper deck of an A380. But I was frozen. Here was exactly what I’d been waiting for, but after months of hard work, I couldn’t bring myself to drain all my miles on a single flight.

Eventually, I compromised and booked myself a cash ticket from Chicago to New York, and then another one from New York to Frankfurt on Singapore’s A380 route. My total out of pocket cost for these two tickets was barely $450, and I still got to fly first class from Frankfurt to Delhi for only 60,000 miles. I got an eight-hour daytime flight and access to the first class terminal while essentially “buying back” 80,000 United miles for just $450.

While the routing was brilliant, nesting three tickets on three different itineraries with just a few hours in between each was a mistake I’ll never make again. It was a clear, sunny day as we started taxing out of O’Hare, only to end up 40th in line for takeoff after an hour-long ground stop. I had to get my bags in JFK and change terminals, and I made it to the gate just as my flight to Frankfurt started boarding. Of course, once I arrived at the first class terminal all my troubles washed away.

Photo by Ethan Steinberg / The Points Guy
When you’re departing from the first class terminal you get to skip the crowded gate area and get chauffeured across the tarmac directly to your plane. (Photo by Ethan Steinberg / The Points Guy)

What’s in my wallet now?

My wallet has ebbed and flowed over the years as card benefits and my own travel preferences have changed. Since I got started in this world back in 2015, I’ve applied for a grand total of 41 credit cards. Thirteen of those applications were rejected, but at age 23 I’ve still held a total of 28 different credit cards over my lifetime.

I currently have 14 open credit card accounts, split between the primary six I carry in my wallet and the ones that only come out on special occasions:

I also have the following cards at home, and will take them out as needed for specific purchases or to leverage card-specific benefits:

The information for the Chase Freedom, American Express Platinum Card for Schwab, Amazon Business American Express card have been collected independently by TPG. The card details on this page have not been reviewed or approved by the issuer. 

Advice for beginners

If you’re thinking I’m crazy having had 28 credit cards already at the age of 23, you’re certainly not alone. Most of my friends and family don’t understand what I do and some definitely think I’m breaking the law somehow. If you’re just starting out and trying to figure out where to go next, here’s my advice:

  • It’s okay to start small. It’s easy to look at someone taking flashy first class flights and staying in tropical paradises and get scared. Analysis paralysis is real. But you don’t need to try and outdo TPG himself to get real value out of credit card rewards. Start small. Don’t bite off more than you can chew. I always tell my friends that if all you do is get one free domestic flight a year, that’s better than zero. Once you get your feet wet, you can decide how far and how fast to scale.
  • Think long term, and always have a plan. When you open your first credit card (possibly ever), it can be hard to imagine opening 5 in a 24-month span and blowing past Chase’s 5/24 rule. I blew past my five in the first four months, and many other people I know are surprised by how fast that limit sneaks up on them. But even once you get deeper into things, having a plan is always a good idea. When I open a new credit card I ask myself three questions: “How much do I expect to use this card after I earn the bonus? What do I want to use these bonus points for? Is this card a long term keeper, or one that I’ll likely close after the first year?”  Thinking these things through helps me maintain a balanced wallet and protect my credit score as I continue applying for new cards.
  • Learn the ins and outs of credit scores. Many of the most dangerous myths about credit cards are rooted in misunderstandings of how credit scores are calculated and what factors affect them. Learning and understanding these things will not only save you from making expensive mistakes, but you may even be able to help your friends and coworkers understand that credit cards aren’t scary if you pay your bills on time.
  • Practice searching for award space even if you aren’t traveling. I tell anyone who asks that I’ve learned more about how points and miles work from mocking up trips I never took than from the ones I actually did. Spend some time searching for award space for trips you might want to take in the future, and you’ll learn trends about award availability, what airlines fly the routes you’re interested in, and how much you should expect to pay.
I've come quite a long way from my days of Southwest only redemptions! Photo by Ethan Steinberg/The Points Guy
I’ve come quite a long way from my days of Southwest only redemptions! (Photo by Ethan Steinberg/The Points Guy)

Bottom line

I still remember the feeling of pure elation I had when I got approved for the Chase Sapphire Preferred during my sophomore year of college (still to this date the only instant approval Chase has ever given me). Four years and 27 cards later, I’m still thanking myself for some of the decisions I made early on. Many of the cards I opened in those first 6 months will stay open forever, continuously boosting my credit score and rewarding me for getting an early start.

Featured image by Ethan Steinberg / The Points Guy

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