25 Thoughts I’ve had after Learning to Travel Hack with Credit Cards.

In Feb 2013, my beach real estate purchase fell apart, and I was frustrated.  I wanted to spend a big chunk of the summer at the beach, and I began scouring the internet for cheap travel options. Luckily, I discovered Frugal Travel Guy.  FTG lead me to posts by Frequent Miler, The Points Guy, Travel is Free, and many other bloggers who dispense methods to efficiently abuse take advantage of credit cards, loyalty programs, and promotions.

Mrs. JumpStart and I started with 6 credit card applications on the first day, and I have been hooked ever since.  During the last 4 years, I have applied for at least a hundred credit cards, been on lots of free planes (sometimes in first class), had lots of free hotel nights (sometimes suites), and cycled hundreds of thousands of dollars through credit cards.  The techniques and opportunities have changed quickly over the years, and I have relied on these awesome bloggers to help me keep up.

The following thoughts flow through my head, and now seem completely normal/justified.  I doubt any of my friends/colleagues will understand them (except Bill), but I hope it will be entertaining for other travel hack addicts.

25 Thoughts I’ve had after Learning to Travel Hack with Credit Cards.

  1. I can’t afford $59 to stay in that crappy bargain hotel, and so I’ll just stay at the Intercontinental for free instead.
  2. Crap! The Uber ride away from the airport was way more expensive than the plane ticket.
  3. I’ve never stayed at this brand of Hotel. I am a platinum member here.  What free stuff do I get?
  4. All I have to do is charge $25k this month on my credit card to get ______. No problem.
  5. Why does this bank value me as a customer? They continue to give me stuff, but I’ve never paid one dime in interest or fees ever.
  6. No, please don’t cancel my order. It wasn’t a mistake duplicate order. (There are 7 orders.)
  7. No. It wasn’t a mistake duplicate application. (I applied for 7 cards.)
  8. This guy sitting next to me in business class. Is he actually rich, or did he get this flight with miles too?
  9. I’ve earned 120k British Airways miles, and spent 80k of those miles on flights. I’ve never been to the UK, and never been on a British Airways plane.
  10. What Visa category is this business?
  11. It’ll be cheaper to fly there, than to buy gas for the car trip.
  12. What am I going to do with all these 1-800 Flower bouquets and Sears junk?
  13. I only earn $52k per year, but I could charge $82k on Chase cards today.
  14. I only earn $52k per year, but according to my credit report, I have $235k in available credit.
  15. I’ve already spent my $50K limit at Staples this year, but I can’t find a pen anywhere in my house.
  16. I know it’s cheaper at Amazon, but what are the portals paying?
  17. If they would let me use split transaction swipes to buy that house, it would be mine.
  18. So, you’re bragging to me about a single free flight after using the same credit card, exclusively for all your spend, over an 18 month period? Moron. Please let me teach you.
  19. My credit score has drifted too high, and now I really need to do some apps.
  20. Just how many Alaskan Airline cards have I had now? Like a million?
  21. I need something from Lowe’s, but the Lowe’s quarter is over. Should I:
    • Buy a Lowe’s card online and go through an online portal?
    • Grab a gift card at Kroger and go through an online portal?
    • Grab a gift card at Staples before heading to Lowes?
    • Do I have any AMEX gift card to liquidate?
  22. Is this guy in front of me paying for groceries with an IHG credit card. Moron. Is he freaking crazy?
  23. Yes, I’d definitely rather spend 35k Hilton points than 15k Starwood points.
  24. This deal can’t last long. Who is running the company, and what are they thinking?  Better hit this hard before it dies.
  25. Remember the good ole days of the double browser trick, Vanilla Reload cards, open jawed flights with stopovers, red birds, blue birds, and the mint?

Leave any other thoughts in the comments.  Special thanks to all the bloggers spreading the word about these great deals.

Posted in Credit cards.


  1. I entered the game literally the same month I’m pretty sure as the Vanilla card option was shut down. Definitely had me scrambling with my strategy, but figured it out. Heading to Japan in the spring–even got the $50 surcharge cancelled out with points!

    • Our first applications included Hilton and Hawaiian Airlines that could be transferred to Hilton. I really wanted to stock up on free hotels more than airlines at the time. It felt like it was 5 minutes after we got the Hilton points in our account when Hilton devalued their points and made it like 90,000 points to stay in a top hotel.

      I got a redbird card after finally having an excuse to be in Richmond. I only got to load the card once with my credit card before Target shut that down.

      You gotta grab what you can get quick in the travel hack game.

      I’ve got to get to Asia one of these days. Have a great trip Femme.

  2. Ok, so I didn’t get all the references, but that’s because I’ve never travel hacked. I take my rewards as cash, which I know isn’t as lucrative. One of these days I’ve got to get into travel hacking!

    • You can’t go wrong with cash back. I like being forced to spend my rewards on travel. It’s kind of like getting a gift card that makes you go to a restaurant.

    • My biggest obstacle to actually taking the trips is the Roanoke airport. Only American and United. I can drive about 5 hours or less to lots of airports though.
      I have lots of summer unemployment time, but that is when it is most difficult to book award travel.

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