How I Play Credit Card Roulette to Fund my Racing Season

So this is the story of how I abuse part of the financial system to fund my race season and parts of my vacations.

I first started credit card roulette in 2019 when I was working as a consultant and traveling a lot. I first picked up a Hilton Honors credit card and waited for the best offer on a Delta SkyMiles Gold card. Because I was having work expenses (that were reimbursed) I crushed the minimum to pick up the introductory offers in like 3 weeks, so I kept my SkyMiles card as my primary card but began picking up more credit cards every 3 months.

Credit cards with a $0 annual fee don’t have great introductory offers but I’ll sign up for them all the time because you usually have to spend $1000 in three months and you get it. That shit is pretty easy—I think I have at least 15 different $0 annual fee cards from the last three years.

The annual fee cards (which basically cost like $95/year) have better introductory offers. I fleeced Alaska Air and Hilton Honors Surpass for their introductory offers which typically require you to spend $3000 in the first 3 months.

I don’t really care about canceling cards or my credit score either, it’s over 800 and even with playing the system it hasn’t been under that in at least a decade. I’d typically sign up for two and cancel an annual fee card. FYI if it’s a $0 annual fee card you never have to close it! However you can call and say you want to close it and then they’ll make you an offer like spend $500 in three months then get 5000 points or miles. Then in a few months I’ll to cancel the card again and then they’ll make you another offer.

Next, if you sign up someone on your account you’ll get like 2500 or 5000 points or miles. Don’t do this if you can’t trust them to wreck your credit by maxing out your card or putting you into debt. There are only two people I’m comfortable enough doing this with that I know won’t screw me over and it’s because they’re comfortable enough to have me on theirs.

Now Hilton cards are special, first of all…their points are inflated, they’re only worth like 0.5 cents per point, but there is a catch, you get 3 points for every dollar you spend on Hilton card for the basic shit which makes those points worth 1.5 cents for every dollar spent. Marriott cards work like 0.8 cents per dollar spent. Delta SkyMiles and pretty much all major US airlines are worth 1.5 cents per dollar which is why I kept that as my primary card.

FYI most of these annual fee cards have an amount you need to spend in a year and you get a flight credit or points. For Delta you need to spend $10k in a year and get $100 credit, I got those from 2019-2022. For Hilton Honors it varies depending on what you sign up for as part of their offer but if I spent $15k in a year I got a free weekend night at any point value which I spend on expensive hotels, I picked up three of those too.

You’re about to ask me “How did you spend $25k in a year as a single man with no dependents on your credit cards?” Well, I was involved in a major lawsuit and had medical bills regarding my case that weren’t covered since I couldn’t work (this no insurance). So I’d rack up some major monthly bills and just pay it all off with part of my insurance money. FYI…I have no credit card debt and never have, I’ve also never carried a balance in my adult life.

Hilton Grand Vacations Timeshare offer…Okay so periodically Hilton will offer you a good deal on a 4-day 3-night stay in some place fun but you gotta listen to their Timeshare pitch for two hours and they’ll give you 15k points (sometimes more) too. Look, take the offer and go have fun. I just took my mom with me to Vegas at one of their resorts for like $200 and I just told them “No thanks, I don’t want it” and we went about our merry way. You gotta say “no” though because it’s a scam—we had a blast.

Hilton Grand Vacations are completely unrelated to the Hilton Hotels and I don’t know why they even associate themselves with that operation because I very much enjoy staying at their hotels. Jenn and Ross Cannon got me on the Hampton Inn kick because I’ve stayed at some pretty shitty hotels for races in the past.

Delta has a shopping Chrome extension that offers better value than Rakuten or RetailMeNot. I’ve earned like 70k SkyMiles on there.

If a guy with brain damage can play credit card roulette then anyone can. Oh, so here’s the approximate haul in a 3-year span to fund my racing:

Delta SkyMiles — 400k SkyMiles, 3-$100 flight credits

Alaska Air Miles — 75k miles + companion pass (les $122 fees)

Southwest Rapid Rewards — 65k points

Hilton Honors — 900k pts (a Hampton Inn averages like 30k pts/night) +3 free weekend nights

Radisson — 50k points (2 nights)

IHG — 40k points (1 good night) — 4 free nights

Wyndham Hotels — 15k points (2 nights)

Park-n-Fly Airport Parking — 8 free days

National Rent-a-car — 2 free rentals

Oh, I also acquired a shitload of free drink tickets as a consultant but ended up giving them away when I got sober January 1, 2020. I picked a hell of a time to get sober too.

It feels good to write again, I’ve been on a six month hiatus.

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