Last week I flew from Chicago to Charlotte, rented a car, and stayed in a Marriott hotel for 3 nights—all for free. On top of that, I accumulated 35,000 flight miles and got a free rental car upgrade. Some people think free trips are beyond their reach, but it is surprisingly simple to do.
I did something completely uncharacteristic of myself by leaving the family behind for a solo weekend trip to FinCon, a conference for financial bloggers, freelancers, & businesses. Though I had a bit of a rocky start, it turned out to be an amazing experience.
Here’s what I mean by rocky start.
I had a really smooth flight from Chicago to Charlotte, and I got the rental car with no problems. After a quick stop at the hotel, I headed downtown. I found a parking spot and emerged from the parking garage onto the streets of Charlotte ready to take the conference by storm.
The first guy I happened to see stopped me and asked if I had any spare change. He clarified that he didn’t even care if I had change and that he was just really hungry. Well thanks to the ridiculous Illinois toll way system (seriously Illinois, you’re the worst), I had no spare change. I did, however, have one last protein bar.
I apologized to the guy that I had no change and offered him my protein bar. He became annoyed, and he said “Man I’m diabetic, I can’t have no protein bar!” I was taken back by his sudden change of tone, so I just started to head toward the conference.
As I was walking away, he said “I bet you would help if I was white.”
Okay. I almost never get angry or offended. Seriously. Almost never. And I can’t remember the last time I had a confrontation with a stranger. In fact, I recently took a personality test that told me “You keep a level head, no matter the situation. You don’t get riled up easily, and you don’t jump into situations without first thinking through the short and long term results of your actions.” That pretty much sums me up.
Well, in this moment, all that went out the window. For some reason this guy really struck a bad chord with me, and I reacted before I thought. I turned around and started walking back toward him yelling “I’M TRYING TO HELP YOU AND YOU’RE CALLING ME A RACIST!!? I’m not sure what I said after that, but I kept walking toward him. In my mind I was wondering “Uhhh Mark what are you doing?”
I think I surprised him, and luckily he started walking the other way as he continued to talk trash. Now that I was fired up and in a bad mood, I turned around and headed down the street to check into the conference.
Back to reality
Luckily, all that rolled off my back pretty quickly as I got in there and started interacting with all of the awesome people I had only ever met online.
It was so cool to spend 3 days soaking up all of the energy of like-minded finance nerds and passionate entrepreneurs. There was also a lot of talk about flexibility, leaving the rat race, growing your business, etc.
But now I’m back home and readjusting to the fact that I have a family to support and a full-time job.
There is nothing quite like coming back from all of that only to return to your fortune 500 company on a Monday morning while you hang around the copy machine and ask each other how your weekends were [cue throw up sound]. I shudder even thinking about it.
But I digress. Let’s get to how I funded my trip.
Credit card benefits: The beginning
I’ve been playing the credit card game for at least the last 5 years, which has yielded me several thousands of dollars of cash and benefits. Before that, I always assumed taking advantage of credit card benefits involved some sort of financial trick that was beyond my ability to comprehend or execute.
When I found out my older sister was making $500 here and $500 there off of credit cards, I instantly became more interested. I thought if she (a microbiology major) could do it, then why couldn’t I? Heck, I was a CPA. If anyone could figure out how to make some free money, I should be able to.
Once I got my first $500 from taking advantage of the Chase Sapphire Preferred credit card bonus, I was hooked. Then I got one for Amanda. Then I did the same thing with the Chase Sapphire Business card, first for me, then for Amanda. That’s $2,000 alone.
Credit card general rules of thumb that I follow and recommend
Don’t waste your time with non-bonus spending benefits
If you are trying to earn twice the points by eating at restaurants or paying for gas, you are likely wasting your time (and money). Focusing on sign-up bonuses rather than everyday spending rewards yields far greater value.
For example, say the sign-up bonus is 50,000 points after spending $3,000 during the first three months. That equates to about 17 points for every dollar spent! Normal spending with most credit cards will yield 1-3 points per dollar spent. There is absolutely no comparison. Stick with sign-up bonuses.
Do not spend more than you usually would
If I were 100% against credit cards, this would be the reason why. If you are not disciplined, it is extremely easy to spend more than you normally would with cash or a debit card. Why? Because you don’t have to worry about how much you have in the bank. It’s natural to become lazy and just default to the credit card.
That’s why I recommend only using them for certain routine or large purchases. I use credit cards for groceries, gas, and large purchases (life insurance, car insurance, medical bills, home owners insurance, etc.).
Pay off the balance so as not to incur interest
This is probably the most common rule of thumb. Pay off the balance every month. If you don’t trust yourself to do this, then don’t get a credit card. Credit card interest rates are obscenely high, and you do not want get caught in that trap.
I recently got the The Citi / AAdvantage Platinum Select MasterCard (American Airlies). Sign-up bonuses change frequently, but when I signed up, the bonus was for 50K flight miles for spending $2K during the first 3 months. It wasn’t hard to spend $2K with normal purchases. We could knock that out with groceries alone.
But again, do not spend just to get points. That would be like getting a mortgage just for the tax deduction. It doesn’t make sense. Only use the card for what you would normally spend.
I booked the flight a month in advance, and it cost me about 25K of the 50K points I earned from the bonus.
More free points
Airlines will occasionally promote their credit cards during the flight. They were promoting the same card with a sign-up bonus of 35K points after spending $1,500 during the first 3 months. Now in many cases, you can’t earn a sign-up bonus twice from the same card (although I have done it).
I could have just assumed that was true in this case, but I asked the flight attendant if I would still qualify for the promotion even if I was an existing cardholder. He said I would still be eligible, so you better believe that I signed up. With those 35K points, I earned back the point cost of my flight plus some.
Free rental car
Most airlines have partnerships with rental car companies and hotels. When you redeem your points, you can opt for another service instead, though it may not be as good of a value. Some people really get into extracting the maximum value from every single point, but I just don’t want to spend my time doing that. I booked an economy size car for another 24K points.
Free rental car upgrade
Rental car upgrades are some of the easiest freebies available. You just have to know who to ask. When I arrived at the rental car desk, the person asked me all the typical questions about if I wanted satellite radio, GPS, insurance, etc., all of which I declined. She was all business. She gave me the contract, and I headed out to the lot.
When I arrived, I met a friendlier woman waiting for me. She was just going to let me go straight to get my little economy car and drive off, but I started asking her questions about the car, probably appearing a little bit clueless to her. She mentioned that I was tall, and I said, “Why yes I am. I’m very tall.” It didn’t take her long to offer me a standard size vehicle at no extra charge.
I am a pretty loyal Marriott customer. I’ve only ever had one bad experience in the dozens of times I’ve stayed there.
Similar to what I did with the Chase Sapphire cards, I have taken advantage of the sign-up bonuses for the Marriott Rewards Premier Credit Card (and business card version) for both me and Amanda.
Before you sign up, you will want to check to see if they have ever run a better sign-up bonus in the past. If they have, it’s almost certain they will be offering it again in the future, in which case you’ll want to hold tight.
To maximize my Marriott points, I try to find the hotel with the lowest category. A category 1 hotel costs the fewest points, and a category 9 costs a ton of points. Charlotte happened to have a category 1 hotel just a few minutes from downtown. In my experience, that almost never happens. I have stayed in many 2s, 3s, and 4s, but the 1s are hard to come by.
I called them beforehand and asked why they were a category 1. She just laughed at me when I asked if they were in the ghetto. After staying there, I’d guess it was rated a 1 because it is not as newly remodeled as most, but it was still nice.
How to find the best credit cards
I’ll tell you what I do. I just go to nerdwallet’s credit card bonus offers page and sort according the largest sign-up bonuses. Sidenote: This is not a sponsored post. Nerdwallet makes a killing from people signing up with their credit card links. I, however, make nothing 😐
So as soon as I meet get my 50K points for my current Gold Delta SkyMiles Credit Card sign-up bonus and the AAdvantage inflight bonus I signed up for, I’ll head over to that page again and see what the best offer is that I haven’t taken advantage of.
Between Amanda and me, we’ve probably gone through about 50 credit cards. Rather, I’ve gone through 50 cards for both of us. I’m always switching the cards around in her wallet.
Most credit card points experts probably wouldn’t recommend it, but I’ve cancelled most of them, and my credit score is still hovering around 800, but that’s a whole other discussion.
We currently have about 350K flight and hotel points (some of which are redeemable for cash & gift cards). That might sound like a lot, but they are pretty easy to burn through if you’re not careful.
Hopefully this gives you an idea of what’s possible. There are a lot of resources out there for people who want to take advantage of these benefits. One resource I especially appreciate is points with a crew. It’s great that singles and DINKs (dual income no kids) can travel the world for free, but what about families? Dan felt the same way and now writes about how he does this with his wife and 6 kids.
I’d be happy to answer any specific questions any of you credit card newbies might have. Just shoot me an email.
Whatever you do, don’t say I didn’t offer, because you know what might happen then.
Is there something holding you back from taking advantage of credit card rewards?