Guest Post On Credit Card Churning

Level 2: Value Investor

Welcome Avatar! This is a guest post from

BowTied Bum

who walks through utilizing the credit card system for higher rewards (cash/credit). For those with no interest in back story you can jump straight to the section called “Part 2: Now”

**Generally speaking**, churning likely applies most to people who fall into one of three categories: 1) younger side with extra time, 2) married or with a biz so you can have two different “entities” with cards and 3) anyone with free time on their hands in a white collar position.

Part1: Personal Story

My father-in-law was born and raised in Eastern Europe. Growing up, his life was pure hell. Rations... Waiting several hours in line for toilet paper, oranges, bread, etc was the norm. Rampant alcoholism was the norm. Men (not him) taking their frustration out on their wife and children was the norm. The sad thing was, no matter how ambitious you were, no matter who strong minded you were, there was no hope. There was no internet, no WiFi money, and zero chance at elevating your status. I could only imagine what that would be like.

Naturally, as a man, you do whatever you can to help your family. Shortly after his kids were born, was able to flee Eastern Europe for Western Europe, where he was able to start a better life for him and his family. Literally risked it all for his family, at a time where apartments and houses were bugged and you could get persecuted for fleeing.

Fast forward a few years, this man has a zest and passion for life and loves to travel the world. But due to circumstances, didn’t have a lot of disposable income to do so. My wife and I would always offer to pay for his flights and hotels, so that he could join us on trips, but as an old school strong minded man, he always refused. It pained us that he would miss out on potential trips, simply because he didn’t want us to pay for him.

It wasn’t until I was able to convince him and prove to him, that I was traveling the world for free on credit card points (and willing to cover his flights too), that he would join us. See, if I paid out of pocket, he was adamant about paying his own way and wouldn’t accept. This meant that I wouldn’t get to know him at all. The credit card churning and points game, literally was the difference in whether or not I got to know my father in law or not. I’ll be forever grateful for getting the opportunity to connect with him thanks to this crazy game.

I finally convinced him that we were not paying out of pocket for any of this, and I forwarded the hotel and flight confirmations that showed a $0 charge. We’ve been on over five international family trips together, and he’s got to spend precious time with my daughter. The two of us have gotten to be good friends, and will continue to travel the world together for as long as he is able to.

2 Magical Weeks in Paradise: How I Did it Then, and How I Would Do it Now

Intro: A few years ago, my wife and I spent two weeks in Hawaii. One in Maui and one in Kauai. We flew from the east coast, and did not pay out of pocket for airfare, hotels, excursions, rental cars, and even flights between islands. Here’s how we did it back then.

Hotels

Maui: A few years ago, the Starwood Preferred Guest (SPG) program was the clear winner in the hotel rewards game. Starwood offered a lucrative Personal and Business card. Points were extremely flexible with lots of airline transfer partners, and you could get a 5th night free when you used points to redeem 4 hotel nights. Savy credit card churners were able to earn tons of SPG points and book exotic vacations all over the world for free. It was a great time.

Since then, SPG merged with Marriott, and their rewards ecosystem took a hit. However, all the SPG points converted to Marriott points at a 1 SPG to 3 Marriot points ratio. Suddenly our 140,000 SPG points (earned from P1 and P2 earning the signup bonus from the SPG Personal and Business card) turned into 420,000 Marriott points, and we were able to book 7 free nights at Sheraton Maui Resort & Spa in Lahaina, and still have points left over.

At the hotel, we told them it was our honeymoon (break the rules not the law) and we got upgraded to an ocean view.

Kauai: Kauai is a much sleepier island. There’s hardly an nightlife and fewer restaurants. We came here to hike and visit remote beaches. We got one single credit card for this trip: The Hilton Aspire Card. It comes with a $450 annual fee, but includes a $250 resort statement credit, $250 airline credit, $100 property credit, and Diamond Status which includes room upgrades, free breakfast, complimentary drinks, and more. Needless to say this card pays for itself each year, but you can also downgrade it to a no-annual fee card after the first year if you want.

Hawaii is not a place you want to visit and stay on property the whole time. Especially in Kauai. We stayed at the Hilton Garden Inn Kauai Wailua Bay, because it was in the middle of the island and close to the airport. This made day trips easy and we got to see the entire island during our week

That one single credit card we got, covered an entire week’s stay here, free complimentary breakfast, and two complimentary evening cocktails. We enjoyed the pool, but we mostly used this hotel as a place to crash at the end of the day after day trips elsewhere. If you want to see Kauai and marvel at its beauty, this is a fantastic option. If you want to go to Kauai and stay in the pool all day and stick to the property (can’t imagine why), there are other options.

Flights

East Coast to Maui: This was fairly straight forward. My wife and I have been banking up as many Amex Membership Rewards points as we possibly could.

Membership Rewards points are fantastic for transferring to airline partners for first class and business flights. Domestic flights often aren’t as good of a deal, and it’s often times better to just pay cash. By holding the Amex Schwab Platinum card, we were able to cash out our points at 1.25 cents per point (now 1.1 cents per point) and just pay cash for our flight.

We flew from the east coast to LAX, and then LAX to Maui

Maui to Kauai: We were able to save a ton of money, by transferring Amex MR points to Hawaiian Airlines, and then booking the round trip flight directly through Hawaiian Airlines using points. Two adults, round trip, for 30,000 HawaiianMiles was an absolute steal.

Rental Cars

Maui: There is a shortage of rental cars in Mauai and the price is usually astronomical. We decided to use our Chase points here, and redeem them for a statement credit to pay for our car. We used Turo, which is essentially AirBnB for cars. We paid under $600 (with a promo code for first time) for 8 days in Maui. Our experience? Could not have been better. We’ve heard about how some people wait hours to get their rentals from the Maui airport. We simply opened our Turo app, which gave us detailed instructions on how to find our car. We walked a couple minutes to the parking lot, where we found our card, opened the door, and got the keys from the glove compartment. It could not have been easier.

Kauai: Despite such a successful experience with Turo in Maui, we booked this trip in advance and didn’t know how Turo would go, so we booked a rental car for Kauai using Chase Ultimate Rewards points, redeeming the points for 1.5X through the Chase travel portal.

Excursions

The nice thing about Hawaii is while it’s expensive to get there and expensive to stay, some of the best activities are free once you’re there. Some of the best hiking in the world. Some of the best picturesque beaches in the world. Again, if you’re staying at your resort all trip, you’re doing it seriously wrong.

Maui: We booked a Molokini & South Maui Coast Tour with a company called Redline Rafting Company. This was a half day rafting and snorkeling tour where we got to see sharks, snorkel in water that offered hundreds of feet of visibility, and it was a great way to see the island. Highly recommend. Even better, we got to use redeem Chase points for 1.5X through the Chase travel portal. This cost $300 for both of us or 20,000 Chase UR points. Magical day.

Kauai: For those of you who’ve seen Jurassic Park. Remember when they flew past that waterfall in the helicopter? Well, that was in Kauai. Naturally, that was an absolute must for me. While there are several options, Blue Hawaiian Helicopters is the company you want. The experience was even better than I could have imagine. We used Chase Ultimate Rewards points to cover it for both of us, however, we paid $100 in cash (each) to be able to sit in the front of the helicopter. One of the coolest things I’ve ever done.

Not cheap, but worth every penny (especially when it was free with points)

Part 2: Now

With the SPG/Marriott merger and devaluation, I’d do things a little bit differently now.

The BowTiedBum members in the Slack community earning $50+ WiFi money each night (or 6,250 Chase Ultimate Rewards points) are jumping for joy and ready to tell their wives to pack their suitcase. That Hilton Garden Inn we talked about above? You can earn enough for a free night roughly every 3 days with the methods in the Slack Group. There’s also amazing Hyatt opportunities on each island that we’ll cover, so we can put all those Chase points to good use.

Let’s get right into it.

Hotels

Maui: Forget that Sheraton hotel. For Maui we’ll be focusing on two options: Hyatt Regency Maui Resort and Spa for a great use of our Chase Ultimate Rewards points, or Ka'anapali Beach Hotel (right next door) for a more budget friendly option.

The Hyatt is in a great location and the redemption options are great, with nights starting at 30,000 points. You’ll see the cash rate is double, so you’ll be able to redeem points at over 2 cents per point.

The BowTiedBum members in the Slack group playing this game with a P2 (second player spouse, parent, etc) will earn a free night here every 5 days. The play here is simple. Earn as many Chase Ultimate Reward points as you can by following the Q1 and Q2 plan as well as the methods taught in the paid Substack and Slack Group.

If you want a more budget friendly option, the Ka'anapali Beach Hotel works too. It’s very close by, and in a great area. You can book this in a few ways.

1. Directly through the Chase Travel Portal at 1.5X if you have a Chase Sapphire Reserve

2. Use the Chase PayYourselfBack to redeem for a statement credit against any gas charge for 1.25 cents per point (if you are still paying for gas, see below)

3. Cash out your Amex points at 1.1 cents per point if you have a Schwab Platinum card

Either way, you can’t go wrong. If you’re flush with Chase points (everyone in the Paid BowTiedBum community should be), the Hyatt is definitely a nicer hotel and a great choice. If not, the other hotel is a fine alternative.

Kauai: The Grand Hyatt Kauai Resort & Spa is a spectacular hotel and a great redemption option at 30,000 points per night. This hotel can often cost you about $1,000 a night cash, so your points will be worth over 2.5 cents per point here. If you book far enough in advance, you can also find off-peak dates for less than 30,000 points per night, making it an even better redemption.

My advice? If you have dates locked in, book as early as possible as this hotel fills up quickly.

If you want a more budget friendly option, the Hilton Garden Inn (mentioned above) works too. You can book this in a few ways.

1. Directly through the Chase Travel Portal at 1.5X if you have a Chase Sapphire Reserve

2. Use the Chase PayYourselfBack to redeem for a statement credit against any gas charge for 1.25 cents per point (if you are still paying for gas, see below)

3. Cash out your Amex points at 1.1 cents per point if you have a Schwab Platinum card

4. Get the Hilton Aspire Card and redeem your Hilton points

Flights

The BowTiedBum community members following the Q1 and Q2 plan should be building a nice portfolio of points by now. I’d recommend heading over to point.me and purchasing a 24 hour pass for $5. Here, you’ll be able to choose your preferred airlines, preferred class (economy vs biz/first class), number of stops, etc. You simply choose your rewards currency, do a search, and point.me will automatically find the best use of your points.

Note that transferring your points to partner airlines isn’t always the best value, particularly when you are flying domestic. If this is the case, you can book flights in a similar fashion as the method mentioned earlier:

1. Directly through the Chase Travel Portal at 1.5X if you have a Chase Sapphire Reserve

2. Use the Chase PayYourselfBack to redeem for a statement credit against any gas charge for 1.25 cents per point (if you are still paying for gas, see below)

3. Cash out your Amex points at 1.1 cents per point if you have a Schwab Platinum card

If you are flying in between islands, definitely check out the Hawaiian Airlines transfer option, as that will often be a much better value.

Excursions

I wouldn’t change a thing here. See the “Excursions” section above. I’d stress the importance of leaving the property as much as possible and seeing all that each island has to offer.

Conclusion and Next Steps

While this post covered a loose plan to visit Hawaii for two weeks for free, I didn’t go into detail in how to earn the points. My paid substack

BowTied Bum

covers that in depth. As a paid member, you’ll get access to the Slack Community, where you can ask questions, connect with others, and share your wins. My Substack includes a step by step plan for each quarter, that discusses the best cards to apply for and how to generate a ton of points.

The goal for each member is to earn $10,000+ within their first year, and I break that down into a separate plan for each quarter, to make it easier to ensure success.

Additionally, the paid Substack discusses several manufactured spending options, which allows you to put a lot of spend on your credit card and quickly convert it into cash or money equivalents

There’s been a lot of success stories so far in 2023, and if you’re interested in joining, I recommend reading those and then reading their comments in the Slack Group. There’s no reinventing the wheel here. People that follow the steps and take action win. Twitter DM’s are open if you have any questions or comments.

Good luck and WAGMI.

Disclaimer: None of this is to be deemed legal or financial advice of any kind.

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Disclaimer: None of this is to be deemed legal or financial advice of any kind. These are *opinions* written by an anonymous group of Ex-Wall Street Tech Bankers and software engineers who moved into affiliate marketing and e-commerce. We’re an advisor for Synapse Protocol 2022-2024E.

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