My good friend and I were at lunch with our wives discussing how to optimize his current development project and the subject of credit cards came up. I realized I haven’t shared the system I use in my personal and business life that has allowed me and my family to travel for free and stay in hotels for free for years. When I left my W2 role 6 years ago, I went from having an expense account to being responsible for all of my own expenses. I did some research and this is what I came up with:

The Chase Card Trifecta: This is from “The Points Guy”. I use the Chase Sapphire for our personal expenses, the Ink Business Preferred for my business and the Ink Business Cash for our real estate business. At any given time we usually have $5k-$10k in value in our points! Free flights? Yep! Free hotels? Yep! Upgrades? Yep! Read the article, see if it makes sense and put this system in place for you.

Amazon Prime Credit Card: My partner, Brandon Abbott, told me he expenses everything on his Amazon Prime card. So I checked it out. Since I call Amazon/Whole Foods my “second mortgage” (we spend ~$2000 combined monthly), I thought this would make sense for Whole Foods and Amazon purchases. Remember we are feeding 4 and stocking our AirBnBs, usually from Amazon. 5% back? 2 boys who eat a foot-long sub as a “snack”? We are getting over $100 back a month with this card. Yeah, this makes sense!

Citi/AAdvantage Executive World Elite Mastercard American Airlines: One thing I’ve learned in traveling hundreds of thousands of miles in my career; loyalty pays. If you like an airline or hotel chain, use their loyalty programs. I chose American Airlines for the Charlotte hub. I can fly from Asheville to Charlotte or Dallas to almost anywhere. Oh, and if I miss a flight to Charlotte? I can drive and still catch my connection. Sometimes it’s easier or cheaper to drive the family to Charlotte and get a flight from there. One February we had an ice storm; no flights out of Asheville. Se we drove to Charlotte that morning and caught our flight to Austin. Try that through Atlanta! Another trick I use? Fly out of Charlotte and hire a car to drive you there. I get 2 straight hours of time to work in the back seat and a direct flight. I got the extra credit card so I get free bags, upgrades and Admirals Club membership. Getting on the plane ahead of everyone, with a free bag, then feeding your family of 4 for free in between flights in the Admirals Club? Sweet! Oh, don’t forget to use the free TSA Pre√ credit, then you and your travelers can avoid the lines. This is key when using all your points that you exchanged via the Chase Rewards program. I just got upgraded to First Class coming back from SLC. Nice perk. Oh and when they sent me some checks with 18 months of 0% interest a couple of years ago? I used a check to pay for my pool and paid it off 18 months later. That money was used to invest at 15%. Investing $40,000 at 15% for 18 months = $9,450 compounded. That’s called arbitrage!

Marriott Bonvoy: Again, loyalty matters. I’ve found Marriott to be a great option. Courtyards are everywhere, have nice lobbies and you can stay at nicer, boutique properties as well. Even short-term house rentals. You can swap points from Chase (I just exchanged at 1.5x rate). Jess used these points to pay for a hotel for a girls’ weekend. Since she “paid” for the hotel, her friends are paying for everything else for her. She used our points to book the flight as well. We get free upgrades on our rooms, access to the Concierge level (free food for our 2 boys – always a consideration) and free high-speed internet. We get upgraded about 50% of the time as well.

So now you know the system I use to combine credit cards to maximize the dollars we spend and turn them into free experiences for my family. However I still pay for certain trips through my business.

You don’t have to use this exact system for you. Do what makes sense for you and the loyalty programs you enjoy. But if you optimize a system like this, you will create thousands of dollars of value that you can enjoy and use for time with your loved ones!