Upgrading Your Travel with Credit Card Points

Today, I’ll share the best of my conversation with lifehacker, financial optimizer, and podcast host ​​Chris Hutchins​​.

Chris was co-founder and CEO of Grove (acquired by Wealthfront), co-founder of Milk (acquired by Google) and a partner at Google Ventures. He was also the former Head of New Product Strategy at Wealthfront. Now, he’s building his award-winning podcast ​​All the Hacks​​ full-time.

All the Hacks​ is one of my favorite podcasts and I highly recommend you check it out if you want to learn from Chris’s fanatical research and world-class guests (​​Sahil Bloom​​, ​​Derek Sivers​​, ​​Tony Hawk​​, ​​Bill Perkins​​, and ​many more​.)

Let’s dive in.

The Points Game

Chris is a credit card point master. At one point, Chris ​held over ten million credit card points​. (Chris, I hope you’ve spent a good chunk of those by now).

So, it should come as no surprise that his number one piece of advice for upgrading your travel experience is, simply, “play the points game.”

Before we dive into a few of his strategies, I offer a warning:

Do not make purchases to earn credit card points.

Credit card points are rewards for spending that you would have done anyway. They are often worth pennies on the dollar.

Pay off your credit cards entirely each month.

Never carry a balance. You will pay interest rates of 25% or higher. If you already have credit card debt, pay that off before worrying about playing the points game.

Now, let’s get into it.

Chris’s Card Stack

Chris uses 7 credit cards:

  • Chase Freedom Flex (5X Points on Rotating Categories)
  • Amex Gold (4X Points on Dining & Groceries)
  • Amex Platinum (5X Points on Flights)
  • Marriott/Hilton Cards (6-7X Points on Hotel Stays)
  • Chase Sapphire Reserve (3X Points on Travel & Dining)
  • Amazon Prime Visa (5X cash back on Amazon)
  • Capital One Venture X (2X Points on everything else)

No matter where he’s spending, he’s earning maximum rewards. He also got welcome bonuses for most of these cards, often valued at more than $1,000.

*If you’d like to apply for any of these cards, you can easily research and apply from ​the “Credit Cards” link​ on my website. It’s an easy way to support my newsletter, so thank you for all of you who’ve already done so*

How to Use & Earn Credit Card Points

The three easiest ways to earn credit card points are:

  1. Welcome Bonuses: When you get a new credit card and spend a certain amount, you’ll often earn large bonuses up to 100,000 points
  2. Referrals: If your friends or family need a new credit card, you can often send them your referral link to earn 15,000 points or more
  3. Spending Bonuses: In your credit card portal, check to see if specific vendors are offering promotional rewards. Today’s sponsor, ​Card Pointers​, has browser extension that adds Amex and Chase offers to your cars with just 1 click.

The best ways to use your credit card points are through transfer partners. With the occasional exception, like Chase to Hyatt, airlines tend to offer the most reward value.

For example, Chris recently booked ​business class flights to French Polynesia​ for 220,000 Chase Points. These flights are normally priced at $4,783 round-trip, meaning his credit card points offered a 12.9% cash back return.

One thing that Chris taught me that I love is that you don’t need to get a perfect deal when using points for it to be worth it.

“I’ve spent so much time optimizing for a dollar-per-point value that I’m doing myself harm,” he said. “It’s time to burn down our points balance instead of just looking for the absolute best deals (although I’m sure I’ll still look).”

Rapid Fire

Cole: What tools do you use to organize email?

Chris: ​Superhuman​

Cole: What financial apps do you use?

Chris: Copilot, ​Kubera​, and ​Trustworthy​

Cole: Did you get a virtual assistant? If so, where did you find them?

Chris: Yes, ​Oceans​ and it was amazing.

Cole: Besides points, what’s your favorite travel hack?

Chris: Book your hotel directly with the hotel and email to tell them you’re excited to stay there. More often than not, you get upgraded, an amenity, or some other perk.

Cole: Any hacks for vacation rentals?

Chris: Take the main photo from the VRBO or Airbnb and put it in ​Google Image Search​ to find other sites that rent the same property for less.

Cole: Favorite international destination?

Chris: Japan for sure. Check out ​my Japan episode​ to learn more.

Cole: If you could give your younger self one piece of advice about managing money, what would it be?

Chris: Treat every dollar deposited in your account as savings and every purchase as a decision to spend your savings.