This is why you shouldn’t let AI guide your points strategy: an epic fail by ChatGPT.

My second biggest mistake in points and miles: The Chase Business Ink Premier does not have transferrable points

I am a travel hacker. I’m borderline obsessive about it. I listen to the podcasts, read all the updates, and I’ve racked up over 6 million points since I started this hobby. I’ve taken my family on really epic trips using credit card points. BUT. Lest you believe someone like me wouldn’t make a mistake at this point – I definitely did. And a BIG, dumb one at that. 

I blindly trusted AI to help me choose my next business card, and it backfired. 

How it happened

I was in a time crunch trying to choose a new business card for our next Venture X location. Things are so fast paced after a new lease gets signed and we just needed a new card, fast, so I consulted my former best friend, ChatGPT about which card I should get next. Chat KNOWS me, ok? It knows I’m a travel hacker and has coached me through many, many card openings before. But in hindsight, I was always the one guiding the conversation in the past. This time, I asked Chat straight up: Which business card should I open next? The answer sounded confident and reasonable. And since it does know sOooOOoo much about me, I trusted it.

It pointed me to the Chase Ink Business Premier.

I opened it immediately, without hesitation, and we we’re off the to race.  There is so much to do and so many expenses right after lease signing.  From building signs to flooring to setting up internet and buying furniture, as a business owner, this is PRIME time to rack up the credit card points. I was so busy with getting our business set up, I didn’t even have time to look in my portal or think about transferring points out for a vacation. I just swiped my card, knowing my points would be there when I was ready to transfer them out. 

The Big Whoopsie

What ChatGPT failed to flag for me is that the points on the Ink Business Premier are not transferable. Not to airline partners, not to hotel partners, and not to another Chase card. The other Ink cards (Cash and Unlimited) let you move your points into a Sapphire or Ink Preferred account, where they become transferable. The Chase Business Premier is the only one where you can’t do that. That was how I figured out that I had screwed up. I tried to move the points I had earned into my other transferrable Chase account (like I do all the time from my other Ink cards) and the option to combine points wasn’t there.

Quick side note for the newbies: transferrable points are really the ONLY points we care about in the points and miles and travel hacking world! They’re so much more valuable than points that you can only use in the bank’s travel portable. We’re talking drastically more valuable: 1 cent per point in the portal vs upwards of 4-6 cents per points when you transfer the points out to partners (more if you’re an expert!) If you’re new, you can start here to learn more. 

When I ran into the roadblock of trying to combine these points with my other Chase points, I went back and consulted Chat and asked why it wasn’t working. ChatGPT actually told me that it was a glitch and I should call Chase! It wasn’t until did more research and pressed the issue further that it finally relented and said the classic, “Good catch, my mistake, that card cannot actually combine points with other the Chase Sapphire Preferred or Chase Business Ink.” Meaning, the points were trapped in that non-transferrable account.

To make it more confusing, Chase’s terms call them “Ultimate Rewards points” on this card too. So a quick search, or a quick AI answer, can easily make it look like the same currency as the cards travel hackers love. But it IS NOT, my friends, it is not.

I only found this out after I had racked up 300,000 points. OUCH. Big ouch. 

What those points are actually worth

Instead of having 300,000 transferrable points, I have 300,000 points that are only usable inside the Chase portal. They do still redeem at 1 cent-per-point, so I’m not totally out of luck. I have about $3,000 sitting there. But in a transferable currency, points like these can be worth far more when used for things like business class flights or high end hotel stays. So while I didn’t lose the points, I lost the opportunity to transfer them for a much higher value. That lost opportunity is roughly a $6000+ loss, at minimum.

Using AI for points and miles strategy 

AI is great for brainstorming, comparing options, explaining concepts and even planning trip itineraries But it should not be your final decision maker. Before opening any card:

1. State your goal in the prompt (for example, “I want points I can transfer to airline and hotel partners”).
2. Ask directly: “Are the points on this card transferable to partners? Show me where the card issuer says so.”
3. Verify on the issuer’s official page, and with a trusted points site or community.
4. Check whether the card’s points can be combined with your other cards.
5. I’d recommend using Claude over ChatGPT. You can create a project in Claude that you can continue to work on over time. It has been more reliable for me. 

The Takeaway

I have three takeaways for you. Lessons from the trenches, if you will.

1. On the bright side, I’m about to gain the most experience I have ever had in booking travel through the Chase portal. My tentative plan is to use it to use part of it book our hotel in Osaka, Japan for our big Japan/Korea trip next spring. I might also book our flights from Japan to Korea, depending on what I can find using points.
2. This brings up a good point: sometimes, the cash price DOES make more sense than the points price, if you have the ability to use either one. I find this most often with Marriott hotels. The points price just doesn’t make sense when you compare the it to the cash price (which is why I almost never stay at Marriott.) It’s always good to check the cash vs. points price when booking travel. Even if it would technically be “cheaper” to pay with cash than points, it can still make sense to book with points if this was something that was out of reach for you if you had to pay cash. Then using points is a great deal because it made an otherwise impossible trip, possible!
3. AI can be a great research assistant but it isn’t perfect. It requires specificity and always a reconfirmation. Tell your friends. Use me as the example. Friend’s don’t let friends get duped by AI.

Also in case you’re new here, this is just my second biggest points and miles mistake. If you want to learn about my BIGGEST mistake, you can read about it here: My Biggest Mistake In Points and Miles.