133. 7 Keys to Better Award Flight Bookings

Point Me To First Class

Devon Gimbel MD

Finances, Education, How To, Travel, Credit, Expenses, Card, Cards, Society & Culture, Professionals, Tips, Personal, Places & Travel, Business, Points, Rewards

5 • 1K Ratings

🗓️ 15 September 2025

⏱️ 49 minutes

🔗️ Recording | iTunes | RSS

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Summary

You’ve built up a stash of transferable credit card points. Maybe you’ve been working hard to optimize your cards, your categories, and your spending. But when it comes time to actually book the flights you’ve been dreaming about, you hit a wall.

You’re not alone. For most points travelers, the hardest part isn’t earning points — it’s redeeming them for the best value. That’s why in this episode, I’m sharing the seven keys that make the difference between endlessly searching without results, and booking award flights that let you travel better, more often, and for less.

I’ll walk you through how to identify your transfer partners, understand transfer ratios and timelines, leverage alliances and partnerships, and master booking calendars so you can finally unlock the outsized value your points hold.

Whether you’ve only booked through your credit card’s portal or you’ve tried transferring points before and got stuck, these seven keys will change the way you approach award flights.

Turn your expenses into points and save tens of thousands of dollars a year on your wishlist travel. Don’t miss out! Click here http://www.pointmetofirstclass.com/pointsmadeeasy to know more about my comprehensive online program, Points Made Easy. Enrollment opens on September 20, 2025 to September 27, 2025.

Transcript

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0:00.0	Welcome to Point Me to First Class, the only show for employed professionals, entrepreneurs, and business owners who are looking to optimize their higher than average expenses to travel the world.
0:10.7	I'm your host, Devin Gimble, and I believe that your expenses are your greatest untapped asset, if you know how to leverage them.
0:17.8	Ready to dive into the world of credit card points and miles so you can travel more, travel better, and travel often. Let's get started.
0:29.8	Hello, everyone. Welcome back to the podcast. I hope your week is off to a great start. Tell
0:35.3	me if this sounds familiar. You're on board with the
0:38.1	idea that your expenses can fund incredible travel experiences via credit card points. You're on your
0:43.7	way expanding your rewards card portfolio to further maximize your points earning potential,
0:48.6	and you could already be sitting on a large transferable points balance, or you will be soon. All that time and effort
0:56.3	you've been putting in to learn the basics of how points works and optimizing your points
1:01.1	earning is all in preparation for the main objective of award travel, using those points to book
1:06.7	incredible travel experiences while saving significantly on your cash cost of travel. And if you're intent on
1:13.5	getting the most value from your points possible, you likely know that the way to do that isn't to use
1:19.0	your points for travel booked directly through your credit card account and as affiliated travel
1:23.7	portal is to transfer your valuable points out of your credit card account and into
1:28.3	transfer partner airline or hotel loyalty accounts and book your flights and hotel stays
1:33.1	from those loyalty accounts instead. But that is easier said than done sometimes because getting
1:39.4	the most value from your transferable points isn't always as simple as transferring your points out of your
1:45.8	credit card account and then finding an amazing award deal, especially when it comes to booking
1:50.9	award flights. And this is where the waters of award travel, especially unlocking the outsized
1:57.3	value that points can hold can become a bit murky. This jump from earning points or
2:03.5	having points, even millions of them, and booking fantastic award flight deals can be the hardest
2:09.5	obstacle that most of us face in the learning curve of award travel. And it's here where many folks
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