Episode Description

If you’ve ever hesitated before transferring points—or wondered if a redemption was “good enough”—this is the episode you’ve been waiting for.

In this conversation with Greg Davis-Kean (a.k.a. Frequent Miler), we unpack how to think more strategically about the value of your points. Whether you’re sitting on a big stash or navigating your first transfer, you’ll hear expert insight into when to redeem, when to wait, and how to use point valuations as a guide—not a rule. We also dive into the psychology behind redemption pressure, real examples of high-value bookings, and why your goals should always shape your strategy.

Turn your expenses into points and save tens of thousands of dollars a year on your wishlist travel. Don’t miss out! Click here to know more about my comprehensive online program, Points Made Easy.

What You’ll Learn from this Episode

• How Frequent Miler calculates point valuations—and why it’s not just math
• When a “low” redemption might still be the best decision
• The two types of people in the points world—and which one Greg identifies with
• Why comparing cent-per-point value can be misleading
• The case for using points to save cash vs. chase aspirational travel
• How to avoid analysis paralysis and use your points with confidence

Featured on the Show:

• Follow me on Instagram
• Get on the waitlist for the Points Made Easy Course here!
• Get My Cash-Back Credit Card Cheat Sheet!
• If you have any questions or you want me to dive deeper into a specific topic, email me here: podcast@pointmetofirstclass.com
• Episode 121: Chase’s New Card Just Dropped
• Visit the Frequent Miler Website
• Reasonable Redemption Value Blog Post
• Points Path Search
• Gondola Hotel Search Engine

Click here to download full episode transcript

Enjoy the Show?

• Don’t miss an episode, follow the podcast on Apple Podcasts, Spotify, Stitcher, or RSS.
• Leave me a review in Apple Podcasts.