126. How Much Is a Point Really Worth? A Deep Dive with Frequent Miler’s Greg Davis-Kean

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

🗓️ 28 July 2025

⏱️ 55 minutes

🔗️ Recording | iTunes | RSS

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Summary

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.

Get full show notes and transcript: https://pointmetofirstclass.com/point-worth-frequent-miler/

Want to shape the show? Take the Point Me To First Class listener survey and share what you love and want more of! https://docs.google.com/forms/d/e/1FAIpQLSeAPfb3wIaphMn_NoQzm_fljydsivTELQwh7pYoxrI2uTFoKQ/viewform?usp=header

Eager to learn the secrets of award travel so that you can turn your expenses into unforgettable experiences? Join the Points Made Easy course waitlist here: https://pointmetofirstclass.com/pointsmadeeasy

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.
0:29.7	What is the value of a point? And with so many different types of points and miles available
0:35.3	to earn and use for travel, from transferable points
0:38.4	to airline miles to hotel points, how does the value of a point impact the decisions you make
0:43.7	around rewards credit cards to use and whether to transfer points or potentially use them
0:49.1	to book travel through a credit card travel portal. To answer that question, I've invited
0:53.1	Greg Davis KeKean of the
0:54.5	frequent miler team to the podcast today. Greg is an icon in the points in miles world,
0:59.3	offering some of the most informed, interesting, and entertaining analyses of trends in points
1:03.4	and miles on his blog, the Frequent Miler Facebook group, and their wildly popular Frequent Miler podcast.
1:09.8	Today, Greg dives in to how he and his team assign
1:12.7	relative redemption values to different points currencies, the personal preferences that affect how
1:17.9	he values different points currencies, and what he predicts might change with points values
1:22.5	in the next year. If you've ever wondered what exactly a point is worth, this is the conversation for you. I hope you
1:29.5	enjoy. Greg, I want to get your take on a conversation that seems to pop up whenever something
1:35.6	significant happens in the world of points or miles, whether it's something like a new all-time
1:40.4	high welcome bonus is getting offered or an airline program is devaluing its award flight
1:45.1	options. I feel like invariably, a ton of people will come out and say points and miles are
1:50.0	just worthless now. They're less valuable than they've ever been before. And then equally as many
1:54.4	people will argue, no, no, no, we're actually in the golden age of award travel right now and points
	...

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