The Path to Becoming an Expert in Points & Miles with Devon Gimbel
Author: Chris Hutchins
May 14, 2025
Duration: 1:08:18
#227: An actionable 4-step framework to master points and miles while maximizing personal value. We cover high-yield earning strategies like paying processing fees, bulk ordering, and leveraging business expenses, plus tactics for scaling award travel for multiple people. We also explore alternate pathways to earn and redeem points without chasing “perfection.”
Devon Gimbel is the founder of Point Me to First Class, an educational platform and podcast that teaches people to maximize their spending for extraordinary travel rewards. She is also a double-board certified physician.
Link to Full Show Notes: https://chrishutchins.com/rethinking-points-and-miles-devon-gimbel
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Resources Mentioned
Devon: Point Me To First Class | Podcast | Instagram
Free Starter Guide to Points
Dunning Kruger Curve
Payment Platforms
Plastiq
Melio
Zil Money (Coupon Code: ATH300)
Venmo Business
Airlines with Great Award Availability
Emirates
Condor
Singapore Airlines
Rakuten: $40 bonus here
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ATH Podcast
Ep #166: Best Award Search Tools for Booking Flights with Points & Miles with Greg the Frequent Miler
Leave a review: Apple Podcasts | Spotify
Email for questions, hacks, deals, and feedback: podcast@allthehacks.com
Full Show Notes
(00:00) Introduction
(02:31) Devon's Non-Traditional Approach to the Points & Miles Game
(05:38) Stage 1: Peak of Mount Ignorance
(08:18) Stage 2: Valley of Despair
(09:41) Stage 3: Slope of Enlightenment
(13:06) One of the Biggest Mistakes People Make in the Points & Miles World
(14:47) Lessons from Chris' Skiing Experience
(21:03) Stage 4: Unconscious Competence
(23:48) Why the Learning Curve Never Stops
(27:08) Identifying High Yield Opportunities for Yourself
(29:54) How to Evaluate If Credit Card Fees Are Worth It
(38:43) The Importance of Understanding Earning Rates
(40:26) Ways to Leverage Business Expenses
(43:43) Maximizing Award Travel When Booking for Multiple People
(48:16) Airlines That Have Good Award Availability (Fifth Freedom Flights)
(55:00) Why You Should Practice Looking for Award Deals
(58:11) Rakuten Bulk Ordering to Earn Flexible Points
(1:01:37) Setting Alerts for Deals
(1:03:49) Alternate Pathways to Earn and Redeem Points
(1:09:12) Using a Venmo Business Profile to Make Payments
(1:10:13) Where to Find Devon
Connect with Chris
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