The Path to Becoming an Expert in Points & Miles with Devon Gimbel

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 Partner Deals DeleteMe: 20% off removing your personal info from the web Upwork: Free job posting to find, hire, and pay top freelance talent NetSuite: Free KPI checklist to upgrade your business performance Bilt Rewards: Earn the most valuable points when you pay rent Green Chef: 50% off your first meal kit with code 50ALLTHEHACKS For all the deals, discounts and promo codes from our partners, go to: chrishutchins.com/ 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 Savewise: 20% off with ALLTHEHACKS20 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 Newsletter | Membership | X | Instagram | LinkedIn Editor’s Note: The content on this page is accurate as of the posting date; however, some of our partner offers may have expired. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. Learn more about your ad choices. Visit megaphone.fm/adchoices

Ever feel like there's a smarter, more efficient way to navigate your finances, your travels, and your daily routines? That's the core question driving All the Hacks: Money, Points & Life. Hosted by Chris Hutchins, this podcast is built on a simple, powerful idea: maximizing value doesn't mean sacrificing enjoyment. Instead, it's about the strategic choices that free up resources-both money and time-for what truly matters. Chris approaches life as a series of systems to be optimized, drawing from his own experience saving millions through meticulous analysis. The conversations here are practical and wide-ranging, moving seamlessly from credit card points strategies and investment philosophies to the less tangible hacks for personal fulfillment. You'll hear from a diverse roster of experts and icons, including Tim Ferriss, Tony Hawk, Codie Sanchez, and Gary Vaynerchuk, who all bring their unique perspectives on building wealth and designing a compelling life. Each episode feels like a focused workshop, offering actionable advice you can use immediately, whether it's planning a luxury vacation for a fraction of the cost or rethinking your approach to career and leisure. This isn't just about frugality; it's about unlocking freedom and excitement through smarter decisions. Tune in for a consistently insightful blend of tactical moves and deeper conversations that challenge the conventional trade-offs between spending, saving, and living well.
Author: Language: English Episodes: 100

All the Hacks: Money, Points & Life
Podcast Episodes
How Much Are Points and Miles Worth in 2025? [not-audio_url] [/not-audio_url]

Duration: 1:06:42
#245: Ever wonder what points are really worth? I'll break down the different types of points, how to calculate their value, and the biggest mistakes people make along the way. You’ll also learn when cash back might be t…
How I Saved $10,000+ on Luxury Hotels [not-audio_url] [/not-audio_url]

Duration: 57:56
#244: I'll explain how I saved over $10k on luxury hotels in Costa Rica and Carmel Valley using points, free nights, and elite perks. I’ll walk you through every step, from how to book with points, when to buy them on sa…
Deep Dive on Capital One Credit Cards and Miles (+ Why I Love Them) [not-audio_url] [/not-audio_url]

Duration: 1:03:56
#242: Chris dives into the Capital One credit card lineup, breaking down earning structures for miles and cash back, exciting benefits, and redemption strategies. He also covers the best 2-card combo, transfer partners,…
Earn More Points with New Cards, Bonuses, and Challenges in 2025 [not-audio_url] [/not-audio_url]

Duration: 56:15
#241: We cover new credit cards, increased welcome bonuses, and major changes to existing cards and their benefits. Plus, learn how to rack up thousands of points through airline and hotel challenges and giveaways. Link…
18 Tactics for Booking Travel with Points & Miles [not-audio_url] [/not-audio_url]

Duration: 54:44
#238: Chris shares 18 tactics he’s used to get the best deals booking flights and hotels with points. Learn how to leverage flexibility, navigate transfer partners, use the right tools, identify “sweet spots,” avoid high…
How to Design a Rich Life at Any Income with Ramit Sethi [not-audio_url] [/not-audio_url]

Duration: 1:00:59
#237: Start living your rich life today regardless of your income. Learn how to spend without guilt, track the four key financial numbers that matter most, harness the power of decisiveness, and avoid the common traps th…
Deep Dive on Amex Credit Cards and Membership Rewards Points [not-audio_url] [/not-audio_url]

Duration: 1:45:22
#236: Chris reviews and ranks the full American Express lineup of 30+ cards. He also breaks down Membership Rewards, transfer partners, approval rules, card-linked offers, unique perks, and more. Link to Full Show Notes:…