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Point Me To First Class

Devon Gimbel MD
Point Me To First Class
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  • 133. 7 Keys to Better Award Flight Bookings
    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.  
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  • 132. From Frustration to $150K in Points Redemptions
    What does it really look like to transform your travel with credit card points? In this special episode, you’ll hear directly from Dr. Faryal Michaud, a past Points Made Easy student who went from feeling confused and frustrated by points to booking over $150,000 worth of award travel. From Qsuites to the Maldives, South Africa, Tahiti, and beyond, she shares the exact turning points that changed how she approached earning and redeeming points. You’ll hear how she overcame the frustrations so many people face in the beginning, the first redemptions that boosted her confidence, and how points have since emboldened her to experience life-changing trips she never thought possible. Faryal’s story is proof of how powerful this skillset can be—not just for one trip, but for a lifetime of travel. 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.  
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  • 131. Unpopular Opinion: Top 5 Reasons You Should Book Travel Through a Credit Card Travel Portal
    Think booking through your credit card travel portal is always a mistake? Not so fast. Last week, I shared five reasons why you’ll want to avoid making travel bookings through your credit card portal. But that’s not the whole story. There are also situations where using your card’s travel portal can be the smarter move. In this episode, I’m breaking down the five most compelling reasons to consider booking flights, hotels, or car rentals through your credit card’s portal — from points-earning opportunities to unlocking annual credits and even finding better award pricing than transfer partners. I’ll share the key tradeoffs, what this means for real-world bookings, and my own approach to when portal bookings actually make sense in my travel 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 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. Want to know what’s really possible with your points? Don’t just take it from me—hear from members who’ve used Points Made Easy to completely change the way they travel. From business class flights to dream vacations, their results speak for themselves. Watch their stories here - https://points.pointmetofirstclass.com/points-made-easy-success-stories
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  • 130. Top 5 Reasons to Avoid Booking Travel Through Credit Card Travel Portals
    If there’s one thing nearly every points traveler has done at least once, it’s book a flight, hotel, or car rental directly through their credit card’s online travel portal. With promises of 5x, 8x, even 12x bonus points, it can feel like the obvious choice. But as I share in today’s episode, those tempting multipliers often come at a serious cost—and the reasons why may surprise you. In this episode, I walk through the top five reasons you should avoid booking through credit card travel portals like Chase, Amex, Citi, and Capital One. From losing out on elite status perks and upgrades to paying more for the same flights or hotel rooms, I reveal the hidden downsides that don’t show up until it’s too late. You’ll also hear real-world stories from travelers who faced everything from missing reservations to costly rebookings—all because they used a portal instead of booking direct. Even more importantly, I’ll explain how using your points through a portal can devalue them by 2–10x compared to transferring to partners. I share specific examples, including how I used Chase points with Hyatt for a $65,000+ stay that would have cost 3.6 million points through the portal. Whether you’re new to points or have been booking this way for years, this episode will help you avoid costly mistakes and make smarter choices with your rewards. 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. Want to know what’s really possible with your points? Don’t just take it from me—hear from members who’ve used Points Made Easy to completely change the way they travel. From business class flights to dream vacations, their results speak for themselves. Watch their stories here - https://points.pointmetofirstclass.com/points-made-easy-success-stories
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  • 129. Fan Favorite: The Psychology of Learning & Mastering Points Travel
    In this week’s episode, we’re re-airing a fan favorite that so many listeners have loved and revisited. If you missed it the first time, or just need a refresher, this is one you don’t want to skip. I love discussing discrete award travel topics like individual rewards credit cards and how best to leverage them, or the specific airlines and hotels that offer the best value for points. But today, I’m covering something that never gets talked about in the points travel world and yet is one of the secrets to becoming more proficient when it comes to points travel: The Dunning-Kruger Effect and how it relates to award travel competency and success. The Dunning-Kruger Effect is a type of cognitive bias that causes people to overestimate their knowledge or abilities, particularly in areas where they have little to no experience. While this may be an unfamiliar concept, you can probably already see why having some background on the Dunning-Kruger Effect makes all the difference when you’re learning something new, like points travel. Tune in to discover how the Dunning-Kruger Effect is impacting how you approach the hobby of points travel. I’m showing you the different stages of the journey when learning the ins and outs of points travel, and how to keep moving through the stages until you reach a point of confidence and competence. On September 20th, 2025, I’m opening up enrollment for Points Made Easy. Enrollment will only be open for one week and this is your last opportunity to join the course this year, so get on the waitlist here: https://pointmetofirstclass.com/pointsmadeeasy Get full show notes and transcript: https://pointmetofirstclass.com/psycholoy-points-travel/ 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
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About Point Me To First Class

Point Me to First Class is a show for employed professionals, solopreneurs, entrepreneurs, and business owners with higher-than-average personal and/or business expenses who want to learn to leverage them into credit card points to spend on travel. Your expenses are your greatest untapped asset - but learning how to use them to travel the world doesn’t have to be confusing or complicated. Each week, Devon Gimbel shares valuable tips, tools, and strategies to help you uplevel your skills earning and redeeming credit card points and shows you how to spend them on incredible travel experiences. Interested in learning more about working with Devon? Visit www.pointmetofirstclass.com to learn more. This podcast is for you if you find yourself asking questions like: How do I earn credit card points and use them for travel? How can I make my expenses benefit me? How can I earn as many credit card points for as little spending as possible? How to maximize value from credit card points. How to earn credit card points for travel. Turn credit card points into travel.
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