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PODCAST

Point Me To First Class

Devon Gimbel MD

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

society & culture places & travel

All Episodes

01:09:45

122. Listener Q&A: Adding a Third Points Currency,...

Point Me To First Class ·

2025/06/30

This episode is all about your questions—and real answers. I’m back with another listener Q&A, tackling the exact points and miles decisions you’re working through right now. Ever feel like you're making credit card decisions in a vacuum? From wondering if it's time to add Capital One or Mesa to your rewards card portfolio, to recovering from redemption regret, I’m walking through the strategy behind each question so you can move forward with more clarity and confidence. We’ll cover how to think

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56:05

121. Chase’s New Business Card Just Dropped & The CSR...

Point Me To First Class ·

2025/06/23

Chase just launched a new business credit card and rolled out changes to the Chase Sapphire Reserve—but are these updates actually worth getting excited about? In this episode, I’m joined once again by Kelly from The Points and Miles Doc for a candid review of what’s new in the Chase ecosystem. From rising annual fees to underwhelming credits and a business card that looks a lot like what already exists, we’re breaking down the updates—and what they really mean for your wallet. We also talk about

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01:20:15

120. The biggest surprises (and letdowns) of 2025 so far

Point Me To First Class ·

2025/06/16

Have you been wondering what’s really happening in the world of credit card points and award travel this year? In this episode, I’m joined by Kelly, The Points and Miles Doc to break down the biggest shifts in 2025 so far. From major devaluations to standout sweet spots, we’re giving you an honest look at what’s working now—and what’s not. We also dive into how international programs are outperforming U.S.-based ones, which transfer partnerships are showing real value, and why flexibility is more

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28:41

119. Alaska Airlines Sweet Spots: Amazing Ways to Use...

Point Me To First Class ·

2025/06/09

Have Alaska miles—or thinking of transferring your Amex points before the June 30 deadline? In this episode, I’m breaking down some of the most valuable ways to redeem Alaska Airlines miles right now. From low-cost domestic redemptions to hard-to-find international business class flights, this guide walks you through the sweet spots that make Alaska’s program one of the most valuable in points travel. You’ll also learn what not to do with your Alaska miles (even if it looks like a good deal), plus a

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38:25

118. Jet-Set with JAL: Bilt’s Boldest Transfer...

Point Me To First Class ·

2025/06/02

Have you ever dreamed of flying to Japan in business class—without paying out of pocket? Bilt just made that a lot easier. In this episode, I’m joined by award travel strategist Ben Komenkul to talk about the newest (and most exciting) Bilt Rewards transfer partner: Japan Airlines. This partnership opens the door to premium flights across Asia and around the world—and it’s not just for those planning a trip to Tokyo. Ben and I walk through everything from low-cost regional flights and lie-flat

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27:06

117. Making Smart Transfer Moves: When Speculative...

Point Me To First Class ·

2025/05/26

A major points transfer pathway is shutting down—and it's got a lot of people wondering: should I move my Amex points to Alaska Airlines before the door closes? In this episode, I break down the fast-approaching June 30 deadline to transfer Amex points to Hawaiian Airlines (and from there to Alaska), and walk you through my personal decision—including the 4-step framework I use for evaluating speculative points transfers. If you’ve ever wondered whether it’s smart to move points to a transfer

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25:26

116. The Award Travel Trick Hiding in Plain Sight:...

Point Me To First Class ·

2025/05/19

If you’ve ever struggled to find award space—especially in business class—this is the episode you’ve been waiting for. In this episode, I’m diving into a unique but often overlooked type of airline route called a fifth freedom flight. These flights are legal exceptions in commercial aviation that allow an airline to fly between two foreign countries, neither of which is their home base—and for points enthusiasts, they offer some of the best award availability, better cabin experiences, and unique

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43:38

115. Rhythms, Routines, and REM: Expert Tips to...

Point Me To First Class ·

2025/05/12

No matter how dreamy your destination is, there’s one thing that can make or break your trip: sleep. In this episode, I’m joined by sleep therapists Leah Corkum and Marlee Boyle, co-founders of Sleep-Works, a Canadian-based virtual sleep education company helping individuals and families improve their sleep health. With certifications in CBT for insomnia, clinical sleep health, and years of experience in both nursing and respiratory therapy, Leah and Marlee bring a holistic and practical approach to

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30:56

114. Finally! Turning Your Mortgage into Points: How...

Point Me To First Class ·

2025/05/05

There’s finally a card that rewards you for the one expense that’s been completely ignored in the points world: your mortgage. In this episode, I’m talking with Kelley Halpin, CEO of Mesa, about the first credit card that lets you earn points for mortgage payments—plus other major homeowner expenses like daycare, utilities, and home improvement. Kelley shares what makes the Mesa card unique, how its rewards system works, and why it’s designed to serve a segment of consumers that’s long been

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20:10

113. 4 Ways to Maximize Points for Costco Spend...

Point Me To First Class ·

2025/04/28

Whether your Costco haul includes a 5-pound bag of almonds or a giant sectional sofa, one thing is certain: you’re probably not spending just a few bucks. If you’ve ever wondered how to earn more credit card points on your Costco runs, this episode walks you through four smart, strategic ways to maximize rewards—whether you’re shopping in-store, online, or through a workaround like Instacart. You’ll learn which cards work, which ones don’t, and how to pick the best method based on your spending

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14:40

112. Best Ever or Big Mistake? 3 Steps to Evaluate if...

Point Me To First Class ·

2025/04/21

A limited time elevated credit card bonus offer sounds amazing—so should you go for it? In this episode, I break down how to evaluate elevated credit card welcome bonuses so you can make a smart, strategic decision. Using the current Chase Sapphire Preferred offer as a real-world example, I walk through the three questions you need to ask before jumping on any limited-time offer: ✔ Are you even eligible? ✔ How will this card fit into your overall points and travel goals? ✔ What’s the opportunity

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01:06:42

111. Life, Travel, and Money Hacks with Chris Hutchins

Point Me To First Class ·

2025/04/14

What does it look like to fully optimize your life—not just financially, but how you travel, make decisions, and spend your time? In this episode, I’m joined by Chris Hutchins, host of All the Hacks, for a fast-paced conversation about how to get more value, joy, and efficiency from everything you do. We talk about optimizing credit card rewards, streamlining travel, removing decision fatigue, and using money as a tool—not just for freedom, but for alignment with your values. If you're the kind of

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42:01

110. 2025 Tax Payment Updates You Need to Know with...

Point Me To First Class ·

2025/04/07

With changes to credit card processing platforms and fee structures for 2025, the strategy for paying taxes with a credit card—and earning points while doing it—has shifted. In this episode, I’m joined by my good friend and points expert Dr. Sujatha Murali to walk you through the major changes in tax payment processing for 2025—and how to earn huge amounts of points while minimizing fees. We share our personal strategies for navigating quarterly tax payments, which types of cards to prioritize (and

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35:06

109. How to Pack Smart for Travel Without Sacrificing...

Point Me To First Class ·

2025/03/31

Have you ever stood in front of your suitcase, overwhelmed, unsure what to pack—or panic-ordered outfits days before a trip that you’ll never wear again? You’re not alone. In fact, this episode might be exactly what your suitcase (and closet) needs. In this episode, I’m joined by Cassandra Sethi, personal stylist and founder of Next Level Wardrobe, who shares her system for making packing simple, efficient, and actually fun. We talk about how to get more outfits with fewer pieces, avoid the most

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15:27

[BONUS EPISODE] Points Made Easy student success...

Point Me To First Class ·

2025/03/27

Whether you’ve been hoarding points for years, afraid to redeem them, or unsure how to make luxury travel feel possible—this episode will show you how quickly things can change. In this episode, you’ll hear from three Points Made Easy students who went from: ✔️ Avoiding annual fees and fearing a drop in credit score → to traveling 7+ times in a year ✔️ Treating points as too complex to learn → to booking luxury hotels and multiple international trips ✔️ Thinking first class was only for high-powered

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16:48

[BONUS EPISODE] Points Made Easy Student Success...

Point Me To First Class ·

2025/03/26

Whether you're sitting on a pile of unused points, overwhelmed by redemption options, or wondering if luxury travel is even realistic for your life—this episode is proof that it’s all within reach. In this episode, you’ll hear from three Points Made Easy students who went from: ✔️ Using points for gift cards → to flying business class across the world ✔️ Avoiding international travel with young kids → to booking their first family trip in business class ✔️ Feeling unsure about how to use points

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43:43

108. Credit Card Points Transfers: Do’s, Don’ts, and...

Point Me To First Class ·

2025/03/24

As someone who has booked over $192,000 worth of travel using points just this year, I've learned that mastering the art of points transfers is the key to unlocking incredible travel experiences. But knowing when and where to transfer your points isn't always straightforward or intuitive, especially when you're new to this hobby. In this episode, I share 10 do's and don'ts of credit card points transfers. You'll hear my hard-won wisdom on everything from transfer ratios to avoiding common

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09:16

[BONUS EPISODE] - Points Made Easy course open now...

Point Me To First Class ·

2025/03/22

Whether you’re just getting started with points, sitting on a stash you don’t know how to use, or trying to figure out how to level up your redemptions—this episode is for you. In this episode, you’ll hear real stories from Points Made Easy students who went from: ✔ Feeling stuck with points they didn’t know how to use → to booking luxury trips effortlessly ✔ Only using one credit card → to strategically earning hundreds of thousands of points ✔ Thinking business class was out of reach → to booking

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37:28

107. Skill Stacking Your Way to Better Points...

Point Me To First Class ·

2025/03/17

Do you feel confident in your points redemption skills, or do you suspect you might be missing out on better deals? With a little knowledge and practice, you can learn to stack the key skills needed to get incredible value from your points, and I'm showing you how this week. Tune in as I break down the six key levels of points redemption skill stacking. I explain how to know which level you're at currently, the specific skills to focus on building, and how to reach the next level so you can

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35:14

106. Lessons Learned & Top Tips from Running...

Point Me To First Class ·

2025/03/10

I share my top tips for running successful award flight searches gleaned from years of experience booking award travel. Let's dive into the key differences between searching for cash flights versus award flights, and how to overcome the challenges of information overload and limited award seat inventory. I break down the most important mindset shifts and practical strategies you can start using today to increase your chances of finding your dream award flights. Get full show notes and

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192 results

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