Devon Gimbel MD
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. I...
Author
Devon Gimbel MD
Category
Podcast website
Latest episode
Jul 6, 2026
Where to listen?
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Episodes
125. Maximizing the Citi Ecosystem with Dr. Suzy Spadafora 21.07.2025 59:22
Ever feel like Citi cards get overlooked in points conversations? If you've written off Citi's ecosystem—or just haven't known how to make it work for your travel goals—this episode is full of smart, real-life strategy. Dr. Suzy Spadafora returns to discuss the strengths (and limitations) of the Citi points ecosystem. From the points earning cards Citi offers to putting their transfer partner menu...
124. Mid-Year Points Update: What I Burned, Booked & Learned 14.07.2025 42:03
Ever wonder what's actually possible with points? In this episode, I'm taking you behind the scenes of how I've already booked and taken 5 international trips in 2025—spending 2.9 million points on award flights and hotels, and saving over $150,000 in travel costs. From a spring break family trip to Paris to a spontaneous 2-day Tokyo adventure, I'm walking you through exactly how I planned, booked...
123. Using Real Estate Spending to Maximize Credit Card Points with Jaina Pallasigui 07.07.2025 33:02
Have you ever wondered how real estate investments could help you travel more—without spending more? In this episode, I'm joined by Jaina Pallasigui, a public health professional, real estate investor, and points enthusiast who turned her real estate expenses into business class flights and luxury hotel stays around the world. From managing short-term rentals to using insurance reimbursements and...
122. Listener Q&A: Adding a Third Points Currency, Booking Emirates First, and Points Regret 30.06.2025 1:09:45
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 beh...
121. Chase's New Business Card Just Dropped & The CSR Gets An Update—Here's Why We're Not Impressed 23.06.2025 56:05
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...
120. The biggest surprises (and letdowns) of 2025 so far 16.06.2025 1:20:15
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 outperfor...
119. Alaska Airlines Sweet Spots: Amazing Ways to Use Alaska Miles (That You Might Be Missing) 09.06.2025 28:41
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 tra...
118. Jet-Set with JAL: Bilt's Boldest Transfer Partner Yet 02.06.2025 38:25
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 plann...
117. Making Smart Transfer Moves: When Speculative Points Transfers are Worth It (And When They're Not) 26.05.2025 27:06
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 spec...
116. The Award Travel Trick Hiding in Plain Sight: Fifth Freedom Flights 19.05.2025 25:26
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 poi...
115. Rhythms, Routines, and REM: Expert Tips to Manage Jet Lag & Sleep Disruption While Crossing Time Zones 12.05.2025 43:38
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 exper...
114. Finally! Turning Your Mortgage into Points: How Mesa is Flipping the Script on Rewards 05.05.2025 30:56
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 i...
113. 4 Ways to Maximize Points for Costco Spend (Without Overcomplicating It) 28.04.2025 20:10
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'...
112. Best Ever or Big Mistake? 3 Steps to Evaluate if Best-Ever Welcome Offers are Right for You 21.04.2025 14:40
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 el...
111. Life, Travel, and Money Hacks with Chris Hutchins 14.04.2025 1:06:42
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...
110. 2025 Tax Payment Updates You Need to Know with Dr. Sujatha Murali 07.04.2025 42:01
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...
109. How to Pack Smart for Travel Without Sacrificing Style with Cassandra Sethi 31.03.2025 35:06
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,...
108. Credit Card Points Transfers: Do's, Don'ts, and Pro Tips 24.03.2025 43:43
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...
107. Skill Stacking Your Way to Better Points Redemptions 17.03.2025 37:28
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...
106. Lessons Learned & Top Tips from Running Thousands of Award Searches 10.03.2025 35:14
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...
105. Turn Payroll into Points: A Game-Changing Strategy for Business Owners with DeAndre Coke 03.03.2025 35:51
In this episode, I'm joined by DeAndre Coke, a financial advisor and an avid traveler who was ranked by Forbes as one of Virginia's top financial security professionals for two consecutive years. DeAndre shares his experience using an innovative platform called Zil Money to pay payroll with his credit card, racking up huge amounts of valuable rewards points in the process. Discover which credit...
104. Expert Answers to Your Top Award Travel Questions: Listener Q&A 24.02.2025 53:06
Whether you're a seasoned pro or just starting out in the world of award travel, this episode is packed with actionable advice and real-world examples. I break down complex topics like transferable points currencies, positioning flights, and maximizing leftover gift card balances in a way that's easy to understand and apply to your own travel goals. So grab a pen and paper (or just hit that book...
103. CME Secrets: Unlock International Travel with Dr. Courtney Downes 17.02.2025 35:26
Are you a medical professional looking for ways to leverage your CME funds for travel? I'm joined by Dr. Courtney Downes, a board-certified emergency medicine physician, Points and Travel strategist, and founder of Prescription to Travel MD. She helps healthcare professionals optimize credit card points and travel hacks for accessible leisure, adventure, wellness retreats, and CME. Discover how...
102. Maldives Dream Vacation: Booking, Business Class & Insider Tips 10.02.2025 1:12:34
From finding award availability to navigating the unique transportation logistics of getting to and from the Maldives, I walk you through everything that went into planning this ambitious trip. I also share my honest review of the flights we took, what it was like staying at the luxurious Park Hyatt Maldives, and how I kept food costs under control at the resort. If the Maldives is on your trave...
101. Behind the Points: How the Travel Mom Squad Built a Thriving Travel Business 03.02.2025 48:49
The Travel Mom Squad shares their journey from humble beginnings to becoming one of the most influential voices in the award travel industry. We dive into the challenges they faced along the way, the strategies they used to overcome them, and the lessons they learned as they grew their business. Get ready for an inside look at how these three powerhouse women are changing the face of award trave...
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