Devon Gimbel MD

Point Me To First Class

Society EN ↓ 198 episodes

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...

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Author

Devon Gimbel MD

Category

Society

Podcast website

pointmetofirstclass.com

Latest episode

Oct 26, 2026

Where to listen?

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Episodes

141. Listener Q&A: Canceling Cards, Transfer Partner Confusion & Shopping Portals vs. Welcome Bonuses 10.11.2025

This episode is all about your questions—and real answers. I'm back with another listener Q&A, tackling the points and miles decisions you're actually making right now. From whether it's possible to move points between airline partners to deciding if that old United card still deserves a spot in your wallet, we're covering it all. We'll walk through when to hold or cancel airline cards, how to dec...

140. Points Path: The Tool That Shows You the Best Value for Every Flight 03.11.2025

Ever look at Google Flights and wonder, "Should I use points for this or just pay cash?" If you've ever felt unsure about which option gives you the best value, this episode is for you. In the final episode of our Streamline, Stack, and Save mini-series, I'm joined by Julian Kheel, former editorial director at The Points Guy and senior editor at CNN, now founder of Points Path — a browser extensio...

139. Stack Shopping Portals and Card Offers for Bigger Rewards with Savewise 27.10.2025

Do you ever find yourself opening multiple tabs, comparing shopping portal payouts, and trying to figure out which site is going to give you the most rewards for your online shopping — only to give up before you actually earn the points? If that sounds familiar, today's episode is for you. In this Streamline, Stack, and Save mini-series episode, I'm joined by Avneesh Kohli, founder of Savewise, a...

138. How to Track, Manage, and Maximize Your Credit Cards with Travel Freely 20.10.2025

Have you ever opened a new credit card for the welcome bonus, only to forget how much you've spent or when the deadline hits? Or maybe you're juggling multiple cards and can't remember which one to use next. In this next episode of our Streamline, Stack, and Save mini-series, I'm joined by Zac Hood, founder of Travel Freely, an app that helps you track your credit cards, sign-up bonuses, and annua...

137. Stop Guessing, Start Earning: How CardPointers Does the Work for You with Emmanuel Crouvisier 13.10.2025

Do you ever forget which credit card to use for a purchase — or worry you're missing out on bonus points and statement credits? It's easy to lose track when every card has different categories, offers, and perks. This episode is part of our Streamline, Stack, and Save mini-series, where we're exploring tools and strategies that simplify how you earn and redeem your points and miles. I'm joined by...

136. Mini Retirements: Redefining How You Work, Rest, and Live with Jillian Johnsrud 06.10.2025

Do you think you have to wait until your sixties before you can retire? Maybe not. At least not the way we've been taught. In this episode, I'm joined by Jillian Johnsrud — author, podcast host, and coach — who challenges the idea of a traditional retirement in favor of taking mini retirements throughout your life and career. Jillian never expected to retire early, so she hatched a plan to retire...

135. Amex Platinum Cards Refresh: What's New, What's Missing, and What We Really Think 29.09.2025

Back in June, Chase refreshed its personal Sapphire Reserve card and introduced the Chase Sapphire Reserve Business card, complete with highest ever annual fees for rewards cards. Not to be outdone, American Express quickly followed with its own updates to the personal and business Platinum Cards. Now that the details are here, it's time to look at what's changed and what it means for cardholders....

134. The New Era of Award Travel: What's Changing and How to Adapt 22.09.2025

If you've been in the points game for years, you've probably noticed how much has changed recently. And if you're newer, you might be wondering if you're already too late. In this episode, I share why I don't believe we're in the "golden age" of award travel right now — but also why points are still incredibly valuable if you know how to adapt. Over the last couple of years, the rules around earni...

133. 7 Keys to Better Award Flight Bookings 15.09.2025

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,...

132. From Frustration to $150K in Points Redemptions 08.09.2025

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...

131. Unpopular Opinion: Top 5 Reasons You Should Book Travel Through a Credit Card Travel Portal 01.09.2025

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 conside...

130. Top 5 Reasons to Avoid Booking Travel Through Credit Card Travel Portals 25.08.2025

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 epis...

129. Fan Favorite: The Psychology of Learning & Mastering Points Travel 18.08.2025

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...

128. The New Citi Strata Elite: Game Changer or Missed Opportunity? 11.08.2025

If a $595 annual fee premium credit card hits the market, should it automatically earn a place in your wallet? In this episode, I take a detailed look at Citi's newest addition to the transferable points landscape: the Citi Strata Elite Card. From its standard 80,000-point welcome bonus to the elevated 100,000-point offer available through certain channels, we'll walk through exactly what you get...

127. Lounge Access Update: Credit Card Changes, Perks & Picks with Traci Siegel 04.08.2025

If you've ever been confused about airport lounge access—what counts, what's changed, and what's still worth it—you're not alone. In this episode, I welcome back guest Traci Siegel for an updated look at lounge access using rewards credit cards in 2025. We unpack the biggest changes to credit card lounge access this year, including new restrictions on who gets in and when. From premium travel card...

126. How Much Is a Point Really Worth? A Deep Dive with Frequent Miler's Greg Davis-Kean 28.07.2025

If you've ever hesitated before transferring points—or wondered if a redemption was "good enough"—this is the episode you've been waiting for. In this conversation with Greg Davis-Kean (a.k.a. Frequent Miler), we unpack how to think more strategically about the value of your points. Whether you're sitting on a big stash or navigating your first transfer, you'll hear expert insight into when to red...

125. Maximizing the Citi Ecosystem with Dr. Suzy Spadafora 21.07.2025

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

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

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

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

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

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

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

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

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...

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