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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

01:05:39

141. Listener Q&A: Canceling Cards, Transfer Partner...

Point Me To First Class ·

2025/11/10

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 decide between co-branded and transferable points programs based on your travel goals, and how to decide

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49:23

140. Points Path: The Tool That Shows You the Best...

Point Me To First Class ·

2025/11/03

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 extension that works seamlessly within your browser when you're searching flights to show you whether points or

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56:10

139. Stack Shopping Portals and Card Offers for...

Point Me To First Class ·

2025/10/27

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 powerful tool that shows you exactly how to combine the best shopping portal payouts with card-linked

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01:02:05

138. How to Track, Manage, and Maximize Your Credit...

Point Me To First Class ·

2025/10/20

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 annual fees — so you can stay organized, hit your goals, and never miss a reward. Zac built Travel Freely

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42:20

137. Stop Guessing, Start Earning: How CardPointers...

Point Me To First Class ·

2025/10/13

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 Emmanuel Crouvisier, creator of CardPointers, an app that helps you track your cards, bonus categories,

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59:17

136. Mini Retirements: Redefining How You Work, Rest,...

Point Me To First Class ·

2025/10/06

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 often. Inspired by the idea of sabbatical years, she began sprinkling mini retirements throughout her

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01:00:44

135. Amex Platinum Cards Refresh: What’s New, What’s...

Point Me To First Class ·

2025/09/29

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. In this episode, I’m joined by Kelly, the Points and Miles Doc to walk through the Amex Platinum cards

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29:00

134. The New Era of Award Travel: What’s Changing and...

Point Me To First Class ·

2025/09/22

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 earning and redeeming points have shifted faster than ever. Credit card issuers are tightening welcome bonus

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25:04

[BONUS EPISODE] Real Student Stories: Points Made...

Point Me To First Class ·

2025/09/20

Whether you’re brand new to points, sitting on years of unused balances, or simply overwhelmed by redemption options—this bonus episode proves that travel transformations are possible for anyone. In this special compilation, you’ll hear from three Points Made Easy students who each started at very different points in their journey but all ended up unlocking unforgettable travel through points: ✔️ Going from never having used a single points card → to booking five business class seats ✔️ Holding

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48:51

133. 7 Keys to Better Award Flight Bookings

Point Me To First Class ·

2025/09/15

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

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01:03:57

132. From Frustration to $150K in Points Redemptions

Point Me To First Class ·

2025/09/08

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

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41:07

131. Unpopular Opinion: Top 5 Reasons You Should Book...

Point Me To First Class ·

2025/09/01

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

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39:06

130. Top 5 Reasons to Avoid Booking Travel Through...

Point Me To First Class ·

2025/08/25

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

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29:49

129. Fan Favorite: The Psychology of Learning &...

Point Me To First Class ·

2025/08/18

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

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35:58

128. The New Citi Strata Elite: Game Changer or...

Point Me To First Class ·

2025/08/11

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 when you open this card. You’ll hear how its bonus categories actually work, why the time-restricted

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48:27

127. Lounge Access Update: Credit Card Changes, Perks...

Point Me To First Class ·

2025/08/04

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 cards like the Amex Platinum and Capital One Venture X to underrated options and family-friendly picks,

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54:43

126. How Much Is a Point Really Worth? A Deep Dive...

Point Me To First Class ·

2025/07/28

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 redeem, when to wait, and how to use point valuations as a guide—not a rule. We also dive into the

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59:22

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

Point Me To First Class ·

2025/07/21

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 to the test, we cover everything you need to know to decide if Citi cards deserve a spot in your wallet

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42:03

124. Mid-Year Points Update: What I Burned, Booked &...

Point Me To First Class ·

2025/07/14

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, and flew these points-funded getaways. You’ll hear the real numbers—how many points each trip

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33:02

123. Using Real Estate Spending to Maximize Credit...

Point Me To First Class ·

2025/07/07

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 big-ticket renovations to her advantage, Jaina shares the exact strategies she uses to turn every

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192 results

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