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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

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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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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161 results

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