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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

29:38

158. Before You Pay Your Taxes by Credit Card: Avoid...

Point Me To First Class ·

2026/03/09

If you're planning to pay taxes by credit card this year, now is the time to set up your strategy—not the week before tax day. Every year, I see posts from people whose tax payment plans went sideways at the last minute. A declined charge, payments that didn't post, a payment that went to the wrong card—these problems are stressful on their own, but they're especially problematic when you're troubleshooting them on tax day. Listen in as I walk through the five key considerations for turning tax

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43:11

157. Shifting My Strategy: Why I'm Pursuing Status in...

Point Me To First Class ·

2026/03/02

For the first time in over a decade, I'm actively chasing status in multiple loyalty programs—and it's a major shift from my usual points strategy. Historically, status hasn't been a focus for me beyond Hyatt Globalist. But this year, I'm pursuing top-tier or near top-tier status in four programs: Hyatt Globalist, Bilt Platinum, Air France Flying Blue Platinum, and American Airlines Platinum Pro. Listen in as I walk through why these specific statuses suddenly jumped to the top of my priority

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37:11

156. Making Large Family Award Travel Actually Work...

Point Me To First Class ·

2026/02/23

Today we're picking up where we left off last week with Dr. Alison Curfman—and diving into what happens after the flights are booked. Part 1 covered how Alison finds award flights and books hotels for her family of six to eight people when they travel. In Part 2, we're talking about execution—the systems and strategies that make those trips actually run smoothly. Listen in as Alison shares her approach to managing overnight flights with kids, minimizing food costs, and keeping complex multi-city

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48:04

155. Planning Award Travel for Large Families with...

Point Me To First Class ·

2026/02/16

If you've ever thought award travel isn't possible with a large family or group, this episode will change your mind. In Part 1 of this conversation, I sit down with Dr. Alison Curfman, a pediatric emergency physician, entrepreneur, and relentless optimizer who regularly travels the world with her family—typically six to eight people depending on whether au pairs or grandparents join. After co-founding a healthcare company that scaled to a nine-figure valuation, Alison transitioned into advisory

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29:37

154. The Most Memorable Credit Card Points Lessons...

Point Me To First Class ·

2026/02/09

Have you ever wondered what points lessons other travelers learned the hard way—so you don't have to? Today's episode is a little different. I recently crowdsourced the biggest points lessons learned in 2025 from members of my community, and the responses were so good. Some were tactical, others were mindset-shifting, and more than a few had me laughing because they highlighted mistakes that are just so relatable in this hobby. In this episode, I'm sharing the most insightful, surprising, and

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30:48

153. Avios Explained: Understanding Transfers &...

Point Me To First Class ·

2026/02/02

In a hobby full of rules, Avios prove to be an exception—and understanding how they work can unlock some of the best award flight opportunities available. In this episode, I'm breaking down everything you need to know about Avios, the points currency used by British Airways, Qatar, Finnair, Iberia, Aer Lingus, and several other airlines. One crucial aspect of Avios that makes them unique among points currencies is their ability to move between partner accounts, which creates opportunities you

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48:47

152. Building Wealth Beyond Travel: Financial...

Point Me To First Class ·

2026/01/26

If you've ever wondered what's the difference between just saving money versus creating wealth that actually matters, this conversation is for you. In this episode, I'm joined by Lauren Oschman, founder of Vestia Personal Wealth Advisors, who grew up watching her interventional cardiologist father work incredibly hard while struggling to balance wealth building with being present at home. That experience shaped her entire approach to financial planning, which she now brings to nearly 600 physician

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01:33:19

151. Bilt's 3 New Cards: A Complete Analysis &...

Point Me To First Class ·

2026/01/19

Have you ever wondered if earning points on your mortgage or rent is actually worth the math? Or whether a card that earns two times points on everything can really compete with what you're already holding? Bilt just released three brand new credit cards, and they're more complex than any card launch I've seen in a while. This isn't just about welcome bonuses and bonus categories— there's an entirely new internal currency called Bilt Cash, along with processing fees to calculate, and real formulas

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01:41:23

150. 2025 Points Year in Review: How We Used Our...

Point Me To First Class ·

2026/01/12

Today we're picking up where we left off last week in our 2025 points recap. In this second part of our year-in-review series, Dr. Andrea Mabry and I continue to break down the travel we actually booked with all those points we earned in 2025. We're sharing the total value of travel we booked, our average redemption values, and the specific trips we planned—from family vacations to aspirational first class products. We also reveal what we've already booked for 2026, including trips worth over

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01:17:44

149. 2025 Points Year in Review: A Look Back at...

Point Me To First Class ·

2026/01/05

Do you ever wonder what cards other people have, how they use them, and exactly how many points they're earning each year? I'll be honest—I'm nosy when it comes to other people's points, and I love getting a peek inside someone else's points earning strategies. In this first part of a two-part year-in-review series, I've invited Dr. Andrea Mabry back to the show to break down everything that shaped our points earning in 2025. This has become one of my favorite Point Me to First Class traditions, and

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20:48

148. Your Year in Points Review: How to Audit, Learn,...

Point Me To First Class ·

2025/12/29

Have you ever taken a step back and actually evaluated what your points did for you over an entire year? In this episode, I'm inviting you to do your own Year in Points Review—a way to look at how you earned points, how you used them, and whether your approach to earning and redeeming rewards helped you reach your travel goals. I walk through why a year-end points review is worth doing, including how it helps you evaluate what you did well, what you could do better, and how having clear data makes

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47:31

147. 2025 in Points and Miles In Review (Part 2): Key...

Point Me To First Class ·

2025/12/22

What really changed in the points and miles world this year—and how should that shape your strategy going forward? In part two of our 2025 Year in Review, Kelly and I continue breaking down one of the most transformative years we've seen in award travel. Beyond rising annual fees and tightening loyalty programs, this year revealed deeper structural shifts in how airlines price awards, who gets access to the best redemptions, and what flexibility actually looks like going forward. We dig into the

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01:07:09

146. 2025 in Points and Miles In Review: The Biggest...

Point Me To First Class ·

2025/12/15

In this episode, we bid farewell to 2025 with a year-in-review analysis of the biggest news, changes, and trends in rewards, credit cards, and award travel over the last 12 months. This episode is part one of a two-part year-in-review series, and I'm joined by Kelly, the Points and Miles Doc, to break down the biggest changes, surprises, and shakeups in the points and award travel world over the last year. In this first half of the conversation, we focus on the biggest wins and disappointments of

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49:14

145. Behind the Scenes at World of Hyatt: Loyalty,...

Point Me To First Class ·

2025/12/08

Have you ever wondered what exactly goes on behind the scenes in loyalty programs—and what drives executive decisions about what to offer, add, or take away from their members' experience? In this episode, I get to do exactly that. I'm joined by Laurie Blair, Hyatt's Senior Vice President of Global Marketing and Loyalty, for a rare behind-the-scenes look at how Hyatt designs a program that travelers actually feel loyal to. We talk about what truly sets the World of Hyatt program apart, how they make

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49:45

144. Inside Rove: The Loyalty Program Reshaping...

Point Me To First Class ·

2025/12/01

There's a new player in the rewards space, and it's changing what's possible for earning points even if you never open another credit card. In this episode, I'm joined by Carissa Rawson, Director of Travel and Marketing for Rove, a fast-growing loyalty platform that combines a travel booking portal with an online shopping portal so you can earn transferable miles on hotel stays, flights, and everyday purchases. Whether you're new to points or you've been in the hobby for years, Rove offers earning

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11:58

143. Your Holiday Points Prep Checklist: 5 Steps to...

Point Me To First Class ·

2025/11/24

This week marks the biggest points-earning opportunity of the entire year—especially if you're planning to shop online. While everyone else is focused on Thanksgiving prep, points and miles travelers know this is the week to turn everyday purchases into tens of thousands (or more) of bonus points. In this short and focused episode, I'm sharing my 5-step points-earning prep checklist for holiday spend—the exact steps I complete before, during, and after the holiday shopping surge to stay organized,

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48:03

142. How Points Become a Tool for Freedom, Joy & the...

Point Me To First Class ·

2025/11/17

Travel is never just about the destination — it's about what the journey makes possible. In today's episode, we explore how learning to earn and use credit card points isn't just a smart financial decision. It's a pathway to freedom, abundance, and experiences that reflect the life you actually want to live. From upgraded flights to dream hotels, points can turn everyday expenses into extraordinary opportunities. No one embodies that transformation quite like Dielle Charon. A former social worker

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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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169 results

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