Devon Gimbel MD

Point Me To First Class

Society EN ↓ 182 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...

Author

Devon Gimbel MD

Category

Society

Podcast website

pointmetofirstclass.com

Latest episode

Jul 6, 2026

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Episodes

175. Why Aeroplan Belongs in Every Traveler's Award Strategy 06.07.2026

Have you ever transferred miles into a program and then realized you only ever use it to book the same handful of flights everyone else does?   Air Canada Aeroplan might be the most useful airline program that US travelers consistently overlook, and after this conversation I think you'll see why so many experienced points and miles enthusiasts treat it as a core part of their strategy. Today I'm t...

174. United MileagePlus Upgrade Awards: How to Book Polaris for Less Cash and Miles 29.06.2026

If you've ever looked at United Polaris business class prices and thought they were completely out of reach, you're not alone. They can be outrageously expensive to book whether you're eyeing paying cash or points.   But what if there was a third path - something between paying full cash for a premium ticket and redeeming a massive amount of miles outright? Miguel Rueda, from the Let's Get to the...

173. London on Points: Awards, Taxes & Insider Tips 22.06.2026

Have you considered London as your next award travel destination but weren't sure where to start?   London is one of the most accessible and rewarding destinations for both beginner and experienced award travelers, but it comes with unique challenges that most people don't anticipate. The city's accessibility makes it ideal for your first international points trip, yet the mechanics of award prici...

172. Autopilot Flight Repricing: Save Money on Flights After Booking with Sam Hollander 15.06.2026

Most travelers think booking a flight is the finish line. They hit purchase and consider the deal done.   Sam Hollander knew something they didn't: the booking is actually just the beginning. When domestic airlines permanently removed change fees during the pandemic, they accidentally created an enormous opportunity for travelers to save money after they've already booked their flights and hotels....

171. 143 Venture Business Applications: Surprising Predictors of Approvals & Denials with Katie's Travel Tricks 08.06.2026

Have you ever wondered why Capital One's approval decisions feel completely random - approval for some, denial for others, with almost no rhyme or reason?   Capital One has a well-earned reputation for being unpredictable with credit card approvals. When Katie from Katie's Travel Tricks saw the launch of the new Capital One Business Venture card, she decided to move beyond anecdotes and collect re...

170. Earn 10x Chase Points! The Paze Strategy Explained 01.06.2026

Have you heard about the quiet Chase promotion that could be one of the biggest points-earning opportunities we've seen in years?   In May 2026, Chase launched a promotion through the digital payment platform Paze that allows cardholders to earn 10 times Chase Ultimate Rewards points on eligible transactions—and up to 14 times on certain cards through the end of 2026. Dr. Michelle Walther and I di...

169. Kyoto with Kids, Travel Mistakes & the Full Trip Cost: Japan Spring Break Breakdown 25.05.2026

Have you ever fallen so in love with a city that you started seriously considering moving there?   That's exactly what happened to us in Kyoto. In part two of our Japan spring break trip recap, my husband Brandon and I continue our family travel story as we settle into five nights at the Park Hyatt Kyoto, a property so beautiful that I can confidently say it's the most stunning hotel I've experien...

168. A $111k Family Trip to Japan for $1,660: How It Started 18.05.2026

Have you ever been tempted to completely change your vacation plans because of an irresistible points deal?   That's exactly what happened when Japan Airlines did a random first class award dump last April. I couldn't resist jumping on the opportunity to book our family of four in first class to Tokyo - even though it meant splitting us across two different flights and completely scrapping our ori...

167. The Woman Dancing in the Sahara Arrived Terrified - Why the Right Adventure Trip Brings You Home to Yourself 11.05.2026

Have you ever felt like you're so caught up in your daily roles and responsibilities that you've lost touch with who you are beneath all of that?   Dr. Stacey Funt, a radiologist, health coach, and founder of LH Adventure Travel, believes that travel has the power to help us reconnect: not just with the world around us, but with ourselves. She curates wellness and adventure group trips for women t...

166. The Payroll Points Strategy Update: Cards, ROI & Best Practices with DeAndre Coke 04.05.2026

If you're a business owner who pays payroll for yourself or your employees, you might be sitting on one of the biggest untapped points-earning opportunities in your business—and it doesn't require opening new cards or chasing welcome bonuses.   DeAndre Coke, a financial advisor and points expert, returns to the show to give us a much-needed update on earning credit card points for payroll expenses...

165. Pack Your Bags for Austin: The 2027 Points Conference You've Been Waiting For 27.04.2026

If you've ever wished you could talk about points and miles with people who are just as enthusiastic about it as you are—without worrying about annoying anyone—this episode is for you.   Dr. Andrea Mabry and I are officially announcing the 2027 Point Me to First Class Conference, taking place in Austin, Texas from April 29th through May 2nd at the Hyatt Regency Austin. After the incredible respons...

164. Credit Card Product Changes: 5 Strategic Ways to Strengthen Your Portfolio 20.04.2026

If you've been holding the same credit cards for years, you might be missing out on one of the most underutilized strategies for building a stronger, more cost-effective rewards card portfolio.   Product changes don't get the same attention as opening new cards for big welcome bonuses or booking aspirational travel. But they offer surprising benefits that can help you lower annual fees, acquire ca...

163. Listener Q&A: Bilt vs Amex, Spending Toward Status, & Rethinking Points Fundamentals 13.04.2026

Have you ever wondered if the advice you're following about credit cards and points is still relevant—or if the landscape has shifted enough that the old "rules" no longer apply?   In this listener Q&A episode, I'm answering your questions on everything from Rakuten rewards strategy and Chase credit card approvals to hotel booking during peak travel times and whether hotel status is worth the spen...

162. Where Japan Airlines Miles Fit in Your Award Travel Strategy with Michael Gandara 06.04.2026

If you've been transferring points to the same airline programs over and over, you might be missing out on one of the most fascinating but overlooked loyalty programs in the points world - Japan Airlines Mileage Bank.   Now that Japan Airlines is a direct transfer partner of Bilt, Capital One, and Rove, accessing this program is easier than ever. But given how new this is to many of us, you may no...

161. Points Earning Unicorns: Risk vs. Reward for Outsized Deals with Dr. Sujatha Murali 30.03.2026

Have you ever seen a points deal that looked too good to be true? 250 Avios per dollar spent. 240 American Airlines miles per dollar. Those kinds of multipliers make you do a double-take and for good reason. Deals like these are as enticing as they are uncertain.    In this episode, I'm joined by Dr. Sujatha Murali to talk about what I call points earning unicorns—rare, outsized opportunities wher...

160. The Uncapped Value of Hilton Free Night Certificates with Jess Field 23.03.2026

If you've been focused on earning hotel points, you might be overlooking one of the most powerful strategies for saving money on luxury hotel stays—and it doesn't require hundreds of thousands of points.   In this episode, I'm joined by Jess Field of Points Talk Squad to break down exactly how Hilton free night certificates work and how you can strategically earn and use them for maximum value. Hi...

159. The Hyatt Award Chart Overhaul: Points Strategy Shifts with The Points and Miles Doc 16.03.2026

Over the past decade, Hyatt has had one of the most beloved hotel loyalty programs in the points world—and a big reason for that has been its simple, predictable award chart that made it possible to get incredible value from Hyatt points. That's (potentially) about to change as Hyatt recently announced a major overhaul to its award chart structure that will introduce dozens of new pricing levels a...

158. Before You Pay Your Taxes by Credit Card: Avoid These Points-Killing Mistakes 09.03.2026

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 tro...

157. Shifting My Strategy: Why I'm Pursuing Status in Multiple Programs This Year 02.03.2026

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...

156. Making Large Family Award Travel Actually Work with Dr. Alison Curfman (Part 2) 23.02.2026

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 a...

155. Planning Award Travel for Large Families with Dr. Alison Curfman (Part 1) 16.02.2026

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-fo...

154. The Most Memorable Credit Card Points Lessons from Real Travelers 09.02.2026

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...

153. Avios Explained: Understanding Transfers & Maximizing Award Flights 02.02.2026

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 p...

152. Building Wealth Beyond Travel: Financial Planning for High-Earners with Lauren Oschman 26.01.2026

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 e...

151. Bilt's 3 New Cards: A Complete Analysis & Strategy Guide 19.01.2026

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 entir...

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