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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

33:29

181. The Two Ways to Search for Award Flights, and...

Point Me To First Class ·

2026/08/17

Have you ever run an award search, come up empty, and quietly wondered whether the flights you want are even out there? That frustration usually comes down to one thing, and it isn't that the flights don't exist. It's that most of us were never taught how to search for them well. In this episode I break down two ways to search for award flights outside your credit card travel portal, where transferring points to airline partners can turn a one to one-and-a-half cent point into two, five, even ten

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18:31

180. Estimating Your Points Earning Potential: What...

Point Me To First Class ·

2026/08/10

Have you ever wondered whether there's still travel value hiding inside the expenses you already have, points you could be earning but aren't, with no real way to know for sure? That's one of the few questions in this hobby I've never been able to answer for you, and it's probably one you've quietly wondered about yourself. We have a rough way to gauge how well we redeem points, our cents per point at least gives us a benchmark, but there has never been a clean way to know whether the expenses you

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01:09:43

179. Listener Q&A: Real Points Decisions, The Case...

Point Me To First Class ·

2026/08/03

Have you ever had a points question where every source online seems to contradict the last, and what you really want is for someone to walk you through how to actually decide? In this listener Q&A episode, I'm answering the questions you have sent in on everything from choosing your next credit card and where to credit your cash-paid flights to which Hyatt award is worth using, when. But the biggest topic I dig into is the Chase change to how its points transfer to Hyatt, and what that should, and

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53:18

178. How to Earn Points on Your Savings, Not Just...

Point Me To First Class ·

2026/07/27

If you've ever looked at the cash sitting in an emergency fund, a business account, or your tax reserves and wished it could earn travel points the way your spending does, this conversation is for you. For as long as I've been earning points and miles, one piece has been missing. We've gotten very good at earning points on the money we spend, but almost no one has offered a way to earn transferable points on the money we save. That's what made Symphony worth a close look, and I sat down with

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01:26:55

177. Mid-Year Points & Miles Review 2026: The 6...

Point Me To First Class ·

2026/07/20

If you've been paying attention to points and miles this year and something has felt off, like the ground keeps shifting under the rules you thought you understood, you are not imagining it. I'm joined again by my good friend and points expert, Kevin Zanes, to make sense of it all. We are hitting pause at the halfway mark of the year to ask what the biggest stories in points, miles, and award travel have really been so far, and more importantly, what those changes tell us about where this whole

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01:11:56

176. Two Points Experts, Two Takes on Park Hyatt Cabo...

Point Me To First Class ·

2026/07/13

If you've been eyeing one of Hyatt's newer Mexico resorts and wondering whether it's actually worth your points, you're not alone. I'm joined this week by Michele from Fancy Travel Pointers, and the two of us have both separately stayed at Park Hyatt Los Cabos at Cabo del Sol and Alila Mayakoba within the last six months. Instead of each doing a solo review, we decided to sit down and compare notes, since we booked, stayed, and experienced both properties independently and didn't come away

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01:08:51

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

Point Me To First Class ·

2026/07/06

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 talking with Anshul Singh of Points, Miles, and Bling, who has spent years inside the Aeroplan ecosystem

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42:59

174. United MileagePlus Upgrade Awards: How to Book...

Point Me To First Class ·

2026/06/29

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 Points podcast, shares about a strategy within the United loyalty program that most travelers either

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01:00:20

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

Point Me To First Class ·

2026/06/22

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 pricing, taxes and fees, and hotel value require strategy to maximize your redemptions. Today I'm talking

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41:24

172. Autopilot Flight Repricing: Save Money on...

Point Me To First Class ·

2026/06/15

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. Sam founded Autopilot, a platform to help solve the problem most travelers face: they don't have the

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56:19

171. 143 Venture Business Applications: Surprising...

Point Me To First Class ·

2026/06/08

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 real data. She surveyed her audience about their approval and denial experiences, gathered nearly 150

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01:10:18

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

Point Me To First Class ·

2026/06/01

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 discuss why we were initially skeptical of this opportunity and why we've become convinced it could be

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58:36

169. Kyoto with Kids, Travel Mistakes & the Full Trip...

Point Me To First Class ·

2026/05/25

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 experienced anywhere in the world. Brandon and I share our honest take on each Kyoto activity we did as a

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54:21

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

Point Me To First Class ·

2026/05/18

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 original Mexico plans. For the first time in this podcast's history, my husband Brandon joins me at the

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36:07

167. The Woman Dancing in the Sahara Arrived...

Point Me To First Class ·

2026/05/11

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 to some of the most transformative destinations on earth, from trekking the Inca Trail to exploring the

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45:42

166. The Payroll Points Strategy Update: Cards, ROI &...

Point Me To First Class ·

2026/05/04

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 using the Zil Money platform. We first talked about this strategy back in Episode 105 last year, but

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35:47

165. Pack Your Bags for Austin: The 2027 Points...

Point Me To First Class ·

2026/04/27

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 response to our first conference in Chicago, we knew we wanted to do this again—and this time, we're giving you

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38:05

164. Credit Card Product Changes: 5 Strategic Ways to...

Point Me To First Class ·

2026/04/20

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 cards that are no longer open to new applicants, and even stack spend thresholds in ways that compound

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01:38:33

163. Listener Q&A: Bilt vs Amex, Spending Toward...

Point Me To First Class ·

2026/04/13

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 spend. But the biggest topic I tackle is one I've been thinking about a lot lately: how my fundamental

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54:03

162. Where Japan Airlines Miles Fit in Your Award...

Point Me To First Class ·

2026/04/06

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 not yet be familiar with its incredibly powerful sweet spots—both for flying on Japan Airlines operated

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192 results

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