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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

31:02

188. The Transferable Points Report Card: Grading...

Point Me To First Class ·

2026/10/05

You can have a small fortune in points between two people and still not be able to book the trip you want. That's the trap this episode is built to help you avoid. Combining or sharing points with a partner, a spouse, or a family member sounds like it should be simple, but every points currency plays by its own rules, and a couple of them won't let you share points with someone else at all. Knowing which is which, well before you've found the award you want to book, turns out to be one of the

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50:44

187. Atmos Rewards Explained: Alaska Airlines'...

Point Me To First Class ·

2026/09/28

Some of the most valuable miles in award travel belong to a program most people have written off. For years, Alaska Airlines miles were easy to overlook, and unless you lived in Alaska or flew the airline often, you probably had little reason to think about them. My guest, Betsey Wilson of Become Travel Rich and Alaska Airlines University, has spent more than two decades in this program and knows it better than anyone I know. As she explains, the real value of these miles, now part of the revamped

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01:19:06

186. Around the World in Five Days: How We...

Point Me To First Class ·

2026/09/21

Planning an entire trip around one airline seat is a backwards way to travel, and every so often it's exactly the right one. My friend Andrea and I have wanted to fly first-class Singapore Airlines Suites on the A380 for years. When we two award seats on their newest first class on a long-haul flight, we built a five-day trip around the world around them, five flights, and almost no regard for where any of it landed on a map. What follows is the whole story, the planning, the flying, and the

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57:29

185. Which Points Get Your Family to Asia in Business...

Point Me To First Class ·

2026/09/14

Collecting a big pile of points is not the same as being able to book the flights your family wants. That gap shows up nowhere more clearly than when you're trying to get your whole family into business class to Asia. This week my guest is Maria Fung, founder of Maria Points the Way, who helps families use points and miles to reach Asia and Asia-Pacific. When Maria moved from Hong Kong to the US, she did everything the points world tells you to do, and soon found it wasn't getting her family

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39:21

184. Hotel Planner Points: How to Earn Points for Any...

Point Me To First Class ·

2026/09/07

Some of the biggest points opportunities have nothing to do with your credit card at all. It turns out hotels quietly reward the person who books an event with them, a conference, a retreat, a wedding, a family reunion, and most people have no idea. They're called planner points. To unpack them, I sat down with Rachel Posada Fletcher, who spent years as an event manager negotiating exactly these kinds of hotel contracts. And the best part is you don't have to plan events for a living to earn

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01:16:44

183. Is the Bilt Palladium Card Worth It? A Six-Month...

Point Me To First Class ·

2026/08/31

Six months ago, Bilt rebuilt its entire rewards program, including releasing the new premium Palladium card with its promise of earning transferable points on rent and even mortgage payments, drawing a lot of attention in the points world. Today we are following up on what it's actually been like to carry and use the Bilt Palladium card now that the shine has worn off and real life has set in. Kelly and I have almost identical points philosophies, which is exactly why it's so much fun that Bilt is

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56:50

182. Behind the Scenes of Seats.aero with Keith Van

Point Me To First Class ·

2026/08/24

Have you ever wondered what your award search tool can see that you can't? My guest this week is Keith Van, who leads community at Seats.aero, one of the award search platforms I reach for most. What made this so fun for me is that his team sees something the rest of us never do. They can watch how travelers everywhere are searching for award space all at once, which means they notice patterns in demand and in availability that none of us could piece together alone, and a few of the ones Keith

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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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199 results

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