Point Me To First Class
by 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 redeeming credit card points and shows you how to spend them on incredible travel experiences.Interested in learning more about working with Devon? Visit www.pointmetofirstclass.com to learn more. This podcast is for you if you find yourself asking questions like: How do I earn credit card points and use them for travel? How can I make my expenses benefit me?How can I earn as many credit card points for as little spending as possible?How to maximize value from credit card points.Ho
Episodes
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191. The Southwest Companion Pass Shakeup: What's Changing and What to Do Now
The way almost everyone has earned the Southwest Companion Pass is about to disappear, and the window to still do it the old way is closing. For years, the Companion Pass has been one of the most valuable, and most reachable, perks in points and miles, a buy-one-get-one on nearly every Southwest...
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190. Mind the Cap: How to Avoid Dropping From 5x Points to 1x
There's a good chance one of your best rewards cards quietly stopped paying its full bonus rate months ago, and never said a word about it. It's called a bonus category spending cap, and more of the cards you carry probably have one than you'd expect. These limits are one of the quietest ways to...
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189. The Hotel Points Program You're Probably Overlooking: ALL Accor with Dr. Suzanne Manzi
One of the most useful hotel programs in my wallet right now is also the most boring, and that turns out to be exactly why it works. That program is Accor, and it tends to get overlooked in the points world, often by the very people who would get the most out of it. My guest, Dr. Suzanne Manzi…
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188. The Transferable Points Report Card: Grading Every Currency on Points Sharing
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...
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187. Atmos Rewards Explained: Alaska Airlines' Loyalty Program, Partners, and Best Uses
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...
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186. Around the World in Five Days: How We Reverse-Engineered an Epic Award Trip
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...
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185. Which Points Get Your Family to Asia in Business Class?
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...
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184. Hotel Planner Points: How to Earn Points for Any Event
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…
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183. Is the Bilt Palladium Card Worth It? A Six-Month Review of Bilt 2.0
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...
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182. Behind the Scenes of seats.aero with Keith Van
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…
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181. The Two Ways to Search for Award Flights, and Why You Need Both
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…
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180. Estimating Your Points Earning Potential: What Your Expenses Are Worth
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...
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179. Listener Q&A: Real Points Decisions, The Case for Chase, and New Award Sweet Spot
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...
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178. How to Earn Points on Your Savings, Not Just Your Spending
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…
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177. Mid-Year Points & Miles Review 2026: The 6 Changes That Matter Most
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...
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176. Two Points Experts, Two Takes on Park Hyatt Cabo and Alila Mayakoba
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...
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175. Why Aeroplan Belongs in Every Traveler's Award Strategy
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...
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174. United MileagePlus Upgrade Awards: How to Book Polaris for Less Cash and Miles
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...
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173. London on Points: Awards, Taxes & Insider Tips
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...
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172. Autopilot Flight Repricing: Save Money on Flights After Booking with Sam Hollander
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...
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171. 143 Venture Business Applications: Surprising Predictors of Approvals & Denials with Katie's Travel Tricks
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...
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170. Earn 10x Chase Points! The Paze Strategy Explained
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...
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169. Kyoto with Kids, Travel Mistakes & the Full Trip Cost: Japan Spring Break Breakdown
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...
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168. A $111k Family Trip to Japan for $1,660: How It Started
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...
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167. The Woman Dancing in the Sahara Arrived Terrified - Why the Right Adventure Trip Brings You Home to Yourself
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…
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166. The Payroll Points Strategy Update: Cards, ROI & Best Practices with DeAndre Coke
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,...
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165. Pack Your Bags for Austin: The 2027 Points Conference You've Been Waiting For
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...
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164. Credit Card Product Changes: 5 Strategic Ways to Strengthen Your Portfolio
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...
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163. Listener Q&A: Bilt vs Amex, Spending Toward Status, & Rethinking Points Fundamentals
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…
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162. Where Japan Airlines Miles Fit in Your Award Travel Strategy with Michael Gandara
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...
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161. Points Earning Unicorns: Risk vs. Reward for Outsized Deals with Dr. Sujatha Murali
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…
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160. The Uncapped Value of Hilton Free Night Certificates with Jess Field
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…
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159. The Hyatt Award Chart Overhaul: Points Strategy Shifts with The Points and Miles Doc
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...
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158. Before You Pay Your Taxes by Credit Card: Avoid These Points-Killing Mistakes
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…
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157. Shifting My Strategy: Why I'm Pursuing Status in Multiple Programs This Year
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…
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156. Making Large Family Award Travel Actually Work with Dr. Alison Curfman (Part 2)
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...
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155. Planning Award Travel for Large Families with Dr. Alison Curfman (Part 1)
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...
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154. The Most Memorable Credit Card Points Lessons from Real Travelers
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...
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153. Avios Explained: Understanding Transfers & Maximizing Award Flights
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…
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152. Building Wealth Beyond Travel: Financial Planning for High-Earners with Lauren Oschman
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…
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151. Bilt's 3 New Cards: A Complete Analysis & Strategy Guide
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...
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150. 2025 Points Year in Review: How We Used Our Points, Chose Programs & Planned 2026 Travel (Part 2)
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…
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149. 2025 Points Year in Review: A Look Back at Cards, Strategies & Earning (Part 1) with Dr. Andrea Mabry
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...
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148. Your Year in Points Review: How to Audit, Learn, and Plan Smarter
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...
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147. 2025 in Points and Miles In Review (Part 2): Key Changes, New Realities, and What Comes Next
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...
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146. 2025 in Points and Miles In Review: The Biggest Wins, Disappointments & Shifts - Part 1
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...
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145. Behind the Scenes at World of Hyatt: Loyalty, Care & the Future of Travel with Laurie Blair
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…
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144. Inside Rove: The Loyalty Program Reshaping Points & Miles
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…
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143. Your Holiday Points Prep Checklist: 5 Steps to Maximize Seasonal Spending
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…
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142. How Points Become a Tool for Freedom, Joy & the Life You Want to Live with Dielle Charon
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...
About this show
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.Interested in learning more about working with Devon? Visit www.pointmetofirstclass.com to learn more. This podcast is for you if you find yourself asking questions like: How do I earn credit card points and use them for travel? How can I make my expenses benefit me?How can I earn as many credit card points for as little spending as possible?How to maximize value from credit card points.Ho
Hosted by
Devon Gimbel MD