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Point Me To First Class — Places & Travel
Point Me To First Class

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.
How to earn credit card points for travel.
Turn credit card points into travel.

Copyright: © 2024 Devon Gimbel MD LLC All Rights Reserved

Latest Episodes:

193. Shopping Portal Superstacking: How to Earn Points Three Ways on One Purchase Nov 09, 2026

Show notes

In the two weeks around Black Friday and Cyber Monday last year, I earned over 335,000 points from online shopping portals alone.

That's roughly the value of two credit card welcome bonuses, earned on shopping I was going to do anyway, without opening a single new account. And with card approvals getting harder to come by, learning to squeeze more out of everyday online spending has gone from a nice bonus to a real strategy.

Doing that well comes down to three strategies: the simple habit most people skip, a gift card technique that can multiply your earnings several times over, and a more advanced move I call super stacking that turned a single purchase into 29 times the points. These strategies work all year, but they shine during the holiday shopping period, when portal rates hit their highest of the year. If any of your holiday shopping is happening online, this is the episode that turns it into a serious points opportunity.

Get full show notes and transcript: https://pointmetofirstclass.com/how-to-stack-shopping-portals

Eager to learn the secrets of award travel so that you can turn your expenses into unforgettable experiences? Join the Points Made Easy course waitlist here: https://pointmetofirstclass.com/pointsmadeeasy

192. What the Data Reveals About Earning More Points with Shopping Portals and Card-Linked Offers Nov 02, 2026

Show notes

Your favorite shopping portal may not be the best one to always use, and millions of data points can prove it.

My guest is Avneesh Kohli, the founder of SaveWise, a tool I use literally every day to find the best points-earning opportunity for whatever I'm about to buy. Beyond helping with individual purchases, SaveWise has indexed tens of millions of shopping portal rates and card-linked offers across thousands of merchants, which means Avneesh can see patterns in this world that no individual shopper ever could. And some of what he's found challenges things the points community has long taken as true.

Avneesh and I get into which shopping portals the data says deliver the most value, some of which will surprise you, and the single best day of the week to shop online if you want the highest rates. We dig into what the numbers reveal about card-linked offers, including which issuers quietly offer the best deals and where the real value is hiding. And because we're heading into the biggest points-earning season of the year, he shares what the data says about shopping smart around Black Friday and Cyber Monday. If you use shopping portals and card-linked offers, even casually, this is the episode that will make you better at it.

Get full show notes and transcript: https://pointmetofirstclass.com/best-shopping-portals-points-data

Eager to learn the secrets of award travel so that you can turn your expenses into unforgettable experiences? Join the Points Made Easy course waitlist here: https://pointmetofirstclass.com/pointsmadeeasy

191. The Southwest Companion Pass Shakeup: What's Changing and What to Do Now Oct 26, 2026

Show notes

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 flight that can be worth thousands of dollars. Then Southwest announced a sweeping overhaul of its Rapid Rewards program, and starting January 1, 2027, the companion pass works on completely different rules. My returning guest, Katie of Katie's Travel Tricks, has taught people how to earn this pass for years, and she's here to break down exactly what's changing and what it means for you.

Katie and I get into why these changes gut the strategy most people have relied on, why Southwest's own framing of the news is more spin than substance, and the narrow window that still exists this year to earn a companion pass under the old rules, if you act in time. We also take on the bigger question, whether chasing a companion pass still makes sense at all going forward, and what to do instead if it doesn't. If earning a Southwest Companion Pass has been anywhere on your radar, this is the episode to hear before you make your next move.

Get full show notes and transcript: https://pointmetofirstclass.com/southwest-companion-pass-changes

Eager to learn the secrets of award travel so that you can turn your expenses into unforgettable experiences? Join the Points Made Easy course waitlist here: https://pointmetofirstclass.com/pointsmadeeasy

190. Mind the Cap: How to Avoid Dropping From 5x Points to 1x Oct 19, 2026

Show notes

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 leave points on the table, and they catch even seasoned points travelers off guard.

In this episode, I walk through which popular cards have these caps and which don't, how to tell whether you're close to hitting one, and what to do when you are, because there are more ways around a cap than most people realize. The goal isn't to collect more cards for the sake of it, it's to keep the money you're already spending earning at the rate you signed up for. If you've ever picked a card for one great category and funneled all your spending to it, this episode will help you make sure those points are still landing where you think they are.

Get full show notes and transcript: https://pointmetofirstclass.com/credit-card-spending-caps

Eager to learn the secrets of award travel so that you can turn your expenses into unforgettable experiences? Join the Points Made Easy course waitlist here: https://pointmetofirstclass.com/pointsmadeeasy

189. The Hotel Points Program You're Probably Overlooking: ALL Accor with Dr. Suzanne Manzi Oct 12, 2026

Show notes

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, is the one who got me paying attention to it, and she knows the program inside and out.

We talk through what makes Accor so different from the hotel programs most of us default to, why its quietest qualities turn out to be its most useful ones, and the kinds of trips where it has come through for me when my usual strategy couldn't. If you travel internationally, travel with a family, or just want a dependable backup for the moments your favorite program comes up empty, I think you'll finish this one seeing Accor very differently.

Get full show notes and transcript: https://pointmetofirstclass.com/accor-points-explained

Eager to learn the secrets of award travel so that you can turn your expenses into unforgettable experiences? Join the Points Made Easy course waitlist here: https://pointmetofirstclass.com/pointsmadeeasy

188. The Transferable Points Report Card: Grading Every Currency on Points Sharing Oct 05, 2026

Show notes

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 quietest but most important parts of planning travel with another person.

I walk through all six major transferable currencies: Amex, Chase, Citi, Capital One, Bilt, and Rove, and grade each one on how easily it lets you combine points with someone else. Not all of them pass. More useful than the grades, though, is what to do about them, the setup worth doing now so the points you've earned together are usable when the trip you want finally appears. If you earn points with a spouse, a partner, or anyone you travel with, this is the housekeeping that keeps you from finding out too late that half your points are stranded in the wrong account.

Get full show notes and transcript: https://pointmetofirstclass.com/combine-credit-card-points-with-partner

Eager to learn the secrets of award travel so that you can turn your expenses into unforgettable experiences? Join the Points Made Easy course waitlist here: https://pointmetofirstclass.com/pointsmadeeasy

187. Atmos Rewards Explained: Alaska Airlines' Loyalty Program, Partners, and Best Uses Sep 28, 2026

Show notes

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 Atmos Rewards program, shows up somewhere most people never look.

Betsey and I get into why this program has been so easy to dismiss, why that's been a mistake, and what makes it, in her words, one of the most generous loyalty programs out there. She shares where she's still finding standout value, which redemptions have gotten harder, and how to think about the Atmos credit cards and elite status without getting lost in the fine print. If you've ever looked at Alaska miles and decided this program wasn't for you, this conversation might change your mind.

Get full show notes and transcript: https://pointmetofirstclass.com/atmos-rewards-alaska-miles

Eager to learn the secrets of award travel so that you can turn your expenses into unforgettable experiences? Join the Points Made Easy course waitlist here: https://pointmetofirstclass.com/pointsmadeeasy

186. Around the World in Five Days: How We Reverse-Engineered an Epic Award Trip Sep 21, 2026

Show notes

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 frankly ridiculous decision-making it took to pull it off.

We get into how a trip like this comes together, why it turns the usual way of planning award travel on its head, and whether spending this many points on a few days of flying was worth it. You'll also hear our candid take on every cabin we flew, where we agreed, where we didn't, and which experiences lived up to the hype.

Whether Singapore Suites is already on your wish list or you just want a fresh way to think about award travel, my hope is you come away seeing that a dream flight doesn't have to wait for the stars to align over your home airport. Listen in as you learn that sometimes the smartest move is to grab the seat when it appears and let the rest of the trip take shape around it.

Get full show notes and transcript: https://pointmetofirstclass.com/singapore-suites-around-the-world

Eager to learn the secrets of award travel so that you can turn your expenses into unforgettable experiences? Join the Points Made Easy course waitlist here: https://pointmetofirstclass.com/pointsmadeeasy

185. Which Points Get Your Family to Asia in Business Class? Sep 14, 2026

Show notes

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 home in the cabins she wanted. That led her to build a completely different approach, one that reverses the usual order, starting with the exact trip you want and working back to the points that get you there.

Maria and I get into why this goal trips up so many families, and why the usual points playbook quietly works against you here. She walks through the destination-first approach she built, a framework she calls the ASIA Method, and the shifts that make several premium seats far more attainable than they look. Whether Asia is an occasional trip to see relatives or a business class dream that has felt out of reach, you'll come away thinking about the whole thing differently.

Get full show notes and transcript: https://pointmetofirstclass.com/family-award-travel-to-asia

Eager to learn the secrets of award travel so that you can turn your expenses into unforgettable experiences? Join the Points Made Easy course waitlist here: https://pointmetofirstclass.com/pointsmadeeasy

184. Hotel Planner Points: How to Earn Points for Any Event Sep 07, 2026

Show notes

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 and benefit from planner points.

Tapping into this points earning potential comes down to simply knowing the opportunity is there and being willing to ask for it. Rachel gets into how these rewards work, the ways a single event can pay off on more than one front, and what she wishes more people understood before signing a hotel contract. If you run a business, help pull together events at work, or have a big celebration on the horizon, I think you'll finish this one seeing your next gathering as more than just an expense.

Get full show notes and transcript: https://pointmetofirstclass.com/hotel-planner-points

Eager to learn the secrets of award travel so that you can turn your expenses into unforgettable experiences? Join the Points Made Easy course waitlist here: https://pointmetofirstclass.com/pointsmadeeasy

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