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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:

118. Jet-Set with JAL: Bilt's Boldest Transfer Partner Yet Jun 02, 2025

Show notes

Have you ever dreamed of flying to Japan in business class—without paying out of pocket? Bilt just made that a lot easier.

In this episode, I'm joined by award travel strategist Ben Komenkul to talk about the newest (and most exciting) Bilt Rewards transfer partner: Japan Airlines. This partnership opens the door to premium flights across Asia and around the world—and it's not just for those planning a trip to Tokyo.

Ben and I walk through everything from low-cost regional flights and lie-flat business class options to more advanced redemptions like partner bookings with Emirates or Korean Air. We also share the biggest tips and pitfalls to know before transferring your Bilt points, including how to avoid JAL's 60-day award booking delay and why their mileage expiration policy might not work for everyone.

If you've been curious about using Bilt points—or want to understand when this program can unlock premium cabin value—this is a must-listen.

Get full show notes and transcript: https://pointmetofirstclass.com/book-japan-airlines-with-bilt-rewards/

Want to shape the show? Take the Point Me To First Class listener survey and share what you love and want more of! https://docs.google.com/forms/d/e/1FAIpQLSeAPfb3wIaphMn_NoQzm_fljydsivTELQwh7pYoxrI2uTFoKQ/viewform?usp=header

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

117. Making Smart Transfer Moves: When Speculative Points Transfers are Worth It (And When They're Not) May 26, 2025

Show notes

A major points transfer pathway is shutting down—and it's got a lot of people wondering: should I move my Amex points to Alaska Airlines before the door closes?

In this episode, I break down the fast-approaching June 30 deadline to transfer Amex points to Hawaiian Airlines (and from there to Alaska), and walk you through my personal decision—including the 4-step framework I use for evaluating speculative points transfers.

If you've ever wondered whether it's smart to move points to a transfer partner without a specific booking in mind, this episode will help you weigh the risk and make a decision you can feel confident in—whether it's for this opportunity or any future bonus or expiring partnership.

Get full show notes and transcript: https://pointmetofirstclass.com/speculative-points-transfer-guide/

Want to shape the show? Take the Point Me To First Class listener survey and share what you love and want more of! https://docs.google.com/forms/d/e/1FAIpQLSeAPfb3wIaphMn_NoQzm_fljydsivTELQwh7pYoxrI2uTFoKQ/viewform?usp=header

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

116. The Award Travel Trick Hiding in Plain Sight: Fifth Freedom Flights May 19, 2025

Show notes

If you've ever struggled to find award space—especially in business class—this is the episode you've been waiting for.

In this episode, I'm diving into a unique but often overlooked type of airline route called a fifth freedom flight. These flights are legal exceptions in commercial aviation that allow an airline to fly between two foreign countries, neither of which is their home base—and for points enthusiasts, they offer some of the best award availability, better cabin experiences, and unique route opportunities around the world.

I'll walk you through the history behind these flights, how to spot them, and the exact routes worth checking out to Europe, Asia, Africa, and even the Caribbean. Whether you're hunting for better premium cabin space or just want a smoother flight, fifth freedom flights should absolutely be on your radar.

Get full show notes and transcript: https://pointmetofirstclass.com/fifth-freedom-flights-points-strategy/

Want to shape the show? Take the Point Me To First Class listener survey and share what you love and want more of! https://docs.google.com/forms/d/e/1FAIpQLSeAPfb3wIaphMn_NoQzm_fljydsivTELQwh7pYoxrI2uTFoKQ/viewform 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

115. Rhythms, Routines, and REM: Expert Tips to Manage Jet Lag & Sleep Disruption While Crossing Time Zones May 12, 2025

Show notes

No matter how dreamy your destination is, there's one thing that can make or break your trip: sleep.

In this episode, I'm joined by sleep therapists Leah Corkum and Marlee Boyle, co-founders of Sleep-Works, a Canadian-based virtual sleep education company helping individuals and families improve their sleep health. With certifications in CBT for insomnia, clinical sleep health, and years of experience in both nursing and respiratory therapy, Leah and Marlee bring a holistic and practical approach to sleep support that goes far beyond just tips and tools.

We talk about how travel disrupts sleep, what actually causes jet lag, and why light exposure, sleep environment, and the way you use (or misuse) melatonin can all have a big impact on how you feel before, during, and after a trip.

Whether you're a frequent flyer, a parent navigating time zone shifts with kids, or just trying to avoid that foggy, post-vacation exhaustion, this conversation is packed with practical strategies from professionals who know the science—and the real life struggle—of sleep and travel.

Get full show notes and transcript: https://pointmetofirstclass.com/sleep-while-traveling-jet-lag-tips/

Want to shape the show? Take the Point Me To First Class listener survey and share what you love and want more of! 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

114. Finally! Turning Your Mortgage into Points: How Mesa is Flipping the Script on Rewards May 05, 2025

Show notes

There's finally a card that rewards you for the one expense that's been completely ignored in the points world: your mortgage.

In this episode, I'm talking with Kelley Halpin, CEO of Mesa, about the first credit card that lets you earn points for mortgage payments—plus other major homeowner expenses like daycare, utilities, and home improvement. Kelley shares what makes the Mesa card unique, how its rewards system works, and why it's designed to serve a segment of consumers that's long been overlooked by traditional credit card programs.

If you've ever wished one of your biggest monthly bills could earn serious points—this card just might become your new favorite.

Make sure to check out the Mesa Homeowners Card - no annual fee, earns points on your mortgage and comes with $800+ in home benefits! Use my referral link to get 5,000 bonus points when you get approved.

https://mesa.onelink.me/odOT/gge86l53?referral_code=htx8f5

Use my code to apply: htx8f5

Terms apply.

Get full show notes and transcript: https://pointmetofirstclass.com/mesa-credit-card-earn-points-mortgage/

Want to shape the show? Take the Point Me To First Class listener survey and share what you love and want more of!

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

113. 4 Ways to Maximize Points for Costco Spend (Without Overcomplicating It) Apr 28, 2025

Show notes

Whether your Costco haul includes a 5-pound bag of almonds or a giant sectional sofa, one thing is certain: you're probably not spending just a few bucks.

If you've ever wondered how to earn more credit card points on your Costco runs, this episode walks you through four smart, strategic ways to maximize rewards—whether you're shopping in-store, online, or through a workaround like Instacart. You'll learn which cards work, which ones don't, and how to pick the best method based on your spending habits and points goals.

This episode is your go-to guide for getting the most out of every Costco trip—without having to overhaul your strategy or juggle a dozen cards.

Get full show notes and transcript: https://pointmetofirstclass.com/maximize-points-costco/

Want to shape the show? Take the Point Me To First Class listener survey and share what you love and want more of!

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

112. Best Ever or Big Mistake? 3 Steps to Evaluate if Best-Ever Welcome Offers are Right for You Apr 21, 2025

Show notes

A limited time elevated credit card bonus offer sounds amazing—so should you go for it?

In this episode, I break down how to evaluate elevated credit card welcome bonuses so you can make a smart, strategic decision. Using the current Chase Sapphire Preferred offer as a real-world example, I walk through the three questions you need to ask before jumping on any limited-time offer:

✔ Are you even eligible?

✔ How will this card fit into your overall points and travel goals?

✔ What's the opportunity cost of applying right now?

Whether you're new to points or deep in the game, this episode will help you avoid shiny bonus syndrome and make elevated offers work for you—not the other way around.

Get full show notes and transcript: https://pointmetofirstclass.com/evaluate-elevated-credit-card-bonuses/

Want to shape the show? Take the Point Me To First Class listener survey and share what you love and want more of! 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

111. Life, Travel, and Money Hacks with Chris Hutchins Apr 14, 2025

Show notes

What does it look like to fully optimize your life—not just financially, but how you travel, make decisions, and spend your time?

In this episode, I'm joined by Chris Hutchins, host of All the Hacks, for a fast-paced conversation about how to get more value, joy, and efficiency from everything you do. We talk about optimizing credit card rewards, streamlining travel, removing decision fatigue, and using money as a tool—not just for freedom, but for alignment with your values.

If you're the kind of person who loves a smart system, a good travel hack, or just wants to make everyday decisions easier and more intentional, this episode is packed with ideas and inspiration.

Get full show notes and transcript: https://pointmetofirstclass.com/travel-money-life-hacks-chris-hutchins/

Want to shape the show? Take the Point Me To First Class listener survey and share what you love and want more of!

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

110. 2025 Tax Payment Updates You Need to Know with Dr. Sujatha Murali Apr 07, 2025

Show notes

With changes to credit card processing platforms and fee structures for 2025, the strategy for paying taxes with a credit card—and earning points while doing it—has shifted.

In this episode, I'm joined by my good friend and points expert Dr. Sujatha Murali to walk you through the major changes in tax payment processing for 2025—and how to earn huge amounts of points while minimizing fees.

We share our personal strategies for navigating quarterly tax payments, which types of cards to prioritize (and avoid), and how to use PayPal strategically to unlock the lowest fees possible when paying taxes with certain rewards cards. Whether you're paying $5K, $50K, or more in taxes, this is a must-listen if you're serious about turning expenses into travel.

Turn your expenses into points and save tens of thousands of dollars a year on your wishlist travel. Don't miss out! Click here to know more about my comprehensive online program, Points Made Easy.

Get full show notes and transcript: Want to shape the show? Take the Point Me To First Class listener survey and share what you love and want more of!

109. How to Pack Smart for Travel Without Sacrificing Style with Cassandra Sethi Mar 31, 2025

Show notes

Have you ever stood in front of your suitcase, overwhelmed, unsure what to pack—or panic-ordered outfits days before a trip that you'll never wear again? You're not alone. In fact, this episode might be exactly what your suitcase (and closet) needs.

In this episode, I'm joined by Cassandra Sethi, personal stylist and founder of Next Level Wardrobe, who shares her system for making packing simple, efficient, and actually fun. We talk about how to get more outfits with fewer pieces, avoid the most common packing mistakes, and how to feel stylish and comfortable—whether you're heading to Paris or just to the airport.

If travel packing always feels like a puzzle you can't solve, this episode will help you finally crack it.

Get full show notes and transcript: https://pointmetofirstclass.com/stylist-travel-packing-guide/

Want to shape the show? Take the Point Me To First Class listener survey and share what you love and want more of!

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