Point Me To First Class
Point Me to First Class is a podcast for employed professionals, solopreneurs, entrepreneurs, and business owners who want to leverage their higher-than-average personal or business expenses into credit card points for travel. Each week, host Devon Gimbel shares tips, tools, and strategies for earning and redeeming points, maximizing their value, and turning them into incredible travel experiences. The show addresses common questions about earning points efficiently, using expenses as an asset, and converting points into trips. It aims to make the process of using credit card rewards for travel simple and accessible.
Episodes
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 I break down two ways to search for award flights outside your credit card travel portal, where trans
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 quietly wondered about yourself. We have a rough way to gauge how well we redeem points, our cents per po
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 card and where to credit your cash-paid flights to which Hyatt award is worth using, when. But the big
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 very good at earning points on the money we spend, but almost no one has offered a way to earn transfera
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 pause at the halfway mark of the year to ask what the biggest stories in points, miles, and award tr
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 within the last six months. Instead of each doing a solo review, we decided to sit down and compare no
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 many experienced points and miles enthusiasts treat it as a core part of their strategy. Today I'm t
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 premium ticket and redeeming a massive amount of miles outright? Miguel Rueda, from the Let's Get to the
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 accessibility makes it ideal for your first international points trip, yet the mechanics of award prici
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 enormous opportunity for travelers to save money after they've already booked their flights and hotels.
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 launch of the new Capital One Business Venture card, she decided to move beyond anecdotes and collect re
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 transactions—and up to 14 times on certain cards through the end of 2026. Dr. Michelle Walther and I di
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 Kyoto, a property so beautiful that I can confidently say it's the most stunning hotel I've experien
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 Tokyo - even though it meant splitting us across two different flights and completely scrapping our ori
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 with the world around us, but with ourselves. She curates wellness and adventure group trips for women t
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, returns to the show to give us a much-needed update on earning credit card points for payroll expenses
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 Austin, Texas from April 29th through May 2nd at the Hyatt Regency Austin. After the incredible respons
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 aspirational travel. But they offer surprising benefits that can help you lower annual fees, acquire ca
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 credit card approvals to hotel booking during peak travel times and whether hotel status is worth the spen
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 Rove, accessing this program is easier than ever. But given how new this is to many of us, you may no
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 Dr. Sujatha Murali to talk about what I call points earning unicorns—rare, outsized opportunities wher
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 Hilton free night certificates work and how you can strategically earn and use them for maximum value. Hi
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 announced a major overhaul to its award chart structure that will introduce dozens of new pricing levels a
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 wrong card—these problems are stressful on their own, but they're especially problematic when you're tro
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 programs: Hyatt Globalist, Bilt Platinum, Air France Flying Blue Platinum, and American Airlines Platinum Pro
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 systems and strategies that make those trips actually run smoothly. Listen in as Alison shares her a
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 family—typically six to eight people depending on whether au pairs or grandparents join. After co-fo
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 were mindset-shifting, and more than a few had me laughing because they highlighted mistakes that are
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, Iberia, Aer Lingus, and several other airlines. One crucial aspect of Avios that makes them unique among p
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 father work incredibly hard while struggling to balance wealth building with being present at home. That e
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 launch I've seen in a while. This isn't just about welcome bonuses and bonus categories— there's an entir
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, our average redemption values, and the specific trips we planned—from family vacations to aspirational
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 year-in-review series, I've invited Dr. Andrea Mabry back to the show to break down everything that shape
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 helped you reach your travel goals. I walk through why a year-end points review is worth doing, including
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 loyalty programs, this year revealed deeper structural shifts in how airlines price awards, who gets a
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 break down the biggest changes, surprises, and shakeups in the points and award travel world over the l
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 Global Marketing and Loyalty, for a rare behind-the-scenes look at how Hyatt designs a program that travele
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 portal with an online shopping portal so you can earn transferable miles on hotel stays, flights, and ever
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 points. In this short and focused episode, I'm sharing my 5-step points-earning prep checklist for holiday sp
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 want to live. From upgraded flights to dream hotels, points can turn everyday expenses into extraordinar
141. Listener Q&A: Canceling Cards, Transfer Partner Confusion & Shopping Portals vs. Welcome Bonuses
This episode is all about your questions—and real answers. I'm back with another listener Q&A, tackling the points and miles decisions you're actually making right now. From whether it's possible to move points between airline partners to deciding if that old United card still deserves a spot in your wallet, we're covering it all. We'll walk through when to hold or cancel airline cards, how to dec
140. Points Path: The Tool That Shows You the Best Value for Every Flight
Ever look at Google Flights and wonder, "Should I use points for this or just pay cash?" If you've ever felt unsure about which option gives you the best value, this episode is for you. In the final episode of our Streamline, Stack, and Save mini-series, I'm joined by Julian Kheel, former editorial director at The Points Guy and senior editor at CNN, now founder of Points Path — a browser extensio
139. Stack Shopping Portals and Card Offers for Bigger Rewards with Savewise
Do you ever find yourself opening multiple tabs, comparing shopping portal payouts, and trying to figure out which site is going to give you the most rewards for your online shopping — only to give up before you actually earn the points? If that sounds familiar, today's episode is for you. In this Streamline, Stack, and Save mini-series episode, I'm joined by Avneesh Kohli, founder of Savewise, a
138. How to Track, Manage, and Maximize Your Credit Cards with Travel Freely
Have you ever opened a new credit card for the welcome bonus, only to forget how much you've spent or when the deadline hits? Or maybe you're juggling multiple cards and can't remember which one to use next. In this next episode of our Streamline, Stack, and Save mini-series, I'm joined by Zac Hood, founder of Travel Freely, an app that helps you track your credit cards, sign-up bonuses, and annua
137. Stop Guessing, Start Earning: How CardPointers Does the Work for You with Emmanuel Crouvisier
Do you ever forget which credit card to use for a purchase — or worry you're missing out on bonus points and statement credits? It's easy to lose track when every card has different categories, offers, and perks. This episode is part of our Streamline, Stack, and Save mini-series, where we're exploring tools and strategies that simplify how you earn and redeem your points and miles. I'm joined by
136. Mini Retirements: Redefining How You Work, Rest, and Live with Jillian Johnsrud
Do you think you have to wait until your sixties before you can retire? Maybe not. At least not the way we've been taught. In this episode, I'm joined by Jillian Johnsrud — author, podcast host, and coach — who challenges the idea of a traditional retirement in favor of taking mini retirements throughout your life and career. Jillian never expected to retire early, so she hatched a plan to retire
135. Amex Platinum Cards Refresh: What's New, What's Missing, and What We Really Think
Back in June, Chase refreshed its personal Sapphire Reserve card and introduced the Chase Sapphire Reserve Business card, complete with highest ever annual fees for rewards cards. Not to be outdone, American Express quickly followed with its own updates to the personal and business Platinum Cards. Now that the details are here, it's time to look at what's changed and what it means for cardholders.
134. The New Era of Award Travel: What's Changing and How to Adapt
If you've been in the points game for years, you've probably noticed how much has changed recently. And if you're newer, you might be wondering if you're already too late. In this episode, I share why I don't believe we're in the "golden age" of award travel right now — but also why points are still incredibly valuable if you know how to adapt. Over the last couple of years, the rules around earni
133. 7 Keys to Better Award Flight Bookings
You've built up a stash of transferable credit card points. Maybe you've been working hard to optimize your cards, your categories, and your spending. But when it comes time to actually book the flights you've been dreaming about, you hit a wall. You're not alone. For most points travelers, the hardest part isn't earning points — it's redeeming them for the best value. That's why in this episode,
132. From Frustration to $150K in Points Redemptions
What does it really look like to transform your travel with credit card points? In this special episode, you'll hear directly from Dr. Faryal Michaud, a past Points Made Easy student who went from feeling confused and frustrated by points to booking over $150,000 worth of award travel. From Qsuites to the Maldives, South Africa, Tahiti, and beyond, she shares the exact turning points that changed
131. Unpopular Opinion: Top 5 Reasons You Should Book Travel Through a Credit Card Travel Portal
Think booking through your credit card travel portal is always a mistake? Not so fast. Last week, I shared five reasons why you'll want to avoid making travel bookings through your credit card portal. But that's not the whole story. There are also situations where using your card's travel portal can be the smarter move. In this episode, I'm breaking down the five most compelling reasons to conside
130. Top 5 Reasons to Avoid Booking Travel Through Credit Card Travel Portals
If there's one thing nearly every points traveler has done at least once, it's book a flight, hotel, or car rental directly through their credit card's online travel portal. With promises of 5x, 8x, even 12x bonus points, it can feel like the obvious choice. But as I share in today's episode, those tempting multipliers often come at a serious cost—and the reasons why may surprise you. In this epis
129. Fan Favorite: The Psychology of Learning & Mastering Points Travel
In this week's episode, we're re-airing a fan favorite that so many listeners have loved and revisited. If you missed it the first time, or just need a refresher, this is one you don't want to skip. I love discussing discrete award travel topics like individual rewards credit cards and how best to leverage them, or the specific airlines and hotels that offer the best value for points. But today, I
128. The New Citi Strata Elite: Game Changer or Missed Opportunity?
If a $595 annual fee premium credit card hits the market, should it automatically earn a place in your wallet? In this episode, I take a detailed look at Citi's newest addition to the transferable points landscape: the Citi Strata Elite Card. From its standard 80,000-point welcome bonus to the elevated 100,000-point offer available through certain channels, we'll walk through exactly what you get
127. Lounge Access Update: Credit Card Changes, Perks & Picks with Traci Siegel
If you've ever been confused about airport lounge access—what counts, what's changed, and what's still worth it—you're not alone. In this episode, I welcome back guest Traci Siegel for an updated look at lounge access using rewards credit cards in 2025. We unpack the biggest changes to credit card lounge access this year, including new restrictions on who gets in and when. From premium travel card
126. How Much Is a Point Really Worth? A Deep Dive with Frequent Miler's Greg Davis-Kean
If you've ever hesitated before transferring points—or wondered if a redemption was "good enough"—this is the episode you've been waiting for. In this conversation with Greg Davis-Kean (a.k.a. Frequent Miler), we unpack how to think more strategically about the value of your points. Whether you're sitting on a big stash or navigating your first transfer, you'll hear expert insight into when to red
125. Maximizing the Citi Ecosystem with Dr. Suzy Spadafora
Ever feel like Citi cards get overlooked in points conversations? If you've written off Citi's ecosystem—or just haven't known how to make it work for your travel goals—this episode is full of smart, real-life strategy. Dr. Suzy Spadafora returns to discuss the strengths (and limitations) of the Citi points ecosystem. From the points earning cards Citi offers to putting their transfer partner menu
124. Mid-Year Points Update: What I Burned, Booked & Learned
Ever wonder what's actually possible with points? In this episode, I'm taking you behind the scenes of how I've already booked and taken 5 international trips in 2025—spending 2.9 million points on award flights and hotels, and saving over $150,000 in travel costs. From a spring break family trip to Paris to a spontaneous 2-day Tokyo adventure, I'm walking you through exactly how I planned, booked
123. Using Real Estate Spending to Maximize Credit Card Points with Jaina Pallasigui
Have you ever wondered how real estate investments could help you travel more—without spending more? In this episode, I'm joined by Jaina Pallasigui, a public health professional, real estate investor, and points enthusiast who turned her real estate expenses into business class flights and luxury hotel stays around the world. From managing short-term rentals to using insurance reimbursements and
122. Listener Q&A: Adding a Third Points Currency, Booking Emirates First, and Points Regret
This episode is all about your questions—and real answers. I'm back with another listener Q&A, tackling the exact points and miles decisions you're working through right now. Ever feel like you're making credit card decisions in a vacuum? From wondering if it's time to add Capital One or Mesa to your rewards card portfolio, to recovering from redemption regret, I'm walking through the strategy beh
121. Chase's New Business Card Just Dropped & The CSR Gets An Update—Here's Why We're Not Impressed
Chase just launched a new business credit card and rolled out changes to the Chase Sapphire Reserve—but are these updates actually worth getting excited about? In this episode, I'm joined once again by Kelly from The Points and Miles Doc for a candid review of what's new in the Chase ecosystem. From rising annual fees to underwhelming credits and a business card that looks a lot like what already
120. The biggest surprises (and letdowns) of 2025 so far
Have you been wondering what's really happening in the world of credit card points and award travel this year? In this episode, I'm joined by Kelly, The Points and Miles Doc to break down the biggest shifts in 2025 so far. From major devaluations to standout sweet spots, we're giving you an honest look at what's working now—and what's not. We also dive into how international programs are outperfor
119. Alaska Airlines Sweet Spots: Amazing Ways to Use Alaska Miles (That You Might Be Missing)
Have Alaska miles—or thinking of transferring your Amex points before the June 30 deadline? In this episode, I'm breaking down some of the most valuable ways to redeem Alaska Airlines miles right now. From low-cost domestic redemptions to hard-to-find international business class flights, this guide walks you through the sweet spots that make Alaska's program one of the most valuable in points tra
118. Jet-Set with JAL: Bilt's Boldest Transfer Partner Yet
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 plann
117. Making Smart Transfer Moves: When Speculative Points Transfers are Worth It (And When They're Not)
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 spec
116. The Award Travel Trick Hiding in Plain Sight: Fifth Freedom Flights
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 poi
115. Rhythms, Routines, and REM: Expert Tips to Manage Jet Lag & Sleep Disruption While Crossing Time Zones
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 experi
114. Finally! Turning Your Mortgage into Points: How Mesa is Flipping the Script on Rewards
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 i
113. 4 Ways to Maximize Points for Costco Spend (Without Overcomplicating It)
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'
112. Best Ever or Big Mistake? 3 Steps to Evaluate if Best-Ever Welcome Offers are Right for You
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 el
111. Life, Travel, and Money Hacks with Chris Hutchins
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
110. 2025 Tax Payment Updates You Need to Know with Dr. Sujatha Murali
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
109. How to Pack Smart for Travel Without Sacrificing Style with Cassandra Sethi
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,
108. Credit Card Points Transfers: Do's, Don'ts, and Pro Tips
As someone who has booked over $192,000 worth of travel using points just this year, I've learned that mastering the art of points transfers is the key to unlocking incredible travel experiences. But knowing when and where to transfer your points isn't always straightforward or intuitive, especially when you're new to this hobby. In this episode, I share 10 do's and don'ts of credit card points
107. Skill Stacking Your Way to Better Points Redemptions
Do you feel confident in your points redemption skills, or do you suspect you might be missing out on better deals? With a little knowledge and practice, you can learn to stack the key skills needed to get incredible value from your points, and I'm showing you how this week. Tune in as I break down the six key levels of points redemption skill stacking. I explain how to know which level you're
106. Lessons Learned & Top Tips from Running Thousands of Award Searches
I share my top tips for running successful award flight searches gleaned from years of experience booking award travel. Let's dive into the key differences between searching for cash flights versus award flights, and how to overcome the challenges of information overload and limited award seat inventory. I break down the most important mindset shifts and practical strategies you can start using
105. Turn Payroll into Points: A Game-Changing Strategy for Business Owners with DeAndre Coke
In this episode, I'm joined by DeAndre Coke, a financial advisor and an avid traveler who was ranked by Forbes as one of Virginia's top financial security professionals for two consecutive years. DeAndre shares his experience using an innovative platform called Zil Money to pay payroll with his credit card, racking up huge amounts of valuable rewards points in the process. Discover which credit
104. Expert Answers to Your Top Award Travel Questions: Listener Q&A
Whether you're a seasoned pro or just starting out in the world of award travel, this episode is packed with actionable advice and real-world examples. I break down complex topics like transferable points currencies, positioning flights, and maximizing leftover gift card balances in a way that's easy to understand and apply to your own travel goals. So grab a pen and paper (or just hit that book
103. CME Secrets: Unlock International Travel with Dr. Courtney Downes
Are you a medical professional looking for ways to leverage your CME funds for travel? I'm joined by Dr. Courtney Downes, a board-certified emergency medicine physician, Points and Travel strategist, and founder of Prescription to Travel MD. She helps healthcare professionals optimize credit card points and travel hacks for accessible leisure, adventure, wellness retreats, and CME. Discover how
102. Maldives Dream Vacation: Booking, Business Class & Insider Tips
From finding award availability to navigating the unique transportation logistics of getting to and from the Maldives, I walk you through everything that went into planning this ambitious trip. I also share my honest review of the flights we took, what it was like staying at the luxurious Park Hyatt Maldives, and how I kept food costs under control at the resort. If the Maldives is on your trave
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