Point Me To First Class

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 exists, w...

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 outperforming U.S....

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 travel.

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 tri...

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 p...

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 enthu...

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 b...

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 reward...

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 ...

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 eve...

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 mo...

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 s...

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...

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 transfers. You'll hear my hard-won...

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 at currently, the specific skills t...

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 today to increase your chances of f...

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 cards offer the best earning rates ...

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 bookmark button) because you won't want...

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 to tap into your CME allowance for ...