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 big-ticket renovations to her advantage, Jaina shares the exact strategies she uses to turn every investment dollar into reward points.

We also talk through the mistakes many real estate investors make with credit cards, how to keep your strategy simple, and why some of your biggest expenses may be the key to unlocking unforgettable trips.

This episode is full of creative insights—whether you're deep in the real estate world or just curious about new ways to maximize your spending.

Get full show notes and transcript: https://pointmetofirstclass.com/real-estate-points-hacking/

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

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 behind each question so you can move forward with more clarity and confidence.

We’ll cover how to think about applying for “no lifetime language” Amex offers, why you might want to move credit lines between Chase cards, and what to do when your points plan feels a little off-track. This episode is packed with honest takes, strategic insight, and practical tips grounded in real-life scenarios.

Get full show notes and transcript: https://pointmetofirstclass.com/listener-qa-credit-card-points-strategy-2025/

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

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, we’re breaking down the updates—and what they really mean for your wallet.

We also talk about how these cards stack up against competitors like Amex and Capital One, when the new benefits might be worth it, and why we’re not jumping to add either of these to our travel strategy just yet. If you're holding the Chase Sapphire Reserve or considering a new business card, this episode will help you make a more informed decision.

Get full show notes and transcript: https://pointmetofirstclass.com/chase-sapphire-reserve-business-review-2025/

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

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.-based ones, which transfer partnerships are showing real value, and why flexibility is more important than ever.

Whether you’ve been feeling excited by the new opportunities or frustrated by unexpected roadblocks, this conversation will help you reset your strategy for the second half of the year and beyond.

Want more help using your Alaska miles wisely?

Join me for a live workshop on June 21st at 10am CDT where I’ll walk you through the best Alaska Airlines sweet spots and the tools I use to find them fast—so you can stop second-guessing and start booking. Click here to save your spot - https://points.pointmetofirstclass.com/offers/g9uBpeJK

Get full show notes and transcript: https://pointmetofirstclass.com/mid-year-award-travel-review-2025/

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

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.

You’ll also learn what not to do with your Alaska miles (even if it looks like a good deal), plus a few rare redemptions that are great in theory—but nearly impossible to actually book.

Whether you already have Alaska miles or you're considering a speculative transfer, this episode will help you use those points with confidence and strategy.

Want more help using your Alaska miles wisely?

Join me for a live workshop on June 21st at 10am CDT where I’ll walk you through the best Alaska Airlines sweet spots and the tools I use to find them fast—so you can stop second-guessing and start booking. Click here to reserve your spot - https://points.pointmetofirstclass.com/offers/g9uBpeJK

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

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

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

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/