June 01, 2026

Travel Rewards 101 | Devon Gimbel from Point Me to First Class

1 hour 17 minutes

Devon Gimbel just booked over $250,000 in travel last year using credit card points—but she's the first to tell you award travel isn't "free." It's a strategy for 10x-ing your existing travel budget by strategically matching your routine spending to the right credit cards. Since ChooseFI's original Travel Rewards 101 in 2017, the landscape has matured: annual fees are higher, issuer rules are stricter, and new players like Bilt have revolutionized the game by letting you earn points on rent and mortgage payments. Yet the fundamentals remain: with deliberate card selection and an understanding of transferable points currencies, it's still entirely possible to unlock one to two meaningful trips per year—whether that's economy flights to national parks or first-class seats to Tokyo.

Key Topics Discussed

00:00:00 - Introduction and State of Travel Rewards in 2026

Brad introduces Devon Gimbel and discusses how travel rewards have evolved since ChooseFI's first Travel Rewards 101 episode in 2017. They address whether earning significant travel value is still possible despite higher annual fees and stricter rules.

00:05:30 - The Evolution of Award Travel Community

Devon reflects on how the travel rewards community has matured since 2013-2014, moving from a monotone focus on premium cabin travel to showcasing diverse travel styles including domestic trips, family travel, and national park adventures.

00:11:45 - Getting Started: First Steps for Beginners

Devon outlines how beginners should approach travel rewards by analyzing their top spending categories and selecting one or two intentionally chosen credit cards with strong bonus categories rather than immediately pursuing dozens of sign-up bonuses.

00:16:20 - Sign-Up Bonuses vs. Everyday Spend Strategy

Discussion of the balance between chasing new card welcome bonuses and building a sustainable credit card portfolio with strong category bonuses. Devon explains why a hybrid approach works better for most people than constantly opening new cards.

00:22:15 - Understanding Bonus Categories

Deep dive into how credit card bonus categories work, why they matter, and how strategic matching of spending patterns to bonus categories can dramatically increase points earning without changing spending behavior.

00:30:00 - The Power of Flexibility

Brad and Devon discuss various dimensions of flexibility in travel rewards including travel dates, destinations, airports, cabin class, and types of points currencies. They share contrasting examples from their recent Japan trips.

00:38:45 - Transferable vs. Fixed Points Currencies

Devon explains the critical difference between transferable points programs (Chase, Amex, Capital One, Bilt, Citi) and fixed airline/hotel programs, comparing them to Visa gift cards versus single-merchant gift cards.

00:47:30 - The Rise of Bilt Rewards

Discussion of how Bilt has emerged as a major transferable points currency, offering the ability to earn points on rent and mortgage payments while providing strong transfer partners that directly compete with Chase Ultimate Rewards.

00:55:00 - Credit Card Issuer Restrictions in 2026

Devon outlines how credit card eligibility rules have tightened, including Chase's evolving restrictions and once-per-lifetime language similar to American Express, emphasizing the importance of deliberate card selection.

01:02:15 - Calculating Travel Value and Points Redemption

Devon shares her methodology for calculating the value of points redemptions using her family's Lufthansa first class trip as an example, discussing the difference between 'free travel' and maximizing travel budget value.

01:12:30 - How Devon Earns 6 Million Points Annually

Transparent discussion of Devon's points earning including business expenses, mortgage payments through Bilt, quarterly taxes, shopping portals, and strategic use of bonus categories, with acknowledgment that her situation differs from average users.

01:22:00 - Partnership Strategy for Couples

Devon explains why couples should avoid automatically adding each other as authorized users and instead should each apply for cards individually to double welcome bonuses and access to certain benefits.

01:29:45 - Essential Tools and Resources

Devon recommends key tools including Travel Freely for card organization, Card Pointers for tracking benefits and credits, SaveWise/GetSaveWise for shopping portal aggregation, and her Point Me to First Class podcast and community.

01:34:20 - Shopping Portal Strategy and SaveWise

Detailed explanation of how shopping portals work and Devon's strategy of waiting for high-bonus periods (like 20x points on Viator) to book travel activities and tours, demonstrating patience-based optimization.

Notable Quotes

Devon Gimbel: "This is not about spending money that you don't have, that you don't want to spend. This is you just spending the money you were going to spend anyway, but really leveraging those expenses to maximize your points."

Devon Gimbel: "I don't consider award travel free travel. I think there's certainly a way that you can do it where you defray as much out-of-pocket cash cost as possible, but I've always thought about it as how do I take my existing travel budget that is a cash-based budget, how do I actually 10x that or 20x that using points?"

Brad Barrett: "This is the equivalent of paying for all of your expenses with a debit card, with checks, with an ACH transfer. It is not bad, but it is such a missed opportunity."

Devon Gimbel: "Credit card companies do not tell you the best way to use your points. If you're ever going to redeem your points through the options they give you, their points are going to have a very low ceiling of value. You are never going to break through that ceiling."

Devon Gimbel: "Transferable points are exceptionally flexible. Airline and hotel points and miles are not flexible."

Key Takeaways

Identify your top 1-2 spending categories over the past year and select credit cards with strong bonus categories that match those expenses.

If you're new to travel rewards, prioritize getting one solid transferable points earning credit card (Chase, Amex, Capital One, or Bilt) before considering fixed airline/hotel cards.

Set up automatic payments for all credit cards to ensure you pay statements in full every month and never carry a balance.

If you're partnered, discuss applying for credit cards individually rather than adding each other as authorized users to maximize welcome bonuses.

Download organizational tools like Travel Freely (free) or Card Pointers (paid) to track your cards, annual fees, and benefits.

Install SaveWise or visit GetSaveWise.com to start comparing shopping portal bonuses before making online purchases.

If you're a renter or have a mortgage, research Bilt Rewards to start earning points on your housing payments.

Learn the difference between redeeming points through your credit card portal vs. transferring to partners—transfers typically offer 2-5x better value.

Before applying for new cards, research issuer restrictions like Chase 5/24 to strategically sequence your applications.

Create a running list on your phone of upcoming travel expenses (tours, activities, transport) and wait for high shopping portal bonuses before booking.

Resources and Links

Point Me to First Class

Travel Freely

Card Pointers

SaveWise / GetSaveWise

ChooseFI Credit Cards Page

ChooseFI Episode 594 with Noah (tools discussion)

Original ChooseFI Travel Rewards 101 (Episode 9, 2017)

Support the Show
We work hard to keep ChooseFI ad-free for a clean listening experience. The easiest way to support us is to use our Top Recommended Cards page when signing up for your next travel rewards credit card.

...more

View all episodes

By ChooseFI

4.8

50485,048 ratings