Are you waiting to travel "someday" when you have more time or money? Portland realtor Bret Crawford shares how he went from barely earning enough Southwest points to flying free multiple times a year – and why the book Die with Zero convinced him to stop waiting. In his 60s, Bret's embracing the "go-go years," traveling as much as he can before he gets to the "slow-go" and then "no-go" years. Whether you're in your go-go years or approaching your no-go years, this episode is your reminder that tomorrow isn't guaranteed. Start using those points and making those memories NOW.

In this episode, Bret shares:

• Booking 10-13 free trips annually (New Orleans, Los Cabos, Palm Springs, Hawaii and more!)
• Leveraging Hyatt points for stays in prime locations
• Planning a dream family Hawaii trip for his adult kids – paying for everyone's flights with points
• His strategy for booking multiple options, then choosing what works best for his wife's teacher schedule

About Families Fly Free: Ready to stop waiting and start traveling? Families Fly Free teaches families a simple system to fly for free using travel rewards. Join our community at FamiliesFlyFree.com.

Think transferring Chase Sapphire points to Southwest will get you closer to Companion Pass? Think again. In this episode, I'm clearing up the biggest confusion around earning the Southwest Companion Pass—because the rules aren't what most people assume. I'll walk you through:

• The major mistakes people make (including that Chase transfer trap)
• Why "bonus points" don't always mean what you think
• The smartest, simplest path to earning the Pass—without cobbling together points from a dozen different places
• How to have a Southwest Companion Pass for nearly 2 full years (yes, really)

If you've been piecing together your Companion Pass strategy through Google searches and forum posts, this episode will save you from costly mistakes and wasted time.

Ready to master the full system? Join Families Fly Free to get the complete roadmap, perfect timing strategies and step-by-step personalized guidance so you never miss out on this valuable perk: https://www.familiesflyfree.com/join

Got questions about Families Fly Free? Text me at 844-403-2263.

Music Credit:

Inspiring Optimistic Upbeat Energetic Guitar Rhythm by Free Music | https://soundcloud.com/fm_freemusic

Music promoted by https://www.free-stock-music.com

Creative Commons Attribution 3.0 Unported License

https://creativecommons.org/licenses/by/3.0/deed.en_US

The travel rewards landscape is shifting, and 2026 requires a new approach. In this episode, I'm walking you through 6 specific changes you need to make to keep flying your family for free—whether these are strategies you've clung to for years or adjustments necessitated by recent bank and airline policy changes.

What you'll learn:

• Why constantly opening new cards needs to stop (especially with Chase's new restrictions)
• To pay attention to the cards that earn you the most points in every category
• To stop wasting your spending on airline cards
• How to stop paying the listed points price for both flights and hotels
• The uncomfortable truth about lounge access for families in 2026
• How to simplify your approach while still meeting all your free travel goals

✨ Learn my simple, step-by-step Fly Free Formula™ for how to maximize your miles to always fly your whole family free and beyond with personal support, a customized plan and live content, along with travel inspiration in my Families Fly Free membership:

👉 Join: https://www.familiesflyfree.com/join

Got questions about Families Fly Free? Text me at 844-403-2263.

Music Credit:

Inspiring Optimistic Upbeat Energetic Guitar Rhythm by Free Music | https://soundcloud.com/fm_freemusic

Music promoted by https://www.free-stock-music.com

Creative Commons Attribution 3.0 Unported License

https://creativecommons.org/licenses/by/3.0/deed.en_US

Ever wonder if you can really cover an entire international vacation with points—not just flights, but hotels, vacation rentals and more? In this episode, I walk you through exactly how I took 3 of us to Costa Rica and saved more than $10,000 strategically using miles and points.

Here's what you'll learn:

• How breaking Southwest flights into segments can save you thousands of points
• The incredible Hyatt Andaz redemption that delivered 7 cents per point in value—my best points redemption ever
• How to use Capital One or Chase points to cover vacation rentals and other expenses
• Real numbers of points paid and cash saved
• Critical car rental warnings for Costa Rica that could save you hundreds and major headaches

If Costa Rica is on your bucket list or you want to see exactly how to maximize multiple points currencies for a trip step by step, this episode breaks it all down.

Bottom line: $10,000+ saved for an unforgettable family adventure!

Did you accidentally earn your Southwest credit card bonus too early this year? You're not alone! Every year, people reach out who've made timing mistakes with their Companion Pass strategy—and it's happened more than usual in 2025 thanks to those amazing 100K+ credit card offers. In this episode, I break down exactly what went wrong, why timing matters so much at year-end, and most importantly—what you can do about it. 

You'll learn:

• Why earning your pass in December 2025 vs. January 2026 costs you a whole year of benefits
• Quick ways to finish earning the remaining points before year-end (if that makes sense for you)
• How to pivot your strategy to card combinations for 2026-2027
• Why this mistake isn't the end of the world—just a detour to Plan B

If you've been stressing about your Companion Pass timing, take a deep breath. I've got you covered!

In this week's episode, I share with you all my best tips for maximizing the number of miles and points you can earn on your holiday shopping. You'll learn how to:

• Earn airline AND flexible points inside shopping portals
• How to earn points IN store
• How to stack points-earning
• How to get EXTRA discounts on top of earning points
• How to earn points at Amazon and Target

Use all the points you earn for your family's free travels in 2026! Happy shopping!

Ready to stop wasting points and perks and make travel rewards EASY? Join Families Fly Free, my popular travel membership where I teach you my Fly Free Formula and show you a simple system to fly your whole family for free for life with the support you need for success. Stop doing it alone and join hundreds of families just like you who've saved $6 million+. Learn more at FamiliesFlyFree.com/Join.

Forgetting travel credits, letting points expire, missing credit card bonuses—sound familiar? You're not alone. In this episode, I'm sharing 1 simple strategy to stop leaving money on the table and start maximizing every mile and perk you already have: simplify by conducting a card audit.

I'll walk you through how to decide what cards to keep, to close and to set aside, so you can take a big sigh of relief!

Plus, I'm giving you my free "5 Ways to Simplify Your Travel Rewards Strategy" guide. Text SIMPLIFY to 844-403-2263 to grab it. 

If you're tired of DIY-ing this alone and want a proven system that takes the guesswork out of flying free, join hundreds of families inside Families Fly Free at familiesflyfree.com/join.

Because you can't recall the memories you never make...

This week I’m chatting with Families Fly Free member Dave Banks—a dad of 4 from rural Oregon—who went from “credit cards are only for emergencies” to saving $2,367 on just 2 trips using my simple system. Dave shares how he and his wife flew to the Florida Keys for as low as 5,000 points each way with the Companion Pass, why the Families Fly Free Community has been the biggest surprise, and how the support inside Families Fly Free helped him go from skeptical to all-in.

You’ll learn:

• Dave’s weekly habit that keeps spending responsible yet rewarding
• How he pushed through a points hiccup and why it was worth it
• Why smaller airports like Boise can still unlock big wins
• The quote that guides his travel: “You can’t recall the memories you never make”

Ready to make those memories with ease like Dave?
Join Families Fly Free to start using miles and points with ease so you can make more family memories by flying free forever.

👉 Start here: https://www.familiesflyfree.com/join

Staying successful with Southwest means keeping up with nonstop change — and that’s where I come in. In this episode I break down the latest boarding scoop from the Wall Street Journal and everything else they've announced in the last few months.

I discuss the simple way to avoid paid seat headaches — lost seats on changes, messy expiring credits and poor points-plus-cash value — by booking in points and using the right Southwest card so you get an assigned seat without paying extra.

I round things out with some good news: 

• free Wi-Fi for Rapid Rewards members starting today!
• new aircraft features
• new routes like Alaska and the Caribbean

Plus, I share what we do and don’t know yet about the Southwest Companion Pass for next year.

Want real-time answers to change in the travel rewards industry and a plan that fits your family's travel style? Join Families Fly Free for my simple Fly Free Formula, personal support and up-to-the-minute guidance — the price increases October 29. Get started at FamiliesFlyFree.com/join 🧳✈️

Related Episodes:

• 199 |❓Your Families Fly Free & Travel Rewards Questions Answered by Members: Open House Replay

• 193 | 🎯 Southwest Changes Simplified: New Fares, Assigned Seats, Bag Fees - Oh My!

• 186 | New Rules, Same Free Perks? How to Outsmart Southwest’s Changes

❓Got questions about how Families Fly Free can help your family travel to more places using miles and points BEFORE the price goes up soon?

In this episode, I share a replay of a recent 🧑‍🧑‍🧒‍🧒 Families Fly Free Open House with 4 current members on hand to answer attendees' questions honestly and directly. We had a HUGE turnout and so many great questions AND answers from our amazing members.

Some of the questions included:

• Do I have to have a Southwest Companion Pass to get my value from the membership? (Answer: No ;-) - 2 of our panelists don't even have one!)
• Do I have to spend a lot of money on credit cards to earn all these points?
• Does it involve closing and opening a lot of credit cards?
• Does it work for international travel?
• Do I always have to fly Southwest?
• Is it worth it to pay the annual fees on travel cards?
• Is this a one-time fee or does it renew every year?
• And TONS more!

Dive into this episode to get all your questions answered about this life-changing membership and hear how it's about so much MORE than the information that will help your family fly free in the simplest possible way. It's the people, the real-time info, the support, the continuing knowledge you gain, the hacks and the list goes on. It's everything you need to not just learn, but take action and be successful year after year.

✅ Join Families Fly Free at FamiliesFlyFree.com/Join

Want an invitation to the next Open House? Get on my email or text alert list.
👉 Join my email list at FamiliesFlyFree.com/Email
📱 Get text alerts by texting FLYFREE to 844-403-2263 (no more than 1/week)

Still have questions?
Email me at [email protected]
Text them to me at 844-403-2263