Episodios

  • 209 | When You Can Fly Free JUST to Try on a Wedding Dress: Success Story with Rachel Elston
    Apr 9 2026

    Families Fly Free is closing to new members on Friday, April 17 as I transition it into a smaller, private community.

    If you’ve been listening for a while and have thought about joining, this is your last opportunity to be part of it before close the doors forever. Inside this amazing membership, you’ll learn a simple, proven way to fly your family for free — with my support, helpful tools, a library of content and a community of people actually doing it alongside you.

    Going forward the only way to access Families Fly Free will be to already be a member. For this last opportunity, I've dropped the price to $995 (regularly $1,250).

    👉 Join now before doors close permanently on Friday, April 17 at: https://www.familiesflyfree.com/join


    Rachel says "I found my thing" when it comes to travel rewards and suggests "you can't go wrong investing in memories." Learn how this mother of grown kids has upgraded her travel rewards skills to take her family on a trip not "if" but "when" and "where" ever they want. She's even been able to fly to California for "lunch" and to take her daughter on a flight just to try on a wedding dress. What's her secret sauce? Listen to the episode to find out.

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    47 m
  • 208 | Travel During Your "Go-Go" Years: Success Story with Bret Crawford
    Feb 3 2026

    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.

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    39 m
  • 207 | ✈️ Which Points Qualify for the Southwest Companion Pass?
    Jan 20 2026

    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

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    15 m
  • 206 | 🛑 6 Things Travel Rewards Enthusiasts Need to Give Up in 2026
    Jan 9 2026

    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

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    32 m
  • 205 | 🐒 Costa Rica Case Study: How I Used Points to Save $10,000+ on Flights, Hotels & an Airbnb
    Dec 30 2025

    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!

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    57 m
  • 204 | ✈️ Did You Make This Common Year-End Southwest Companion Pass Mistake?
    Dec 19 2025

    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!

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    31 m
  • 203 | 🛍️ How to Earn Maximum Points on Your Holiday Shopping to Fund Next Year's Travels
    Dec 2 2025

    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.

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    43 m
  • 202 | 🛑 Stop Wasting Points & Perks: How to Do a Credit Card Audit
    Nov 19 2025

    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...

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    29 m