How to Fly $30,000 First Class for $4,000

December 30, 2022

Episode 129


Want To Travel More and Save Money? Listen To The Podcast.

What if you could travel more and save TONS OF MONEY? ( We're talking THOUSANDS of dollars…)

Today’s episode starts off with great advice – never pay retail prices! Or at least, Matt Bennett never pays retail. As owner and founder of, Matt has spent years perfecting the art of never paying full price for airline travel.

So how do you get this amazing deal? With five simple strategies that Matt has perfected over the years.

  1. Buy Miles: Did you know you could buy miles? Companies like Amex allow customers to buy miles outright without having to buy a product to earn miles. (He also let me know that Amex has sales where miles are discounted!)
  2. Find the Routes with the Best Seats: Do you want your first class experience in an old 1970's-style airplane or a nice new plane? Obviously, you want the newer plane and Matt knows what routes those planes fly.
  3. Accidental Bucket List Experience: Keep your mind open! So what if you have to fly to Melbourne to get to Sydney? You might fly in on the perfect day for an Australian Open in Tennis.
  4. Travel like a King, Queen, or Rockstar: Don’t outright buy a first class upgrade—put yourself on a waitlist. Even if that means picking up the phone sometimes.
  5. Turn your Business Trip into a Vacation: Do those pesky business trips get in the way of having a real vacation? Or is your boring plane going to Puerto Rico without you? Take advantage of your business trips. Add an extra stop to the beach before returning home. Fly to Prague for a Summit and stop in Italy while you’re there. The possibilities are endless—and cheaper.

You’ll have to listen to the whole episode to hear about each strategy in detail and find out how Matt has used his knowledge to help find people millions of deals on flights. That’s a lot of vacation memories. Let's get started!

Key Takeaways

  • (2:15) Matt Bennett’s money mindset
  • (9:18) How many upgrades? Upwards of 70 million!
  • (9:40) Cool Strategy 1: You’re still collecting Delta Sky Miles?
  • (17:20) Cool Strategy 2: Find the routes with the best seats
  • (22:23) Cool Strategy 3: Accidental Bucket List Experience
  • (26:39) Cool Strategy 4: Travel like a King, Queen, or Rockstar
  • (29:47) Cool Strategy 5: Turn your Business Trip into a Vacation
  • (32:00) Combine the strategies for the biggest bang for your buck

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