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👋 Hi Reader,

Happy Saturday! Here's a sneak peek of today's newsletter:

• 💰 How we save $20k on a luxury Europe trip
• 🚨 Last call: Companion Pass for 2 years + 120k points
• 📱 Best iPhone 16 trade-in deal
• 🎉 Million mile giveaway!
• 🛒 Sam’s Club membership for just $15
• 🎁 Huge savings on gift cards!
• 🩺 Highest ROI $100 health test and more!

As always, I hope you enjoy reading and please forward this to someone who might enjoy it too! And if that's you, make sure to subscribe ​here​ so you don't miss out on amazing deals in the future.

Thanks so much!

-Chris

💰 Saving $20k on a Luxury Europe Trip

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We celebrated our 40th birthdays in Europe and ended up saving over $20,000 booking with points. We shared our entire process we used to find deals on business-class tickets and a five-star resort. My wife Amy also joined me to share highlights and recommendations from the trip!

🛫 Travel, Points & Miles

🎉 Best Rewards Programs and Million Mile Giveaway!

​point.me just released their report on The World’s Best Airline Rewards Programs and is also giving away 1+ million Flying Blue miles since Air France-KLM claimed the top spot. Giveaway ends on 10/15!

🛫 Last Call: Southwest Companion Pass for 2 Years

I previously shared how the best-ever 120k welcome bonuses on two Southwest business cards will help you earn Companion Pass for a year. However, if you time things correctly, you should be able to earn it for two years (2025/2026). I wrote up a post ​​here with more details.

• ​​Card 1​: 60k bonus points after $3k spend in 3 months, plus an additional 60k after $15k spend in 9 months.
• ​​Card 2: 80k bonus points after $5k spend in 3 months, plus an additional 40k after $15k spend in 9 months.

Note: These offers expire on 9/17/2024 at 8am ET and for compliance reasons, we can't include the names of all cards/banks in this email.

💺 D.O.T. Puts Pressure on Frequent Flyer Programs

The D.O.T. is demanding transparency from major airlines regarding their frequent flyer programs. I have no idea what comes of this, but it's super interesting to see them looking into points devaluations, dynamic pricing, and lack of transparency in fee structures.

🚀 Where to Credit​: Maximize Your Miles

If you're ever flying on an airline you don't normally fly, I recently heard about an amazing site called Where to Credit that shows you which partner's frequent flyer programs give you the most for your flight.

🤑 Latest Deals

📱 How to Save the Most on the New iPhone 16!

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Pre-orders for the iPhone 16 are live and there are some amazing deals to be had. My friend Stetson Doggett (founder of bestphoneplans.net) knows more about US cell phone plans than pretty much everyone and recently did in-depth analysis of trade-in credit from all the major U.S. phone carriers. If you've been considering changing carriers, also check out this video he made on the best phone plan at every price point.

It might be worth calling up your carrier to see what offers they have. Despite getting a $1,000 trade-in credit from T-Mobile last year, they offered us the same deal again for upgrading to an iPhone 16 Pro.

🤑 Up to 40% off Amazon with Amex

American Express cardholders can once again save up to 40% on Amazon by redeeming as little as 1 Membership Rewards® point. This is a targeted offer so check this link to find out what you’re eligible for!

🎁 Pepper Rewards: Huge Cash Back on Gift Cards

The Pepper Rewards gift card app has been offering some crazy gift card deals the past few weeks. Earlier this week, I got 12% off Amazon Gift Cards, which was amazing. Deals go quickly, but new customers get 2x points for the first 15 days with a referral code (mine is 612342).

The points system is a bit confusing – you earn "points" instead of cash back, and you get the base (4x) points instantly while bonus points pay out a few weeks later. So when I got 12x on Amazon, it was 4x right away (worth 4% back) and 8x in 3 weeks (worth 8 more % back).

🛒 $15 Sam’s Club Membership (Save $35!)

New members can get a Sam’s Club membership (normally $50) for just $15 with this limited-time offer expiring on 9/27. I did this last year and honestly haven't gotten much value from it, so probably not worth it unless you're pretty sure you'll use it, but if so, it's a great deal.

🎯 Target Car Seat Trade-in Event

From 9/15 to 9/28, you can trade in old, expired, damaged or outgrown car seats and boosters at Target and get a 20% off Target Circle™ Bonus, good for car seats or select baby gear until 10/12.

🕵️ Great Finds

🎙️ Howard Marks + Morgan Housel: The Impact of Debt

I love Howard Marks' Behind the Memo podcast, but his recent episodewith Morgan Housel on the impact of debt was one of the best podcast episodes I've listened to this year. They discuss ideas from one of Howard’s memos which was inspired by Morgan’s article How I Think About Debt. I highly recommend giving this a listen!

🩺 The Best $100 to Spend on Your Health

As someone who's had cholesterol issues for most of my life, I really loved seeing this article call the coronary calcium score test "the highest ROI $100 you can spend on your health." After years of following conventional advice for my high cholesterol and having no improvement, my calcium score is what led to take a more aggressive course of action, which has lowered my cholesterol significantly!

📝 New Free E-Signature Platform

My go-to for e-signatures used to be HelloSign, but since being acquired by Dropbox, there's no free option. Then I got excited when Google Docs launched free e-signature, but so far, I'm unimpressed. So naturally, I was so excited to see Agree launch free e-signatures last week and am hoping it'll be my go-to service in the future.

💬 Parting Thoughts

As always, thanks so much for reading - I hope you enjoyed it!

Please feel free to reply to this email with any thoughts, feedback or even if you just want to say hi! :)

Chris