👋 Hi Reader,

Happy Sunday! A note before we get into it: the newsletter just crossed 100,000 subscribers this week, which is genuinely surreal. Thank you for being one of them. The fact that this lands in your inbox every weekend and you actually open it is something I don't take for granted.

I also took an extra day this week to restructure how the newsletter works. The goal is to spend less time on the long list of every deal that crossed my desk and more time on the things that actually deserve your attention — while still keeping the comprehensive list at the end for anyone who wants to scan it. Here's what that looks like:

• 📋 My Past Week: a bike lesson gone wrong, a 3D printer save, and a few automation experiments
• ⭐ My Top Picks: Hyatt's award chart shake-up, save $$ on flights you've booked, 50% off Disney Cruise kids, and more
• 🍿 My Recommendation: a new HBO show worth your time
• 📰 The Rest of the Week: JAL/ANA doubling fuel surcharges, 25% Citi bonus to LHW, business class award deals, and more

If you've been forwarded this, you can subscribe here. And if you have a friend who'd find this useful, I'd be grateful if you sent it along.

Chris

🤖 The Custom Everything Era with Kevin Rose

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This week, my good friend Kevin Rose and I dig into how AI is reshaping the way we use software. The big idea: we're entering an era where it's faster to build your own tool than to download someone else's. We get into how we're actually using AI day-to-day, what we're sharing with these models, and what it means for jobs, trust, and creativity.

💸 Take Control of Your Money Today

Today’s newsletter is brought to you by… Copilot Money​

​​​​Copilot Money​​ is the personal finance app I use and trust almost every day to stay organized and confident about where our money is going.

It’s a beautifully designed money-tracking app that pulls your spending, net worth, and investments into one dashboard you can access on iPhone, Mac and Web. With Copilot Money, you can set flexible spending and savings goals, stay ahead of renewing subscriptions, and trust that your data is never sold.

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📋 My Past Week

• When I first learned to ride a bike, I remember turning around to see my parents' faces light up that I was doing it on my own, then running straight into the mailbox and getting a few stitches on my head. Well, my youngest daughter took after me this past week and turned around to see how proud we were and tumbled right over her handlebars. She was right, we were very proud, and fortunately she only got some scrapes and avoided the ER.
• On a happier kid note, I loved getting to take my two daughters out for a breakfast date this week, and it was even better that we did it somewhere I could pay with our Amex Hilton credits. We make an effort to have some 1:1 time with our kids (or 1:2 time in this case) and as much as I love doing things with the whole family, we also think some single parent time is important too.
• My dad somehow lost one small lego piece on the DC-3 we got him for his birthday, which Lego would have had to ship from Denmark. Fortunately, this was a great opportunity for our 3D printer to get him the piece in less than 20 minutes. It actually took two prints, because I didn't use auto-orient the first time.
• In an effort to "buy more time", I spent the weekend trying to automate a lot of the manual processes I do on a regular basis. This week it was automating Invoicing and Award Searching and early results are very promising. I was really looking forward to building this out on the new GPT 5.5 models, but they were down right as I started this project, so that'll have to wait until next week.
• Finally, I restructured the newsletter to be more focused on my goal of highlighting the top things each week, so I hope you like what I did. Please reply and let me know!

⭐ My Top Picks

The most actionable money, points, and travel items I came across this week. Some weeks that's 7-8, others just 3-4. I'd rather keep it short than waste your time.

🏨 Hyatt Award Changes: 112 Hotels Moving Up

Hyatt just announced its biggest award chart change in years and it's not great. Starting 5/20, 112 properties are moving up at least one category and only 24 are moving down. This is on top of broader award price hikes across the board. Free night certificates will still work regardless of tier, but if you've been eyeing a Hyatt redemption, book before 5/20 to lock in today's price. Full details here.

✈️ Save Money on Flights You've Already Booked

I recently started using ​Autopilot​, a service that automatically tracks your upcoming flights (American, Delta, United, Alaska, and JetBlue for now), and any time the fare drops by $20+, they rebook the same ticket and issue you airline credit for the difference (your flight, seat, and cabin don't change). It's free to track flights, and you only pay 15-25% of the savings if they save you money. And with this link​, you get your first $100 in savings processed free.

🔍 Google Hotels Adds Price Tracking Alerts

If you need an option for tracking Hotel prices, Google Hotels now lets you set alerts on a hotel and dates, and get an email if/when the rate falls. This is especially useful if you ever make refundable hotel bookings that you can easily cancel and rebook.

🏨 Top Travel Portal Boosts Hotel Redemptions to 2.5cpp

A popular card issuer's travel portal just bumped their hotel redemptions to 2.5¢/point on a curated list of 11 luxury hotels. The list is small but includes some genuinely aspirational properties in the US, Europe, Asia and the Caribbean. At 2.5cpp, this is a fantastic value for your points. Full list of hotels and details here.

🎿 Free Marriott Night When You Renew Your Ikon Pass

If you ski as often as our family does, you're probably holding an Ikon Pass. And if you're renewing for 2026-27, ​there are 5 Renewal Rewards​ to choose from, with the standout being a Marriott Bonvoy Free Night Award worth up to 25K points (which you can top off with 25K more to book up to a 50K-point property). Other options include $50 off your renewal, up to $100 off Backcountry.com plus a Premium membership, 2 free rental days from Ski Butlers, or $25 monthly mountain credits. This offer is valid through 7/31 for U.S. and Canada residents.

🚢 50% Off Disney Cruise Line Kids Fares

If you've got kids under the age of 18, Disney's new ​Together at Sea offer​ gives 50% off the cruise fare. However, you do need 2 adults paying full fare, the sailing can't already be discounted, and suites/concierge services are excluded. Book by 6/14 for sailings between October 2026 and March 2027. The offer even applies to existing bookings in the window, so you can call Disney to adjust.

🍿 My Recommendation

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Amy and I have been really enjoying Rooster on HBO. It's a new Bill Lawrence comedy (Ted Lasso, Shrinking) starring Steve Carell as a best-selling thriller author who shows up at the New England college where his daughter teaches, just as her marriage is falling apart. Episodes are only 30 minutes and it's had us laughing a lot.

📰 The Rest of the Week

Everything else worth knowing this week, organized by category. Skim to whatever's relevant to you.

💳 Credit Cards & Points

• Citi: 25% Bonus to Leading Hotels of the World (through 5/16)​
• Capital One: Quicksilver → Discover, Adds 3% Gas/Grocery​
• LifeMiles: Another Devaluation (3rd in a year)​
• Citi: AT&T Points Plus Card Refresh (new bonus + credits)​

✈️ Airline News & Promos

• Air France/KLM : ​10K miles on economy from the US​
• ANA & JAL: Doubling Fuel Surcharges from North America​
• Cathay Pacific: ​Up to 4,380 miles for completing challenges​

🏨 Hotel News & Promos

• Accor: ​Up to 3x pts in Asia, Africa and Middle East (4/20 - 8/31)​
• Hyatt: ​20% points back on Las Vegas awards (4/3 - 7/31)​
• IHG: ​5K points in Middle East, Africa & South Asia (4/21 - 6/21)​
• IHG: ​3K bonus points for new members after 1st stay​
• Marriott Homes & Villas: ​40K points on 2+ nt stays (4/27 - 1/3)​

💎 Award Deals

• 🇦🇪 Abu Dhabi: Biz class from 70K Etihad miles​​
• 🇳🇱 Amsterdam: Biz class from 60K Virgin points​​
• 🇯🇴 Amman: ​​Biz class from 70K Royal Jordanian miles​​
• 🇦🇷 Argentina: ​​Biz class from 50K Atmos points​
• 🇬🇧 London: Park Hyatt London for 5K/night​
• 🇪🇸 Madrid: ​​Biz class from 40.5K Iberia Avios​​

🔗 Card-Linked Offers

• Air France/KLM: ​$250 off $1,250 or ​$400 off $2,000 (5/31)
• AT&T Wireless: ​$75 off $100​ (4/30)
• Citi Travel Hotel Bookings: ​$50 off $300​ (5/14)
• Fox One: $19.99 off $19.99 (5/16)
• Go Rentals: ​20% back, up to $200​ (8/5)
• Hilton: ​10% off, up to $65​ (5/15)
• Leading Hotels of the World: ​$150 off $700+​ (7/31)
• Marriott: ​10% off, up to $80​ (5/15)
• The Parking Spot: $10 off $50+ (5/15)

To find and activate offers across all your cards in one place, I love using CardPointers (30% off here)

🛒 Points on Sale

• British Airways: 1.64¢ each with up to a 40% bonus​
• Marriott: 0.89¢ each with a ​targeted 40% bonus​

🎁 Gift Card Deals

• Amex: Up to 10K bonus miles for Delta gift cards​
• BJs.com: ​10% off Lowe's, Panera, Gap & more​
• Meijer Mperks: ​7,500 points for a $100 Visa gift card​
• Newegg: 8% Off $250 Lowe's Gift Cards​
• Staples.com: ​15% off Ulta, Cheesecake Factory & more​

For 5-12% off brands like Uber, Doordash, Instacart, Airbnb & more, check out my relaunched gift card site.

💬 Parting Thoughts

This is the first issue with the new format. Hit reply and tell me what you think — I read every response. 🙏

Chris