👋 Hi Reader,

Happy Saturday! Hope your weekend is off to a great start! Here are some quick highlights of today's newsletter:

• 💳 Up to 15x points on United, Newegg, Sephora and more
• 🛠️ The AI Tools I'm Building for Everyday Optimization
• 📖 Great new book on risk, volatility and long-term wealth
• 🔄 Rare 30% transfer bonus to Southwest
• ❓ Ask me anything on credit cards, points & miles
• ✈️ JetBlue + United elite perks are now active
• 🏨 Last call to book Hyatt awards before 5/20 increase

If you enjoyed reading this newsletter, I'd really appreciate it if you would forward this to a friend who might too! And if that's you, make sure to subscribe here. Thank you so much!

Chris

🛠️ AI Tools I'm Building to Replace Spreadsheets

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Is AI making it possible for the average person to live a fully optimized life? My friend Anish Acharya and I swap notes on how custom AI tools are replacing our spreadsheets and reshaping the way we work, learn, create, and relate to each other. We'll dig into why I abandoned OpenClaw, the architecture mistakes many people are making, and what happens when the subsidies on all these AI tools go away.

💰 Smart Q2 Tax Moves to Make Right Now

Today’s newsletter is brought to you by… Gelt​

Tax Day has passed, but if you filed an extension, the clock is still ticking, and there are real moves to make before October. Q2 is actually the best time to bring in a pro who'll make sure you're in good hands.

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Right now, Gelt is offering two Q2 specials for business owners who are ready to get serious about their taxes. Find out if you qualify here.

📋 My Past Week

• Our girls still love rock climbing and it's been really fun to keep up with the tradition of trying to take them every week or two. I miss getting to climb more often, but one of these days they'll be old enough to be my belay partners and I can do a bit more climbing myself.
• Cleaning the solar panels on our roof is one of those home maintenance tasks that never seems urgent enough to prioritize. But it had been almost a year, the days are getting longer, and we finally decided to tackle it (and turn it into a family activity). The good news: we saw a noticeable boost in energy production. The bad news: we also discovered one of the panels was cracked and needs to be repaired, which will sadly probably cost more than any future production for that single panel.
• One of the kids in my daughter's class had a birthday party at the Marine Science Institute, where they went out on a research ship and got to interact with a bunch of sea creatures. It was such a unique idea and everyone had an amazing time. Since we weren't able to join on the boat, we had lunch at Hurrica, a new restaurant that was amazing. Worth checking out if you're ever near Redwood City and want a meal on the water.
• With the Hyatt award rates going up on 5/20, we’ve been making all of our bookings for the next year. Since award reservations are generally refundable, we’ve even made a few speculative bookings. And if you have Globalist status, Points Advance will let you make bookings without needing to have the points when you book (though you'll eventually need them).

⭐ My Top Picks

💳 10-15x on United Airlines & More via Paze

A few popular bank cards just quietly added a 10x bonus on Paze checkout, which is a new wallet/checkout platform. The list of merchants is small, but notably includes United Airlines, Newegg (which sells gift cards), Dunkin', Sephora and more. It's capped at $1,500/month in spend (15K bonus points) and good through the end of the year, which could mean up to 105k bonus points. This stacks on top of normal credit card earning, which could mean earning up to 15x on these purchases. Details in the post above on which cards qualify.

🙋 Upcoming AMA on Credit Cards, Points & Miles

I love getting a chance to answer all your questions, so I'll be recording an "ask me anything" episode next week, focused on credit cards, points & miles. If you have any questions to share, please add them here. The AMA episode after that will be on Money/Investing, so feel free to add questions on that topic as well. Thanks in advance!

🤖 Amex's $300 ChatGPT Credit is Live

If you've got an Amex Business Platinum or Business Gold you can now get $300/mo back on a ChatGPT Business account. Enrollment on the Amex site/app is required and ChatGPT Business requires a minimum of two users, which is $50/mo (though codes like this might cut that in half). At $50/mo with 7 months left in the year, the $300 credit would cover most of the cost for two accounts. For next year, if you have two of these cards, it'd cover the cost for two users for the entire year. I think this one is definitely worth checking out if your ChatGPT usage doesn't require the $100 or $200 plan.

✈️ JetBlue + United Reciprocal Elite Perks Live

The next phase of the JetBlue/United Blue Sky partnership is now active, and TrueBlue and MileagePlus elites get reciprocal priority boarding, preferred seating, free checked bags, and same-day standby when flying the other airline. While it's better than nothing, I do wish it included preferred seating at booking for top-tier elites.

🔄 30% Bonus to Southwest from a Popular Bank

A popular bank just launched a 30% transfer bonus to Southwest through 6/5. This is only the second-ever bonus to Southwest and bigger than the last one. While it's hard to get outsized value from Southwest points, in my recent searches I consistently saw ~1.35¢ per point. That means with this bonus you could be getting ~1.75¢ per point, which is pretty decent value. Just know that points don't count toward Companion Pass or Southwest status.

⚾ Capital One: Free Drinks + Cheap MLB Tickets

Two fun Capital One perks landed:

1. ​Free handcrafted drinks every Monday at Capital One Cafés from 5/25 through 9/28. No purchase or card required, just enroll and add the QR code to your wallet.
2. June and July dates are now bookable for the Cardholder Exclusive MLB seats at 5,000 miles each. They only have 4 seats available per game, so the good ones go fast. Avoid anything labeled "Powered by VividSeats."

🍿 My Recommendation

Ben Carlson just released Risk and Reward, a new book on how to handle market volatility and build long-term wealth. I really enjoyed reading an advanced copy to prep for my episode with Ben, which comes out next week. The book is full of great context on past crashes, inflation, lost decades and bear markets – but the bigger takeaway is how to think about risk, time horizon and staying invested when things inevitably get uncomfortable.

📰 The Rest of the Week

💳 Credit Cards & Points

• Intuit: New 2% Business Card with a $300 SUB – plenty of better 2% cards with higher bonuses.
• Mastercard: New Lounges in HKG & GRU (free for World Legend cardholders) – No plans to be in Brazil or Hong Kong, but they look beautiful

✈️ Airline News & Promos

• Amex Biz Gold: FedEx Ending as $20/mo Credit Option – I've never used this credit on FedEx, so not a big deal to me
• Delta: Up to $80 Uber Credit for Flying Comfort​
• Industry: Summer Airfares Up 20%+ YoY – I'm definitely feeling this as we're booking some upcoming travel
• JSX: Red Stripe Sale from $199 One-Way​
• United: SFO–Sapporo Nonstop + ORD–Tokyo Narita Daily – I'd love to go to Hokkaido, so I'm excited for this.

🏨 Hotel News & Promos

• Accor: Mega Offer: Up to 40% Off Americas​
• Choice: 8K Bonus Pts Every 2 Stays​
• Marriott × Starbucks: Sip, Share & Earn Sweepstakes + $5 GC​

💎 Award Deals

• 🇭🇰 Hong Kong: Delta One from 85K SkyMiles​
• 🇮🇪 Ireland: Aer Lingus Biz from 45K Alaska​
• 🇮🇹 Italy: Biz Class from 55K Flying Blue​
• 🇬🇧 London: Virgin Upper Class from 29K + ~$700​
• 🇵🇫 Tahiti: LAX–PPT from 24K Cap1 Miles​

🏦 Bank / Brokerage Bonuses

• Ally Invest: $200 Bonus on $1K Deposit (Existing Ally Customers) – Small bonus, but easy for Ally customers
• SoFi Invest: 2% Bonus, $100K Cap (5-yr Hold) – 2% is a fantastic bonus, but not worth it for a 5-year hold. I'd be interested if it were 1-2 years

💬 Parting Thoughts

Thanks so much for reading! Hit reply and let me know what you think – I read every response. 🙏

Chris