May 16, 2026

๐Ÿ’ฐ My Top Picks, Recommendation & More (5/16/26)

๐Ÿ’ฐ My Top Picks, Recommendation & More (5/16/26)

This week, we'll cover getting up to 15x points on United, Newegg, Sephora and more, the AI tools I'm building for everyday optimization, a great new book on risk, volatility and long-term wealth, rare 30% transfer bonus to Southwest, you can ask me anything on credit cards, points & miles, JetBlue + United elite perks are now active and a heads-up on the last call to book Hyatt awards before 5/20 increase and more! 

Advertiser Disclosure

๐Ÿ› ๏ธ AI Tools I'm Building to Replace Spreadsheets 

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.


๐Ÿ“‹ 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 โ€‹Marine Science Instituteโ€‹, 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 โ€‹Hurricaโ€‹, 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, โ€‹Points Advanceโ€‹ will let you make bookings without needing to have the points when you book (though you'll eventually need them).

โญ My Top Picks

๐Ÿ’ณ 10-15x on United Airlines & More via Paze

A few popular bank cards just quietly added a โ€‹10x bonus on Paze checkoutโ€‹, 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.

๐Ÿ™‹ 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 โ€‹add them hereโ€‹. The AMA episode after that will be on Money/Investing, so feel free to add questions on that topic as well. Thanks in advance!

๐Ÿค– Amex's $300 ChatGPT Credit is Live

If you've got an Amex Business Platinum or Business Gold โ€‹you can now get $300/mo back on a ChatGPT Business accountโ€‹. Enrollment on the Amex site/app is required and ChatGPT Business requires a minimum of two users, which is $50/mo (though codes โ€‹like thisโ€‹ 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.

โœˆ๏ธ 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 โ€‹reciprocal priority boarding, preferred seating, free checked bags, and same-day standbyโ€‹ when flying the other airline. While it's better than nothing, I do wish it included preferred seating at booking for top-tier elites.

๐Ÿ”„ 30% Bonus to Southwest from a Popular Bank

A popular bank just launched a โ€‹30% transfer bonusโ€‹ 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.

โšพ Capital One: Free Drinks + Cheap MLB Tickets

Two fun Capital One perks landed:

  1. โ€‹Free handcrafted drinks every Monday at Capital One Cafésโ€‹ 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 โ€‹bookable for the Cardholder Exclusive MLB seats at 5,000 miles eachโ€‹. They only have 4 seats available per game, so the good ones go fast. Avoid anything labeled "Powered by VividSeats."

๐Ÿฟ My Recommendation

Risk and Reward: How to handle market volatility and build ...

Ben Carlson just released โ€‹Risk and Rewardโ€‹, 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.


๐Ÿ“ฐ The Rest of the Week

๐Ÿ’ณ Credit Cards & Points

โœˆ๏ธ Airline News & Promos

๐Ÿจ Hotel News & Promos

๐Ÿ’Ž Award Deals

๐Ÿฆ Bank / Brokerage Bonuses

 


Editor’s Note: The content on this page is accurate as of the posting date; however, some of our partner offers may have expired. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.