💰 My Top Picks, Recommendation & More (5/30/26)
This week, we'll cover three new 80-90K Southwest welcome bonuses, maybe opening a Bay Area studio for builders, why an 800+ credit score can still get denied, AA blocking close-in partner awards, whether AI is actually creating more work, and more!
🏦 The Hidden Rules of Credit Card Approvals
Learn how to dramatically improve your odds of getting approved for the credit cards you actually want. I'll break down the hidden system banks use to evaluate applications, why your credit score matters far less than you think, and the real factors driving denials, from credit-to-income ratios to recent inquiries to each issuer's internal model.
📋 My Past Week
- I'm a big fan of Colin & Samir's work in the creator world and really enjoyed joining them at their Press Publish LA event this week. As someone who works at home without a team, getting to spend a day with other creators talking about the future of our work was so fun (and honestly necessary). I highly suggest you all try to find at least one in-person event or meetup this year with people who share your profession or hobby.
- The event is actually pushing me to consider something I've been thinking about for the past year: opening a physical space for builders and tinkerers. Think a shared workshop where you could 3D print a prototype, hack on an interesting AI project, laser cut a sign or solder a circuit board alongside other curious builders. If that resonates with you and you live in the bay area, on/near the peninsula, let me know here:
- While in LA I stayed with a close friend for 2 nights and it was so great to have so much time together that it felt like we got past the catching up stage and were just hanging out. After having kids I don't feel like we often get to do that and it was really fun.
- My youngest daughter loves taking photos. Everywhere we go, she asks to borrow our phones and take photos. The end result is that we have 1000s of random photos, mostly of her fingers, the ground or a wall. But amongst all that are some really fun photos that I never would have captured myself, like this:
⭐ My Top Picks
💳 Southwest Personal Cards: Up to 90K Point Bonuses
Right now, three personal Southwest cards have elevated welcome offers of 80-90K Rapid Rewards points, which I value at $1,000+ of travel. Even better, the spend requirements are lower than many similarly valued offers and the welcome bonuses will leave you more than halfway towards companion pass. Full details on the offers here.
✈️ American Is Blocking Close-In Partner Awards
Bad news for those who book American flights with partner miles. It appears AA is blocking nonstop domestic saver award space within ~6 days of departure, while keeping those same seats bookable with AA miles. This is a huge bummer for people like me, who often use Alaska or Avious to book last-minute domestic flights. There hasn't been an official announcement, so things could change in the future.
🪒 My Recommendation
I'm a huge fan of the content around AI and Tech that Dan Shipper and the team at Every have built. But I specifically loved the long-form piece they recently published called After Automation, which is about how AI progress is creating more work for humans, not less, which is something I'm personally feeling a lot right now. While a lot of their writing and the apps they've built are part of a subscription (with a 30-day trial), their AI & I podcast is free and they actually put out this episode on the After Automation piece I linked above.
📰 The Rest of the Week
💳 Credit Cards & Points
- Bank of America: BofA Rewards Launch is Live — I was hoping for cool new perks, but only got a mediocre streaming credit.
- Citi: Custom Cash No Longer Accepting New Applications
✈️ Airline News & Promos
- American: Adding Starlink Wi-Fi to 500+ Aircraft — I can't wait for Starlink on all flights, the experience is amazing.
- Bilt: June Rent Day — Up to 125% Transfer Bonus to TAP — Between the limited uses of TAP and a cap of 100k points transferred, I'm passing on this one.
🏨 Hotel News & Promos
- Hilton: 2K Points/Stay + 4K Points on 4+ Nights (6/1 - 8/15)
- Hyatt: Early 13-Month Award Access for Elites & Cardholders — TBD if this will be a "perk". I assume most people booking Hyatt's far out already have status or a Hyatt card.
- IHG: 3rd Night Free on Premium Rooms (EMEA & Asia)
- Hyatt: Some Park Hyatts Reclassifying as "Resorts" to Dodge Late Checkout — This feels like it shouldn't be allowed.
- Marriott: Up to 10K Bonus Pts/Stay at 121 Luxury Properties
- SLH: Free Club 03 Top Tier Status, No Stays Required — Sadly this won't work for bookings if you want to earn Hilton points.
💎 Award Deals
- 🇦🇷 Argentina: US to Buenos Aires Biz/First From 50K/75K Alaska
- 🇦🇺 Australia: DFW/LAX to Sydney First From 110K
- 🇧🇪 Belgium: IAD to Brussels Biz From 60K Aeroplan
- 🇯🇵 Japan: Park Hyatt Tokyo Reopens, Nights From 35K Hyatt
- 🇵🇹 Portugal: TAP Biz to Lisbon/Porto From 60K Aeroplan
- 🇪🇸 Spain: Iberia Biz to Madrid From 40.5K pts
🔗 Card-Linked Offers
- Hertz: $75 Back on $325+, Citi Offer
- JetBlue: $50 Back on $400+, Citi Offer
- UberEats: $15 Back on $25+, BankAmeriDeals
🛒 Other Deals
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.
Founder / Host
I love sharing my quest to optimize and upgrade my life. Previously I was Head of New Product Strategy at Wealthfront, co-founder and CEO of Grove (acquired by Wealthfront), co-founder of Milk (acquired by Google) and a Partner at GV, where I focused on seed and early stage investments.
💰 My Top Picks, Recommendation & More (6/27/26)
