40. Are cruises cool or an impending disaster?
Putting Virgin Voyage's Millennial playground to the test.
Today’s letter includes: a tiny island's accidental internet jackpot, the biggest wealth transfer in history, celebrity drug dealers, the wordless subway ad that actually works, and why boring parents make the funniest kids.
Hi friends.
Have you ever been on a cruise? I think they are fairly common for “family reunions planned by grandparents” type trips. But recently, they seem to conjure up more reactions around biological imperatives running amok — I think we can thank the the bad PR from Triangle of Sadness and Netflix’s Trainwreck: Poop Cruise.
I have been on a few cruises as a kid. What I remember most is that cruises used to offer true digital detox—you were literally at sea with no service, no WiFi for multiple days in a row. This Friday, I’m testing that theory on my first cruise in years with my dear old dad. I’m genuinely curious to see how well the WiFi works now; Virgin Voyages offers it for free, but they are constantly urging you to upgrade to Premium (which I did not do).
I’m also curious to see how it will feel to be on a Virgin cruise. My CEO keeps reminding me that one of our investors, Bain Capital, holds the majority stake. And it does seem somewhat “innovative” for an old industry (the first leisure cruise sailed in 1844).
When I looked into my ship’s programming I laughed to myself —sushi, tattoos, K-BBQ, drag brunch, bathhouses—it genuinely feels like they asked ChatGPT to list “things millennials like.”
They’ve taken the old revenue streams, like buying expensive watches onboard to avoid taxes and turned them into events. And yes I will be attending, “Rolex: It’s time to collect - At this event, our Swiss timepiece expert gives Sailors an informative presentation on the history of Rolex, and the benefits of buying pre-owned…while sipping on complimentary champagne and scotch.” Thank you for asking.
But just as I am finally about to learn why people like Rolexes so much, they’re already out.
Due to said cruise, no party talk next week. Instead you’ll find a deep dive into offline as the new status symbol and why tech founders are swapping their luxury watches for rare books.
Rumor has it that Substack is suppressing free content. If you’d like to resist the algorithm pushing paid content only, then liking, sharing, quoting and restacking this newsletter will help! <3
I’m sure your group chat was discussing Chappell Roan’s outfit. Now that’s what I call confidence! Kendrick Lamar made Grammy history with five wins, overtaking Jay-Z as hip-hop’s most decorated artist. Bad Bunny’s Debí Tirar Más Fotos became the first Spanish-language album to win Album of the Year.
The federal government entered a partial shutdown after missing the January 31 deadline but it ended when 21 democrats broke party lines and voted to pass it. Also there are ICE billboards all over San Francisco.
Sweet girl! Lorde is donating six figures of her merch sales to Minnesota Immigrant Funds.
I’m not going to read the 3,000 Epstein files documents but I don’t want to “look like a thicky, thicky dumb, dumb in front of all my mates!”
Charli xcx wrote about the death of cool and I finally read it. The people in the comments section lost their minds. I don’t understand wanting to spend time to go on a tirade on a celeb post. But you do you! I did enjoy imagining Julia Fox drones delivering packages.
“But if Julia Fox did have a custom Mcdonald’s meal and a clothing line with Target and little Julia drones were delivering everyone’s Amazon packages, would this mass exposure make Julia Fox uncool? I honestly don’t think so because I’m sure she’d find a Warholian way to make it all make sense.”
— Charli XCX on her Substack
Carlos Alcaraz defeated Novak Djokovic to win his first Australian Open title, becoming the youngest man ever to complete a career Grand Slam at 22.
You can get $1000 from this ill-named tax vehicle. Trump Accounts are a new investment option for minors with a one-time $1,000 contribution for US-citizen children born between 1/1/2025 - 12/31/2028. If you have a kid that fits those dates, here’s a helpful guide.
Melania’s red carpet was black. Also they did not let journalists in for the premiere of the documentary, so it looks like journalists had to pay for the matinee (see below). Friend of the letter, Betsy Klein reports!
G2 acquired a bunch of other software review sites. Market consolidation alert!
Rich kids get richer. Wealthy families are about to pass down $38 trillion worldwide over the next decade, with Gen X and millennials set to inherit $4.6 trillion in real estate alone.
The new collaboration between Morris & Co. and Zara Home is giving Wuthering Heights.
What celebrity won’t GLP-1s hire? Tom Brady, Justin Long, now Serena Williams and Rebel Wilson. The other night we joked that my friend’s cousin was an “early adopter” because she’s been on Ozempic for over two years.
NYC Landlords will finally have to provide air conditioning. This is very good because temperatures are getting more and more extreme.
My new company name is about to make Anguilla some money. Anguilla, a tiny British territory with just 16,000 residents, is absolutely crushing it thanks to a lucky internet accident. Back in the early days of the web, they were assigned the country-specific ".ai" domain suffix. Domain registrations now account for a quarter of the island's entire revenue. They made $39 million in 2024 alone, with projections hitting $70 million for 2025. The number of .ai domains exploded from 50,000 in 2020 to over 1 million this month. Meanwhile, islands with less sexy domain extensions like ".tv" (Tuvalu) are probably wondering where they went wrong.
Do people really not know what Pumpernickel is? Come on, order more pumpernickel bagels!
Rachel Sennott’s parents are both accountants. I listened to her Good Hang episode on the drive back from skiing and was delighted to learn that such a funny person could spawn from accountants. Her parents met at the same firm and dated secretly before popping out 5 kids. She also said the best stuff happens to her when she is “at rock bottom,” to which Poehler replied: “Rejection is God’s protection!”
I kind of love this copyless David OOH ad. I saw it in the NYC subway and it immediately caught my eye. Awkward timing though with Peter Attia being linked to Epstein and parting ways with the company.
Here’s why they can get away with the minimalism:
The product is obvious and physical. Even if you haven’t heard of it, you can tell it is an edible pre-packaged good.
They did full car buyouts.
The product packaging is unique — the gold is alluring and the brand is giving 80’s boom boom aesthetic.
They’re hoping it’s alluring enough that you will simply take out your phone and Google it. I’d love to see their NYC traffic MoM since the ad started running. That’s where my adoration of the brand ends however. I don’t think my values overall align with the company. This is a fascinating deep dive into the company, its products, and VC backers from Joe Hovde though if you want to learn more.
Thanks for reading!
Thanks so much for sharing! Hope the cruise is great :)