In today’s issue: The mogul who bought back her empire, billboards that break the algorithm, and AI that runs your ads for you.
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Notes from a messy desk
Hi from a rocky beach in Ibiza 👋
Last week, I launched the newest summer cohort of Business Class—and then launched myself off a cliff into the Mediterranean sea. Between rocky swims and salty dinners, I’ve been watching a fresh wave of founders roll into the Lounge.
Yes, this is my first time in Ibiza. No, it’s not all drug-fueled raver paradise. It’s also a quiet paradise. Remote beach paradise. Gorgeous-rural-drive, rustic-outdoor-dining, highly-spontaneous-everything-is-only-30-minutes-away paradise. I was set to head back on Monday (Ryan Air, FML) but decided last minute to extend the trip until a few hours before yesterday’s kickoff call (thanks, Amex points!), to milk every moment of sun before I returned to rainy London where this fresh tan will be fully wasted.
I felt a little guilty. But mostly, I felt, for lack of a better word, authentic — because this is truly what’s possible when you work for yourself. As I promoted the last hours of enrollment on Friday from a seaside rock, I realized how corny pre-recorded promo content can feel. It turns out people don’t want polish. They want real, which is a lot more pleasant (and easier) than a blinding ring light in your face.
Not every business can be run from a beach, and not every founder wants that. But part of my mission is to help founders reimagine what freedom looks like. It’s not about snake oil or selling a fantasy. It’s about designing your work to support your life—not the other way around.
If you missed enrollment, you can join the waitlist for the next time we open.
Wheels up,
Sophia
P.S. If you ever come to Ibiza, skip the clubs. Go for the sea bass and the sound of cicadas. 10/10.
Collabs on my radar
The Edie Parker collaboration with Wes Anderson’s The Phoenician Scheme on a glass pipe and gemstoned lighter case is gorgeous and genius. You can now buy Selena Gomez’s horchata-inspired OREOs. You can also soon buy Dr. Squatch soap bars made with Sydney Sweeney’s actual bathwater. Dancing with the Stars’ Rylee Arnold has her own pink lemonade with Swoon. Khy dropped a collection with Turkish-British designer Dilara Findikoglu. Like it? Loathe it? Gap continues to kill it with their collabs, this time with Malbon, “the coolest brand in golf.” The Acne Studios x Moomin collection is fun. Stylist Veneda Carter is dropping a collab with Nike this month and it looks extremely cool. There was a pop-up in Copenhagen for the collection over the weekend. There’s now an exclusive MOMA edition of the Polaroid camera, but the coolest part is the MOMA film with artist quotes. The Fold collection made with Liberty fabric is gorgeous. Up There and Coffee Supreme made a sick stackable mug. Veronica Beard and HEAD Sportswear just dropped a collection for anyone spending time on the courts this summer. Very into this sculpted sports bra and legging set. Wölffer Estate, a winery in the Hamptons, designed a bottle of Rosé inspired by NARS makeup. Kinda cute to bring to a summer barbecue.
Collab report: Last issue, subscribers were most into the Farm Rio x Starbucks merch collab, the STAUD x Birkenstock sandals, and the Tibi x L.L. Bean tote.
Shop my favorite brand collabs.
Links to make you smarter and more interesting
Nectar just came out of stealth with $10.6M in funding, co-led by GV and True Ventures. I backed Nectar at the pre-seed through Trust Fund, and I’m so proud to be in the earliest cohort of believers behind Farah and Misbah Uraizee — two brilliant sisters and former Meta leaders building the agentic social commerce platform modern brands have been waiting for. Nectar gives brands real-time insights, full-funnel attribution, and DM campaigns converting at over 12%. This is the operating system for commerce in the attention economy. Thrilled to watch them build what so many brands desperately need.
TikTok Shop isn’t the free rocket ship it used to be. In 2025, sellers are seeing fewer organic views and more pressure to spend on ads to stay visible. If TikTok is part of your sales funnel, start thinking like a media buyer, not just a content creator. AKA budget like it’s an ad-first platform, because that’s where it’s headed.
Huda Kattan just bought back the brand that made her a mogul. After 12 years, $450M+ in annual sales, and one less skincare detour, she’s back in full control of Huda Beauty. It’s a full-circle moment that brought me back to something I commented on last week:
’s piece on how female founders are expected to be both the operator and the face. Visibility is the price of admission and Huda’s been paying it longer than most.OnlyFans billboards gave one creator a 200% spike in subscribers and another thousands in extra monthly revenue. OnlyFans creators are investing thousands into physical ads because you can’t get shadowbanned on Olympic Boulevard. And it’s working. Top performers like Chloe Amour and Meighan Baker are bypassing algorithms and buying visibility IRL. Amour’s L.A. billboard brings in around 70 new subscribers a day. The billboards are part reach, part flex, and part content farm: creators post them online to double their value. It’s a playbook worth watching – not just for adult creators, but for anyone with a saturated or controversial niche, a bold brand, and a product that converts attention into revenue.
“Billboards can’t be shadowbanned, can’t be muted, and can’t be scrolled past,” Creators Inc. founder Andrew Bachman told
. “When everybody’s going Jetsons, going Flintstones, is kind of a flex. And for a world that now lives online, nothing hits harder [for these creators] than seeing your name and your face lit up in the real world.”Meta’s AI is about to make ads from a single product photo and budget goal – and run them for you. The program will whip up the whole ad – images, videos, copy – and figure out exactly who to show it to on Facebook and Instagram. It can also personalize ads in real time, showing different versions based on factors like location (i.e. a car ad might show mountain roads to viewers in snowy regions). For founders and creatives without a production team or deep ad know-how, this could be a game changer.
The bachelorette party scene just turned into a $650 million industry, and it’s reshaping how people plan and spend on celebrations. Guests are dropping over $1,300 each on multi-day trips dripping in custom decor, matching merch, and curated experiences. For founders, that means huge demand for fresh ideas that make planning easier and more affordable – whether that’s clever party swag, smart shortcuts for busy hosts, or services that take the party planning stress off. There’s room to win by solving the chaos behind these over-the-top celebrations.
Victoria’s Secret went dark for two days last week, and that blackout probably wiped out millions in sales. Security breaches have spiked this year, and fashion brands like Dior, Marks & Spencer, and Harrods all experienced cyberattacks over the last few months. These hits aren’t just tech headaches, they’re business killers.
BoF broke down how smart brands stay a step ahead:
Hire a cybersecurity boss who gets it. Someone who lives and breathes protecting your brand, not just a part-time IT fixer.
Ditch custom Frankenstein sites that haven’t been updated in years. Move to platforms like Shopify that keep patching holes before hackers find them.
Run simulated hacks regularly. Test your defenses with real fire drills. You want to find weak spots before they become headlines.
Get crystal clear with your customers if you get hit. Own it, explain what you’re doing to fix it, and why their trust is your top priority. Transparency is your best damage control. Maybe even have the messaging written out ahead of time so you’re not scrambling with PR in the middle of a crisis.
Train your team on phishing and scams like their paychecks depend on it. Because, honestly, they do. One click can sink you.
Prada just bought Versace for $700 million less than in 2018, and E.l.f. dropped $1 billion on Rhode… even with tariffs and a shaky economy. While most brands are playing it safe, the ones with cash and guts are doubling down, buying up discounted assets and betting on growth. Waiting for perfect clarity is how you get left behind. Smart risk-taking now builds the future winners.
Creator jobs exploded from 200K to 1.5 million in just four years. That’s a 7.5x jump, and creator media revenue is growing five times faster than traditional media. New tools like Substack and CapCut make it way easier for anyone to build a business off their content.
50+ people make more than $1 million on Substack, according to CEO Chris Best. I’d love to know who these people are – did they have pre-existing audiences carry over from other platforms? Are they brands? What’re their playbooks? Dish.
Gen Z will probably sell their data because they already give it away for free. Youth polling company Generation Lab just launched a tool paying users $50+ a month to track their online habits, turning personal data into a straight-up commodity.
Coming back from vacation shouldn’t feel like punishment. A few founders finally did what most of us say we’ll do and let AI handle the mess.
Lindsey Scrase, COO at Checkr, used AI to summarize meetings and Slack threads after a 9-day trip to Japan
Erin DeCesare, CTO at ezCater, had Glean spit out a one-pager of decisions made, what was still open, and how her team was feeling after a six-week sabbatical
Melanie Rosenwasser at Dropbox swears by Copilot for email triage and planning, and said it gave her 30% of her time back
Link report: Last issue, subscribers were most into the Business Class Summer Cohort launch (!!), the marketer’s guide to Reddit trends, and the Seed 100 list of the best early-stage investors of 2025.
More from my rich universe of endeavors
I may include affiliate links, which means I receive commission on purchases made from some of the links. But I’ll only show you stuff I really like.
The beaches there are incredible—unreal water, and riding bikes along the shoreline? Chef’s kiss. I also went to UNVRS (formerly Privilege Ibiza when I was there), which is the largest nightclub in the world. It was absolutely wild. If you’re still there, it’s worth checking out just for the experience. Just make sure you know where the exits are—seriously. That place is massive, and when I was ready to leave, I couldn’t figure out how to get out… though to be fair, that might’ve had something to do with how many drinks I’d had.
M