Are brands getting petty?
Vrbo’s confusing new billboards, and why betting 50% of your business on a single product is a bad idea (duh)
March 28, 2025 | London, UK
Hi there, and welcome back to The Brandsider: the weekly newsletter exploring how great companies use brand as a business lever. Subscribe for insider takes on brand-led business strategy - from breaking down major headlines to deep dives on the brands getting it right.
It’s been a minute, but only because The Brandsider is officially moving to Fridays.
Since it’s a round-up, it just makes good business sense. Plus, I always look forward to reading The Stanza on Friday mornings, and I like to imagine someone might feel the same about The Brandsider one day.
Momentum is finally building. The months I spent trying out different approaches, platforms, content types did pay off. And now it’s time to execute.
As I get into the flow, I’ve been thinking a lot about my role and editorial boundaries as a content creator. I cover a lot of ground in my videos every week - both in quantity and breadth. And because I’m not an expert in every industry (nor do I claim to be one), mistakes are unavoidable. Angles I miss, things I misunderstand, nuances I overlook.
And people are, of course, always keen to point them out (thanks TikTok). Or like yesterday, when I misread the new campaign for California Pizza Kitchen (weird, I know) - and got called out on LinkedIn. My stomach dropped when I realized I hadn’t understood the full story, but I was honest about my shortcomings. The person and I discussed; now have plans for an intro call. Yay!
So while the potential of a making mistake publicly was paralyzing at first - especially as a recovering perfectionist - I’m realizing my value isn’t to get everything right. It’s to surface connections others miss, spark new conversations, and create space for the people who do know the details to jump in.
I look forward to having a research team fact check every word before posting. But until then? Prioritizing output, staying curious, and being transparent about my limits feels like the only way forward. Or at least that’s what I’m telling myself.
But for now, let’s get into what happened this week…
Mentioned in this week’s letter: Vrbo, AirBnB, Tesla, Hims, Hers, 23&me, H&M, Starbucks, Sephora, Doordash, Klarna, Unilever, Ben & Jerry’s, Open AI
✨ Where Business Meets Brand
Deeper analysis, as covered on IG / TikTok / YouTube Shorts
Vrbo’s challenger attempt: strategic or just petty?
Brand rivalries are nothing new - but they seem to be heating up. Hatch is going after Apple. Tony’s Chocolonely after Cadbury. And Vrbo is now going up against AirBnB. WSJ even wrote a piece on it (highly recommend)
But what makes the difference between a true challenger brand - and one that just comes across as “confused as they are desperate”?
In this piece, I explore how great challenger brands don’t just poke the leader - but challenge the very belief system it stands for. Creating a tribe for those who never felt like they could quite relate to the incumbent. I’d be keen to hear your thoughts on what that space might look like for Vrbo.
Hims & Hers’ big gamble
When GLP-1s became a thing, Hims & Hers quickly jumped on the bandwagon: positioning as affordable source for weight-loss drugs. They even pledged to tackle America’s obesity crisis with their recent Super Bowl ad.
But the secret to their affordability? Compound GLP-1s, which the FDA is now cracking down on.
This puts the whole model at risk. GLP-1s now make up 50% of Hims & Hers’ revenue, and thousands of customers rely on them for access. If the company can’t deliver, it’s not just a business problem, it’s a direct hit to the brand’s core promise of accessibility.
Tesla’s ‘founder’ liability
Tesla is officially the worst-performing stock on the S&P 500 this year: a case study in the double-edged sword of a founder-led brand. For years, Elon Musk was the brand. But what happens when your founder alienates your core audience?
After Musk’s recent political moves - from historical Trump campaign donations to leading DOGE - the backlash has been real. Boycotts, stock dumping, and viral bumper stickers later… the business is feeling the brand fall out.
I break it down here:
🎥 Bonus: Day in the Life
I filmed a day in my life video on Tuesday, which included both my corporate workday and the BTS of creating the Challenger Brand carrousel from scratch. So fun to make this type of content - especially to capture the early stages of building The Brandsider.
📈 Intel Files
A roundup of stories caught my attention this week
🧬 23&me has officially filed for bankruptcy. But what the heck is happening to the genetic data of its 15M customers? As one of the businesses’ core assets, the data is fair game to be sold in a bankruptcy sale. Well that’s terrifying, for so many reasons. State authorities and legal experts are urging past customers to delete their data from the platform. (WSJ, Wired)
👚 Apparently H&M - alongside all its retailer friends - is attempting a comeback. I haven’t bought clothes from H&M in probably 7 years, but I do religiously shop from & Other Stories, one of their brands targeted at professional-age women who have too much money to spend on sweaters. I’m wondering how H&M’s controversial attempt at normalizing AI models (nope, will always be weird to me) will fit into this. (BBC, Business of Fashion)
🏡 AirBnB seems to be unbothered about its tiff with Vrbo as it gears up for bigger and better things. The WSJ reports that Airbnb is ramping up marketing spend and hiring ahead of a big announcement in May - where it will expand its revenue streams beyond home sharing. They launched Experiences a few years ago, and that was both a brand-aligned and a smart business move. So I’m excited to see what Brian Chesky and the team will create next. (WSJ)
☕️ We all know Starbucks is going through a corporate turnaround and nostalgia-driven brand overhaul (video coming soon). But did you know baristas are expected to jot down handwritten notes on every cup they serve? What started as a spontaneous gesture is now being mandated - and it’s backing up queues. Can a forced moment of kindness still feel genuine? Or does turning it into a requirement ruin the magic? Of both the interaction - and the brand. (Bloomberg UK)
💄 There’s a rumor that Sephora will stop selling sex toys by the end of the year. And I’m wondering if this a brand issue, or simply a demand one. A few years ago, sexual health was all the rage… with brands like Dame and Maude popping off. But now with social conservatism on the rise, and the age of beauty buyers plummeting (leading to the wonderful Sephora kid phenomenon), I think the retailer might be trying to align their stance with their new audiences - and the parents who fund them.
🌯 I think we’ve reached peak capitalism: you can now pay for your food delivery in installments. Klarna, the Swedish BNPL (buy now, pay later) company, has struck a deal with Door Dash — promising a better, ‘interest-free’ alternative to credit cards. But considering American household debt reached an all-time high last month, and that Klarna can absolutely charge late fees on missed payments - this is very concerning. I rewatched The Big Short this week, and thought this meme was bang on. French fry tranches coming soon. (Fortune)
🍦 One of the truly iconic brand-led companies is discovering the limitations of corporate. Ben & Jerry’s - which has always stuck to its social justice ethos like its life depends on it - is claiming Unilever ousted their CEO. It seems the parent company wasn’t aligned with the executive’s outspoken social policy takes. Ben and Jerry, the founders, are considering buying the company back to maintain ideological independence. (Reuters)
🖼️ ChatGPT released a new image generation model, and it’s… insane. I was working on the Challenger Brands post the day it was came out - and asked it for an ‘Up movie' style set of me surrounded by challenger brand paraphernalia. Took some back and forth, but I truly can’t believe the output. The possibilities for this are endless, and I haven’t even started looking into campaign / brand creatives. (Tech Crunch)
🩵 Quick hits
Amy Poehler launched a podcast, and I’m fully bought in. It’s the exact opposite of Meghan’s sterile cooking / lifestyle / craft show no one can relate to.
Parker’s obsessed with this new font by Pangram Pangram Foundry
I read (and pay for) a lot of newsletters. My current fave? As Seen On by Ochuko Akpovbovbo
Onwards
My priority for next week will be to start engaging with the broader brand/marketing/business creator community. Until now, I’ve been building the Brandsider within the confines of my network - albeit publicly.
There’s something to be said about earning your spot - honing your lane, getting in the reps - before taking part in the conversation. But I’m getting to that point now, and I know from building Boldest that it’s through community engagement that things really start to take off.
Time to start showing up.
If you’re also working on something - creative, ambitious, scary - I’d love to hear about it. And if you’re in London, Parker and I are playing with the idea of hosting dinners for creative entrepreneurs. If that sounds interesting, don’t hesitate reach out :)
Already looking forward to the next one,
xoxo,
The Brandsider