๐ฐ Millennial Heart Break
Millennials were getting our first jobs out of college when brands like Everlane and Allbirds introduced us to a new idea: that buying things could be an act of integrity. We weren't just consumers, we were conscious consumers of ethical production, sustainable wool, and radical transparency. And brands and customers alike were absolutely swooning.
This weekend, I taught a storytelling workshop to eight entrepreneurs for The Jazba Collective, and I used Everlane as one of my favorite case studies: a brand that used the power of storytelling to make its mark. The brand introduced us to terms like "radical transparency," showing customers exactly what their clothes cost to make: materials, labor, shipping, and the markup. They didn't just sell a product, they sold us a feeling of integrity of choice.
Less than 24 hours later, I saw the news that broke the internet (and millennial souls): Everlane was acquired by Shein, one of the world's most prominent ultra-fast-fashion platforms.
๐๏ธ If You're New Here
This is The Messy Middle, a newsletter about the leadership journey no one tells you about. I'm Arshiya Kherani, an executive and founder coach and speaker. I write about the things most people skip in professional spaces: identity shifts, and what it actually takes to lead with intention when the path isn't always clear.
This week...
๐ The Brand I Wanted To Be
Everlane didn't invent sustainable or ethical fashion, but they invented the language and the story that made ethical manufacturing suddenly look scalable and accessible to investors and customers. Everlane's trademarked radical transparency model gave us an itemized breakdown of what $98 pants actually cost, and a narrative that made us feel good about the splurge when fast fashion was selling the same silhouette for $30.
And as a brand owner in the 2010s myself, Everlane was my role model. I was building Sukoon Active, a modest activewear brand with ethical and sustainable manufacturing practices in place. My dream was to be the Everlane of that space. I loved everything about their messaging, and the conviction with which they made values feel like a competitive advantage.
What I know now, having built a values-driven brand myself, is that the story and the work have to move together. Everlane actually did this for more than a decade, and over the last few days I started to really wonder, where did they go wrong? And how do you build a brand that can grow without eventually having to sell out the thing that made it worth buying in the first place?
๐ก So Where Did It Go Wrong
In my research, I came across a tweet from Nan Yu, an early CTO at Everlane. The pandemic wiped out Everlane's core wear-to-work market almost overnight. It turns out that the brand took on absolutely awful financing terms just to survive the pandemic, and as a result, they've been heading towards this acquisition for a few years now.
Yu says, "it's a pretty sad day for the people who built it."
I know that feeling. Sukoon went under during the pandemic too. I will not pretend that my bootstrapped 6-figure brand was in the same category of a $250 million valuation DTC darling, but I did have a similar experience in that that during the pandemic, the math stopped working for my brand.
โจ A Powerful Story Can't Save A Business
A powerful story can build a brand, but it can't save a business. When the market suffered, costs went up, competitors became more prominent, and the financing terms came due, the story didn't matter anymore for Everlane: the math needed to math.
Everlane had to sell to survive, but it begs the question: why are millennials so mad? And why is Everlane's story, even its story of selling to the anti-Everlane, still an incredible case study in brand storytelling?
Because it demonstrates that an entire generation of loyal customers bought so deeply into their story that they built an entire identity around this brand. Consumers aren't experiencing the cap table, they're experiencing the betrayal that comes with selling the value system they bought into.
That's the power of storytelling. Everlane made people feel less shitty about contributing to a system inherently linked to climate change; Everlane made us feel like the exception to buying cute things.
In fact, I would argue that the internet is outraged today because Everlane may have been almost too good at storytelling. So good that when the business decisions didn't match the story, we took it personally.
๐ And They're Not The Last
Everlane isn't the first brand to sell out and break our hearts, and it won't be the last. We have watched brand after brand get built on a story, scale on that story, and then get acquired by the exact thing the story was positioned against. The story doesn't survive the cap table.
And every time it happens, we're shocked. We feel betrayed, unfollow, and rage post our disappointment. Everlane sold to a fast fashion giant. Allbirds is now an AI company. Outdoor Voices' founder was pushed out before it was acquired by private equity and lost its hold in the millennial wardrobe. The real question is: what does it actually take to build a brand where the story and the business can survive each other?
I'm not saying don't believe in brands; what I am saying is story is that powerful. Powerful enough to build a $250M valuation, and powerful enough to make us question what we're really buying into after all.
The brands that will last (or at least not break our hearts)...are the ones where the story and the substance actually stay in alignment; where the values continue to show up in the hard decisions instead of just in the marketing.
I wonder as a founder with a brand that went under myself...at what cost did brands like Everlane, Allbirds, and Outdoor Voices choose to survive?
๐ฅจ Snacks
๐ฎโ๐จ This Week In The News: Is THIS really the most future proof career choice?
โ Save The Date: Building a portfolio career? Join me for this FREE roundtable on how to talk about it on May 28th.โ
๐ฌ Uncomfortable Truth: Toxic bosses are on the rise. According to Glassdoor, workplace reviews were 6.7 times as to reference toxic management than they were in 2026.
๐บ What To Watch: Speaking of breaking the internet...Devil Wears Prada 2 did not disappoint. One of my favorite lines, "you look like a nervous cat."
See you next week,
Arshiya
๐ PS: If you're building a values-driven brand and you want the story and the substance to actually match, book a 90-minute Power Session with me and let's make sure your story has the follow-through that your business model can match.
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