Forwarded this email? Click here to get your weekly slice.

 

🪩 Volume 128 | March 18, 2026

 

Remember when Starbucks decided it wanted to be a restaurant?

 

Paninis. Hot sandwiches. A food menu so ambitious it could compete with your local café. It made sense on paper—people are already here, they're already spending money, why not give them more to spend money ON? Growth is growth, right?

 

Except the coffee got worse. Baristas who were hired to pull perfect espresso shots were suddenly managing a hot food line. The thing that made Starbucks STARBUCKS—that specific, reliable, ”I know exactly what I'm getting” experience—got real fuzzy. And customers noticed.

 

They eventually scaled it back. But, I don't think the instinct was wrong. When something is working, leaning in feels not just logical, but OBLIGATORY. Like, you found the thing! You cracked the code! Of course you're going to push on it. The tricky part is knowing the difference between leaning in and tipping over—and that line is a lot blurrier than any business book will tell you.

 

This week we're looking at two brands that found the thing, pushed on it, and tipped. Not all the way over—but enough that they had to stop, look around, and make some hard calls…

 

—

 

 

 

Week 3 of 4 is here; missed the first 2? Check them out below:

 

Week 1: Volume 126 | 🥳 More money DOESN'T have to mean more problems

Week 2: Volume 127 | 🥳 When the underdogs hit it BIG

 

NOW INTO THE MEAT N POTATOES!

 

 

 

If you were online between 2014 and 2019, you know the Glossier era. The millennial pink, the boy brow, the feeling that buying a $14 face wash was somehow also a personality statement.

 

Emily Weiss built the whole thing as a literal community experiment—she ran a beauty blog called Into The Gloss, spent years asking her readers what they actually wanted, and then just... built it. Sans: focus groups, retail distribution deals or wholesale partnerships (what a feat!) 

 

All it was, was her, her readers, and a direct line between the two. And you’ll never catch me complaining about brands that listen to their audience.

 

It worked SPECTACULARLY. By 2021, Glossier had hit a $1.8 billion valuation riding the DTC wave, and had more than 5 million customers globally. Two out of every five women between 18 and 34 in the U.S. had heard of the brand. That's insane brand awareness for a company that started as a blog.

 

And then they went to Sephora.

And launched foundation.

And opened 11 brick-and-mortar stores (I will never forget visiting the store in NYC!)

And hired aggressively.

 

But then the waters got dicey when they started chasing new customers instead of deepening relationships with the ones they already had.

 

To be fair—the stores were GOOD. Like, genuinely impressive as brand experiences. Their SoHo flagship had a live selfie broadcast feed, 15-foot product tables, and a wet bar for trying skincare. Their physical locations converted at 50% on average—higher than most retail concepts period. The stores weren't the mistake.

 

 

One analyst put it plainly: Glossier "probably grew too fast, delivered a product that wasn't resonating with their consumer who was aging, and was hyper-focused on acquisition and not retention." Meanwhile, the beauty space had simultaneously filled up with brands that felt exactly like early Glossier—Merit, Kosas, Jones Road, Tower 28. Brands that were doing the ”Skin first. You but better.”" thing at a sharper price point, without corporate bullshit.

 

The Reddit beauty community clocked this YEARS before the business did. There were threads calling it as early as 2020—noting that newer launches weren't hitting, that the brand had gone from feeling like a friend's recommendation to feeling like a costume.

 

Fast forward to February 2026 (yes, LAST month): new CEO Colin Walsh cuts nearly a third of the company—about 54 people from a 170-person team. His stated mission: To get back to being a ”skin-first brand” that moves ”with the speed of culture”. Which is… a pretty accurate description of what Glossier was in 2016. The correction is essentially a walk back to the original thing that worked.

 

For your business: Your community will tell you what's wrong before your revenue does. The signals were in the Reddit threads and the TikTok callout videos years before Glossier's numbers reflected it. → Are you actually listening to your customers? Or just tracking revenue on a spreadsheet? ←

 

 

 

 

Sweetgreen had a genius idea in 2018. They called it the Outpost program.

 

The concept: instead of waiting for office workers to come to them, they'd bring the salads directly into the office buildings. Designated Sweetgreen pickup areas, placed inside corporate lobbies and break rooms, built specifically for the midday corporate lunch crowd.

 

By early 2020 they had nearly 800 of these locations running. Investors LOVED it. It felt like the future of fast casual—frictionless, tech-forward, meeting customers where they were...literally.

 

 

Overnight, 800 pickup locations became 800 pickup locations inside empty buildings. App order volume fell by two-thirds. Their urban restaurant locations—which made up the bulk of their footprint—saw business declines ranging from 40% to 80% across the country. Sweetgreen cut 20% of its corporate workforce. It was a bloodbath.

 

Here's a question I keep bouncing around my noggin, and I want you to think about it too: did COVID actually break Sweetgreen, or did it just speed up something that was always going to happen?

 

The Outpost program was clever, but it wasn't really a consumer play. It was a B2B play dressed up as one.

 

Sweetgreen wasn't building relationships with individual customers—they were building relationships with employers. The person eating the salad was almost incidental (😅).

 

The real customer was the office building facilities manager who said yes to putting a pickup station in the lobby. The moment that person's employees stopped showing up, the whole thing evaporated.

 

Even without a pandemic, that model had a ceiling. Remote work was already creeping up before 2020. WeWork was collapsing. The ”everyone commutes to a downtown office forever” assumption was shakier than it looked. COVID didn't create the vulnerability—it just made it impossible to ignore.

 

 

If you're Sweetgreen, you rebuild. And er, they're still figuring it out… they invested a ton into the “Infinite Kitchen” to have robots and automations “making food” to solve their operational issue, and reported even worse earnings. Ha! (Hopefully they stop trying to be a tech company now).

 

For your business: If your best sales day depends entirely on something you don't control—an algorithm, an office reopening policy, one wholesale account, one platform—that's not a business model, it’s a bet. What's your single point of failure, and what happens the day that thing goes away?

 

Glossier and Sweetgreen are two brands with two very different problems, but one shared truth:

 

Glossier forgot who it was talking to. Sweetgreen forgot what it was standing on. Both chased a version of themselves that was bigger, broader, more—and both eventually had to stop, look around, and make the uncomfortable decision to get smaller before they could get better.

 

That takes guts. It's easy to keep pushing when things are going sideways and hope the next quarter turns it around. It's much harder to say: the thing we built isn't working the way we built it, and we need to be honest about that. Correcting requires a level of introspection and strategic clarity that most brands—frankly, most people—aren't willing to do. (I’ll admit I’ve had to do this a number of times in my own business over the years, restructuring the business, making strategic hires and fires, and things of that nature). The fact that these brands are IN a position to correct at all means they still have something worth saving.

 

Two brands launched discounted products recently and I can’t stop thinking about it. One did it brilliantly…and the other—not so much.

 

Apple launched the MacBook Neo — a $599 MacBook. As in, an actual Apple laptop, aluminum body, Liquid Retina display, all-day battery, for five hundred and ninety-nine doll hairs. For context, the MacBook Air—previously Apple's entry-level laptop—now starts at $1,099. The Neo is literally half the price. Apple called it ”breakthrough”. The CFO of Asus called it ”a shock to the entire market”. It launched earlier this month and reviewers are losing their minds over it.

 

Peloton announced a refurbished bike at a discount. Last week, the Peloton homepage (since changed) advertised the refurbished Original Bike for $695. Their headline: ”our lowest price yet”.

 

It’s easy to view these as the same situation: “Two premium brands launched products at more accessible price points. Cool.” But when we dig into it deeper—and you know that’s the name of my game here—it’s clear one of these strategies is not like the other.

 

Apple's Neo feels like a calculated brand architecture move—the Neo has real limitations (less RAM, no backlit keyboard, fewer ports) that are clearly designed to make the $1,099 Air feel worth the upgrade. It's a deliberate entry point, built to bring new customers into the ecosystem without negating the benefits of the premium tier. Ok, smart.

 

Peloton's sub-$700 bike feels… different. It's a refurbished unit, perpetually on sale, front and center on the homepage of a brand that spent years telling you that serious fitness required serious investment. That's less ”brand architecture" and more ”we need to move units.”

 

Here's a question worth sitting with: at what price point does a premium brand stop being premium? And is that actually a bad thing?

 

Maybe the answer is that premiumness was never really about the price, but instead about the experience, the community, the feeling of being in on something. Glossier charged $14 for a face wash and it felt luxurious. Peloton charged $2,500 for a bike and it felt like a club. If the price comes down but the experience stays, maybe nothing is lost. But if the price comes down AND the experience gets fuzzy—that's the Starbucks food menu all over again.

 

--

Week 4 is the one I've been building toward: Lessons for creative founders from everything we've covered this month. We're taking all of it: the brands that scaled carefully, the ones that stayed bootstrapped, the ones that had to correct—and translating it strategy you can bite into—and apply to your own business.  See you then. :)