Sara Blakely's October 2021 sale of Spanx may be the best-timed consumer exit of the entire cycle. Bootstrapped for 21 years, sold majority control at $1.2B, and the buyer's equity has now gone to zero.

The arc: in 2000, Blakely started Spanx with $5,000 saved from selling fax machines door to door. By 2012 she was the youngest self-made female billionaire on the Forbes cover. In October 2021, Blackstone bought majority control at $1.2B, on ~$300–400M of revenue and $50–80M of operating earnings, financed with a first-lien term loan. Blakely kept a significant minority, became Executive Chairwoman, and gave every employee two first-class tickets and $10,000. All-female board, all-female deal team, Oprah and Reese Witherspoon co-investing. It was the deal of the year.

Then the category turned. Between 2021 and 2026, Skims went from ~$145M in revenue to ~$1B, and didn't just take share, it changed what shapewear was, from compress-and-hide to enhance-and-show. Spanx was the leader of a category whose premise had flipped.

This is where my day job kicks in, because the mechanics of what happened next are the ones I see constantly in smaller situations. A first-lien term loan sized against 2021 earnings doesn't shrink when the business does. By summer 2026, the private credit loan was marked at 70 cents on the dollar. In July, an out-of-court restructuring handed control to the senior lenders, HPS and Oaktree among them. The debt was amended and extended; Blackstone's $1.2B equity was effectively written to zero; Blakely formally exited the board. No bankruptcy, no headlines, just the capital structure quietly working as designed.

Clapping for Sara Blakely and everyone who sold in 2021.

What does it take to get acquired for nine figures by a legacy incumbent? Here's the cleanest recent answer: take seven share points off the category leader in three years.

Goodles grew its US shelf-stable mac and cheese share from 0.8% to 7.8% since 2023, while Kraft fell from 42.2% to 36.6%. Last week, Barilla, the fourth-generation family-owned Italian pasta giant, agreed to acquire it.

The playbook is one regular readers will recognize immediately: the sleepy-aisle pattern. Find a shelf that hasn't been reformulated in decades, rebuild the product for the modern consumer with better-for-you ingredients and upbeat branding, and let the incumbent's inertia do the rest. Goodles blends wheat flour with chickpea protein and nutrient-dense vegetables, kale, pumpkin, shiitake, into flavors named Cheddy Mac and Twist My Parm. It's a box of mac and cheese that a parent can feel fine about.

The capital efficiency: ~$20M raised in total, including L Catterton at an $88M valuation in 2023, against a nine-figure exit three years later. Compare that to the DTC-era brands that raised $100M+ to reach similar revenue.

But the founding team is what made this inevitable rather than lucky. A serial founder. An ex-Kraft brand manager who knew exactly how the incumbent thinks. Gal Gadot for reach. And the former president of Annie's, the original BFY mac and cheese, which itself sold to General Mills for $820M in 2014. This team had already run the exact play once. They knew the aisle, the buyer, the acquirer's logic, and the exit.

And a note on the buyer: Barilla is family-owned, private, and patient, the same profile as Ferrero, who we covered buying both ends of the cereal K last month. The most aggressive acquirers of American challenger brands right now are European family companies with permanent capital and no earnings calls.

Challenger CPG has been on an absolute roll for liquidity these past 18 months. Great for the ecosystem, and a reminder that a sleepy aisle is only sleepy until someone wakes it up.

Quince proved there's a $10B business in selling luxury-quality basics from the same factories the luxury brands use. Now Atorie wants to do the same thing as a marketplace, and just raised ~$10M from a16z speedrun, Night Capital (the creator fund that includes MrBeast), and Lightspeed's Jeremy Liew.

The distinction matters. Quince is a merchant: it designs and sources the product, owns the customer, and pushes inventory risk upstream to factories that hold stock until an order ships, we covered that machine when it beat Everlane. Atorie is a marketplace: the factories themselves are the sellers. Same supply insight, different business model, and the difference is the entire bet. A marketplace has thinner margins but doesn't carry the merchandising burden, and it can scale supply without a buying team.

The traction: founded in 2024, $5M in revenue last year, on pace to 10x this year. Founder Redouane Ramdani grew up in a family that manufactured for French luxury, he knows the factory side from the inside, which is the hardest side of this model to access. Atorie's stated plans include helping creators launch clothing lines quickly: luxury-tier factories on one side, creator audiences on the other, and the marketplace in between taking a cut of both.

The macro window is what makes the timing interesting. Between 2019 and 2024, the luxury houses raised prices 50–100% on core products, deliberately pricing for the top of the K. It worked until it didn't. Luxury has now spent two years in a slowdown. Every price increase widened the gap between what the product costs to make and what the consumer pays. Quince was the first business to arbitrage that gap at scale. Atorie is betting the gap is wide enough for a marketplace to live in too.

The risk is the one every marketplace faces: Quince's moat is a curated, consistent customer experience. A marketplace of factories is, by definition, less curated. Whether creator-led demand can substitute for merchant-led quality control is the question the next $50M of revenue will answer.

CACs only go up. Consumer wallets are tight. Most DTC brands respond by quietly lowering their efficiency targets and calling it strategy.

Jordan Nathan has never flexed below Caraway's ROAS floor. Not once since launch. That kind of discipline sounds simple, hold the line, don't chase growth you can't afford, but holding a ROAS floor for six years while scaling into one of the most recognizable homeware brands in DTC raises an obvious question: how do you keep hitting the number when acquisition only gets harder?

Jordan's answer is a marketing calendar he calls rolling thunder. Every single month, Caraway has something to talk about. A product launch. A color drop. A partnership. A promotion. The calendar is engineered so there is never a quiet period, never a stretch where the brand is running the same ads at the same people hoping efficiency holds.

Most brands go dark between launches. They pour everything into a big moment, then coast on stale creative for four months while CAC creeps up and ROAS erodes. Then they panic, discount, and break their own pricing architecture to hit the quarter. Rolling thunder is the structural answer: new things to say keep creative fresh, fresh creative keeps efficiency high, and high efficiency means you never have to choose between growth and your floor.

And it compounds backwards into product strategy. Caraway plans launches five years out, because the marketing calendar can only roll if the product pipeline feeds it.

Three things from the conversation worth taking with you:

Raising sixty checks when every obvious investor had already backed a competitor. The cookware category was crowded with funded players when Caraway launched. Jordan's fundraise is a case study in going wide when you can't go deep.

Price higher than you think you can. Caraway's pricing architecture is the reason the ROAS floor is holdable, margin is what buys you the right to be disciplined.

"Impossible to ignore" as a creative brief. What that phrase actually means operationally, and why it's the standard every Caraway ad has to clear.

🎧 Watch on YouTube, listen on Spotify.

In October 2021, Headspace merged with Ginger at a $3B valuation, a landmark deal of the digital mental health boom. Axios reported the company is being sold to Sword Health for $200–300M.

Beyond the 90% haircut, consider what's being sold. The combined entity raised $500M+. Founded by a former Buddhist monk, it helped invent consumer mindfulness as a category. Nearly 600 employees, enterprise contracts, a global brand. All of that was real, and none of it translated to lasting market value.

In the same month, I've covered Function Health raising $450M in growth financing, Neko Health raising $700M at a ~$7B valuation, and Happy Health raising $75M for their FDA-cleared diagnostic ring.

Two wellness cycles are passing each other in opposite directions. The 2019–2021 cohort; meditation, mindfulness, teletherapy (Cerebral, Pear Therapeutics, Babylon), is being liquidated or sold at steep discounts. The 2024–2026 cohort; diagnostics, biometrics, clinical-grade prevention, is being funded at record levels.

What changed is what the consumer is willing to pay for. The first cohort sold a feeling: calm, support, presence. The second sells a number: biomarkers, blood panels, a ring that tells you something clinically true about your body. It's the same shift we've tracked in food (from "better-for-you" to "protein per calorie") and in bottled water (from a story to a lab test). The wellness consumer has moved from wanting to feel better to wanting to prove they're better.

Quick ask: did anything in this issue change your mind about something? Hit reply. I read every one.

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