5HT #123: why Headspace blew it, the fastest-growing sport, and 3 more

I first learned to meditate with Headspace and meditation has been a consistent part of my protocols ever since (more on those below). There’s a tooon of great evidence behind it, and I think everyone should be doing it.

I don’t think any company has done more to popularize and destigmatize meditation in the West than Headspace. In my mind, it’s the app that taught a generation of anxious millennials how to breathe. 😮‍💨

And, last week, it was announced Headspace was being acquired by Sword Health… for less than it raised in venture capital. Though we don’t know all the details, that does noooot seem like a good outcome (it was previously valued at more like $3B after it merged with Ginger.) 

Brutal.

Worse, I think it was perfectly positioned to build a defining consumer health brand and business. So, like, doubly brutal.

Why? Well, Headspace made something that’s perfectly counter-positioned to the crazy, hectic, stressful day-to-day American experience: accessible, fun, and friendly (especially for beginners). Andy Puddicombe’s voice did more to shape how people think about meditation in a friendly, accessible, Western-ish way than any book, monk, or TED Talk ever did.

Plus, some of the smartest people I’ve ever known worked there, including current Oura CFO (just announced it’s going public, nbd) Sean Brecker and Karan Singh (built Ginger). For a while, they were a huge talent magnet attracting the best and the brightest people passionate about consumer health.

Building a business is really hard. Building a business in health is especially hard. So it’s easy to be a Monday morning quarterback when things don’t go to plan. (I guess that’s what newsletters are for, but still.) To me, Headspace blew it when they (1) didn’t realize what business they were actually in and (2) decided to go all-in on healthcare to chase an outlandish VC valuation.

Their main competitor, Calm, seems to have done a much better job of understanding who they are. They knew they weren’t just a tool or a meditation app. Yes, it also did B2B stuff like Headspace. But Calm refused to stop being a brand. It took an equity stake in XpresSpa, which has locations in more than 50 airports. It sponsored election-related programming. It partnered with Hilton to bring Calm content into hotel rooms. It sold Sleep Mist. (Honestly, kudos Calm 👏.)

A friendly approach to meditation may have been how Headspace earned their relationships. But it’s not the only thing they should have been selling forever. If anything, meditation and the broader space of mindfulness have never been more popular AND still never more needed.

Headspace almost certainly should have expanded further into mindfulness, breathwork, and, in particular, offline communities. For example…

So many whats-ifs! And all of which would have felt sooo natural for Headspace, but ultimately, they got stuck. They treated meditation as a product rather than a foothold. And they missed the shape of the landscape as it was evolving. Once they pivoted to basically B2B telehealth, they were then competing with many others—and they lost the thread.

Bottom line: I think a truly great mindfulness brand has yet to be built—and I’m sad Headspace missed its chance to be the one. 🤷‍♂️

I’ve written about tennis 🎾 aka “the world's healthiest sport” a buuunch. But while it may be considered the healthiest sport, it’s not the most popular racket sport these days.

And before you guess, it’s not pickleball, either. 

According to SFIA’s 2026 First Half Game Plan: Key Moves in Sports Participation Report, padel was the fastest-growing activity, increasing 14.5% in just its second year of SFIA tracking. Meanwhile, Pickleball only grew 1.3% in the first half of 2026 after five consecutive years as SFIA’s fastest-growing sport.

Another report tracking worldwide search interest reinforces just how quickly padel is gaining momentum. 🚀

For brands, this is an opportunity to get in early on partnerships and activations—especially as more courts pop up around the US. My advice: get in now, before everyone else starts making a racket 😉. (Sorry.)

Also, worth saying I watched a new movie called The Dink with my wife recently. It was fine (not a strong recommendation), and wooow was I not expecting it to go the way it went.

Remember last week when I told you consumers are spending more on in-person health services? Apparently, some of those wellness dollars are going straight to pasture 🐮.

Your challenge: Predict the next hot animal x wellness collab.

My money’s on duck paddleboard yoga 🦆. You heard it here first.

It’s conference season! 

The one I’m most excited about right now is The Assembly, happening October 13–16. I went last year for its inaugural event and was blown away. Imagine a place where folks from across healthcare, wellness, fitness, hospitality, and other sectors come together to create better consumer experiences and bridge the gaps between industries. A conference with a purpose, imagine that!

It’s also carefully curated and capped at 125 C-Suite leaders and founders. (Fwiw, my ideal conference size is 100ish.)

Last year I got to see friends like Dugal Bain-Kim (Lifeforce), Andrew Katz (Athletic Brewing), Andrew Lacy (Prenuvo), Kelly & Juliet Starrett, Mel Strong (Next Ventures), Michael Wolf (Resort Pass), and so many more. I can’t wait to head back this year, and if you’re interested, you can apply to attend here. 

Here’s my itinerary for the fall:

Hit reply if you’ll be at one of the above and want to grab a coffee, hit the cold plunge together, or try some Fixie Dust 👀.

If you’ve been here for a while, you know I’ve got protocols for days. From cold prevention and supplements to longevity and skincare, I share everything I’m using (and what I wind up ditching). 

Most recently, I went back through alllll my protocols and updated everything. I’m extremely particular (again, if you’ve been here for a while, you know this about me 😂), so if something makes the list, it has truly earned its spot.

One of my favorite recent additions to my at-home fitness protocol is Fat Gripz. They’re basically a removable rubber sleeve that wraps around dumbbells, barbells, and pull-up bars, making the handles thicker so your hands and forearms have to work harder. 💪 They also have a “z” in them, which is just so 90s and I love it.

Grip strength is increasingly being recognized as a reliable marker of overall health. It’s been associated with greater longevity and lower risks of depression, cognitive decline, and type 2 diabetes.

One of the largest studies on the subject followed nearly 140K adults across high-, middle-, and low-income countries—and found that grip strength was a better predictor of all-cause and cardiovascular death than systolic blood pressure. Pretty big deal!

Anyway, rock climbing 🧗continues to be the single best thing I’ve been doing for grip strength, and I continue to go at least 1x a week—and using Fat Gripz makes me a better climber! 

3 other healthyish things I’m into right now: 

Most clicked last week: Nice hand soap as the new status symbol. We use Aesop in our home. 😎

👋 Who are you again? I’m Derek Flanzraich, and I’m in the business of healthyish. I founded two venture-backed startups–Greatist (👍) and Ness (👎)—and helped dozens of brands you know grow including Ro, GoodRx, Midi, BetterHelp, and LMNT. I now run Healthyish Content, plus a few other healthyish things (like Fixie Dust, launching this fall).

Every Thursday, I share what’s hot, what’s not, and what’s next in consumer health. (Disclosure: I invest in and advise companies in this space—when I cover one, I'll say so.) I sometimes add affiliate links, but they influence my picks zero.

See something smart, strange, or seriously overhyped? Hit reply, I respond to every email.