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Aloha 5HTers 👋! Welcome to your latest Sunday edition. I’m coming to you from Kona, Hawaii. So far, I’m into it!

The week wearables became the front door to medicine

A few years ago, I built a credit card whose real job was to make you healthier. It failed.

I'd been chasing what I think of as health's "everyday thing," an object so woven into your day you stop noticing it's there. I bet on the wallet. Recent events convinced me someone finally pulled it off, on the wrist instead.

  • 📰 Google launched the Fitbit Air—a screenless, $99 WHOOP clone with a Gemini coach and no subscription.

  • 📰 WHOOP fired back by offering on-demand video visits with real clinicians and EHR syncing.

A search company gave the hardware away. A fitness-tracker company started hiring doctors. Opposite directions, same bet: the wearable is no longer a gadget. It's the front door to medicine.

The question underneath is the one I've chased my whole career: how do you get people to care about their health before something breaks? 🤔

Preventive health has access and motivation problems (and Future You is a lousy salesman 👎). Here's why the answer might finally be here—and why every earlier attempt face-planted.    

The drawer graveyard

We've tried this before, and it ended in a drawer 🪦. Around the time of my first startup, Greatist, there was an explosion in fitness wearables. The Nike FuelBand was sleek and cool…and gone within two years 😬. Jawbone raised nearly $930M, hit a $3.2B valuation, and liquidated in 2017. The original Fitbit clipped to your belt and counted steps (Google later bought the corpse and just relaunched it as the Air). They all failed for the same reason: a step count is a vanity metric. It tells you what you did, but never what it means, and never what to do next. The signal of hitting (or not) 10K steps/day wore off and died about as fast as the battery (zing!). ⚡

The everyday thing

Everything in health asks you to remember it: book the appointment, log the meal, schedule the follow-up. But a wearable you just, well, wear. The shift hit me the first time my WHOOP guessed a workout I hadn't logged—correctly. A tracker waits for you to tell it things, but this felt like it was paying attention. This was more than just a sleep score. Jawbone and FuelBand begged for attention, but this new generation disappears 🫥. Google made its new Fitbit Air screenless on purpose.

The identity marker

A step-counter signaled "I exercise." An Oura ring signals something stickier. Something more like “I optimize.” I said it on LinkedIn last yearthe new flex isn't a gold Rolex, it's Oura and WHOOP. You've already skipped a beer over your sleep score, trained harder for a recovery number. Our wearables are already making Future You feel like Today You—the whole game in prevention. And once health is identity, it doesn't end up in a drawer. (Just the opposite, you want to show it off.)

One caveat: most people likely won't sport more than one wearable, so we may have a few parallel worlds. Perhaps we’re speaking a few different languages (Recovery vs. Readiness), but all heading in the same direction.

The wearable AI

That’s all relevant. But the biggest change? Wearables no longer just tell you what happened today; AI tells you what to do to make tomorrow better. It measures, interprets, nudges—and repeats. A step count was a dead end. A recovery score read by an AI coach that knows your last three weeks intimately is a conversation. One that can drive personalized, long-term change.

The part doctors already know

The clinical version of this already works. A peer-reviewed study in Mayo Clinic Proceedings last year tracked ~6,000 Medicare patients in Cadence's remote-care program against ~11,000 matched controls: 27% fewer hospitalizations, $1,302 lower cost of care per patient/year, and a 64% drop in heart-failure hospitalizations. (It's Cadence studying its own program, to be fair—but it's peer-reviewed and large, with independent co-authors from MGH, Duke, and Rush.)

The study is blunt about why it works: not the sensor or the feedback loop but clinicians acting on the data. As Cadence founder (and longtime friend) Chris Altchek puts it, tech-enabled care can deliver real savings at scale. The device is the easy part. So why isn't remote monitoring everywhere? Getting people to use the thing. In one Medicaid diabetes program, barely half stuck with daily monitoring!

This is exactly what consumer wearables quietly solved—adherence isn't a fight when the device is already yours. "Keep wearing the ring you love" beats "strap on this clinical monitor." The future isn't your doctor handing you a device: probably your doctor “prescribing” the one already on your wrist and Medicare paying to read it.

Soooo…who wins?

WHOOP is building toward the clinic. Just read its $575M round at a $10.1B valuation by who wrote the checks: Abbott and the Mayo Clinic. You don't get a diagnostics giant and a hospital funding a sleep band. They’re funding the on-ramp to clinical care.

Oura's racing there from the consumer side (newly confirmed IPO filing, ~$1B in sales, 5M+ members). Aaaand Google's coming from the other end with $99 hardware and Gemini. 

Imagine the everything-app healthcare has never had, where your monitoring, records, labs, care, and nudges all live. Amazon swung at it. Google swung at it (maybe a second at bat right now?). Telehealth "one apps" swung at it. They all missed.

But here's why I’m convinced wearables have the best shot anyone's had. 

AI is increasingly making the back of the house cheap/commoditized—records, billing, triage, even a first-pass clinician, all rentable through an API. When the back end is a commodity, the prize moves to the one thing you can't spin up on demand: someone who actually wants to engage with their health every day.

That's the whole game, and it's brutally hard. You can buy the same sensors, rent the same AI, and pipe in the same labs. The one thing nobody can fake is whether you'll want to wear the thing tomorrow.

So the real question of the next five years is almost funny in its simplicity: can a company you love wearing build the boring back end faster than a company that owns the boring back end can build something you love wearing?

I spent years betting the everyday thing would be a credit card. I think I was wrong about the form factor, but I still think I was right about the idea. The pedometer ended up in a drawer, but this one ends at the front door of the whole dang system. 

My money's on the wrist (especially after switching from Oura to WHOOP and not looking back a year ago)—not because the sensor is magic, but because everyone underestimates how rare it is to build something people actually keep on.

🛒 Serotonin shelf

Here are three things I’m currently into this week:

  1. Obsidian (awesome note taking tool I’ll share more on soon!)

  2. Morning Water (brought a zillion of these with us to Hawaii + “5HT” gets you 10% off)

🍿 Brain snacks

👋 Who are you again? I’m Derek Flanzraich—founder of two venture-backed startups in Greatist (👍) and Ness (👎). I’ve worked with brands like GoodRx, Parsley, Midi, Ro, NOCD, and Peloton. I now run Healthyish Content, a premium health content & SEO agency (among other things).

Every Thursday (and now Sunday!), I share healthyish things I feel strongly about. (Disclaimer: I’m more your friend with health benefits. None of this is medical advice.) Also some links are affiliate links, but they influence my decisions zero.

Oh, you also feel strongly about some health things? Hit reply—I’d love to hear it.

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