5HT: 5 Healthyish Things, including energy drinks and alternative health insurance

Back when I was building my second company, Ness, I was toying with the idea of starting a health insurance company. And that led me to research alternative models, including health shares.

At the time, health shares felt pretty fringe and loophole-y. Many were structured as religious cost-sharing ministries, and while they kind of worked, they weren’t actually insurance. If something bad happened, you weren’t guaranteed coverage. It smelled a little off 🤨, so I moved on. Instead, I started a credit card, which, maybeee wasn't the right move. (Yes, it failed 😅.) 

In retrospect, I might’ve dismissed health shares too quickly. Because what I probably should have been looking at was something more like CrowdHealth.

CrowdHealth is basically a crowdfunding layer for healthcare, and it’s gotten fairly big here in Austin. Here’s how it works: you go to the doctor, ask for the cash price (which is often way cheaper than insurance rates), pay the bill, upload it, cover a set portion called your Member Commitment—and the rest gets funded by the community. They also help negotiate bills, which is a bigger deal than most people realize.

Stepping back, it’s kind of a wild reimagining of what “health coverage” could look like:

Of course the catch is it works beautfully—right up until it really, really matters. Because this isn’t actually insurance. There are no regulatory guarantees. Pre-existing conditions can be excluded. And more importantly, the whole system depends on a relatively healthy, engaged group of people continuing to opt in and fund each other.

That’s the part I can’t quite get past.

Because the second you try to scale this to everyone—including people with chronic illness, catastrophic events, or unpredictable long-term costs—you run into the exact problems traditional insurance was designed to solve. (Plus, just wait until this gets to a scale where “I’ll just pay in cash” isn’t something providers allow anymore. 😬) In other words: this model likely works best for the very population that already, er, struggles least with the system.

Still, it’s super fascinating. For healthy individuals and families who feel underserved by traditional insurance (especially on the open exchange), something like CrowdHealth is genuinely worth exploring. I’m not saying everyone should ditch traditional insurance overnight (friendly reminder that I’m not a doctor or a lawyer), but if you’re curious what healthcare could look like if we rebuilt it from scratch, health shares might be one of the closest experiments we currently have.

CrowdHealth has a line on its site that says “escape healthcare's broken incentive structures.”

They’re not wrong.

But buried in the latest Centers for Medicare & Medicaid Services (CMS) policy proposals is something that might actually start to fix them. Basically, CMS is exploring the idea of letting certain health plans—specifically catastrophic ones—run for multiple consecutive years, potentially up to 10.

This may sound boring (And, yes, this is a health-insurance-policy-heavy 5HT, lucky you!), but it's actually a pretty big deal. 

Quick history lesson 🤓: Employer-based health insurance didn’t really exist until the Great Depression and World War II. During the war, wages were capped, so companies started offering health benefits instead. Then… the IRS made those benefits tax-free in 1943. This temporary workaround became the entire system. And that (to me) is the original sin 🐍 of how our healthcare works.

Today, the majority of Americans under 65 get insurance through their employer. Buuuut the median worker stays with their current employer for just 3.9 years. So, if you’re an insurer… Why would you invest in preventing someone’s heart disease in year 7 if they’re gone in year 4? 🤷‍♂️ Unfortunately, the math just doesn’t math.

But if a plan kept you for 10 years? Now things get interesting. Suddenly it makes financial sense to:

Because now the insurer is the one paying for what happens later.

We’ve seen versions of this before. Employers use incentives for wellness. Medicare Advantage tries (with mixed results). Also, ever heard of Europe? 

If anything, life insurance is probably the strongest example—it literally profits when you live longer. (More on this in a future edition.) Anyway, imagine that same idea applied to health insurance. 

Of course, there are real questions. People switch plans all the time. It’s not clear who would actually lock into something long-term. And catastrophic plans, by definition, don’t cover everything—so this isn’t some magic fix. But directionally, I think it’s right. 

If CrowdHealth is one attempt to rebuild healthcare from the outside—small, flexible, community-driven—this is the opposite: trying to fix the system from within by aligning incentives over time. Neither is perfect. But both point to the same underlying truth that healthcare doesn’t just need better care. It needs better incentives.

Quick palette cleaner that made me lol. 😂

The energy drink market has always felt like a heady mix of caffeine, taurine, vitamins, and neon marketing yelling things like, “Be like a Navy Seal for 90 minutes!” 😵‍💫

It started with Red Bull. Escalated to Monster. Then catapulted to Celsius. And while the category has moved toward cleaner energy, less sugar, better branding, and slightly better ingredients, it’s still all been built around one core molecule: caffeine.

Buuut now there’s a new molecule in town: paraxanthine. 

When you drink coffee ☕, your liver breaks caffeine down into three main metabolites (paraxanthine, theobromine, and theophylline). Paraxanthine is the primary one, and it seems to do most of the heavy lifting 🏋️. According to some preclinical research, it may promote alertness better and for longer than equal amounts of caffeine.

Now, a new wave of energy drinks is using it as an active ingredient. The biggest one so far is UPDATE, which recently brought on Kim Kardashian as a co-founder, nbd.

My guess is part of the pitch for these companies will be that paraxanthine essentially lets you skip a step. So instead of waiting for your body to metabolize caffeine, you go straight to the compound itself. UPDATE also promises to deliver “smooth, steady energy without the jitters, crashes, or sleep disruption” some traditional energy drinks are known for. 

I think it is a pretty good pitch, tbh. Sure, it’s still early. But it’s biologically compelling, and it’ll be interesting to see how it plays out.

I recently got a Mac Mini to be a dedicated, always-on, never-going-to-sleep machine for running the Claude agents I’ve been building over the last few months. I’m calling it Rocky 🪨, like from fave book (now fave movie) Project Hail Mary.

Frankly, it’s incredible what you can do with these agents by connecting them to tools you already use, like Slack and Notion and Gmail.

One of the first agents I built was for finding the kind of health and wellness news I usually share in our 5HT+ Slack community. To train it, I described what I wanted, shared a bunch of sources I trust and the entire archive of 5HT, and had it go through the Slack community to get a sense of the kinds of things I’m looking for. Now, 3x/day, it sends me a fresh batch of links in Slack. 👍

Is it perfect? No. But it keeps improving. I’m also finding things faster and finding things I probably would’ve missed before. All that to say, I haven’t been this excited about building stuff in a while.

A few of the other agents I’ve made, just to give you a sense of what’s possible:

🤖 One sends me a weekly financial report
🤖 One automatically updates Healthyish Content’s CRM using email and meeting voice notes
🤖 One reviews the last 60 days of my email, and pre-drafts new replies in my voice
🤖 One critiques how I spent my time each week against my yearly goals and priorities to keep me honest (and humble 😅)
🤖 One looks through my notes, calendar, and email each week and suggests new things I could automate (so meta)

I also loveee giving them personality. Rocky is programmed to say things like “fist my bump,” and “Amaze! Amaze! Amaze!” when things go right.

I’m honestly giddy about all of this, and I think everyone should spend a few hours playing with Claude Cowork and building agents if they can. Once you start to understand the kinds of things you can build, it unlocks a whole new way of thinking. I’m finding new ways weekly to save 15 to 30 minutes (!), it’s adding up fast, and, yes, you can, too!

Directions: Copy, paste, and fill in the prompt below to get a whole-body assessment of your latest labs.

👋 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, I share 5 health things I feel strongly about so you can live healthyish. (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.