Loopy Loops

How learning loops turn into flywheels and how the right ones can pull you to product–market fit

"Have you heard of the Jeff Bezos flywheel story? The napkin sketch is now in the Smithsonian!," I spoke breathlessly to my friend Louie Bacaj in one of our semi-random monthly walk-talks.

I have been fascinated with OODA loops and flywheels recently. I have this gut feeling that they are a key unlock for any limited successes that I have enjoyed. It's too pat to say the goal of a startup is to attain Product Market Fit (PMF). A startup is more like a quest for flywheels. Each turn makes you faster, stronger. Over time, they build durable compounding advantages.

The funny thing is my obsession with flywheels has led to hallucinations. As best as I can tell, the Bezos napkin isn't in the Smithsonian and the napkin itself may be apocryphal.

I have struggled to write this piece because at the back of my head, I have this fear: is this all post-hoc rationalization? A form of survivorship bias?

Is it? You be the judge.

Which brings me to why I'm staring at our Discord chatbot's metrics again.

We vibe-coded a bot persona for Reframe Science, a healthcare self-help community. The idea seemed straightforward enough: surface answers from past discussions so people don't keep asking the same questions over and over. Each interaction should make it smarter. Better answers → more trust → more usage → more data → even better answers.

Sounds great on paper, right? But here's the thing that's keeping me up: is this the loop that actually matters? Or am I just building a really sophisticated hamster wheel?

That's the thing about loops. They're seductive. The numbers tick up (maybe?), you feel productive, the team gets excited. But sometimes you're just spinning toward the wrong destination. And when you're obsessed with flywheels, every rotation starts to look meaningful.

The long road to PMF

Product-market fit doesn't arrive with a push notification. It sneaks up on you through loops.

Most loops are learning loops: you grind, you iterate, you collect clues every time around. They take effort, sometimes a lot, but they sharpen your instincts.

Occasionally — and this is where the magic happens — the grind shifts. Each turn gets easier. The wheel starts pulling instead of you pushing. That’s the moment a loop becomes a flywheel.

The trick isn't avoiding the grind. It's finding the smallest loop that can start pulling. Or at least, that's what I tell myself when I'm staring at those chatbot metrics.

What Hannah Montana taught me

My first real flywheel started with a weird blip in our search logs.

"Hannah Montana backgrounds."

Not just a few searches. Hundreds. We were running an image search engine, and suddenly every tween with a MySpace page needed young Miley Cyrus' wallpaper.

So we threw together a landing page. Nothing fancy—just Hannah Montana backgrounds our users had already handpicked. And then I watched the numbers start curving the chart.

The page climbed Google rankings → brought in more Hannah Montana fans → some of them searched for other backgrounds → we made pages for those → which brought in even more people.

Each turn was easier than the last. We weren't pushing anymore; the loop was pulling.

At our peak, we were updating someone's myspace page more than once every second every day.

I didn't have a fancy name for it then. But that was my first content flywheel, and it started as a throwaway experiment.

The Snag Bar

A couple years later, different loop, same magic. Maybe.

Remember FarmVille? Millions of people clicking through endless bonuses from friends. Fun for about five minutes, then pure grind. Digital farming as a second job.

We built a tool, Snag Bar, that let our users collect all their preferred bonuses with one click. Suddenly our users had an edge—more rewards, faster progress, zero hassle.

But here's where it got interesting. The bonuses often included gifts to send back. So every Snag Bar user made their friends wonder "wait, how are they collecting so fast?"

More users → more shared bonuses → more value for everyone → more users wanting in.

The product literally got better as more people used it. Hannah Montana was powered by content. The Snag Bar was powered by connections..

Thread Reader

Most of my loops I built from scratch. Thread Reader I bought mid-spin.

It solved a real problem: making Twitter threads readable. But the magic was in the mechanism. To unroll a thread, you replied "@threadreaderapp unroll" publicly. Everyone watching saw you use it. Genius, right?

More requests → more visible unrolls → more people discovering it → more requests.

I could see it immediately. The flywheel was already spinning. My job was just to oil it and get out of the way.

Did I see a flywheel because it was there, or because I'd been looking for one?

Three different flywheels, three different mechanisms. Content, connections, and now distribution baked right into the product itself. Each one taught me something about what to look for.

The Four Questions

After watching enough loops spin (and enough sputter to a halt), I've learned to run them through four gut-checks. They sound simple, but skipping one can kill your momentum.

1. The Compass — Are we even heading the right way?

The Discord bot could spin beautifully… straight into irrelevance. Hannah Montana backgrounds were absurd on the surface, but they pulled the right audience at the right moment. Picking the wrong loop is like pedaling hard toward a cliff.

2. The Map — What's each turn teaching us?

A loop with no new insight is just a workout machine. When we saw people searching for MySpace themes to match their Hannah Montana wallpapers, that told us where to go next. If nothing changes in your plan after a few turns, you're not in a loop—you're in a rut.

3. The Pedals — How quickly can we make the next turn?

FarmVille bonuses dropped daily. Our Snag Bar shipped updates just as fast. Momentum dies if your loop waits for quarterly releases—speed is oxygen. The more cycles you fit in, the more chances you give the loop to strengthen.

4. The Oil Can — Can we clear friction before it kills us?

Every loop builds pressure. Hannah Montana nearly melted our servers; Snag Bar nearly drowned us in support requests. If you can't remove bottlenecks fast enough, the loop slows, coughs, and stalls.

Here's where the strange loop comes in. The more you work through these questions, the more you zoom out—seeing the loop from above—only to realize you're right back inside it, pedaling. Except now you understand it differently. You're both the rider and the mechanic, the subject and the observer. And sometimes, that shift in perspective is what unlocks the next turn.

That’s what using Thread Reader felt for the first time. Wow, summoning a bot to create a page is that easy? Oh, everybody gets to see it too? What a great technique! Who is the genius that built this? I want to learn from him.

These aren't four separate levers—they multiply. Get a zero in any one, and the whole thing collapses. But bump even one up, and everything else gets easier. Right loop + fast learning + quick turns + no friction? That's when a loop stops feeling like work and starts feeling like magic.

Can you design a flywheel from scratch?

Here's a thought that's been nagging me: instead of waiting to discover a flywheel, what if you hypothesized it first?

Map out the loop you think can compound. Test if it can even start spinning. See if the physics (or economics/psychology) actually works that way.

I've tried this. On paper, the loops look perfect—arrows pointing to arrows, virtuous cycles everywhere. In practice, some never catch while the dumbest-looking ones suddenly take off.

Still, asking "what would need to be true for this to become a flywheel?" has saved me from chasing dead-end zero progress loops. It forces you to see the system, not just the feature.

The three signs a loop is about to catch

You know that moment, when learning to ride a bike, you stop wobbling and start gliding? That transition from forced effort to natural motion? Loops have that moment too.

Transfer: Each pass leaves something valuable behind

The Discord bot starts with generic responses. But each interaction teaches it the community's language, their trusted sources, their recurring problems. Templates evolve from one-offs to reusable assets. You feel the friction dropping.

Acceleration: Time between cycles compresses naturally

Not because you're pushing harder—because the loop is doing more work. Monthly releases become weekly, then daily, then continuous. When every piece is already spinning, new experiments can catch fire overnight.

Distribution baked into the product

This is the holy grail. Thread Reader showed me this - every unroll created a public "look at this cool tool!" moment. The Snag Bar turned every bonus into a gift that advertised what friends were missing.

When two of these show up together, pay attention. The wheel has probably caught.

For Reframe Science, we're still watching. Smart answers alone aren't enough. But if those answers also train the next response faster, compress time-to-solution, and create shareable artifacts that bring in newcomers? That's when we'll know.

The power of seeing the loop you're in

Will the hamster still run if it knows how the wheel works?

We do - usually on autopilot. We grind away without realizing we're in a loop at all—just shipping features and wondering why growth feels random.

But a loop you can see? You can test it, measure it, accelerate it. You can ask: where's the friction, what would make this turn faster? That awareness—being able to name the mechanics—often separates grinding from compounding.

Closing the loop

Back to those Discord metrics. Maybe we're building our flywheel. Maybe it's just a fancy hamster wheel. Maybe I'm so obsessed with flywheels that I'm seeing them in my coffee swirls.

I'll know it when I feel it—that transition from pushing to pulling, from forcing to flowing. I've felt it before.

Or at least I think I have.

You be the judge.

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How This Got Written (A Loop)

As regular readers already know, I’ve been experimenting with ways to fold AI into my writing (and life).

This was my most significant attempt. I have struggled thinking about this concept of loops and flywheels for months (as Christin Chong, PhD can attest). But I felt unable to turn this into a coherent idea by myself.

Early on, I just jotted thoughts and notes around the subject. But they were disparate and undirected.

After a fun conversation with Louie, and coincidentally right after ChatGPT 5 was released, I finally picked up enough motivation to feed gpt5 with all my diffused notes and ask it to help me come up with a through line and structure.

Conversations with Christin and Louie were my indispensable learning loops to put down my raw, random, intuitions down. ChatGPT helped me gain enough momentum to start the flywheel towards publishing.

I actually spent more time on this than any of my earlier LLM-less pieces. But this one feels more ambitious. Despite taking a dim view on AI-writing, the best editor I know, the ever tender and helpful Sandra Yvonne , gave me really piercing feedback on an early draft. She flagged how the Reframe reference felt disconnected and disjointed. An earlier me would have thrown up my arms in despair. AI-assisted me came through only a little scathed.

I translated Sandra’s notes into specific problems; ChatGPT offered several options. I tried a few and ended up melding a composite of two.

For the first time I enlisted not one, not two, but three AIs. Perplexity grounded my scant research and handled some fact-checking (including convincing me that my Bezos napkin being in the Smithsonian was a hallucination). I often compared responses between Claude and ChatGPT. Louie would probably not be surprised that I found Claude was better at style-transfer, whenever I had trouble with a phrase or a retelling, Claude’s suggestions almost always felt truer to how I would have expressed (if only I had thought of it - a strange loop!)

I am sure many of you may find this form of writing distasteful or fake. But please bear with me, I feel I am just at the initial turns of a fabulous flywheel! I am feeling my way through something more like curating than writing. This lets me run bigger experiments but of course I am losing something too.

AI helps me write and connect ideas faster. But, as Louie warns it can also add wrap shit with bling. Where are the levers for the right win-win?

Twenty years ago, I was already yapping that, in the 21st century, we’ll be managing bots rather than people. We’re living in that world now.

Thanks also to Rick Lewis, Neha Patel and Kathy Ayers for their support and feedback.