⚙ Hi {{first_name_tally|Operator}},

I fell down a Stripe rabbit hole this week. Their 2013 and 2014 blog posts about making all internal emails public.

Now everyone's talking about organization transparency again because of AI agents.

Makes you wonder: if humans can barely handle 400 email lists, what happens when half your coworkers aren't human?

- Rameel

Me when I realize I have to write an essay this week

Operators surrender to the siren song of entropy everyday.

You’ll call growing pains "scaling," but we both know what you’re doing. You’re surrending to physics, to chaos, to the inevitable drift toward disorder that claims every company.

Don’t be like that. Be like Stripe.

Stripe fought back against entropy. By embracing the one value everyone repeated, but never actually committed to.

They made every email public, built 400 email lists, created rules about when not to speak, and constructed what looks like chaos but is actually the most sophisticated anti-entropy machine in Silicon Valley.

2013 Silicon Valley: Everyone's drunk on "radical transparency."

Facebook preached openness while keeping operations opaque. Google said information wants to be free for the public while privately operating with a need-to-know basis for employees. Twitter. Square. Every startup with a ping-pong table and a transparency manifesto somehow never applied to the executive team's actual decisions.

They mistook openness for order.

Claude Shannon warned them in 1948: information and entropy are the same thing. More information doesn't create more order but instead creates disorder unless you build systems to fight back.

When communication costs (scheduling meetings, formal memos) increase, people share what matters. When it's free (cc everyone), you drown.

Most companies surrendered to the flood, but Stripe fought back by making communication expensive again—expensive in brain power, cultural work, infrastructure.

You fight entropy by making information cost something.

To fight back Stripe made emails public by default. But they weren't being idealistic; they were engineering anti-entropy infrastructure.

And this is how they built their open email infrastructure. 

The Technical Architecture

They started with a simple rule: every email list gets a corresponding archive list that any employee can read. Your team discussing payments? That conversation goes to payments@ but also payments-archive@ where everyone can see it.

By 2014, this spawned over 400 lists. Not 400 topics—400 different lists following patterns like:

Then they built Gaps, custom software to manage the chaos. Gaps doesn't try to reduce the lists. Instead, it helps humans navigate them: tracking which of 400+ lists you subscribe to, generating Gmail filters automatically so your inbox doesn't explode, notifying you when new lists spawn (which happens constantly).

Without Gaps, engineers would spend hours just managing email settings. With it, they can subscribe to what matters and filter the noise while keeping everything searchable.

The Cultural Protocols

But software alone doesn't beat entropy. Stripe had to create operating rules for humans:

These were operating instructions for humans interfacing with information systems that exceed cognitive limits.

The Compound Effect

Every archived email becomes permanent, searchable institutional memory. A new engineer with a question about payment processing can search five years of actual discussions. They find not just the answer but the context, the debate, the reasons why.

Questions answered once are answered forever. Knowledge compounds. Meanwhile, entropy stays linear because you're not generating new information to answer old questions.

That's how you win. Make growth work for you, not against you.

Greg Brockman wrote about their 400 lists in 2014. He didn't celebrate. He admitted. "We now have over 400 email lists." That verb choice tells you everything about a company that knows it's in a fight with physics.

Conway's Law: Organizations build systems mirroring their communication structures.

Stripe discovered the inverse. Communication structures reshape organizations. Those 400 lists weren't describing Stripe. They were creating it, each list becoming a gravity well that pulled related work toward it until the organization became what it communicated about.

Most companies fear this. Transparency reveals the real org chart—actual power flows, true bottlenecks, real decision makers—not the PowerPoint version but the physics version that actually determines how work flows and where it dies.

So they surrender. Keep communications private. Pretend the org chart is real. Lose information in handoffs and call it "process."

Stripe fought by making physics visible, then manageable. Once you see the real organization, you can design it.

Fighting entropy costs millions in infrastructure, constant cultural work, brain power that never rests, leadership commitment that can't waver.

When I talk to COOs about this, they get it. Intellectually. Then they calculate the cost and suddenly their excitement evaporates into excuses about culture and timing and product-market fit.

"We'll do it when we're bigger."
"Our culture isn't ready."
"Product-market fit first."

Physics doesn't wait. Every day you don't fight, entropy compounds and the effort to start fighting multiplies until, by the time you're "ready," it's too late.

As your company grows, entropy multiplies. Choose:

1. Surrender openly. Build hierarchies. Accept information loss. Call it "management." At least you're honest about physics winning.

2. Surrender quietly. Pretend small-company communication scales, watch it fail, blame "culture" while physics laughs at your delusions.

3. Fight. Build anti-entropy infrastructure, pay the price in discomfort and dollars, and win advantages others can't match because they've already surrendered.

Stripe chose option three. They built a machine that turns chaos into memory. While competitors repeat context in meetings, Stripe links to emails.

While others lose decisions in handoffs, Stripe has no handoffs—everything's visible, searchable, permanent.

Exhausting? Yes.

Worth it? They're processing $1 trillion annually with knowledge intact.

Can you do it? Wrong question.

Will you do it before it's too late?

Entropy always wins. Eventually.

But eventually isn't today, and the gap between now and eventually is where great companies live.

Stripe built weapons. Costs them millions in infrastructure, thousands of hours in maintenance, constant reinforcement that never ends and never gets easier.

Most COOs don’t lose to entropy because they didn’t understand the physics. They lose because they thought they had more time.