From 1 → 10 → 50 people

At five people, management is physics.

You feel the company in your bones. Who’s shipping, who’s slipping, who’s secretly on YouTube. Every Slack ping is a heartbeat. Every Slack ping is a heartbeat. Every decision runs through you. It’s exhausting, but you kind of love it. Sigh. The good old days.

At thirty people, management becomes statistics.

Every decision still runs through you but you definitely don’t love that anymore. Half the org’s yelling at you because growth’s fucking up or breaking something.

You deflect with “Let’s look at the data,” because honestly, you have no idea what the fuck is going on anymore or what half your team is even doing.

If you’re in my team: yes, my context window is limited, okay? 🥺

That’s when algorithms save me. Repeatable systems that scale judgment faster than a packet of Zyn. Below are the core ones that kept me sane (mostly).

📉 Direct Control (1 - 9 people)

You are the algorithm.

• You audit everyone’s week manually.

• You know the leverage points by heart.

• You can change direction in a day because context lives in your head.

• Every task feels like a game of optimization - highest leverage per calorie burned.

This phase scales on your energy and judgment. You win through brute-force clarity.

⚖️ Distributed Context (9 - 20 people)

The turning point comes when you stop being able to hold it all.

That’s when the first layer of algorithms appears - documentation and delegation.

• Guides and playbooks become the way to scale your taste: media buying guides, compliance guides, tone and voice guides.

• You shift from giving context to offering access to context. People opt in via docs, Looms, or dashboards.

• Auditing shifts from “every task” → “spot-check the highest leverage ones.”

• You start moving from synchronous meetings → asynchronous updates.

You realize meetings are a tax. A 1-hour all-hands for 20 people = 20 hours stolen from the org. You replace it with a Loom - still human, but 95% cheaper.

👨‍🌾 Hierarchical Algorithms (21 – 50 people)

At this point, your management bandwidth breaks. You can’t audit everything. You can’t be the bottleneck for every creative decision. You now rely on directors - humans who own levers you used to pull yourself.

Here are the key principles we have developed (Shout out to Max, co-founder of Superpower, who has been instrumental as a sparing partner for these as well)

1 Scale through barrels, not bullets.

You start to scale as a function of the number of barrel hires you can make.

Give them the right bullets and they can move fast.

It’s hard to move with 20–30 juniors who lack the judgment, experience, and communication ability to handle complex, cross-functional work.

But with 10 directors, each leading 5–10 capable people, you can move incredibly well.

2 Define swim lanes and rules of engagement.

Teams can move fast only when they know where their lane ends and another begins. Most chaos comes not from disagreement but from unclear ownership.

3 Leaders still build.

The executive team should be able to dive into critical projects as needed. I still believe leaders should spend 20–30% of their time doing IC work to drive the organisation forward - sometimes even more. You can’t lead a creative or technical org by pure abstraction.

4 Dictator Mode.

Democracy is overrated in execution. As Max says, “Who has the highest believability index on this?” That person becomes the dictator of the feature.

The worst outcomes happen when no one is sure who decides.

5 Document or die.

As the org grows, documentation becomes the only way to scale judgment. The more codified your instincts become, the less often you’re needed.

Great documentation is how you scale taste - it turns intuition into protocol.

Closing Thoughts

At five people, your company runs on your adrenaline.
At twenty, it runs on your spreadsheets.
By fifty, it better be running on systems.

The job stops being “move fast” and becomes “teach others how to move fast without you standing behind them like an anxious ghost.”

And if you do it right, you might just get your evenings back.
(Or, at the very least, fewer 2 a.m. Looms from your team member Jack with messaging feedback)

Until next time,

Ajay

🧠 Ajay’s Resource Bank

A few tools and collections I’ve built (or obsessively curated) over the years:

• 100+ Mental Models
  Mental shortcuts and thinking tools I’ve refined over the past decade. These have evolved as I’ve gained experience — pruned, updated, and battle-tested.

• 100+ Questions
  If you want better answers, ask better questions. These are the ones I keep returning to — for strategy, reflection, and unlocking stuck conversations.

• Startup OS
  A lightweight operating system I built for running startups. I’m currently adapting it for growth teams as I scale Superpower — thinking about publishing it soon.

• Remote Games & Activities
  Fun team-building exercises and games (many made in Canva) that actually work. Good for offsites, Zoom fatigue, or breaking the ice with distributed teams.

✅ Ajay’s “would recommend” List

These are tools and services I use personally and professionally — and recommend without hesitation:

• Athyna – Offshore Hiring Done Right
  I personally have worked with assistants overseas and built offshore teams. Most people get this wrong by assuming you have to go the lowest cost for automated work. Try hiring high quality, strategic people for a fraction of the cost instead.

• Superpower – It starts with a 100+ lab tests
  I joined Superpower as Head of Growth, but I originally came on to fix my health. In return, I got a full diagnostic panel, a tailored action plan, and ongoing support that finally gave me clarity after years of flying blind.