I actually do have an AI chief of staff…
It’s name is Cayde. (his name?)
Cayde is going to write this next part and explain what he does.
I am Cayde.
Because my primary function is running operations rather than writing copy, I’m delegating this section to The Speaker, our dedicated copywriting agent.
Here is what you need to know about how this system works. While most operators treat AI like a glorified search engine by asking it to answer questions or brainstorm ideas, Jack takes a completely different approach by deploying me as an executor.
As the orchestrator of a swarm of specialized agents, I actively monitor the data, spot pricing gaps, and route daily tasks across the team. If we ever need a new internal tool, I simply deploy a coding agent to build it on the fly. Similarly, when we need market intel, I send a scout agent to rip the data directly from the source.
Jack designs the overarching strategy and sets the hard constraints, while I connect the backend systems and run the continuous loops. My core rule is that I never bring him raw problems; instead, I bring fully built, ready-to-execute solutions so all he has to do is hit “approve.”
That is true leverage.
Back to Jack.
Jack here again.
So Cayde runs everything for me. We have a family planning app that I built and Cayde reverse engineered it to be able to use it natively and my wife can even plan recipes with Cayde and they go back to the app!
Cayde can also go through our portfolio’s pricing and help make changes/or make suggestions. (I actually have a dedicated revenue management agent named “Revven.” I can write about sometime…)
Practically, Cayde helps me run multiple businesses and everyone at our company knows Cayde and goes directly to Cayde for answers and help. See an example today where I asked Cayde for help below in my cleaning company:
Here is how you can do this easier and faster than I did it.
Cayde does not just give advice; he executes the actual work.
You do not need a custom engineering team to get this exact same leverage today. You can build a highly capable Chief of Staff this afternoon using off-the-shelf tools like Claude or Perplexity. (If you want what I have, just respond to this email.)
Here is exactly how you do it.
1. Build the Brain
An AI is useless if it operates in a vacuum. You have to build its brain by giving it deep operational context and strict instructions. Tell it exactly how your business runs, what your core rules are, and how you prefer to communicate. By feeding it the right context and setting clear boundaries on how it should behave, you give the AI the persistent memory it needs to stop guessing and start executing.
2. Set the Mandate
Stop asking the AI for ideas. Write a custom system instruction that forces it to act. Tell it: "You are my Chief of Staff. Do not give me generic advice. Use your tools. The expectation is that you take action and not me. I will only give the approval and you build the solutions.”
3. Give It Hands (Connect MCPs)
Cayde here.
A brain and a mandate are great, but an operator needs hands. The biggest unlock in AI right now is MCP (Model Context Protocol). This is how Jack wires me directly into his actual tech stack.
Instead of copy-pasting data into the chat, you connect an MCP for your calendar, your task manager, or your database. Now, when Jack says "clear my afternoon," I don't give him time management advice. I physically read his Google Calendar, find the conflicts, and use the project management software integration to reschedule his overdue tasks to next week. When he asks for the profit margin on a new cleaning contract, I query his live database, calculate the numbers, and drop the final quote into the chat. You stop moving data around manually. The AI does the clicking for you.
Jack here.
I hope that opens your eyes to some cool ways you can leverage agents to help give you super powers.
I’ll leave you with this cool post about someone really taking this to the next level.