Founder · Operator · Builder

The OS for
running your
business
on systems.

Not theory. A $21M company running in real time — with AI, systems, and the playbook to do the same.

AI Chief of Staff The Creative CEO Mastermind Weekly Newsletter
Start Here →
russ-cos — hermes
$hermes gm
☀️ Good morning, Russ. 7:04 AM. 📬 12 emails → 2 Tier 1 flagged. 📅 Board letter due today. 🎯 Top priority: CHIPS Phase 8.
$hermes "draft reply to Will"
✍️ Drafting in your voice... ✅ Ready. Want to review?
$
12hrs
To build your AI CoS
~$21M
ARR at Design Pickle
11yr
Operator. Not a coach.
Weekly
Live call with Russ
01
📘

The Creative CEO

The playbook for creative operators. Turn your skills into a scalable business without losing your edge.

→
02
🧠

AI Chief of Staff

Build your own AI operating system. Course + weekly live call. Start this week. No coding required.

→
03
🤝

Mastermind

A private room for operators building seriously. Weekly live call. Peer cohort. Application required.

→
The Room

For operators who are actually building.

Not a Discord. Not a group chat. Founders running real AI-powered businesses — building together, weekly.

Apply for Access →
"I took a seven mile walk and basically did the whole chief of staff brief… and it suggested some stuff."
— Chris, Cohort 1
"My AI Chief of Staff just tells me what to do. 'Three things you got to focus on this hour.' Oh, this is a whole game changer."
— Jamie, Cohort 1
📘
The Creative CEO
Russ Perry
#1 Creative Business
The Book
The Creative CEO

A complete playbook for building your creative empire, driven by purpose. 6 frameworks. Battle-tested inside Design Pickle. Available on Amazon.

Get 3 Free Chapters → Amazon →
🥒
Russ Perry

Founder & CEO of Design Pickle since 2015. ~$21M ARR. 350+ global team. YPO member. Author.

I replaced my EA with an AI Chief of Staff. It took 12 hours to build, costs $20/month to run. I teach founders to do the same — so they can get back to running their actual business.

Newsletter

The Operator's Brief.

What I'm building, breaking, and shipping — weekly. Real company. No fluff.

Recent Issues
How I replaced my EA in 12 hours
May 2026
The 3-tier email system I swear by
April 2026
Building AI voice agents: what actually works
April 2026