The Chairman's Circle is a private operating forum for real business operators — people building companies, managing teams, and making high-stakes decisions every day. You don't have to carry the entire burden alone anymore.
Chairman's Circle Online — $497/month · Chairman's Circle PRO — $1,997/month
The entrepreneur mastermind built for real operators.
Entrepreneurs love independence — it's part of the DNA. But independence can quietly turn into isolation, and over time the biggest risks to your business are rarely external. They're the blind spots in your own leadership. If you are still asking why join a mastermind group when you already have a team, that tax is the reason this room exists. If you typed chairman circle, read what a chairman's circle actually is.
Most coaching programs are built for beginners or hustlers. They focus on tactics. The Chairman's Circle focuses on operators — people responsible for teams, systems, capital, strategy, and the long-term trajectory of a company.
Inside the Circle we work on the architectural layer of business: strategy, systems, organizational structure, leadership psychology, and decision frameworks — including Strengths-Based Leadership for founders, the language we use to hire the gap instead of shaming it.
What we actually work on
- Market dynamics — We pressure-test your read of the market, competitors, and positioning.
- Operational bottlenecks — We surface the constraints silently taxing your margin, throughput, and people.
- Leadership challenges — We work on leadership psychology — the real lever behind everything else.
- Strategic pivots — We figure out when to hold, when to pivot, and when to say no.
Two tiers. Both private. Both non-casual.
No contracts. Value-based retention. If the Circle stops helping you grow, you're free to leave at any time.
Chairman's Circle — $497 per month
A private operating forum for founders making high-stakes decisions every day. Veteran mentorship, peer accountability, and a community that will call you out with love.
- Bi-weekly mastermind calls with Steve
- Strategy & hot-seat sessions
- Full Catalyst88 resource vault
- Private peer channel with serious operators
Chairman's Circle PRO — $1,997 per month
Some decisions can't wait until the next call. PRO is Steve on demand: text him, and if he is free you are on a video call in minutes. No appointments to claim, no limits on the asking.
- Everything in Chairman's Circle
- Steve on demand: phone, text, WhatsApp
- No standing calls, no homework, no limits
- Priority advisory for six-figure decisions
- Your fractional Chairman of the Board
What's included
- Bi-weekly mastermind calls — Circle and PRO
- Strategy & Hot Seats — Circle and PRO
- Catalyst88 resource vault — Circle and PRO
- Private peer channel — Circle and PRO
- Steve on demand: phone, text, WhatsApp, no limits — PRO
- Priority direct line for urgent calls — PRO
- Fractional Chairman of the Board role — PRO
Mentorship from a 9-figure operator.
Steve Simonson isn't a theoretical coach. He's a builder — someone who has founded, scaled, and exited multiple companies, built global supply chains, and led international teams across retail, ecommerce, and logistics.
Frequently asked questions
Is there a contract?
No. We believe in value-based retention. If the Circle stops helping you grow, you should be free to leave. Cancel anytime — no further charges once your subscription expires.
How does On-Demand access work?
PRO members get Steve's phone, text, and WhatsApp. No standing calls, no appointments, no team meetings, no homework, and no limits. Most founders text; if Steve is free you are on a live video call in minutes, and if not he gets back to you as soon as he can — video or text, whatever works for you. It is not for casual conversation; it is for the moments a decision needs an experienced perspective now.
Will Steve actually be on every call?
Steve is on the vast majority of calls. From time to time an associate may lead a session when schedules conflict — but the core experience is Steve at the table.
What if I'm not ready yet?
That's okay — over 60% of applicants aren't, and that's by design. Use MyMentorSteve (free, in 69 languages) and the Awesomers podcast until the stars align.