Leadership6 min read
Founder Isolation: The Tax Nobody Invoices
Founder isolation never shows up on an invoice. It costs you in delayed decisions and protected hires. Here is a self-audit, and the free first step.
September 2, 2026Read
Blog
Insights from the trenches.
Strategy, AI deployment, and leadership wisdom from Steve Simonson — written for founders who build, not just dream.
Leadership5 min read
Founder OS vs Spreadsheets: Why Your Forecast Keeps Dying
Founder operating system software vs a spreadsheet forecast: why the spreadsheet quietly dies, and what a connected workspace replaces it with.
September 2, 2026Read
Leadership5 min read
The First 30 Days in Chairman's Circle: What to Expect
What to expect in a CEO mastermind, week by week: orientation, your first hot-seat, and the follow-up that finally makes the accountability stick.
September 2, 2026Read
Leadership5 min read
Founder Community vs Mastermind vs Coach: Three Rooms, Three Jobs
Founder community vs mastermind vs coach: three different jobs, not three tiers. Here is how to pick the right room for your company's stage.
September 2, 2026Read
Leadership5 min read
How Much Does a CEO Peer Group Cost? A Founder's Honest Framework
CEO peer group cost is rarely published. Here is what $497 a month actually buys in Chairman's Circle, and how to judge if the fee is worth it.
September 2, 2026Read
Leadership7 min read
What a Chairman's Circle Actually Is (and What It Isn't)
A chairman circle is Steve Simonson's peer group for scaling operators — not a corporate board and not mastermind theater.
September 2, 2026Read
Leadership14 min read
Why Join a Mastermind Group If You're Already Running the Company
Why join a mastermind group: isolation taxes every call. Peers compress decisions. A real room beats another year of talking to yourself alone.
August 31, 2026Read
Leadership13 min read
Why Hire a CEO Coach If You've Already Built the Company
Why hire a CEO coach if you already built the company: the job changed, unchallenged decisions got expensive, and the bottleneck is still you.
August 31, 2026Read
Leadership13 min read
Why Founders Need a Mentor (And Why the Hard Way Costs the Most)
Why founders need a mentor: the hard way is a curriculum you pay in years. Pattern-matching from someone who already paid compresses the tuition.
August 31, 2026Read
Field Notes28 min read
Amazon Listing CPR: How to Revive a Failing Amazon Listing
Learn how to revive a failing Amazon listing: diagnose lost momentum, rebuild organic rank, use PPC as a lab, and decide whether to save or kill the ASIN.
August 15, 2026Read
Leadership14 min read
Why Founders Don't Have Business Plans (And How Life Changes When They Do)
Why founders skip business plans—and how a living plan (LivePlan-class tools or Catalyst88 Founder OS) improves decisions, cash clarity, and privacy without theater.
August 8, 2026Read
Founder Growth7 min read
Why I'm Not Doing New Year's Resolutions — The 50/50 10/10 2/2 Challenge
Private New Year's resolutions fail founders by February. Here's the public scoreboard alternative Steve Simonson runs with operators: the 50/50 10/10 2/2 Challenge.
July 31, 2026Read