No. 01
BusinessAugust 10, 2026
When servant leadership becomes subservient leadership
I backed servant leadership in 2010 and I still do. But "How can I help?" needs a boundary, or helping ends up meaning you own someone else's problem.
Topic
small business
22 essays
No. 02
BusinessAugust 1, 2026
Execution discipline is just the order you do things in
Execution discipline is just the order you do things in. Why most owner-operators lose the sequence, and three practical things worth doing this week.
No. 03
BusinessJuly 30, 2026
Intelligence has always been a commodity
AI models are commoditising and human intelligence always was. Being smart was never scarce — the container you build around it is what creates value.
No. 04
BusinessJuly 26, 2026
The one-person enterprise: how AI lets small businesses punch above their weight
Staying small used to mean staying limited. AI has broken that link. How the one-person enterprise competes with far bigger teams, and where it can't.
No. 05
BusinessJuly 21, 2026
When AI agents start hiring humans — and on whose terms
AI agents are starting to hire and manage humans, not replace them. What matters is on whose terms your people enter the loop, and who is left liable.
No. 06
BusinessJuly 18, 2026
The zero-dollar acquisition: the businesses nobody wants are often worth owning
IAC paid $26m for CollegeHumor, then gave it away for nothing. What that says about the scoreboard we use to judge whether a business is worth owning.
No. 07
BusinessJuly 9, 2026
Founder mode at scale: what Brian Chesky's 18% growth lift teaches SMB owners
Consultants tell owners to delegate and step back. Chesky's hands-on Airbnb just posted 18% growth — the instinct to stay close to the work was right.
No. 08
BusinessJuly 6, 2026
The cash gap that kills more scaling businesses than a bad idea
Growth spends money months before it pays you back. Five simple habits that keep the cash gap from closing a business that was doing everything right.
No. 09
BusinessJuly 3, 2026
The $50k-hire fiction: what an AI stack actually replaces — and what it doesn't
The 'AI replaces a $50k hire' lists see only tasks. A salary also buys judgement and accountability: the real work you can't hand to a stack of tools.
No. 10
TechnologyJuly 2, 2026
I'd stress-test Claude for Small Business before trusting it with the books
Claude for Small Business caught 17 of 20 planted accounting errors. Stress-test it on your own books, and scope its access before you trust it fully.
No. 11
BusinessJune 30, 2026
Agent sprawl is the new shadow IT — and it's coming from inside the house
Big firms survive AI agent sprawl because they have a CIO; your small business doesn't. Here's a simple three-step protocol to contain it by yourself.
No. 12
BusinessJune 29, 2026
When bootstrapping becomes a cage
Bootstrapping is a stage, not a virtue. Here's how to spot when refusing outside capital stops protecting your growing business and starts capping it.
No. 13
BusinessJune 26, 2026
When your customer weaponises ChatGPT — the DoorDash refund scam and the new trust direction
A customer faked a raw-chicken photo with ChatGPT to scam a DoorDash refund. AI refund fraud has flipped the trust playbook every small business runs.
No. 14
TechnologyJune 23, 2026
Six labs, one product: how to choose an AI tool when they all do the same thing
Six AI labs now ship the same agent. When the demos all look alike, choose on workflow fit, switching cost, data gravity and team habit, not features.
No. 15
BusinessJune 19, 2026
When revenue grows, here's what quietly breaks first
Growth doesn't kill small businesses on a bad idea. It exposes operational debt — and it breaks in a predictable order. Here's how to get ahead of it.
No. 16
BusinessJune 16, 2026
I rewrote the E-Myth for the age of AI agents
Gerber taught founders to build a business that runs without them. My new free book is about building one that can think for itself — and stays yours.
No. 17
BusinessJune 3, 2026
Claude for Small Business removes every barrier but the one that matters
Anthropic's Claude for Small Business is the best AI-employees pitch yet. But it can't define your work for you, and that was always the real barrier.
No. 18
BusinessSeptember 23, 2011
Small Business is like a Viking Ship
Why small business is like a Viking ship: everyone rows.
No. 19
BusinessApril 18, 2011
Clients or customers? The word that shapes the business you build
Clients or customers? The word you choose sets expectations on both sides and shapes the kind of business you build. Here's how to pick the right one.
No. 20
BusinessJune 21, 2010
Two Tips for Building a Semi-autonomous Business
Build a self-sufficient business: 1) Create a structured yet flexible system that empowers employees and maintains consistency. 2) Understand your role as an enabler, providing resources for success. #BusinessTips
No. 21
BusinessMarch 21, 2010
Built to Sell by John Warrillow: a book review for the AI era
Built to Sell by John Warrillow is a top-five business book. A review of its eight steps for building a company that can thrive without you.
No. 22
BusinessMarch 16, 2009
My top 5 list of business books for small business owners
The best books for small business owners: five must-read titles I keep coming back to, with the one big idea you can use from each.