Latest POSTs
Introducing a Dow-Like Index for Entrepreneurial Businesses

At Simple Numbers, the goal was simple: develop a single metric that captures the overall health of the entrepreneurial economy.

I Thought I Knew My Business. AI Proved Otherwise

The ability to analyze nearly a million rows of raw data has exploded some of my core assumptions.

Four Degrees of Communication

Something different happened two weeks ago when about 60 of us gathered at a remote location with spotty Wi-Fi, very little structure, and plenty of unhurried time together.

Six Months Later: AI Exposed Us — and That's a Good Thing

The tools work. But they don't fix bad data or broken processes, or the temptation to trust something just because it sounds right.

What’s Keeping You Up at Night?

Introducing the Sleep 5000: the real measure of a healthy business (and a healthy owner).

Never miss a 21 Hats Podcast episode
When Your Business Is Fine, but the World Isn’t

Everywhere you look, there is risk and uncertainty, but the biggest risk may be in letting the constant flow of unsettling news paralyze you.

EIDL Loans Are Moving Quietly into Collections

And it’s getting ugly, especially for owners who don’t really understand how the process works.

The SBA Is Guaranteeing Far Fewer Loans

As loan counts fall sharply and average sizes rise, the program appears to be drifting away from the smallest businesses it was designed to serve.

When SBA Lending Tightens, Alternative Capital Surges

Small businesses increasingly operate between two interconnected capital systems. When discipline rises in one, demand spills into the other—with consequences that policymakers often overlook.

When a Partnership Starts to Strain

Too many owners either assume a buyout would be impossible or assume it would be simple, without ever running the numbers.

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