The first guess is supposed to be wrong
A division full of tiny software products that couldn’t make money. My first explanation was wrong, and being wrong fast was the only reason I found the right one.
- Note 179 min
- Note 169 min
Buying the Same Revenue Twice
Retained ARR, new ARR, cash and freed-up time are not the same dollar. Sort that out first, then go read the customers you already have.
- Note 157 min
But everybody did their job...
We blame the department showing the bad number. The real cause is usually upstream, in a seam nobody owns, and AI makes it harder to see.
- Note 1411 min
Shrink the Box
When building gets cheap, the cost stops forcing your choices for you. What’s scarce now is the judgment about what’s actually worth building.
- Note 133 min
AI took the effort. Watch what goes with it.
Effort used to be the filter that told you what mattered. AI removes it, and it’s easy to hand over the judgment that was your real value too.
- Note 123 min
Trade up your problems
The goal was never to have no problems. It’s to trade up to better ones. The same problem twice means you patched a symptom.
- Note 113 min
How to see around corners
The people who seem to know what’s coming aren’t psychic. It’s four skills, and the hardest one isn’t the seeing.
- Note 104 min
You can stay in your seat too long
The seat that got the company here isn’t always the one the next stage needs. Stay in it too long and the decision gets made for you.
- Note 095 min
You can’t see the thing you’re inside
You can read every business but your own. Your position is the blind spot, and at $10M–$50M it gets expensive.
- Note 084 min
The research was never the hard part
AI made the looking-things-up free. Judgment, accountability, and an outside eye never got cheaper, and they’re the whole game.
- Note 074 min
Why hiring more salespeople can make stalled growth worse
Adding quota to a funnel that leaks after the close multiplies the leak. The first hire should be a diagnosis, not a rep.
- Note 066 min
The hidden tax inside a $10M company
Somewhere between $5M and $15M, coordination cost starts compounding faster than revenue. Most P&Ls don’t have a line for it.
- Note 053 min
Your funnel may not be the problem
Top-of-funnel is the easiest place to look and the most expensive place to fix. Three questions to ask before you touch it.
- Note 045 min
Where CEOs usually look first, and where I look instead
Marketing, then sales, then the market. I start with the customers you already closed and what happened to them next.
- Note 034 min
Revenue follows decision speed, not effort
Two companies at $5M are not the same company. One reaches $10M in two years. The other takes seven. The difference is almost never the strategy.
What these are
Field notes, longer than the name suggests.
After twenty years and a few hundred businesses, the same patterns keep showing up. These are the ones worth writing down: how I actually think about where revenue gets stuck, worked all the way through instead of boiled down to a checklist. Notes from the field.
Know where this has to go, and not how?
Twenty minutes. Tell me where you want this company to be in two years and I’ll tell you what I’d go look at first.