Hey Reader,
Startups rarely fail with a bang. Most fail with a thousand tiny compromises.
But the ones that get a little traction? The rare combo of relentless founder and a validated idea (the jockey and the horse). So many of them die because they can’t convert that early traction into something bigger.
Often because entropy wins.
You’re doing the work. Motivated. Excited. Probably working harder than ever. Momentum definitely feels real.
And yet...
Things are slipping.
Entropy isn’t inaction. It’s often misplaced effort.
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HYPER RELATED:
Last week, I talked about how motivation isn’t what keeps founders moving, it's just the spark. It’s systems and discipline that deliver the momentum. But systems, especially in startups are almost designed to break down. That’s this week, that's entropy, and it doesn’t care how motivated you are.
Feel familiar?
- Your engineer is suddenly “too busy” for standups.
… Your standup was sacred until that one busy Monday.
- Your sales pipeline? Getting “updated tomorrow.”
… You’re in back-to-backs, so you’ll do it later.
- The tech debt you know is fatal is now “next sprint.”
… Your QA process worked until that urgent hot fix.
- Customer feedback? You’ll “look into it when things calm down.”
… Your customer obsession was solid until that big feature launch.
- Your metrics dashboard? Gathering cobwebs.
… Your metrics review was weekly until it wasn't.
One exception becomes two. Two become normal. Normal becomes chaos.
We've all been there, overwhelming amount of customer promises, missed release dates, competing priorities, and mounting chaos.
You’re a firefighter running around putting out the tiny fires because you don't have the time or money to focus on the inferno, which is just far enough away to be ignored.
Every Slack “ding” is met with the fear it could be an outage or a crisis… because it usually is.
This is why entropy is so dangerous: in the moment, the trade-offs feel completely reasonable and even necessary - you are right to make those trade-offs.
- Metrics don’t matter if the pitch fails and we run out of cash.
- The hot fix gives us the breathing room to get this customer off our back.
- Would you rather me selling or updating hubspot?
This is what makes fighting entropy so f'd up. It disguises itself as prioritization.
To repeat... Entropy doesn’t win with a bang. It wins with a thousand tiny compromises.
I'm pro-chaos. That’s not this.
Chaos is fine. Mayhem is fine. A shit show is expected. It’s supposed to be messy, unscalable and generally impossible.
Entropy is the slow decay of your systems, focus, and execution.
- Chaos is shipping a feature the night before launch.
Entropy is never revisiting it to fix the bugs.
- Chaos is running down 10 leads at once.
Entropy is forgetting to follow up because you’re too busy.
- Chaos is 2am triaging production issues.
Entropy is letting tech debt pile up until it defines your product.
Chaos is the grind. Entropy is when the grind become the standard.
Early days, you are E1 (Entropy of One)
It’s just you (and your upwork engineer!) - you are the chaos generator. No processes exist outside of what is in your head.
That's normal. Thats the trap. When it's just you, chaos feels like speed. It's not. Chaos only works when it's contained by systems. It cannot be the system.
Every decision. Every action. Big and small. From vision to TestFlight builds.
This is E1: Entropy of One. One founder, no systems, pure chaos. It's not innovation. It’s disorder.
You can’t beat entropy. Fact. Every system tends toward disorder.
This isn’t about motivation (we covered that). This isn’t about product-market fit (if you believe in it).
Every founder with a tiny bit of traction thinks they can outwork entropy. You can’t.
You can only try to build systems that force order, even when chaos is trying to crush you.
As you grow, things start to take longer. They just do. Not everyone has the founder adrenaline to live and die with every push to prod, every lost customer, or every missed milestone. They shouldn’t have to.
The goal isn’t to defeat entropy. It’s to delay it. To control its pace.
Entropy comes for every startup. The difference isn’t work ethic or idea validation or even market traction.
It’s systems.
Stay in the fight.
As always, if I can be of service, feel free to grab time.
LFG.
-- James
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