- Uncommon Advice
- Posts
- The Moment I Knew The Old Playbook Was Toast
The Moment I Knew The Old Playbook Was Toast
What 22 years of pattern recognition taught me about what's next.
Nate Kennedy
February 26, 2026
There's a moment in every market cycle where the rules quietly change.
Most people don't notice until it's obvious. By then, the advantage is gone.
I've seen it happen three times in my career:
The shift from direct mail to online (2006). The people who moved early built empires. The people who waited spent years playing catch-up.
The rise of Facebook ads (2012-2014). Same story. Early movers got arbitrage. Late movers got competition.
The platform algorithm wars (2018-2020). Organic reach died. Paid became mandatory. The operators who adapted thrived. The ones who complained got left behind.
Each time, the pattern was the same: a new infrastructure emerged, early adopters got leverage, and within 2-3 years the window of easy advantage closed.
I'm watching it happen again. Right now.
But this one's different. It's not a new traffic source or a new platform. It's a new operating system for how businesses run.
Here's what I mean:
I was talking to a founder last year. A smart guy with a $2M business and a team of 8. He was exhausted. Working 50+ hours a week just to keep things running.
Every time he tried to scale, he had to hire. Every hire added management overhead. The business grew, but so did the complexity.
Sound familiar?
I asked him a simple question: "How much of your team's time is spent on tasks that don't require human judgment?"
He thought about it. Then he said: "Probably 60-70%."
That's the breaking point. That's when I realized the game had fundamentally changed.
For 20 years, the answer to "how do I scale?" was "hire people." Build a team. Delegate. Manage.
That answer isn't wrong. But it's incomplete now.
The new answer is: "Automate first. Then hire for insight."
Every task you automate before hiring creates permanent leverage. Every task you delegate first creates permanent overhead.
This isn't about replacing people. It's about not hiring people to do work that a system should handle.
That shift of automation before delegation is the core of everything I'm building now.
It's why I'm teaching system design. How to identify what should be automated, how to build it, and how to create infrastructure that compounds over time.
Next email, I'll show you what this looks like in practice with some Real numbers and Real implementations my team has done.
For now, I'll leave you with the question that changed everything for me:
What would your business look like if you automated the 60-70% that doesn't require judgment... before hiring anyone else?
It’s Ai’s Time!
Nate Kennedy
P.S. If you're reading this thinking "that's me. I'm the founder working 50 hours to maintain, not grow" then hit reply and tell me what's eating most of your time.
I read every response.
