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I Spent 150 Hours Trying to Replace My EA with AI. Here's the Truth.
Last month, I went all-in on replacing my executive assistant with AI. I bought a Mac Mini for $600. I burned through $700 in Claude tokens. I spent roughly 150 hours planning, architecting, and build
Why AI Won't Replace Your EA (But Will Make Them 10x Better)
Every founder I talk to is asking the same question: “Should I be using AI to replace my assistant?” Here’s what I’ve learned after working with 60+ executives and their EAs: You’re asking the wrong q
What It Means to Be a System Driven Founder
If you ask most people how to build a massive company and be a present husband and father, you get one of two answers. The first: “It’s not possible.” Pick one. The second: “It’s all about balance.” J
Most Founders Don’t Have a Productivity System
I have nearly 40 CEO clients that have let me into the most intimate parts of their work life - their personal productivity workflows. Primarily I’m here to help them with delegation - but lately our
Stop Using Your Email Inbox as a To-Do List
Hey friends, It’s been a minute. I took a pause over the holidays, stepped back, reset a few systems - and now Systems Driven Weekly is back. And I’m starting with a problem I see constantly (and stil
Overcoming Obstacles on the Path to Your Goals
The mindset that keeps you moving forward by focusing on progress, not perfection New Year’s Resolution ReminderAs we step into a new year, consider making this your resolution:commit to continuing fo
Digitize Every Paper in Your Life With a One-Tap System
What if managing your mail didn’t fall on you anymore? Here’s how to make that happen. If you’re like me, you have a massive pile of bills, mail, and paper stacked up somewhere in the corner of your k
Ambition Without Anxiety: Is It Even Possible?
This holiday season, I find myself swinging between two extremes… On one hand, I’m motivated and ambitious. I want to grow my business to $10m+ quickly. On the other hand, the ambition is exhausting.
How I Turned Annual Goals Into a Life Operating System
Most founders set annual goals, but few go deep enough to connect those goals to an identity. Fourteen years ago, my annual planning process was a list of resolutions. The typical kind: Read more book