I built myself an AI executive assistant to get my brain back

Every business owner I know has some version the same problem. That background process running in your head at all times:

Who did I forget to get back to? What's falling through the cracks right now? When's the last time I talked to [important person]? What meetings do I have tomorrow - am I even prepared? Is someone waiting on me right now? Did I ever send that thing I promised?

Every tool and technique that I've tried has been great at making me feel more overwhelmed, and none of them made me feel like I knew what I should be doing next.

I had to manually update statuses, remember where I left off on things, wonder if systems had gotten out of sync.

The gap between "impressive demo" and "actually useful" always left me wanting more.

But after a year of experimenting with AI tools like Cursor, I eventually found Claude Code.

And everything started to click.

Over the course of 5 days, I developed a fully custom system that was wired into my tools, my workflows, and most of all it works the way my brain works.

This system has materially changed how I feel about my work, and how I move through my day. Maybe it can change yours?

The demo that started it all →
Runs entirely on my own devices and accounts Custom tailored to how I work Turns my existing tools into a complete system The more I use it, the more powerful it gets
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Who's Behind This

I'm Alex Hillman.

I've spent my career building things people want and sharing what I learned.

  • I found that I wasn't the only one looking for likeminded professional peers in Philly, and that led to Indy Hall.
  • My partner Amy and I had built businesses with paying customers on day one - people wanted to learn how, so we taught them through Stacking the Bricks.

And now: I built myself an AI executive assistant because I needed a system that could keep up with how my brain works - and nothing out there came close.

What started as a five day experiment has turned into an entire operating system for my work and life. Nothing since Indy Hall itself has changed how I feel about my work the way this has.