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Strategy & Execution·March 15, 2025·7 min read

Why I Rebuilt My Website With AI (and What It Changed About How I Lead)

How working with AI to build a real product changed the way I think about requirements, pivots, and what it means to lead at the edge.

So I rebuilt my website.

I've always believed the best way to learn is to do.

So I rebuilt it from scratch, using the latest AI tools from idea to execution — to see how this way of working changes how you build, and how you lead.

Because at this point, being a product leader isn't just about setting direction. It's about understanding how things actually get built.

And honestly, my previous site was due for some love.

For years it lived on website builders — Bluehost, then Squarespace. Pick a template, set a theme, drop in blog posts. It worked. But the ceiling was always the template.

I wanted to see how far I could actually take it — and stay hands-on with what these AI tools can really do.


Translate ideas into execution

Working this way collapses the distance between an idea and something real.

You're not sitting with abstractions for long. You describe what you want, see it take shape, and immediately understand what's working and what needs to evolve.

That loop — describe, review, refine — happens in minutes.

Over time, it pushes you to be more precise in how you express intent. Layout, interaction, hierarchy, motion. You start describing things in a way that leads directly to execution, not interpretation.

It becomes a tighter connection between what you envision and what actually gets built.

And that carries straight into how you lead teams.


Speed changes how you think about decisions

Working at this pace changes how you approach decisions.

You spend less time debating and more time validating. The cost of trying something drops so low that it's often faster to test than to discuss.

That reinforces a mindset I've always believed in:

Ship. Look at it. Learn. Adjust.

Here, that loop becomes the default — not the aspiration.


The real skill is articulation

The hardest part of working this way isn't technical.

It's being able to clearly express what you want and why.

If something feels off, you have to define what's not working and what the outcome should be. Structure, flow, interaction, hierarchy.

The more clearly you can articulate that, the better the result.

That's the muscle this builds.

The ability to look at something, diagnose it, and describe the outcome in a way that leads directly to execution.

That applies just as much to working with teams as it does to working with AI.


The workflow is a product too

More than a year in, the way I build this site has gone through its own versions.

v1 was Claude Code inside Cursor — an engineer's cockpit. Powerful, but I spent my time in the code.

v2 is where I work now: a Cowork project with full context on the site. I talk through the problem, Claude writes the code straight into the repo, and I review the result live before anything ships. I stay in the conversation; the code stays out of my way.

Same loop I preach everywhere else: ship, look at it, learn, adjust. Applied to the workflow itself.

And the site has become the testbed — every prototype, experiment, and article lands here first. That's what the Playground is for.


This is how product leaders stay relevant

The gap between idea and execution is shrinking fast.

You don't have to imagine what something might look like. You can build it. Test it. Refine it. All in the same sitting.

That changes the role of a product leader.

You're not just defining direction. You're exploring it hands-on. Validating ideas earlier. Making decisions based on something real.

Rebuilding my site didn't just give me a better website.

It gave me a better way of working.

The tools are here.

The question is whether you use them to lead differently, or keep working the same way while someone else moves faster.

Back to ArticlesSteve Black