Why I Keep Starting Over (And Why That's the Point)

In the last few months, I’ve gone from:

AlfredGateman → Auraa → back to the board.

Not iterations. Completely different directions.

Not because I’m unserious. If anything, it’s the opposite.

Alfred

AI layer for customer teams. Sat on top of Gmail / Intercom, understood context, helped you respond better.

Made sense:

  • clear use case
  • easy to demo

But it was just that:

a layer, not a product.

No control. No ownership. Fragile.

Moved on.

Gateman

Guardrails for AI tools. Stop people leaking sensitive data.

Had:

  • real risk
  • real buyers
  • clear positioning

I started building it.

But conversations changed things:

  • felt like DLP
  • enterprise tools already cover parts of it
  • extension friction is real

And the big one:

buyer ≠ user

If users hate it, it dies.

Still solid. Just clearer tradeoffs now.

Auraa

Creator monetisation.

Good story:

  • growing market
  • fragmented tools

Reality:

  • thin margins
  • expensive infra
  • messy legal

Still a decent play. Just not obvious enough.

So yeah, I’m back at the drawing board.

Not because the last ideas weren’t good enough, but because building is the point for me.

AI just makes it easier to try more things, so I will.

That’s the only thing that matters.