Welcome to Scaling Judgment!

Hello friend,

I am Alistair.

In the past decade I’ve experienced the rollercoaster of joining a little-known travel tech startup and helped grow it into a leader in the European vacation rental market. Today I run a commercial organisation across Europe with hundreds of people — and the kind of complexity you cannot learn in business school.

Along the way, I started making investments with my personal savings and quickly realised how differently you think about business when you have skin in the game. From a vacation rental in Portugal to public equities, secondaries, and even some angel investment — I’m building this track in parallel, making my mistakes, and learning a ton.

Scaling Judgment is where I write about judgment — the thing between the data and the decision. In the context of building and scaling organisations across Europe. For operators who want to think like investors, and investors who want to understand execution at scale.

Subscribe if that sounds like your kind of conversation.

You can find me on LinkedIn. I’m always open to connect with curious people thinking about the same problems.