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Pencil sketch portrait of Robbie Stephens

About

A short note.

I’m interested in how businesses actually work as they grow. How decisions get made, how incentives change behavior, and why some systems hold up while others depend on people pushing through every problem.

I started my career at Southwest Airlines, working in commercial and network strategy. Since then, I’ve spent most of my time at Uber building and operating marketplace businesses. The work has crossed strategy, operations, product, and partnerships, along with the everyday details of making a business run.

I like ambitious teams and hard problems. I’m most interested in what happens after an idea looks good on a slide: how customers respond, where the plan starts to break, and what still works once the tradeoffs become real.

This site is where I write down some of the things I keep learning. Some become essays. Others become frameworks or small experiments. Most begin with a question I haven’t been able to leave alone.

Outside of work, I’m usually with my wife, son, and our dog. I enjoy hiking, rugby, aviation, vintage cars, endurance training, and cooking. That usually means making a multi-course meal for friends or putting something on the Traeger. I also like any excuse to build something from scratch.

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