About me
I’ve been in your shoes. That’s the whole point.
I'm Dave Bailey, a CEO coach for founders of venture-backed tech companies. I spent fifteen years building companies myself, including Delivery Hero which IPO'd in 2017, before making coaching my full-time work.


After my operating years I moved into venture capital, and found the hours I loved most were the ones spent helping a CEO think. So I made that the whole job. Since then I've coached 250+ venture-backed CEOs across the US, Europe and Latin America, written hundreds of essays on founder leadership, and taken the ideas to the retreats of leading venture firms and keynotes for EUVC and others.
I've only ever coached CEOs. Not co-founders or execs. Just founders running the companies they built. Do one job for eight years and you start to see the patterns nobody writes about: why brilliant founders get stuck at 50 people, why the advice that saved you at Series A hurts you at Series C, why the loneliest moments come right after the wins.
That's why my coaching comes with more than good questions. You get 500+ frameworks and visual models, built from watching what actually works inside hundreds of scaling companies. Practical tools you can use with your team the same week, not insights you can’t remember a week later.
Right now I'm obsessed with one question: what does great leadership look like when AI is changing every job in your company? I use AI heavily in my own work, and my clients and I are figuring out the answer together, in real companies, in real time.
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