The Optimist: Sam Altman, OpenAI, and the Race to Invent the Future

The Optimist by Keech Hagey is a fascinating portrait of one of the most consequential figures in modern tech, and I came away from it with a lot to think about.

As a fellow Missourian, I couldn’t help but feel a particular kind of pride reading about Sam Altman’s trajectory. There’s something genuinely motivating about watching someone from the same part of the country go on to shape the future of AI. If he could do it, the ceiling feels a little higher for the rest of us.

But this book is far more than an inspirational story. I also read it as a cautionary tale about leadership and people-pleasing. Altman’s story illustrates, sometimes painfully, what happens when leaders tell different stories to different people rather than just saying the hard thing clearly. Alignment matters more than comfort. The messy OpenAI board drama is a masterclass in what misalignment actually costs, and it’s a lesson I’ll carry into my own work.

What also shines through is Altman’s extraordinary talent for fundraising and, more broadly, for influence. He isn’t always the person with the best technical ideas in the room, but he is consistently the person who can inspire others to build remarkable things. That’s a different kind of genius, and Hagey captures it well.

Highly recommend to anyone in tech, product, leadership, or anyone who just wants a gripping inside look at how OpenAI came to be.