I’ve never found a truly great book out there for startup founders and CEOs. Ben Horowitz’s The Hard Thing About Hard Things and Brad Feld’s Do More Faster came close, but even they were missing many topics I believe are important. Many other books, written by non-CEOs about how to be a successful CEO, weren’t even close to good. They were like sex instruction guides written by virgins. They may get a couple of things right, but they fundamentally have no idea what they’re talking about.
Being a good manager is an important part of being a successful CEO, but it’s just a part, and not that central. So books on managing in general are not that useful. This book is focused on the key parts of being a successful startup CEO. It touches on general management in places, but it’s also much more and much different than a management book.
Any CEO will get it wrong. A lot. You’ll make big mistakes that put the future of the company on the line. If you get it right even half the time, you’re doing awesome. This is very different from every other executive role, where it’s a reasonable expectation to be hitting your goals regularly. Being CEO is unique.
So think of this book as a sympathetic source of hard-earned wisdom, from a fellow CEO who managed to get it right about half the time – like most successful CEOs, even those who would never admit to a batting average that low.
I have a wonderful wife, 3 terrific daughters, and a great dog. In my spare time I read history and blog on political topics, including interviewing many of the elected officials here in Colorado (from both parties).
I was CEO & founder at Windward Studios (sold it in 2021)
I've written operating systems (including on the Win95 team at Microsoft), games (including Enemy Nations), applications, firmware, and enterprise web apps.
After Windward I desperately wanted to start another company. Being CEO is like crack cocaine (I assume, never tried it), it’s really hard to let go. But eventually I did. And key to that was deciding that no matter what I did, the one thing it would not be was another start-up.
I called around to a lot of people and long story short, I ended up volunteering to write a program for the Democratic party. Specifics are a secret but it is a Blazor (server side) app that includes a small amount of spatial functionality and will (hopefully) use some AI services.
It’s one hell of a learning curve. Half of what I’m programming in is new to me (Blazor, Entity Frameworks, Spatial, ML services) and the other half I’m 7 years out of date so the knowledge I have is obsolete & forgotten.
I’m having a blast doing it.
I’ll be writing about various stories, challenges, thrills, highs, lows, etc. about being the CEO of a vibrant start-up.
And I’ll add in occasional tidbits on what I am doing now.
Thanks for reading I Don’t Know What I’m Doing! Subscribe for free to receive new posts and support my work.