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A New Book Is On The Way!

Maintaining software: how the best startups do it.
Jun 6, 2025

I’ve had some extra time of my hands lately, so I have been taking classes at Harvard and MIT. They were good, but I lost some of my balance with learning and creating, so I decided to start writing my second book.

My first book was published under another name. I have a lot of experience writing, but not in such a long form, so I didn’t want to take any risks and published it on my own on Kindle. Honestly, it did better than I thought. It was the top seller in software engineering books for two weeks! It’s a short book, so it was priced appropriately and I can’t say I made a million bucks off of it; in fact, after everything settled and the sales came to a halt, I told myself it wasn’t worth the money. And I still believe that. But I remember in Californication when the author Hank Moody’s daughter came up to him with her first book. He promptly told her to put it in a drawer and start on her next one. There’s a lot of truth to that scene. I’ve always been a writer. I was first published as a kid, which felt great at the time, but it was a much shorter format. I should have also put it in a drawer and started this one. I did get to learn the whole process. It’s relatively simple to do on Amazon’s platform, but it meant I had to be a designer, an editor, and a marketer at the same time. I don’t have experience with those things — well I didn’t. But I’ll never be as good as professionals at those things. This time I pitched it to every publisher I could find that covers technical books. Two responded. I talked with one for a bit and they wanted to see a much longer book. They were right, it’s much shorter than what the industry puts out. I’m a short or mid length type of author, so it made total sense. I like to write succinctly; it’s a hazard of my day job. At that point I knew I had to keep working on it. I also made the assumption that they don’t offer much in the editing department, so they probably weren’t what I was looking for.

But I did say there were two.

I've been talking to an editor at what I believe is the second biggest tech book publisher. No name drops yet! But it's huge. They have been using language like "when we have the book approved" and not language like "if the book is approved then", so it seems like their plan is to help me get this book published. And hey, if it does fall through, I'll make the rounds again and see who's interested.

By that time the book will be much longer and refined. It's almost doubled in length from when I first made the pitches and it's continuing to grow. As I wait for said publisher, I've been editing and editing and editing. Some new ideas have come up, I've been making each chapter more complete, and I've restructured it to have better flow. It's something the editors can help with, but the closer I can get it to the final product the better anyway.

As for the book itself, it's about running an engineering organization that is hyper-productive. I've been in this business long enough to see a lot of success and some devastating failures. So I decided to take the best parts of all of the best startups that I've worked with and distill it into book form. I hope to teach engineering leaders how to take their group or groups of people and transform them into true teams. Teams that are collaborative and communicate well. Teams that are autonomous. Teams that are truly greater than the sum of their parts.

I have no idea how long this whole process will take, but I am happy to say something is coming soon™. It's leaps and bounds above my first book in terms of quality completeness. And a professional editor hasn't even got the hands on it yet!

I do know my blog gets a good amount of traffic, so for those who are readers, please do check back in soon, and hopefully I'll have even more to share about my new book that's titled: Maintaining Software: How the best startups do it. And if all goes well, I'll have more exciting news to share soon after this venture, too!