Startup CTO

Over the 2019–2025 I’ve maintained some notes on the process of starting https://www.segmed.ai and developments/beliefs that either turned right, or the ones that were completely wrong. This was mostly to see how I’m doing on a tech/biz decision trajectory. The more I looked at it, the more is started to sound like a story.

Two YC friends picked my brain on some business things and how it could fruitfully be converted into the technical aspects, and both said that there should be a book about the CTOing..

I planned out some lose notes for this book May 2025. It’ll covered initial aspect of development of products in a small team. As of Oct/2025, there’s 71k words in in, with more planned. ETA for the 1st draft would be late Q4 2025. I’m looking for proof-readers, so if you see this, and you’re interested, let me know. I’d drop you watermarked chapter, and if you do well, you’d get printed book free of charge.

I plan to cover everything that employee 0 / co-founder / CTO will see. Culture / cofounder dynamics is covered, and the way to handle working with customers, vendors and suppliers who may often be non-technical. Book follows the gradual decision making steps and process for various stages of the company where you’re the only person programming and shipping the product to the extended team, where you have to make high level decisions on direction, but you’d not be the one executing them. I also covered the process of managing and working with the head of engineering and the first moment where you’re not working hand-by-hand with engineers. If you anticipate that your successful business may end up with 30+ people, this book is for you. I covered everything from starting and developing tech at Segmed. working on all aspects of product: product management, software engineering, ML, deployment into the highly regulated space, and integration.

Outline

(I’ve adjusted the outline)

This book provides essential strategies and insights for technology leaders navigating the unique challenges of startup environments. Drawing from real-world experience leading engineering teams at high-growth companies, it covers:

• Technology Strategy - Building scalable architectures and technical roadmaps
• Team Leadership - Recruiting, developing, and retaining top engineering talent
• Startup Dynamics - Balancing technical debt, speed, and quality in resource-constrained environments
• Executive Communication - Translating technical concepts for board members and stakeholders
• Scaling Challenges - Managing growth from startup to scale-up phases
• Innovation Culture - Creating environments that foster creativity and continuous improvement

Buy the Book

Status: Currently in development - Expected publication: Dec/Jan 2025/2026

Pre-order information and purchase links will be available soon.

Formats Available:

• Paperback - $24.99
• Kindle/eBook - $9.99
• PDF (Direct) - $14.99

Book Details:

• Pages: 280
• Word Count: ~75,000 words
• Reading Time: 5-6 hours
• Language: English
• ISBN: xxx-x-xxxxxx-xx-x

Target Audience

• Current CTOs at startups and scale-ups
• Senior engineers transitioning to executive roles
• Technology leaders in rapidly growing organizations
• Founders taking on CTO responsibilities
• Engineering managers preparing for leadership roles

What You’ll Learn

By the end of this book, you’ll have practical frameworks for:

• Making strategic technology decisions under uncertainty
• Building and leading high-performing engineering teams
• Communicating effectively with non-technical stakeholders
• Managing technical debt while delivering business value
• Creating scalable processes and systems

Follow my blog for updates on the book’s progress and early chapters.