BONUS The Startup CTO's Handbook With Zach Goldberg

In this BONUS episode, we dive deep into the world of startup leadership with Zach Goldberg, author of The Startup CTO's Handbook. We explore the critical transition from engineering to leadership, the art of balancing technical debt with startup urgency, and the communication skills that separate great CTOs from the rest.

"My original training in software engineering was not enough for being a leader. All the people and leadership skills, I had to learn on my own."

Zach's journey to writing The Startup CTO's Handbook began with a stark realization about the gap between technical training and leadership reality. Despite his classical software engineering background, he discovered that the people and leadership skills required for CTO success had to be self-taught. The book emerged from a growing Google Doc of topics and frameworks addressing the leadership and management challenges that CTOs consistently face - from hiring and performance management to making strategic decisions under pressure. Today, we can either buy the digital/print book on Amazon, or read the book on GitHub. 

In this segment, we also refer to the book The Great CEO Within.

"Max only cared about my ability to learn - to get curious about something hard. He wanted to help me deal with complexity."

Zach opens his book with a deeply personal story about his mentor, Max Mintz, who fundamentally changed his approach to learning during what he calls "the most impactful single coffee" of his life. Over 1.5 years of conversations, Max taught him that true learning isn't about accumulating facts, but about developing curiosity for hard problems and building the capacity to handle complexity. This lesson forms the foundation of effective CTO leadership - the ability to continuously learn and adapt in an ever-changing technical landscape.

"As a CTO, the most important 3 things: people, people, people. Do the people have the right energy, the right passion? Assemble the right team."

Zach identifies consistent patterns in startup CTO failures across his experience. The first and most critical mistake is undervaluing people decisions - failing to prioritize team energy, passion, and the right assembly of talent. The second category involves investment mistakes, particularly the challenge of balancing short-term survival needs with long-term technical goals. In startups, the ROI timespan is exceptionally short, requiring optimization for immediate objectives rather than hypothetical scale. The third mistake is treating technology as religion rather than tools, losing sight of what the business actually needs.

"You are optimizing for velocity! What are you doing to help developers get their work done? Look at developer experience as a metric."

Successful startup CTOs understand that velocity - the time from idea to valuable market delivery - is paramount. This requires a fundamental shift in thinking about technology decisions, focusing on features that deliver real customer value rather than technical elegance. Zach emphasizes measuring developer experience as a key metric, recognizing that anything that helps developers work more effectively directly impacts the company's ability to survive and thrive in competitive markets.

"It's like a character progression in an RPG. When we learn one type of skills, we don't learn other types of skills. We make investments every day and we have a choice on where we learn."

Drawing from gaming metaphors, Zach explains how technical professionals often reach Level 100 in engineering skills while remaining Level 1 in management. The skill tree concept highlights that every learning investment is a choice - time spent developing one skill area means less time available for others. For engineers transitioning to leadership, the key is recognizing opportunities to serve as tech leads, where they can begin setting culture and quality standards while still leveraging their technical expertise.

"Pick the high-impact debt, and pay that down. This is not always easy, especially because we also need to pick what debt we don't invest on."

The tension between continuous improvement and startup speed requires sophisticated thinking about technical debt. Using financial analogies, Zach explains that technical debt has both principal and interest components. The key is identifying which debt carries the highest interest rates and can be paid down most quickly, while consciously choosing which debt to carry forward. This approach maintains the healthy tension between quality and speed that defines successful startup engineering.

"The single hardest skill, especially for very tech leaders is that of 'audience empathy.' When you explain ideas to people, you usually assume a lot - but they might not."

According to Zach, the most undervalued communication habit for startup tech leaders is developing audience empathy. Technical leaders often suffer from the curse of knowledge, assuming their audience shares their context and understanding. The solution requires deliberately considering what the audience already knows before crafting any communication, whether it's explaining technical concepts to non-technical stakeholders or providing clear direction to team members.

In this segment we refer to the concept of “the curse of knowledge”, a cognitive bias that occurs when a person who has specialized knowledge assumes that others share in that knowledge.

About Zach Goldberg

Zach Goldberg is a seasoned technical entrepreneur, executive coach, and author of The Startup CTO's Handbook. With a founder's mentality and a passion for systems thinking, Zach helps engineering leaders build high-performing teams. He also founded Advance The World, a nonprofit inspiring youth in STEM through immersive experiences.

You can link with Zach Goldberg on LinkedIn, and visit Zach’s website at CTOHB.com.