The Brand Called You Scaling Startups & Tackling Tech Debt: Insights from Thanos Diacakis, Software Delivery Coach & Fractional CTO
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Aug 6, 2025 
Thanos Diacakis, a seasoned software delivery coach and fractional CTO with over 25 years of experience and seven software patents, shares insights on the tech landscape. He discusses the critical mindset shifts needed to transition between startups and large enterprises. Thanos dives into the dangers of tech debt and the importance of deliberate shortcuts. He offers a practical framework to align tech strategy with business goals and emphasizes hiring for strong engineering fundamentals. Key leadership qualities in scaling culture and the strategic balance of build versus buy are also highlighted.
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From Buttons To Debugging Teams
- As a kid Thanos loved devices with buttons and knobs and that curiosity led him to software engineering.
- He still enjoys solving small puzzles and now delights in debugging teams and processes as larger systems.
Different Paths To Scale
- Startups scale by speed and minimal process while large companies scale through collaboration and specialized roles.
- Leaders must change modes when moving between these worlds to leverage available resources effectively.
Tech Debt Can Become Sovereign Debt
- Tech debt often compounds like sovereign debt when teams never pay it down and can cripple startups.
- Taking intentional, compartmentalized shortcuts early is fine, but avoid irreversible design mistakes.