#371 Balancing CTO-CEO Relationships and Mastering Due Diligence: A Talk with Hutton Henry

In this episode of “The CTO Show with Mehmet,” we dive into the intricate dynamics between CTOs and CEOs, exploring how these relationships can make or break a startup’s success. Our guest, Hutton Henry, founder of Beyond M&A and a seasoned expert in due diligence, shares his valuable insights on how CTOs and CEOs can better align their goals, manage expectations, and overcome common challenges in high-pressure environments. Hutton discusses the importance of understanding the different speeds at which CTOs and CEOs operate, especially post-investment, when new pressures and expectations emerge. He emphasizes the need for effective communication and mutual understanding to prevent friction and ensure that both technical and business objectives are met. We also explore the role of due diligence in the startup journey, with Hutton providing an insider’s view of the process. He highlights the common pitfalls that startups encounter during due diligence, particularly in areas like cybersecurity and technology stack assessments. Hutton underscores the value of conducting due diligence early, even before seeking investment, to create a stronger, more resilient business. Throughout the conversation, Hutton offers practical advice for both CTOs and CEOs on how to navigate their partnership, optimize their collaboration, and prepare for the rigorous demands of due diligence. Whether you’re a founder, tech leader, or investor, this episode is packed with actionable insights that can help you steer your startup toward success. More about Hutton: https://linktr.ee/huttonhenry 01:10 Hutton Henry's Background and Expertise 02:09 Inspiration Behind Hutton's Career 04:34 Challenges in CEO-CTO Relationships 11:07 Investor's Role and Expectations 16:12 Transactional Analysis in Leadership 21:16 The Importance of Training in Tech 22:08 Balancing Speed and Quality in Product Development 23:46 Effective Communication Between CTOs and Founders 24:23 Introduction to Due Diligence 25:03 The Due Diligence Process Explained 27:18 Common Issues Found During Due Diligence 40:57 Advice for Founders and CTOs 42:22 Conclusion and Final Thoughts