I had the privilege of bringing together three brilliant minds - Ran, Amit, and Yossi - for an insightful discussion about the unique mental aspects of being a Chief Technology Officer (CTO) in the startup world.  

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Ran, the founder and CTO of Epsagon, which was acquired by Cisco for $500 million, is a product-building enthusiast who loves hiking and cooking. He is married to Neta and a father of two children.

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Amit, the founder and CTO of Bigabid, has been a programmer since a young age and is a graduate of Mamram. Married to Karin, father of Yuli, and expecting another child. He enjoys drawing and helping fellow entrepreneurs.

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Yossi, the chairman of the Mamram Alumni Association (Israel's first IDF computing unit) and the CEO of the technology training company Fast Lane, leads entrepreneurship programs that guide entrepreneurs from early stages to growth stages. An amateur chef who loves Italy, he is married to Shiran and is the father of two daughters - Yuval and Maya.

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Together, the four of us delved into the most important issues of the entrepreneurial journey from the perspective of the tech entrepreneur.

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The first among them was the decision-making process at the beginning when multiple founders start a startup together, determining who becomes the CEO, CTO, etc. While experience often dictates these roles, aligning expectations is crucial, and tech-savvy founders transitioning to CEO roles need to step back a bit from their technical background to avoid friction, disagreements, and overbearing discussions. Sometimes difficulties arise when two experienced tech founders embark on a journey, and their roles and boundaries of responsibility need to be clearly defined. The CEO, as a co-founder, is the ultimate decision-maker, while the CTO, as a co-founder, takes on a functional role. Over time, the CEO's role may grow and expand, while the CTO's role specializes within the realm of technology. This can create gaps between the two founders.

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There are two main types of CTOs, and their communication styles and management approaches characterize these types:

1. The Inbound CTO: Focuses on hiring, code quality, day-to-day operations, processes, organization and methodologies, future planning, and technological vision. Most CTOs fall into this category and often have less pronounced soft skills.

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2. The Outbound CTO: Typically less skilled in management or architecture but excels in working with customers, dealing with go-to-market strategies, and possessing stronger soft skills.

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Yossi emphasized the importance of the stage at which one becomes a CTO - early in their career or after gaining experience as a team lead in a larger company, which typically leads to more developed soft skills and management abilities.

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Introversion vs. Extroversion

Although every human trait is essentially a spectrum, representing a range of that trait, it is a generalization, but CTOs often exhibit more introverted tendencies, struggling to express emotions or convey technical explanations in a way that resonates with non-technical people.

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Yossi said,

"I don't think nowadays, in 2024, you can be completely shy" suggesting that CTOs must take responsibility and connect with the ecosystem.

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The Unique Challenges CTOs Face

Loneliness: Different from a CEO's loneliness. This loneliness stems from being a co-founder, as investors often spend time nurturing CEOs but leave the CTO on the sidelines. CEOs typically have a support network of peers in similar roles, while a CTO may lack such resources.

Technological complexity: Others may not understand the technological complexity, making it difficult to resolve issues and set realistic timelines.

Perceived importance: The CTO's role may not seem critical enough.

Trust: Does the CEO trust the required technological solution?

Character: CTOs often exist on a spectrum of introversion and extroversion, which can present challenges that other roles in the company may not face.

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Finally, we dove into the entrepreneurs' personal experiences and touched on their individual struggles, emphasizing the entrepreneurial roller coaster we all experience:

Amit shared his first fundraising experience and the anxiety attack that followed, lasting three weeks, with symptoms like ringing ears, a lump in his throat, and blurred vision. He realized he needed help when talking to his co-founder and felt he had to seek professional help. Therapy and medication helped him understand the entrepreneurial roller coaster he was on.

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Ran discussed the difficulty of dealing with employee layoffs and maintaining closeness with his wife and family given his limited time at home. He says there's no magic solution and constantly tries to balance and communicate the importance of both aspects of his life.

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Yossi added that the sheer amount of experiences in a day is overwhelming, making it difficult to share all the details with loved ones and leading to frustration on both sides. He recommended coaching or counseling for everyone and shared his personal experience of seeking a psychologist during the COVID-19 period, with whom he discussed personal and professional matters, which helped him move forward and overcome the crisis he was in.

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My discussion with these three CTOs surfaced many important points about the tumultuous mental and professional journey we all experience as entrepreneurs. I invite you to listen to the full episode to be exposed to the rest of the stories, experiences, conclusions, tools, and solutions we discussed!