by mrandish | 2025-08-08 19:16:16+00:00
> did you feel that most CEOs that you met along your journey were similar to you (passionate, technical founder) or something else (MBA fast-track to an executive role)?

I doubt my (or anyone else's) personal experience of CEOs we've met is very useful since it's a small sample from an incredibly diverse population. The CEO of the F500 valley tech giant I sold my startup to had an engineering degree and an MBA. He had advanced up the engineering management ladder at various valley startups as an early employee and also been hired into valley giants in product management. He was whip smart, deeply experienced, ethical and doing his best at a job where there are few easy or perfect answers. I didn't always agree with his decisions but I never felt his positions were unreasonable. Where we reached different conclusions it was usually due to weighing trade-offs differently, assigning different probabilities and valuing likely outcomes differently. Sometimes it came down to different past experiences or assessing the abilities of individuals differently but these are subjective judgements where none of us is perfect.

The framing of your question tends to reduce a complex and varied range of disparate individuals and contexts into a more black and white narrative. In my experience the archetypical passionate tech founder vs the clueless coin-operated MBA suit is a false dichotomy. Reality is rarely that tidy or clear under the surface. I've seen people who fit the "passionate tech founder" narrative fuck up a company and screw over customers and employees through incompetence, ego and self-centered greed. I've seen others who fit the broad strokes of the "B-School MBA who never wrote a line of code" archetype sagely guide a tech company by choosing great technologists and deferring to them when appropriate while guiding the company with wisdom and compassion.

You can certainly find examples to confirm these archetypes but interpreting the world through that lens is unlikely to serve you well. Each company context is unique and even people who look like they're from central casting can defy expectations. If we look at the current crop of valley CEOs like Nadella, Zuckerberg, Pichai, Musk and Altman, they don't reduce easily into simplistic framing. These are all complex, imperfect people who are undeniably brilliant on certain dimensions and inevitably flawed on others - just like you and I. Once we layer in the context of a large, public corporation with diverse stakeholders each with conflicting interests: customers, employees, management, shareholders, media, regulators and random people with strongly-held drive-by opinions - everything gets distorted. A public corporation CEO's job definition starts with a legally binding fiduciary duty to shareholders which will eventually put them into an no-win ethical conflict with one or more of the other stakeholder groups. After sitting in dozens of board meetings and executive staff meetings, I believe it's almost a certainty that at least one of some public corp CEO's actions which you found unethical from your bleacher seat was what you would have chosen yourself as the best of bad choices if you had the full context, trade-offs and available choices the CEO actually faced. These experiences have cured me of the tendency to pass judgement on the moral character of public corp CEOs who I don't personally know based only on mainstream and social media reports.

> FWIW I doubt that a souped-up LLM could replace someone like Dr. Lisa Su, but certainly someone like Brian Thompson.

I have trouble even engaging with this proposition because I find it nonsensical. CEOs aren't just Magic 8-Balls making decisions. Much of their value is in their inter-personal interactions and relationships with the top twenty or so execs they manage. Over time orgs tend to model the thinking processes and values of their CEOs organically. Middle managers at Microsoft who I worked with as a partner were remarkably similar to Bill Gates (who I met with many times) despite the fact they'd never met BillG themselves. For better or worse, a key job of a CEO is role modeling behavior and decision making based on their character and values. By definition, an LLM has no innate character or values outside of its prompt and training data - and everyone knows it.

An LLM as a large public corp CEO would be a complete failure and it has nothing to do with the LLMs abilities. Even if the LLM were secretly replaced with a brilliant human CEO actually typing all responses, it would fail. Just everyone thinking the CEO was an LLM would cause the whole experiment to fail from the start due to the innate psychology of the human employees.