An employee can be 'fearless' knowing they can find another job. A founder loses this safety net. The psychological burden shifts to a deeply personal responsibility for employees' livelihoods, investors' money, and the vision, making the stakes feel infinitely higher.
A 'no' from a high-value candidate shouldn't be the end of the conversation. The best approach to recruiting is to be persistent over a long time horizon. A rejection today may turn into a hire five years from now if you maintain the relationship.
When an executive leaves, the CEO should step in to run their department directly. This provides invaluable operational context for hiring a replacement and empowers the CEO to make necessary but difficult changes (org structure, personnel) that a new hire would hesitate to implement.
The conventional wisdom for SaaS companies to find their 'second act' after reaching $100M in revenue is now obsolete. The extreme rate of change in the AI space forces companies to constantly reinvent themselves and refind product-market fit on a quarterly basis to survive.
A technical CEO shouldn't ship production code. Their most effective use of coding skills is to build quick demos. This proves a feature's feasibility and can effectively challenge engineering estimates, demonstrating that a project can be completed faster than originally projected.
In a hyper-growth market where demand is at an all-time high, it's easy to mistake a favorable environment for individual skill. This powerful 'current' can hide significant operational flaws, which only become apparent when the market inevitably shifts, as seen in the ZIRP era.
The popular belief that AI companies are inherently more efficient is a misinterpretation of their age. They are still hiring at a rapid rate. Human-intensive functions, like building a large enterprise sales force, still require significant time and headcount to scale, regardless of AI's influence on product development.
While Silicon Valley idolizes new companies, the most impressive feat is sustained relevance. A company like Microsoft surviving and re-capturing dominance across multiple technological generations is statistically harder and more remarkable than a single startup's initial success.
The CEO role is not a joyful or fun job; it's a high-pressure, problem-solving position. Founders who love their craft, like software engineering, often take the CEO title out of necessity to solve a larger problem and bring a vision to life, not because they desire the job itself.