Re-reading old Paul Graham essays is revealing for how much my startup experience has changed my views. I remember this essay resonating with younger me.

Reading it now, I spot the reader-directed flattery much earlier (it literally starts in the title). I also have years of experience with a couple successful and even more failed startup founders behind me.

Maybe this essay was discussing narrowly the breakout YC company founders like Dropbox, AirBnB, Doordash, and the other top successful CEOs they saw. Most things in venture capital focus on the survivorship bias of the best companies and forget the others.

My experience with startups has been the opposite: The founders who "weren't meant to have a boss" either because they told you so themselves or they failed out of big companies due to being unmanageable or fighting their boss were the people who also had conflicts with cofounders and early employees. They'd get into fights with investors and the one or two board members you get after early funding rounds. Since they'd never successfully let themselves be managed or work as a team, they didn't know how to manage other people.

Some of them saw the founder role as equivalent to being king, with employees as their indentured servants who owed them 16 hour days in exchange for 0.05% of their empire, vesting over 4 years.

I haven't been lucky enough to be an early employee at one of the unicorn startups, but the successful startups I was part of had mature leaders who did well in other companies before founding their own. The "not meant to have a boss" founders I worked for are the periods of my career I wish I could go back and erase.