I've heard of "hierarchy-less" company structures being attempted before. I've also heard that each and every one of those attempts always ended up with hierarchies anyway, only now they became "shadow" hierarchies, unofficial and undocumented. Because that's just how human nature works. Not everyone can stay locked in on what every else is doing while still also keeping up with their own responsibilities, so other people get deferred to instead.

Is there happy middle-ground that can be found here? Is there any research out regarding tree-less company structures that may actually work in the real world?

It's not about acting on your own or achieving something for yourself. It's about building something which is only possible with collective effort of hundreds or thousands of humans. The size of such organization needs hierarchy, management and process.

Think of what processes and management was used for pyramid building. And what would have happened if the workers worked without a boss and process.

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.

I was taught to consider the agenda an author has, Paul Graham’s agenda is to invest in startups to earn a massive return on a few winners. Convincing people they should work in startups benefits Paul Graham. Paul Graham would be a nobody if ZIRP never happened, I’m not sure why people listen to him. He just got lucky that money was free to borrow for a decade which forced capital to chase gains anywhere they could.

Some people want to try to die rich and unloved by 40. Some people work to be able to afford what they want to do. Different strokes, eh.

I'm completely self taught as a software engineer. Since I started I had a passion for writing code every single day. My ideas at first were huge and ambitious but as time passed I noticed they became smaller and more "grounded". But that also correlated with my trajectory in my career. The first few jobs I had were small contracts. Working for myself and hustling against overseas engineers charging 1/100th what I wanted to charge. Then, I went to work for a government agency.

I had big ideas of cool solutions we could build to old problems they were dealing with. I implemented a genetic algorithm that reduced the time it took to estimate how to move water from one location to the next from 15 hours down to 30 seconds. But, we couldn't push the solution to production until several committees could meet and discuss it at length. I left that place after a year and now, 10 years later, they're still struggling with their old technology and slow paced processes.

I then went to work for a startup that wanted to do facial biometrics for fraud prevention. When I arrived they had 7 marketing people, a paying customer, but no actual software developed. Me and a few other engineers wrote the core of the application in a few days and then spent the rest of our time there fleshing it out into a real product. We were working 60 to 80 hours a week, nights, weekends, the whole enchilada. It was exhausting physically and emotionally but it was the best job I ever had. I had complete freedom to design everything from the ground up, got stuff pushed to production seconds after I committed my code, and got to develop some pretty innovative solutions for liveness detection and geo-fencing.

I then roamed around for a few years, salary hopping, from corporation to corporation until I landed at a big company. The work was easy and the pay was good. But year after year my love of software engineering started to die. There were no challenging problems to work on, the solutions were cookie-cutter implementations for every project, and the politics were exhausting. What should have taken 2 weeks of work would stretch to 2 months due to unnecessary meetings, and status updates, and leadership constantly changing their mind. And worst of all, I wasn't learning anything new or growing as an engineer.

Toward the end, every single team became a "modernization" team where all they would work on was updating legacy software to "modern" tech stacks. This was obvious busy work because leadership had nothing better to do with the hundreds of engineers they had hired. Eventually, when I had enough money saved up, I decided to retire.

But I always missed working at that startup. The rush, the challenge, the real world solutions we were building that were used by real people and making an impact on their lives was amazing. Now that I'm retired and get to choose what I want to work on I think fondly of those times and wish I could recreate that experience.

If PG thinks we weren’t meant to live this way, I’d like to see him out there fighting for universal housing, universal healthcare, universal education including no-tuition college, higher tax rates for billionaires and upcoming trillionaires, abolishing excessive wealth (e.g., we should tax all wealth and assets over $999 million 100% and/or force employee/community ownership of company shares of excessively wealthy individuals), abolishing for-profit prison labor, etc.

If you think this is extreme I would like you to explain how one person being a millionaire 300 times like Paul Graham is isn’t extreme. And then you realize that Elon Musk is as wealthy as 1000+ Paul Grahams.

I don't need to hear another VC giving a management seminar about how unnatural modern work is. I’d like to see them start changing people’s lives for the better, maybe they could start by advocating for the basic needs of the poorest people in our society or something like that.

Some people (most people?) are perfectly happy with just working a stable job within a giant corporation. Either because they are capable of still finding fulfillment from work despite not having so much control (the kind of control that people who start businesses tend to crave), and/or because they find their fulfillment outside of work entirely.