I always wonder what gives these people the drive to continue. Maybe I’m lazy and lacking vision but if I were worth 2B, I don’t think I would go to the office every day just to get accused of mismanagement when I have to lay people off. I would take my yacht to the Caribbean and slack off.
People enjoy having a purpose and a mission in life. Leading a team of people that you put together, in order to improve a project you started, and knowing that doing so will improve both your lives and theirs, is incredibly fulfilling. Even if the day-to-day is full of hardships. In fact, working to overcome hardship is one of the primary source of meaning in life.
Kids are another example. They're expensive, they're annoying, they ruin your health, they take up your free time, they consume all your resources, and they're inherently needy, selfish, and largely incapable of being grateful. Yet raising kids can be profoundly rewarding and fulfilling, in part because of the hardships, and in part because you're contributing to something bigger than just yourself, which is another crucial ingredient of meaning.
Sitting around on a yacht doing nothing is not so different than moving into your parents' basement and doing nothing, save with better scenery. It's the kind of thing you crave when you're burned out, overworked, and jaded, the same way we crave sleep when we're tired and food when we're hungry. It's a reaction to a state of being. But we only desire sleep until rested and we tire of eating once we're sated.
If you ever get to your tropical yacht vacation you may find that, in much the same way, what you thought was a permanent desire was only a temporary one.
Dreaming of winning the lottery and Going On Permanent Yacht Vacation is precisely the difference between being a worn out low-level worker and being a high-level executive who has all their needs met (or at least has the resources to have them met). With the latter you can have enough resources for you next ten generations and still go to work and optimize shareholder profits while thinking to yourself that you are serving a higher purpose.
The average person enjoys villainizing those who they see as somehow "above" them in standing, whether that's social, financial, or otherwise. They are of course incensed when the people "below" them do the same thing.
Type A people who become CEOs don't dream of sitting around on yachts.
Some might be driven by money, but at a certain level it probably switches to a sense of responsibility, but also, it's intoxicating to be at the top where you don't really have to work in the same way, but get to direct what happens. People enjoy power. People enjoy the secrets of what happens at the top. People enjoy the recognition (within their peer group). etc...
One hardly needs $2B to slack off on a boat in the Caribbean… many people do so on surprisingly nice ~30 foot sailboats you can buy with a few months work at minimum wage, and wild seafood is free
I see a lot of people that say “If I won the lottery I’d….” and then describe something they could definitely do without winning the lottery… which makes me think they still would not actually do so if they won
Sure there is- opportunity cost, the real dangers and skills required to operate a vessel at sea, etc. You can pay a professional crew to do everything for you, but then you'll probably feel pretty useless, and be looked down upon by the people you meet along your journey that do it themselves.
The sea doesn't care how rich you are, and being a helpless dependent is boring and infantilizing no matter how big your boat - and you don't develop skills without taking risks.
Ultimately, I don't think people are often that conscious of their real goals and motivations. It's easy to say you have no choices in life because of financial and time constraints, but I don't think those are the real reasons most people choose to do or not do things.
I don't have billions and I don't manage people (I've been voluntold to manage 1 person a few times, and I'd rather that not happen again), but I have enough that I don't need to work for economic reasons.
I'm working part time anyway, because it keeps me busy and interacting with people outside my home, and it gives me access to interesting real world problems that I can't really access as an individual person on the interwebs. Having other people depend on me to get things done provides motivation to keep moving on things that I can't seem to manage on my personal projects.
If I liked the kind of organizational management work a CEO does and I was good at it, I'd probably get roped into being a CEO.
Ultimately he mentions that being CEO is a rare opportunity to play a more infinite game and practice the craft of getting really good at something that doesn't have an end
Yeah I figure a long shot deep tech project would be better suited to a billionaire. Little to no accountability for the first decade or so, and loads of glory if it somehow works out.
I can understand wanting to continue doing something. What I don't understand is why instead of putting their time and now considerable wealth into more philanthropic pursuits, they decide to continue increasing their wealth, often at the expense of other, less fortunate people.
People who have mission and vision of the future are entrepreneurs because they want to solve problems and help other people not because they want to become rich and sail with yacht.
Listen to Snapchat's founder and CEO Evan Spiegel[0] why he didn't sell to Facebook for $3 billion. He even didn't sell to Google which offered 10x more ($30bn) for Snapchat.
To clarify, I actually kind of get it for businesses that actually have a important mission (using my definition of important of course). If you’re working on curing cancer, I would understand that a CEO doesn’t want to leave even if he’s set for life. I just don’t see entertainment and service businesses like Snapchat or Dropbox as actually meaningful endeavors. To me they are nice to have and something I would work at for money, but I wouldn’t feel like I’m making the world a better place. Maybe that’s exactly the thing I was misunderstanding about those CEOs, they truly think their work is needed and important for the world.
No idea about what big CEOs feel but for me, I would absolutely continue working even if I was a trillionaire someday. What matters and drives me would be impact and influence I could have on society. Have couple billions? Throw them on things I care about and keep getting more to throw at the same.
Some people do exactly that but it's rare that someone will simultaneously have the drive to do something that will generate them billions of dollars and also be willing or able to just stop working at that point.
Also remember once you have that much money a lot of things become basically free, both figuratively ($100,000 to a billionaire is nothing) and literally (comped rooms, gifts, etc for basically every event and your company(ies) end up footing the bill for most of your expenses).
There's plenty of people who make $5-50 million in a windfall and are never heard from again.
True, it’s probably that this drive is what allowed them to be billionaires in the first place.
Just to rant a bit more: the Wordpress situation makes this point even more crazy to me. Mullenweg has about 400m and instead of retiring and enjoying life, he’s arguing with anonymous users on Hacker News. No offense against hacker news but defending my life decisions on HN isn’t exactly the first thing I would do if I could do everything I ever wanted. Like, go buy a plane and take flying lessons, or go scuba diving? Nah, I’d rather justify myself on the internet.
The internet is a direct pipe to every person on earth. You have to acknowledge that this is new territory for humankind.
In fact, internet communication is much closer to dark-age "public square" type communication. Bring your soapbox to the square, talk loudly, gather a crowd, and listen to the crowd jeer or clap. We haven't had that since the industrial revolution pre-1800s (i.e. at the earliest 1700s)
For the forseeable future, we are in a situation where people will "feel" that the most authentic communication is intentionally said in-front of the internet bystanders. So a CEO posting an intimate reply to an individual with billions of people able to see the intimate reply is more "authentic" than everything else.
(Much closer to dark-age communication implies that we are closer to "old" methods of communication that disappeared for the last couple of centuries. We used to have industrial revolution-type communication medium, one-direction broadcast medium.)
I expect a lot of people with that kind of money can't enjoy life as it disconnects them from everyone else. Your friends can't afford to do those things with you, so you either end up buying friends – with all the disillusionment that goes with that – or you turn away from people and get your fix trolling computers instead.
I have a slightly different version of this. There are some other replies here to the effect of "people like to have a purpose in life". But surely "helping people share files" or whatever the Dropbox "mission" is can't be that inspiring, right? I mean, the point of starting a company like that is to make those billions. Maybe to do it successfully you need to delude yourself into thinking that mission is really important, I don't know.
But for me, if I had that kind of business success I'd cash out and go do something that feels actually important. Go get a PhD and take a crack at curing some obscure disease, or setting up a Dyson swarm around the sun, or making a great work of art, or thinking about how to improve elementary education a la Khan Academy; something like that. Then you get to have a real purpose and work toward something that most people don't just by virtue of the fact that it doesn't pay well enough, and you still get to spend plenty of time on your yacht!
The instinct to acquire resources does not have a limit. When homo sapiens evolved, such a limit would not have been a useful adaptation. There were no billionaires then.
Also it's nice to boss people around, probably for the same reason.
You and lots of people say would do something or other. I submit that it's different when you're actually in that position, as opposed to imagining it. Lots of us imagine we're going to go to the gym for years, and give up after a month or two.
Some people have made the (good in my opinion) point that this is actually survivorship bias and a lot of people actually do retire and are never heard from again once they have enough money. So people predicting what they would do aren’t necessarily that wrong, it seems that some people actually do that.
I got from the other comments that he got the 2B by owning part of the now very valuable company, not by working for a salary. Assuming he picked a good enough successor that didn’t completely ruin Dropbox, he should still have pretty much the same net worth without any work, no?
