My Emotions as a CEO(ryancaldbeck.co)
ryancaldbeck.co
My Emotions as a CEO
https://ryancaldbeck.co/2021/10/08/my-emotions-as-a-ceo/
93 comments
I’m currently in that 1,2, 3 trifecta and it’s very challenging most days. It’s been a tough year: co-founder quit along with a few others and investors loosing patience, but I’m trying to keep everything together.
I haven’t given up because I believe in what we’re doing (most days) and I want to see if I’m capable of turning this thing around.
I appreciate this comment a lot. Thank you.
I haven’t given up because I believe in what we’re doing (most days) and I want to see if I’m capable of turning this thing around.
I appreciate this comment a lot. Thank you.
When we are infants, our close social circle enthusiastically encourages us to walk, through every failed attempt, until we walk (and then run) without thinking. As adults I think we generally don't curate a social circle that will give us this enthusiastic encouragement through failure and the burden falls on our self-esteem to summon it from within ourselves.
So two things:
1) For what it's worth, you're not alone. As someone who walks a similar path, I want to give you sincere encouragement to keep going!
2) To the degree that you've already done this, try to build a social circle around you of people who will can relate and enthusiastically encourage you through failure. There may be an international club you could join, a group of CEO friends you can pull together, or maybe you start a Meetup.com group. I don't know what will work for your specific circumstances, but something will.
Best of luck!
So two things:
1) For what it's worth, you're not alone. As someone who walks a similar path, I want to give you sincere encouragement to keep going!
2) To the degree that you've already done this, try to build a social circle around you of people who will can relate and enthusiastically encourage you through failure. There may be an international club you could join, a group of CEO friends you can pull together, or maybe you start a Meetup.com group. I don't know what will work for your specific circumstances, but something will.
Best of luck!
Edit: sorry for the confusion, "PFM" was meant to say PMF (autocorrected and I didn't notice) - product market fit.
Having had that 1-2-3 combination, they were some of the most difficult years of my life.
But the lessons I learned were invaluable and could not have been learned any other way.
And - the next thing I started achieved Product Market Fit right out the gate.
But the lessons I learned were invaluable and could not have been learned any other way.
And - the next thing I started achieved Product Market Fit right out the gate.
What does PFM stand for?
I think he means "Product Market Fit"?
I right-clicked and Looked It Up
Premiata Forneria Marconi is an Italian progressive rock band founded in 1970 and which continues to the present day. They were the first Italian group to have success internationally. The group recorded five albums with English lyrics between 1973 and 1977. During this period they entered both the British and American charts.
Premiata Forneria Marconi is an Italian progressive rock band founded in 1970 and which continues to the present day. They were the first Italian group to have success internationally. The group recorded five albums with English lyrics between 1973 and 1977. During this period they entered both the British and American charts.
Product Farket Mit
product market fit (PMF), the PFM abbreviation are typos i believe.
It seems like a permutation or typo or autocorrect for “product market fit”?
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I'm sorry this person has had such a negative experience of the job. I can relate to some of it, but as a former CEO (up to a team of 20-30) I've not felt lonely or jealous. Does he really think a desire to leave is unique to the c-suite? Apallingly out of touch.
In my experience you get what you sign up to take. As CEO of a company that's taken tens of millions in funding you a) are indepently wealthy b) have other options for fulfilling work c) can apply a massive amount of control to your everyday circumstances. Don't feel like reading 500 emails a day? Delegate more effectively. Feel lonely? Should have made some fucking true friends in your life. Feel an unbearable desire to quit? Figure it out or, you know, quit. I did.
Founder-CEO is a great privilege of a job and this self-pity party is unbecoming of a leader. You don't have to be happy all the time but you do have to face the fact you've chosen this life again and again over many options most people will never have the privilege of having. It's not a life sentence.
In my experience you get what you sign up to take. As CEO of a company that's taken tens of millions in funding you a) are indepently wealthy b) have other options for fulfilling work c) can apply a massive amount of control to your everyday circumstances. Don't feel like reading 500 emails a day? Delegate more effectively. Feel lonely? Should have made some fucking true friends in your life. Feel an unbearable desire to quit? Figure it out or, you know, quit. I did.
Founder-CEO is a great privilege of a job and this self-pity party is unbecoming of a leader. You don't have to be happy all the time but you do have to face the fact you've chosen this life again and again over many options most people will never have the privilege of having. It's not a life sentence.
I read your post before the article, and based on your post, the article is not at all what I expected. The author was clearly respectful and appreciative of the opportunity he was given. This was an honest appraisal of the emotions he felt during that time, which were often not positive. It's the type of vulnerability that we should probably encourage from our leaders, but we are often too immature to handle it.
Your post to me smacks of toxic positivity. It's ok to admit that not everything is great (even though we are just about all of us on this forum lucky and blessed). It's the human condition, and nobody is exempt.
BTW, you do realize he has stepped down and this is a retrospective, right?
Your post to me smacks of toxic positivity. It's ok to admit that not everything is great (even though we are just about all of us on this forum lucky and blessed). It's the human condition, and nobody is exempt.
BTW, you do realize he has stepped down and this is a retrospective, right?
It seems like because he was a CEO of a small company who did not feel these issues that he has some kind of credibility to lambast someone else who does. It's an incredibly toxic attitude to have.
Did we read the same article? I didn't interpret it as a pity-party at all. I haven't been a CEO, but I have been in upper management, and that has been stressful enough for me to know that being a CEO is the last thing I could do.
I just thought this post was an honest discussion of one person's emotions, and I didn't feel that it was too strong one way on the positives or the negatives. If anything I found it helpful putting into context some of my own emotions that I have in leadership positions.
I just thought this post was an honest discussion of one person's emotions, and I didn't feel that it was too strong one way on the positives or the negatives. If anything I found it helpful putting into context some of my own emotions that I have in leadership positions.
Maybe my reading was too coloured by my own emotions and experiences with the job, and I apologize if so, but continuing my rant I have a real problem with anyone who takes very optional and voluntary hardships on and complains they're hard. Especially when the problems he openly talks about are so in his control. Email, really? Tell me about the times your own board tried to oust you or the funerals you missed for a biz dev meeting that went nowhere and maybe I'll take you seriosly.
It makes me uneccessarily mad to read about sacrifice in privilege. CEOs sometimes want to quit the job? How about grunts on deployment? My paternal grandfather was a military man - wartime general. Never heard him complain but did hear a proud story of when he was a platoon commander in the jungle. If his platoon happened on a mine field he'd stand besides the poor sod tasked with defusing it until the job was done. That's leading. That's grit.
Let's have conversations about mental health and sacrifices, but let's not pretend san francisco tech entrepreneurs leading large successful companies are in a uniquely hard place in life.
It makes me uneccessarily mad to read about sacrifice in privilege. CEOs sometimes want to quit the job? How about grunts on deployment? My paternal grandfather was a military man - wartime general. Never heard him complain but did hear a proud story of when he was a platoon commander in the jungle. If his platoon happened on a mine field he'd stand besides the poor sod tasked with defusing it until the job was done. That's leading. That's grit.
Let's have conversations about mental health and sacrifices, but let's not pretend san francisco tech entrepreneurs leading large successful companies are in a uniquely hard place in life.
If you're leading a company of young, mainly unattached folks and don't have other companies depending on your product, then yes, it's more like a gold rush where you all prosper together and the downside of flying the company into a mountain is 'oh, well, we tried and we learned, let's move on to the next thing.'
It's a different matter if your company is staffed by family breadwinners and you have customers that would have serious deletierious consequences if your firm failed. You don't even need to fail, just go through a rough patch and lay off some the workers you hired and trained, or, fail to deliver a project that negatively affects a customer. These are nerve-wracking for CEOs that aren't made of the stuff that can lead firmly through these situations.
Perhaps the better notion is that startup CEOs that really do react poorly to the 'hard stuff' need a plan to move the burdensome work to a 'professional CEO' and step into Chairman/CTO, or somesuch. Keep the fun, keep the equity, offload the hard stuff.
It's a different matter if your company is staffed by family breadwinners and you have customers that would have serious deletierious consequences if your firm failed. You don't even need to fail, just go through a rough patch and lay off some the workers you hired and trained, or, fail to deliver a project that negatively affects a customer. These are nerve-wracking for CEOs that aren't made of the stuff that can lead firmly through these situations.
Perhaps the better notion is that startup CEOs that really do react poorly to the 'hard stuff' need a plan to move the burdensome work to a 'professional CEO' and step into Chairman/CTO, or somesuch. Keep the fun, keep the equity, offload the hard stuff.
Your last paragraph. Correct.
The fear of letting people down can be crippling. To be brutally honest, there is a type of CEO who simply doesn't feel that as deeply as some people, and they tend to do well in the job, especially when times are good.
In my experience, that type of person is not the same type of person who comes up with an idea and creates something out of nothing. You need some real empathy to find product-market fit; you have to actually care about users and early adopters and by extension investors and employees. But that profile I don't think works at a big company, there is a totally different dynamic.
The fear of letting people down can be crippling. To be brutally honest, there is a type of CEO who simply doesn't feel that as deeply as some people, and they tend to do well in the job, especially when times are good.
In my experience, that type of person is not the same type of person who comes up with an idea and creates something out of nothing. You need some real empathy to find product-market fit; you have to actually care about users and early adopters and by extension investors and employees. But that profile I don't think works at a big company, there is a totally different dynamic.
Hence the stereotype of effective CEOs being sociopaths: their empathy is for the money, not anything--or anyone-- else. They can make a lot of decisions that we would consider difficult, in a completely dispassionate manner, and that's how and why they become good for the job.
The article didn't come across as a complaint to me, rather a description of the emotions they experienced while in that role.
I guess what triggers me is the stressors they describe as responsible for those emotions. To me they are meaningless compared to things that really should cause anxiety in a CEO: am I making payroll this month if deal X falls through? Can I land in jail if thing Y turns out to be illegal instead of a harmless hustle? If I fizzle is my professional life over?
The Hard Thing About Hard Things made the same points as the author in much more poignant ways to me, when I read it. No current or future CEO should stress about volume of email or thoughts of another career as a bartender in a tropical island - stress about real problems instead.
The Hard Thing About Hard Things made the same points as the author in much more poignant ways to me, when I read it. No current or future CEO should stress about volume of email or thoughts of another career as a bartender in a tropical island - stress about real problems instead.
I hear you and often I have a similar reaction—why does this person feel X when Y happens because I feel Z when Y happens, so it makes no sense for them to feel X.
So for you, those stressors may seem meaningless. However, to that person, those stressors may feel devastating. Likewise, some things that deeply impact you may seem trivial to them.
I, like you, would imagine that the "am I making payroll this month" would be a larger stressor on a CEO (I've never been one so I haven't been in that situation) than the volume of email I'd receive, and yet I can also imagine the payroll stress is relatively infrequent where the email stress may be a nagging drag, bringing with it incessant uncertainty of 1) whether what I say in an email will be posted to Twitter or used against me in 10 years, 2) news that rockets the company or tanks it, or even 3) an email that notifies me I won't make payroll this month.
I dunno. I say this to you as much as to myself to remind me that while we might all feel very similar emotions, sometimes we attribute very different causes to those emotions.
*edit: and remembering this and actually accepting that other people have different emotional responses to the same stimuli than I do is one of the things that confuses and frustrates me the most.
So for you, those stressors may seem meaningless. However, to that person, those stressors may feel devastating. Likewise, some things that deeply impact you may seem trivial to them.
I, like you, would imagine that the "am I making payroll this month" would be a larger stressor on a CEO (I've never been one so I haven't been in that situation) than the volume of email I'd receive, and yet I can also imagine the payroll stress is relatively infrequent where the email stress may be a nagging drag, bringing with it incessant uncertainty of 1) whether what I say in an email will be posted to Twitter or used against me in 10 years, 2) news that rockets the company or tanks it, or even 3) an email that notifies me I won't make payroll this month.
I dunno. I say this to you as much as to myself to remind me that while we might all feel very similar emotions, sometimes we attribute very different causes to those emotions.
*edit: and remembering this and actually accepting that other people have different emotional responses to the same stimuli than I do is one of the things that confuses and frustrates me the most.
The author described the constant emails as "exhilarating" and something he loved, even if it meant raised adrenaline levels.
> Tell me about the times your own board tried to oust you or the funerals you missed for a biz dev meeting that went nowhere and maybe I'll take you seriosly.
This comes across as gatekeeping and I can only wonder what has riled you up so much about the author's experience to go on this kind of attack.
This comes across as gatekeeping and I can only wonder what has riled you up so much about the author's experience to go on this kind of attack.
> the funerals you missed for a biz dev meeting that went nowhere
I assume you were a CEO and you chose a biz dev meeting over a funeral. No, several funerals in fact.
In that case, that fucking sucks. I'm sorry for your loss.
But, in your words:
> I have a real problem with anyone who takes very optional and voluntary hardships on and complains they're hard
Sounds like you're angry because he made the same decision - to choose work over the other thing. And to then be unhappy about it.
I assume you were a CEO and you chose a biz dev meeting over a funeral. No, several funerals in fact.
In that case, that fucking sucks. I'm sorry for your loss.
But, in your words:
> I have a real problem with anyone who takes very optional and voluntary hardships on and complains they're hard
Sounds like you're angry because he made the same decision - to choose work over the other thing. And to then be unhappy about it.
I can't speak to being a CEO - I'm just a middle manager - but a lot of this, especially the loneliness, resonated with me.
Did I choose management? Yes. Do I have a choice to stop? Also, yes. Do I make enough money either way to have a nice apartment and no real material concerns? That too.
But I'm definitely stressed and lonely. I'm really not sure if this is what's best for my mental health. From the article him and I aren't the only ones with that feeling. My boss, too, has talked about feeling exhausted; when we have events for leads, it feels like we're even more burned out than the rank-and-file.
Lonely is easy to explain. The more you move up, the fewer peers you have. The fewer people you have to look up to and emulate. The more "on your own" you are, expected to operate independently and direct more folks. There's less of a playbook. More acting by intuition. More people looking up at, depending on, and often resenting you. Your relationships with communities of coworkers changes. When they're upset, rather than joining in on the griping and feeling camaraderie you feel either vaguely responsible or unaware of what's really been going on. Whatever it is not just a thing to bitch and moan about - you're responsible.
The stress comes from the same place - feeling a sense of responsibility for all the people in your org, for the company, all of it. It's a much bigger scope than your IC responsibility. It's hard to let go of, to accept that you might not pick the right 2 or 3 of 100 things to focus on, and when you do, there are real consequences for real people. With that kind of scope you're making a lot more mistakes just because there's so much more surface area. Those mistakes matter, too! Hire the wrong person, ignore a team that needs your attention? These are big painful mistakes. People might quit, their careers might languish, an asshole might make people miserable, customers might have a bad day(/month/quarter/etc), etc.
You have to accept a lot of failure in this very difficult job with a huge scope and no real rules or guidance, but that's hard when you're a competitive, success-oriented person.
"But you can quit!" is a valid argument. One the article addresses - it says it takes years to set up for a CEO. For me, it's shorter, but I still feel like it's something that you can't just hire an eager replacement for - for a bunch of reasons. Pick the wrong person, and again, lots of consequences to people you care about.
Somebody in leadership did quit without notice recently - and I saw all their reports bump up to their lead, who was already way stretched thin. Those people won't have real support for a long time. Their new lead is really stretching himself very thin. I hope the person who quit is able to find peace in it (genuinely, I don't think they wouldn't have done it if they felt there were alternatives). But I know I wouldn't be able to.
Sometimes I wonder if there would be an equivalent to a Dwarf Fortress tantrum spiral. Somebody quits, their team flows up, that person then snaps, etc, until half the company is reporting to a handful of people. (and imagine how responsible the CEO would feel if that happens?)
Also - COVID has made all of this worse.
Did I choose management? Yes. Do I have a choice to stop? Also, yes. Do I make enough money either way to have a nice apartment and no real material concerns? That too.
But I'm definitely stressed and lonely. I'm really not sure if this is what's best for my mental health. From the article him and I aren't the only ones with that feeling. My boss, too, has talked about feeling exhausted; when we have events for leads, it feels like we're even more burned out than the rank-and-file.
Lonely is easy to explain. The more you move up, the fewer peers you have. The fewer people you have to look up to and emulate. The more "on your own" you are, expected to operate independently and direct more folks. There's less of a playbook. More acting by intuition. More people looking up at, depending on, and often resenting you. Your relationships with communities of coworkers changes. When they're upset, rather than joining in on the griping and feeling camaraderie you feel either vaguely responsible or unaware of what's really been going on. Whatever it is not just a thing to bitch and moan about - you're responsible.
The stress comes from the same place - feeling a sense of responsibility for all the people in your org, for the company, all of it. It's a much bigger scope than your IC responsibility. It's hard to let go of, to accept that you might not pick the right 2 or 3 of 100 things to focus on, and when you do, there are real consequences for real people. With that kind of scope you're making a lot more mistakes just because there's so much more surface area. Those mistakes matter, too! Hire the wrong person, ignore a team that needs your attention? These are big painful mistakes. People might quit, their careers might languish, an asshole might make people miserable, customers might have a bad day(/month/quarter/etc), etc.
You have to accept a lot of failure in this very difficult job with a huge scope and no real rules or guidance, but that's hard when you're a competitive, success-oriented person.
"But you can quit!" is a valid argument. One the article addresses - it says it takes years to set up for a CEO. For me, it's shorter, but I still feel like it's something that you can't just hire an eager replacement for - for a bunch of reasons. Pick the wrong person, and again, lots of consequences to people you care about.
Somebody in leadership did quit without notice recently - and I saw all their reports bump up to their lead, who was already way stretched thin. Those people won't have real support for a long time. Their new lead is really stretching himself very thin. I hope the person who quit is able to find peace in it (genuinely, I don't think they wouldn't have done it if they felt there were alternatives). But I know I wouldn't be able to.
Sometimes I wonder if there would be an equivalent to a Dwarf Fortress tantrum spiral. Somebody quits, their team flows up, that person then snaps, etc, until half the company is reporting to a handful of people. (and imagine how responsible the CEO would feel if that happens?)
Also - COVID has made all of this worse.
> as a former CEO (up to a team of 20-30) I've not felt lonely or jealous
Re: loneliness, you must have had a tremendous support network of other executives. I find the job rather lonely not because I’m not around people but because the people I’m around don’t understand half the words coming out of my mouth when talking about the top 3 work related challenges I’m having at any given time.
> Feel lonely? Should have made some fucking true friends in your life.
That’s just unnecessarily cruel.
Re: loneliness, you must have had a tremendous support network of other executives. I find the job rather lonely not because I’m not around people but because the people I’m around don’t understand half the words coming out of my mouth when talking about the top 3 work related challenges I’m having at any given time.
> Feel lonely? Should have made some fucking true friends in your life.
That’s just unnecessarily cruel.
Re loneliness I knew zero other executives or business people when I started. I had a great support network of close friends and family, but no one I could confide in. What I think helped me cope (when I could cope) was keeping front and center how privileged I was to have chosen this mountain to climb. I've since met people starting startups literally in the middle of warzones. Can't complain I've had it too rough. Neither has Ryan from the stories which is the point of the cruelty.
If he has had it rougher than it seems, let's hear those stories! Would make for much better blogging than this.
If he has had it rougher than it seems, let's hear those stories! Would make for much better blogging than this.
FYI, you come across as an asshole, then you explain yourself and still seem like an asshole.
I fail to see how the legitimacy of someone’s suffering or emotions is affected by their societal privilege.
Well not the suffering, you're certainly right there. But the internal narrative around that suffering can be challenged, and in being challenged lessen the suffering. In my experience. Doubly so in public.
There are definitely phases. Managing 20 or 30 people feels a lot different than managing a hundred or more. Up until about fifty, you can keep that family\team feeling that you're all in it together. You know everyone, and they all know each other.
But somewhere a few months after a typical A-round, you start walking through the hall and wonder who the hell these people are? Who hired them? Do they really have the company's best interest at heart, or are they just freeloaders?
Probably related to this, around that size you start to get the more toxic kind of politics. You realize people have agendas that they don't admit. The first rule of Fight Club...
I think another way of describing what he calls loneliness would be paranoia. People put so much faith in their leaders, and they are so let down when they think you failed them. The term emotional roller coaster just doesn't do it justice. It sometimes feels more like you're in a blender.
Strangely enough, I plan to do it again. But I think I'll tap out around that phase change if we're lucky enough to get there. It takes a whole different type of human being to take a company from a few million in sales to something impressive enough to make investors really happy they invested in you.
It's certainly not for everybody.
But somewhere a few months after a typical A-round, you start walking through the hall and wonder who the hell these people are? Who hired them? Do they really have the company's best interest at heart, or are they just freeloaders?
Probably related to this, around that size you start to get the more toxic kind of politics. You realize people have agendas that they don't admit. The first rule of Fight Club...
I think another way of describing what he calls loneliness would be paranoia. People put so much faith in their leaders, and they are so let down when they think you failed them. The term emotional roller coaster just doesn't do it justice. It sometimes feels more like you're in a blender.
Strangely enough, I plan to do it again. But I think I'll tap out around that phase change if we're lucky enough to get there. It takes a whole different type of human being to take a company from a few million in sales to something impressive enough to make investors really happy they invested in you.
It's certainly not for everybody.
Does he really think a desire to leave is unique to the c-suite?
I think what he's suggesting is that people might be surprised that even CEOs feel that way. Outsiders tend to assume people with money and power are happy and where they want to be. Escapist fantasies are probably not something most CEOs routinely admit to.
I think what he's suggesting is that people might be surprised that even CEOs feel that way. Outsiders tend to assume people with money and power are happy and where they want to be. Escapist fantasies are probably not something most CEOs routinely admit to.
> Does he really think a desire to leave is unique to the c-suite?
He didn't say that. I read an article about someone openly reflecting on their feelings.
He didn't say that. I read an article about someone openly reflecting on their feelings.
> As CEO of a company that's taken tens of millions in funding you a) are independently wealthy
Raising tens of millions doesn't make you independently wealthy, though it greatly increases the chance you may be someday. To me, independently wealthy means you can stop working and live a very comfortable life using existing funds and the wealth they generate.
Founders who have raised money — even tens of millions — are generally dependent upon the business that raised the money. If they walked away from being CEO, they might be rich on paper, but they also would have just tanked the commercial value of their largest asset (stock in said company).
Raising tens of millions doesn't make you independently wealthy, though it greatly increases the chance you may be someday. To me, independently wealthy means you can stop working and live a very comfortable life using existing funds and the wealth they generate.
Founders who have raised money — even tens of millions — are generally dependent upon the business that raised the money. If they walked away from being CEO, they might be rich on paper, but they also would have just tanked the commercial value of their largest asset (stock in said company).
> Does he really think a desire to leave is unique to the c-suite? Apallingly out of touch.
From what he writes, I think he believes most people think a CEO never thinks about leaving.
After all, why would you leave the company you started?
From what he writes, I think he believes most people think a CEO never thinks about leaving.
After all, why would you leave the company you started?
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>as a former CEO (up to a team of 20-30) I've not felt lonely or jealous
CircleUp is probably 3x as big and C-Level work/responsibility grows exponentially as headcount increases.
CircleUp is probably 3x as big and C-Level work/responsibility grows exponentially as headcount increases.
That seems unlikely, no? How would Jack Welch ever have been about to cope with 10^19 the work as this dude (or me)?
At a certain point it all just ... tops out certainly or we'd have no Presidents. Certainly whoever is the CEO at circleup has had more responsibility than I have ever had, but exponentially more?
I think it's much more likely different people feel stress in different ways, and that what we bring to the job influences our experience.
Not to paint myself as a stoic in any sense, I can remember spells of not being able to sleep for 3 nights in a row out of terror and axiety. But when that happens you must find mechanisms to keep it from happening again. The pain is transient, not intrinsic.
At a certain point it all just ... tops out certainly or we'd have no Presidents. Certainly whoever is the CEO at circleup has had more responsibility than I have ever had, but exponentially more?
I think it's much more likely different people feel stress in different ways, and that what we bring to the job influences our experience.
Not to paint myself as a stoic in any sense, I can remember spells of not being able to sleep for 3 nights in a row out of terror and axiety. But when that happens you must find mechanisms to keep it from happening again. The pain is transient, not intrinsic.
Welch had an annual workforce decimation.
There is no way work/responsibility grows exponentially as headcount increases. Walmart has 2.2 MILLION employees. I doubt Doug McMillon works exponentially harder than a CEO with 1000 employees.
I always appreciate it when folks write about their humanity, in this venue.
Of course, everyone will have their opinion, as to the "validity" or whatever, of what people share here, and I can't always say that I'm thrilled with what these folks write, when they share their humanity, but I'm still glad they do it.
Despite all the technology, infrastructure, money, and culture, the basic work unit in technology is always a human, and humans are complex, emotional creatures. Our relationships with each other, and the teams we build, are what make great product and endeavors.
I have nothing to share about, regarding this chap's journey. We have had different paths in our lives, and I don't really relate too much to this article. I have liked other articles that he's written.
Of course, everyone will have their opinion, as to the "validity" or whatever, of what people share here, and I can't always say that I'm thrilled with what these folks write, when they share their humanity, but I'm still glad they do it.
Despite all the technology, infrastructure, money, and culture, the basic work unit in technology is always a human, and humans are complex, emotional creatures. Our relationships with each other, and the teams we build, are what make great product and endeavors.
I have nothing to share about, regarding this chap's journey. We have had different paths in our lives, and I don't really relate too much to this article. I have liked other articles that he's written.
A sense of inadequacy, jealousy, arrogance and adrenaline are likely interrelated.
You don't feel jealous because someone else has something. You feel jealous because of what you lack.
Arrogance is often a cover up for self esteem issues. Adrenaline suggests a fear that you won't be able to rise to the occasion.
Not everyone will experience that to that degree when in charge. Though we do have the saying "It's lonely at the top" so I fully believe that part is very much the norm.
You don't feel jealous because someone else has something. You feel jealous because of what you lack.
Arrogance is often a cover up for self esteem issues. Adrenaline suggests a fear that you won't be able to rise to the occasion.
Not everyone will experience that to that degree when in charge. Though we do have the saying "It's lonely at the top" so I fully believe that part is very much the norm.
Super insightful. Do you have a background in psychology or just good at joining the dots on human emotion?
I've had intro to psych and a social psychology class in college, plus other classes with a psych component. I also spent years in therapy and was a full-time mom raising special-needs kids for two decades and attended unaccredited classes to help me parent them.
My very "aspie" kids needed a lot of social/emotional stuff explained to them and it had to meet a pretty high bar. They are too literal for the usual explanations to work well.
My very "aspie" kids needed a lot of social/emotional stuff explained to them and it had to meet a pretty high bar. They are too literal for the usual explanations to work well.
Your kids are lucky to have such a switched on hard working Mum. Keep up the good work :)
> Though we do have the saying "It's lonely at the top"
I wonder, is it because it's more lonely at the "top" than at the "bottom", or because people expect the "top" to be less lonely than the "bottom"?
I wonder, is it because it's more lonely at the "top" than at the "bottom", or because people expect the "top" to be less lonely than the "bottom"?
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It's a natural property of the pyramidal structure of most organizations. At the bottom, there are many people in a similar situation to sympathize with, but at the top, there is only one CEO.
I think his own experiences are valid for him, but he definitely generalizes to everyone:
1) I have never once felt loneliness. I dont get close to people at work and never have.
2) adrenaline - Im definitely not addicted to adrenaline. Im more of a stoic. I hate fires so avoid creating fires at all costs. Im constantly gaming worst case scenarios. Fires happen. I do admit I tend to get lazy when things are good and work harder and am more focused when things are falling apart. I dont get an adrenaline rush, instead it is easy to tune out everything except the solution to the biggest problem.
3)constant information flow - Im good at just ignoring things. I have created a structure where I get info from my direct reports and from key people on the ground. I sit in on project standups so I know what is actually going on. We mainly use slack now and so my emails have dropped to almost nothing. I only monitor a few key channels daily.
4) feelings of inadequacy - Im a stoic. I know Im bad at lots of things and that is ok. I dont beat myself up over things I have done wrong.
5) arrogance - I dont really have this as Im constantly second guessing and gaming out worst case scenarios. I almost always let my reports do what they think is right though I will often challenge them.
6) jealousy - I have jealousy over lots of things. But Im also very happy with what I have. If I was told i was going to die in a month, I wouldnt feel that I would have to rush out and do a lot of things that I missed out on. I would mostly do the things I have already been doing and prepare people in my life to be without me.
7)wanting to quit- I have gone through this many times in my life. sometimes I have essentially stopped working and let my mgmt team run things. I try to change up what Im doing every 5 years or so. It is a good way to quit without quitting. Whatever you dont like to do, find someone to do it for you.
8) pride - I dont need accolades, I dont need fancy stuff. I mainly just want to be able to do things I enjoy doing.
1) I have never once felt loneliness. I dont get close to people at work and never have.
2) adrenaline - Im definitely not addicted to adrenaline. Im more of a stoic. I hate fires so avoid creating fires at all costs. Im constantly gaming worst case scenarios. Fires happen. I do admit I tend to get lazy when things are good and work harder and am more focused when things are falling apart. I dont get an adrenaline rush, instead it is easy to tune out everything except the solution to the biggest problem.
3)constant information flow - Im good at just ignoring things. I have created a structure where I get info from my direct reports and from key people on the ground. I sit in on project standups so I know what is actually going on. We mainly use slack now and so my emails have dropped to almost nothing. I only monitor a few key channels daily.
4) feelings of inadequacy - Im a stoic. I know Im bad at lots of things and that is ok. I dont beat myself up over things I have done wrong.
5) arrogance - I dont really have this as Im constantly second guessing and gaming out worst case scenarios. I almost always let my reports do what they think is right though I will often challenge them.
6) jealousy - I have jealousy over lots of things. But Im also very happy with what I have. If I was told i was going to die in a month, I wouldnt feel that I would have to rush out and do a lot of things that I missed out on. I would mostly do the things I have already been doing and prepare people in my life to be without me.
7)wanting to quit- I have gone through this many times in my life. sometimes I have essentially stopped working and let my mgmt team run things. I try to change up what Im doing every 5 years or so. It is a good way to quit without quitting. Whatever you dont like to do, find someone to do it for you.
8) pride - I dont need accolades, I dont need fancy stuff. I mainly just want to be able to do things I enjoy doing.
These (mostly negative) emotional reactions seem pretty reasonable for anyone with so much power/responsibility. I'm not the first to wonder this, but are there ways to successfully run a business without a single CEO taking on all the power/responsibility themself?
Worker co-operation (coops) models [0] exist and can take the form of a dozen employees, or scale to really quite enormous companies like Mondragon[1].
I've come across lots of them in Europe, and a few where I live now in Canada, but I don't know if they're common at all in the US?
[0] https://en.wikipedia.org/wiki/Worker_cooperative
[1] https://en.wikipedia.org/wiki/Mondragon_Corporation
I've come across lots of them in Europe, and a few where I live now in Canada, but I don't know if they're common at all in the US?
[0] https://en.wikipedia.org/wiki/Worker_cooperative
[1] https://en.wikipedia.org/wiki/Mondragon_Corporation
Worker co-ops don't eliminate executive roles, though. They just make it so that executives serve at the pleasure of the members (and are usually elected in some form). Mondragon has a President, who was formerly a Vice President and Managing Director. REI, a US-based co-op, has a more complicated story: https://en.wikipedia.org/wiki/Recreational_Equipment,_Inc.#G...
They still have hierarchy and pay still scales with position in that hierarchy. The ratio of CEO pay to worker pay is generally more equitable, but it is still a ratio. I have no idea what the work-life balance is like, but running a co-op (or a nonprofit, for that matter) still sounds like a stressful job to me.
They still have hierarchy and pay still scales with position in that hierarchy. The ratio of CEO pay to worker pay is generally more equitable, but it is still a ratio. I have no idea what the work-life balance is like, but running a co-op (or a nonprofit, for that matter) still sounds like a stressful job to me.
I'm not sure how much it applies to tech as an industry, but research shows that coops (or, "labor-managed firms") tend to last much longer and be more productive than non-coop companies as well.
https://www.uk.coop/resources/what-do-we-really-know-about-w...
https://www.uk.coop/resources/what-do-we-really-know-about-w...
Thanks for the link, what an interesting pdf.
What I still don't quite understand about coops is how they practically come about? The pdf you linked to says that 84% come into being from scratch. If you need to buy some mechanical equipment and rent a factory, does everyone who joins the coop at the beginning pay into those start-up costs? Or is the investment in the coop usually entirely from the outside like bank loans? Is there ever a distinction between coop members who have invested money into the firm, and those who join later that haven't?
What I still don't quite understand about coops is how they practically come about? The pdf you linked to says that 84% come into being from scratch. If you need to buy some mechanical equipment and rent a factory, does everyone who joins the coop at the beginning pay into those start-up costs? Or is the investment in the coop usually entirely from the outside like bank loans? Is there ever a distinction between coop members who have invested money into the firm, and those who join later that haven't?
I was part of an employee owned company but I had no ownership and was only a contractor.
At some point the company couldn't pay the employees and they took partial ownership. The employees were senior ex-sun types who could forgo money for stock.
It was a pleasant and the darkest (in terms of no lights on). Conversations were about high level technical and no meetings. Great place to work while it lastest.
At some point the company couldn't pay the employees and they took partial ownership. The employees were senior ex-sun types who could forgo money for stock.
It was a pleasant and the darkest (in terms of no lights on). Conversations were about high level technical and no meetings. Great place to work while it lastest.
America is generally pretty allergic to socialist ideas. The tech sector in particular seems to gravitate towards libertarian ideologies, idolizing founders as heroes who single handedly disrupt entire industries and are rewarded with massive wealth.
I’d be really interested to see more product based startups follow the coop model, most of the tech coops i’ve heard of are dev shops. I imagine not being able to take VC money is a big challenge, and a reason we don’t see more tech coops.
I’d be really interested to see more product based startups follow the coop model, most of the tech coops i’ve heard of are dev shops. I imagine not being able to take VC money is a big challenge, and a reason we don’t see more tech coops.
Why couldn’t you take VC money? The VC would just have more shareholders to contend with.
VCs talk to 200 people a month with a single CEO or maybe the odd co-CEO. Along you come with a 20 person co-op leadership structure. Why would they take that dive? They want you to look/act/speak/organize like their previous successes. (Which is the same general reason why non-white males start at such a giant disadvantage )
I think one reason it's harder is because typically VCs pay more money to have more decision making power and many coops are founded on the one member one vote principle. So despite how much money they'd contribute, they'd have no more say than the average member.
The defining feature of a worker coop is that it’s owned by the workers. That means they can’t give shares to VC’s. I’m sure there’s hybrid models where the company is only majority owned by workers, but I don’t know how common they are and I doubt they’re very attractive to VC’s for reasons others have mentioned.
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My understanding of co-ops, while I haven't experienced them first-hand, is that they are still capitalist in nature - they are usually profit driven (though not at the expense of workers), pay is not equal, and the difference is a democratic decision making structure.
> America is generally pretty allergic to socialist ideas.
I think yes, we often feel allergic to government ownership of things (at least that's how I see socialism, which may not be how others see it), yet I don't think that's why many of us don't like coops, as publicly traded companies are owned by many people through the stock markets.
I think what may hinder the rise of coops in the US is ironically our allergy to democracy in business. We seem to love democracy in governance yet prefer top-down authoritarianism in business (and mostly in the military, minus the civilian leaders). Most coops I know strongly emphasize democratic governance, where all shareholders are equal in voting power, and most businesses I know are very far from that.
I think the desire for and familiarity with top-down governance (which seems like authoritarianism to me) that we get in the business world is influencing many of our attitudes towards on democracy in governance, as top-down can be quicker, more adaptive, more efficient, etc
However, I wonder if the perception of being exploited by some of these large companies, especially in the consumer tech sector, will lead to a demand for more democratic/representative governance, as we see with some DAOs and more.
I personally would love to see more coop Clubhouses, Facebook, TikToks, etc. Let the users 1) have more decision making power on the platform and 2) receive more profits from the services.
I think yes, we often feel allergic to government ownership of things (at least that's how I see socialism, which may not be how others see it), yet I don't think that's why many of us don't like coops, as publicly traded companies are owned by many people through the stock markets.
I think what may hinder the rise of coops in the US is ironically our allergy to democracy in business. We seem to love democracy in governance yet prefer top-down authoritarianism in business (and mostly in the military, minus the civilian leaders). Most coops I know strongly emphasize democratic governance, where all shareholders are equal in voting power, and most businesses I know are very far from that.
I think the desire for and familiarity with top-down governance (which seems like authoritarianism to me) that we get in the business world is influencing many of our attitudes towards on democracy in governance, as top-down can be quicker, more adaptive, more efficient, etc
However, I wonder if the perception of being exploited by some of these large companies, especially in the consumer tech sector, will lead to a demand for more democratic/representative governance, as we see with some DAOs and more.
I personally would love to see more coop Clubhouses, Facebook, TikToks, etc. Let the users 1) have more decision making power on the platform and 2) receive more profits from the services.
> yet I don't think that's why many of us don't like coops, as publicly traded companies are owned by many people through the stock markets.
That's not the same thing. The concept of coops is that the people that work in them own them.
That's not the same thing. The concept of coops is that the people that work in them own them.
In some coops yes: worker cooperatives. There are many styles—if you're in the US, you may not know that REI, the outdoor store, is also a coop, albeit a retail one.
Very well said! You might find this talk interesting, it’s about “democracy at work” as a new-ish flavor of socialism. https://m.youtube.com/watch?v=ynbgMKclWWc
Ahh thanks! I'll check it out. I think unfortunately the word socialism evokes so many emotions and different interpretations in people that I try to not use it, although I do like the concept of "democracy at work" :-) perhaps I'll change perspective after the video
I've worked for a couple single founder businesses (not with OP though). I'll never do it again. I think it's much healthier when they have someone on equal footing that can tell them when they're being unreasonable and going in the wrong direction. As a single founder with all the control, it's too easy to just dismiss concerns that employees raise. I guess that's where the arrogance comes from. Absolute power corrupts and all that...
Yep, this is exactly why I left my last startup.
Relevant: https://en.wikipedia.org/wiki/Founder%27s_syndrome#:~:text=F....
Relevant: https://en.wikipedia.org/wiki/Founder%27s_syndrome#:~:text=F....
I've invested twice in Co-CEO managed start-ups. Like everything else, it has its pros and its cons, the one was decidedly more smooth than the other, but in both cases a viable business emerged and both companies are still in business (I've exited the one, am still involved in the other, which has one member from HN in the management).
You could check out self-managed organizations, like Semco in Brazil.
https://semcostyle.us/
You still have executives, but lots of management decisions are made by employees themselves, like decisions about wages and scheduling.
https://semcostyle.us/
You still have executives, but lots of management decisions are made by employees themselves, like decisions about wages and scheduling.
There's an interesting HBR article about Morning Star, a company like that: https://hbr.org/2011/12/first-lets-fire-all-the-managers
Not exactly a CEO but a founder - it can really be rough. You are really the less free person. Every step you take can have huge consequences - there's too many people involved in a deal, there's your team, your clients. You are always on the hook. And it's damn hard to sleep when so much depends on you.
But it is a rewarding experience - shipping your own product for the first time, seeing your teammates grow, working on so many different problems. It's worth it!
But it is a rewarding experience - shipping your own product for the first time, seeing your teammates grow, working on so many different problems. It's worth it!
Nice article I resonate with quite a lot, even as a CTO of a small to mid sized startup. The rest of the management/founder team of course doesn't understand anything I do so I need to have outside support on that. But what's nice is that this caused me to actively search for outside counselling and a support network. It made me aware of my needs and a drive to meet them, either via my network or by doing the work on all the stuff that causes conflicts inside the founder team or negative emotions inside myself. Because if you don't have a manager, you have to manage yourself and learn quite a lot. And I like that.
Worth reading about what personal and professional challenges Ryan Caldbeck faced before leaping in to criticize. He wrote an excellent tear down of a destructive board member appointed by the VC backer.
It's a very poorly understood role and often over glamorized, much like VC itself.
I think CEO should be thought of as a responsibility more than anything. It's going to weigh a lot for obvious reasons.
I think CEO should be thought of as a responsibility more than anything. It's going to weigh a lot for obvious reasons.
I have been a CEO and felt all these same emotions myself. I have been a founder and CEO for 12 years. It gets a lot better than Ryan makes it out to be in my opinion. There are two key things you need to do though to make it better: 1) Never take investors as they add an enormous amount of stress because they literally control your life 2) Delegate and share the wealth. Greed will drive out good people and leave you all the stress.
"Secret desire to leave" - I've interviewed at a company where the founder-CEO told me that he wanted to leave his company. Needless to say, I was relieved when I didn't get the job.
You simply need psychopathy at the top:
https://www.ribbonfarm.com/2009/10/07/the-gervais-principle-...
Things are much easier to understand with the above template.
https://www.ribbonfarm.com/2009/10/07/the-gervais-principle-...
Things are much easier to understand with the above template.
The article would be different, or at least I would read it differently, if it had been titled
My Emotions
instead of
My Emotions as a CEO
But clearly, the author intends this to be informative about the experience of being CEO.
So what is a CEO?
Is it a guy who earns $12 million a year + options at the top of a NASDAQ corporation with 15,000 staff?
Or is it a smart guy hired by a founder (or the founder) of an underfunded venture with no staff and a long path towards making a vulnerable, contested niche pay?
Those are different things, presumably with different emotional challenges.
What does it tell us that the author chose an ambiguous title, which isn't explicitly clarified in or by the article?
My Emotions
instead of
My Emotions as a CEO
But clearly, the author intends this to be informative about the experience of being CEO.
So what is a CEO?
Is it a guy who earns $12 million a year + options at the top of a NASDAQ corporation with 15,000 staff?
Or is it a smart guy hired by a founder (or the founder) of an underfunded venture with no staff and a long path towards making a vulnerable, contested niche pay?
Those are different things, presumably with different emotional challenges.
What does it tell us that the author chose an ambiguous title, which isn't explicitly clarified in or by the article?
The job has its downsides, and the worst thing that can happen to you is 1) be a first-time CEO, 2) have no PFM, and 3) have no safety net. If you hit that trifecta, it's not going to be easy. But here's the deal - you'll get through it, and you'll come out on the other side with a much improved mental model that will allow you to be more successful in your next go around. You may or may not ever achieve market-level compensation, and you may even end up in debt. But it will get easier each time you try, it will come the closest to being your own boss, you will learn more than doing anything else, and most importantly, you won't turn 70 and think of yourself as having not taking enough chances in your life.