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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 lonel

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.

hn_throwaway_99 5y ago
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.
- zemvpferreira 5y ago
  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.
  - n4r9 5y ago
    The article didn't come across as a complaint to me, rather a description of the emotions they experienced while in that role.
    - zemvpferreira 5y ago
      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.
      - jimkleiber 5y ago
        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.
      - 5y ago
cj 5y ago
> 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.
- zemvpferreira 5y ago
  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.
  - cj 5y ago
    I fail to see how the legitimacy of someone’s suffering or emotions is affected by their societal privilege.
    - zemvpferreira 5y ago
      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.
  - cglace 5y ago
    FYI, you come across as an asshole, then you explain yourself and still seem like an asshole.
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nojito 5y ago
>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.
- zemvpferreira 5y ago
  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.
  - kevin_thibedeau 5y ago
    Welch had an annual workforce decimation.
- cortesoft 5y ago
  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.
darkerside 5y ago
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?
- Kranar 5y ago
  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.
seedless-sensat 5y ago
> 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.
gnicholas 5y ago
> 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).
DoreenMichele 5y ago
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.
Aeolun 5y ago
> 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?
danbmil99 5y ago
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.

hn_throwaway_99 5y ago

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.

zemvpferreira 5y ago
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.
- n4r9 5y ago
  The article didn't come across as a complaint to me, rather a description of the emotions they experienced while in that role.
  - zemvpferreira 5y ago
    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.
    - jimkleiber 5y ago
      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.
    - 5y ago

cj 5y ago

> 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.

zemvpferreira 5y ago
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.
- cj 5y ago
  I fail to see how the legitimacy of someone’s suffering or emotions is affected by their societal privilege.
  - zemvpferreira 5y ago
    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.
- cglace 5y ago
  FYI, you come across as an asshole, then you explain yourself and still seem like an asshole.

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nojito 5y ago

>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.

zemvpferreira 5y ago
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.
- kevin_thibedeau 5y ago
  Welch had an annual workforce decimation.
cortesoft 5y ago
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.

darkerside 5y ago

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?

Kranar 5y ago
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.

seedless-sensat 5y ago

> 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.

gnicholas 5y ago

> 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).

DoreenMichele 5y ago

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.

Aeolun 5y ago

> 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?

danbmil99 5y ago

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.