My Emotions as a CEO
ryancaldbeck.co
ryancaldbeck.co
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.
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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.
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.
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!
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 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.
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'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.
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 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.
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.
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.
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.
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.
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.
If he has had it rougher than it seems, let's hear those stories! Would make for much better blogging than this.
CircleUp is probably 3x as big and C-Level work/responsibility grows exponentially as headcount increases.
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.
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?
He didn't say that. I read an article about someone openly reflecting on their feelings.
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).
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.
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?
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.
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.
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.
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"?
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.
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.
Relevant: https://en.wikipedia.org/wiki/Founder%27s_syndrome#:~:text=F....
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?
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 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.
That's not the same thing. The concept of coops is that the people that work in them own them.
https://www.uk.coop/resources/what-do-we-really-know-about-w...
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?
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.
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.
You still have executives, but lots of management decisions are made by employees themselves, like decisions about wages and scheduling.
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!
I think CEO should be thought of as a responsibility more than anything. It's going to weigh a lot for obvious reasons.
https://www.ribbonfarm.com/2009/10/07/the-gervais-principle-...
Things are much easier to understand with the above template.
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?