On the lonely work of running an emerging growth company
The board meeting ends at 4:40. Laptops are closed and directors mumble a few platitudes about the opportunity. The lead investor, who has eleven other companies, is already thinking about the next one. A few minutes later, the CEO is alone in the room again.
I’ve watched this on replay at companies building everything from medical devices to industrial software to consumer brands nobody has heard of yet. Everyone gets to leave and participate in something else. The CEO is the one person who cannot put the company down.
Everyone else has a job. The CEO has all of them.
People who have not run an emerging growth company imagine the version they have seen in the press: the keynote, the funding announcement, the profile with the good photograph. The job itself is closer to plumbing.
There is no crisis communications department, no general counsel down the hall, no head of facilities. No head of anything really. There is a person who is excellent at one thing and is currently doing four. When the VP of Sales resigns on a Tuesday, the CEO owns the pipeline on Wednesday. When the office floods, the CEO calls the landlord. When the biggest customer’s renewal goes quiet, the CEO is the one who notices.
Then there is the category of problems that never appears on an org chart. The co-founder who has stopped believing. The key engineer whose spouse got a job in another state. The investor who committed verbally and is now slow to respond. The wire that must go out Friday against a receivable that is going to land Monday. None of this is in anyone’s job description, so all of it is in the CEO’s.
Why the job is lonely
Here is the part that people outside the role never quite get: the loneliness is a structural feature of the job.
Consider the CEO’s big picture. The employees need to believe the company is going to survive, because they have mortgages and perhaps turned down other offers. The investors need to see conviction, because conviction is most of what they are buying at this stage. The customers need to believe the contract will renew. The board needs a leader who is on top of it.
Every audience requires a version of the CEO that is more certain than the CEO probably always feels. So, the CEO performs the certainty. That’s not dishonesty; it is the job. Additionally, the gap between what the CEO knows and what the CEO can say out loud often widens, and that gap is where the loneliness lives.
I have had a fair number of those conversations at odd hours, usually because a lawyer is one of the small circle in a CEO’s life who is paid to hear the unedited version. What I can say is that the fear is about payroll and whether the people who left their last jobs to come here are going to be all right.
Nobody can make the job less lonely. But after enough years next to people doing it, the ones who came out the other side had a handful of things in common.
Be ready for anything: The thing that nearly kills your company will be a supplier’s bankruptcy, a founder’s divorce, a patent letter from a company you have never heard of, a bank that fails over a weekend. You cannot forecast which. You can be the kind of company that survives surprises: cash position known to the week rather than the month, signed IP assignments rather than assumed, a cap table that will survive diligence, a board that trusts you before you need to deliver bad news.
A related discipline is seeing down the road and around the corner. The CEO is the person in the company whose real job is eighteen months out. Everyone else is paid to be excellent about this quarter. Two questions are worth asking yourself: as CEO at any given time, what must be true eighteen months from now for us to matter, and what would have to break for us to be gone. Then, work backward from both.
Be nice to everyone: This is a moral point, and I believe it is also the most underrated tactical advice in this business. The ecosystem is small, and it has a long memory. The associate you were brisk with in time becomes a partner. The candidate who turned you down runs the company you eventually want to acquire. The junior person you treated well at your last company sends you your best engineer six years later.
A CEO also needs a great deal of help, and people help the ones they like. Reputation is the only asset that compounds faster than equity, and unlike equity, it is entirely within your control. Watch how a founder treats the person who cleans the office and the recruiter who cold-called them. That is the reference check that predicts something.
Believe when nobody else does: At the start, conviction is the one asset that is genuinely yours. Capital, talent, customers, and credibility all come later, and because someone believed you first.
But belief must be distinguished from denial, and the difference is what you do with information. Belief says the destination is right, and I will change anything else to get there. Denial says do not send me the cash report. The best founders I have worked with changed their minds about tactics constantly and about the destination almost never. The ones who failed badly usually had it exactly backward.
Decide: A CEO is paid to decide, with less information than the decision deserves, on a schedule set by other people. Most decisions are reversible and should be made quickly and cheaply. A few are not reversible, and those deserve the slow, expensive treatment. The costly mistake is treating everything like the second category, because the entire company idles behind an undecided question. A team can execute a B-plus decision made on Monday. No team can execute a perfect decision that is still being considered in March.
It does take a village: The myth of the solitary founder has created real damage. The CEO carries the accountability alone, which is precisely why the CEO should not carry the information alone.
Build the board you will need in two years, not the one your current round entitles you to. A director who shows up for the meeting and does nothing between meetings is not neutral; that seat has a cost. The good ones take the call at nine at night and tell you what nobody else will say.
Pick advisors who have done the specific thing you are about to do. Someone who has taken a hardware product through FDA review or a first enterprise deal through a Fortune 100 procurement department is worth more than a famous name who will lend you their logo.
Hire a good lawyer, a good accountant, and hire them earlier than you think you can afford them.
The cheap version of these two can turn out to be the most expensive line item on the cap table. Unsigned IP assignments, options priced off a stale 409A, a handshake with an early contributor that becomes a claim during diligence, revenue recognized in a way the acquirer’s auditors will not accept. Every one of those is a small problem in year one and a valuation problem, or a dead deal, in year five.
Get good admin: The scarcest resource in the company is the CEO’s attention, and most CEOs spend a third of it on work that a capable person could do better than they can. Hire the admin before it feels like a luxury you can’t afford, and then actually use them, which is the part most people get wrong.
The most useful book I know on this is Radical Delegation by Patrick Ewers of Mindmaven, which is specifically about the working relationship between an executive and their assistant. It is practical rather than inspirational. If you have hired an assistant and still feel underwater, that book is the diagnosis.
Take care of yourself. Seriously. The company’s most concentrated point of failure is the judgment of an exhausted human being. Sleep is due diligence on your own decision-making. Exercise is the friend who knew you before any of this, so is the vacation each year when someone else is holding the phone.
Protect your time the way you would protect the source code. Somewhere in the week there needs to be an unbroken block where you do the thinking that nobody else in the company can do, and it needs to be defended against people who mean well. Notice what replenishes you rather than what merely numbs you.
And have at least one relationship outside of work where you are not the CEO. Everyone else in your life needs something from you. You need one person who just enjoys your company and some good conversation.
Loneliness is not the same as alone: The role does not get less isolated with scale. The isolation builds, and the number of people you can be fully honest with shrinks as the number of people depending on you grows.
Isolation is a fact about the seat, not a final sentence. Founders who last build a small circle deliberately, over years. It may include two directors who tell the truth, an advisor who has been through this exact fire, a lawyer and an accountant who have seen the failure modes and will say so, an assistant who protects the calendar, and a person at home who gets the unperformed version. This group may change, but not much.
At the end of the day, it’s the CEO who stays in the room after everyone else has gone. That part does not change.
