In this week's issue

The Lonely Journey of an Entrepreneur
The other day I was talking to a friend about how our parents call all the relatives constantly to stay in touch. We both labelled it as a generational thing, and also as a way to cope with loneliness.
Then I mentioned to her that I never actually feel lonely. I love being by myself and I'm never really alone, because I always have things to do or books to read.
We finished the chat by her saying that according to her therapist, loneliness takes many shapes and forms, and for every person it's different. That's exactly the case of "never say never."
A few days later I had an investor call that really stressed me out. I called my CTO to share a bit about the call, expecting some comfort and support. Instead I quickly realised that this might stress him out too, and in fact I should probably keep most of this to myself.
That's when I understood what my friend's therapist meant.
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The specific loneliness of being the founder
As a CEO, my job is to protect my team from unnecessary stress. My job is also to know everything, take responsibility for everything, set an example, motivate everyone, fire people, fundraise, sell, build partnerships, work with partners, provide customer support, and about a hundred other things I didn't fully understand before I started.
But I'm also human. I have bad days. I make mistakes. I don't know everything.
That's fine. I know what I signed up for. But it doesn't make me feel any less alone on this journey, because most of the time I can't fully discuss it with anyone. I share it all with my husband, who patiently listens - which is honestly good enough for me. Not every founder has that. And even when you do, there are things you can't talk about with a partner either - not because they wouldn't listen, but because they can't hold it the way another founder can.
The uncomfortable thing is that this isn't a personal problem. It's structural. It comes with the job.
What the data actually says
I want to bring some numbers into this, because I think a lot of founders feel this quietly and assume they're the only ones. They're not.
According to The Lonely Entrepreneur's 2026 Founder Reports survey, 87.7% of founders are struggling with their mental health. Nearly half battle anxiety. Only 18.5% know that structured support even exists.
A study cited by the University of California found that 49% of entrepreneurs report at least one mental health condition - depression, anxiety, or ADHD - and one third report two or more. Compare that to 32% of non-entrepreneurs. Entrepreneurs recently rated their loneliness levels at 7.6 out of 10 on average.
A 2024 survey found that 55% of CEOs reported mental health issues in the previous year - a 24 percentage point jump from the year before. Anxiety, depression, burnout, and loneliness were the most commonly cited.
And Harvard Business Review has covered CEO loneliness for over a decade. Roughly half of surveyed CEOs report feelings of isolation, and the majority of those believe it's affecting their performance.
None of this is new information. It's been sitting in peer-reviewed journals for years. Most of it hasn't reached the way we actually talk about founding companies, because founders are structurally incentivised not to say it out loud.
"No one told me how lonely it would be"
The line that hit me hardest when I was reading around this was from Brian Chesky, the co-founder and CEO of Airbnb, talking to Steven Bartlett on the Diary of a CEO podcast in 2023.
Chesky said: "No one told me how lonely it would be, and it doesn't have to be." He described how Airbnb had started with him and his friends. Then they hired people. Then those people became employees, and the informal bonds became formal ones. "As we got successful then we became more of a corporation, there was a chain of command, there were more boundaries. It becomes more formal. And that's the moment your employees become your employees and less your friends. And that gets more and more isolating."
He also said something that I keep coming back to: "Lonely leaders are probably not the best leaders."
I think that's the actual point. The loneliness itself isn't just uncomfortable. It's a business problem. A founder who has nobody to reality-test their fear with will spiral in a way a founder with a genuine peer group won't. The same stressor lands completely differently depending on whether anyone else knows you're carrying it.
Why the "just tell your co-founder" advice doesn't work
The default response most founders get when they mention loneliness is: talk to your co-founder. Talk to your team. Talk to your investors.
The reason that doesn't work is that each of those relationships has a structural reason you can't be fully transparent inside it.
Your team is your team. Your job is to protect them from the doubt you're carrying, not to offload it onto them. Sharing everything with them doesn't make you a "vulnerable leader." It destabilises the people whose confidence in you is a real component of whether the company works.
Your co-founder, if you have one, is closer - but they also have their own load. And on the specific things you're most worried about, you're often worried precisely because they don't yet know. Telling them can be the right move, but it isn't a stress release. It's a transfer of stress.
Your investors are not your therapists. They will smile and nod and then adjust their internal probability of your company succeeding downward. That's a structural fact. It's not a criticism of investors.
Which leaves your partner, your family, and your friends - most of whom love you deeply but genuinely can't hold the specific shape of what you're carrying, because they haven't carried it themselves.
And that leaves the one thing that actually works, which is other founders. Preferably founders at roughly your stage. Preferably in a space where nobody's pitching, selling, or asking for anything.
That's the actual answer. Everything else is a partial one.
What I've started doing
I want to be careful about this section, because I don't want to write another founder self-help post. But there are a few things I've started doing that have genuinely helped, and I think they're worth naming.
One - I stopped trying to process everything with my team. The instinct to share, to be "authentic," to model "vulnerable leadership" is a real one. But there's a difference between being human with your team and outsourcing your emotional load to them. I've become much more careful about which category any given conversation belongs to.
Two - I found two or three other founders I can be genuinely honest with. Not many. Two or three. People at roughly my stage, who are also raising, also building, also getting the same investor emails. When I have a bad call, they get the honest version. When they have a bad call, I get theirs. Nobody is pitching. Nobody is judging. That has been the single most important thing I've built this year, and I built it accidentally.
Three - I stopped treating my husband as a co-founder. He's my partner. He's not my sounding board on every fundraising decision. Turning him into one was making both of us worse. The relationship works better when I bring him the parts he can genuinely engage with, rather than the parts I need him to engage with because I have nobody else.
Four - I stopped treating "always busy, always fine" as a virtue. I used to answer "how are you?" with "great, really busy" reflexively. I've started answering more honestly with the people who can hear it. It's a small thing. It's also, weirdly, the thing that's made the loudest difference.
The point
I'm writing this because a lot of the founders I meet - especially the ones who present as fine, working hard, moving fast, closing rounds - are quietly carrying more than they let on. The data says almost 90% of us are. And most of us have been trained to treat that as a weakness to hide rather than a structural fact to manage.
It isn't a weakness. It comes with the job.
The founders I most admire aren't the ones who never feel lonely. They're the ones who've quietly built a small group of people they can be honest with, who don't confuse that group with their team or their partner or their investors, and who understand that loneliness at the top is a business problem as much as a personal one.
If you're building something right now and you've quietly recognised yourself in any of this, you're not broken. You're not failing. You're doing one of the hardest jobs a person can do, and you're doing it in a structure that was designed to isolate you.
The move isn't to work harder through it. It isn't to pretend it isn't happening. It's to name it, and then build the small, specific set of relationships that can actually hold it.
Because you can't out-work loneliness. Every hour alone at the desk deepens it.
That's the thing my friend's therapist was right about. Loneliness takes many shapes and forms. For every founder it looks different. But the shape it takes for the person at the top of the org chart is one nobody warns you about, and one you can't reason your way out of.
You have to build your way out of it, the same way you build everything else.
Just, in this case, the thing you're building is a small group of people who understand what you're actually carrying.
✅ Know a founder who's quietly carrying too much and pretending they're not? Forward this their way. The sooner more of us admit that loneliness at the top is structural, not personal, the sooner we all start building the specific relationships that can actually hold it.
POLL TIME❓
(👉 Vote now - we’ll share the results in next week’s issue. All votes are anonymous.)
🗳️ When someone asks "how are you?" - how honest is your default answer?
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