Isolation

There are more solopreneur efforts than ever, and while that’s cool, it can also be a seriously dangerous thing.

You can start something without a cofounder, a developer, or even a team, which means isolation can be built into the company from day one.

A solopreneur can build a product, test a market, and run the whole go-to-market motion with AI. That can be an enormous unlock. It also means there may be nobody in the room whose job is to say, “I don’t think that’s right.”

The deeper risk is a workflow that makes you feel heard without giving you independent challenge.

One Person and a Model

Claude can confirm the story you already wanted to believe and produce market research that backs up your wildest assumptions. Used well, it can also help you test those assumptions. The difference is whether you have anyone outside the model who can check the answer.

An AI assistant does not know your customers, your numbers, or what a bad decision will cost the people around you. It is not a mentor. Even when you ask it to argue the other side, you are still the person deciding whether the argument was good enough.

That makes real mentoring relationships more important, not less. Founders need people who can bring context the model does not have, notice when the story sounds too clean, and care enough to challenge it.

How the Drift Happened for Me

For me, isolation started as a matter of geography. In the early years, we worked out of incubators and co-working spaces, surrounded by other founders who’d ask how things were going and expect a real answer. Then we had an office of our own, and later I was mostly working remotely, with nobody nearby for the kind of casual check-in that catches a problem early.

I also never built real mentorship into my life as a CEO, and that’s on me. Nobody took the people away. I stopped making room for them.

Why People Stop Telling Leaders Things

Elizabeth Morrison and Frances Milliken, both at NYU’s Stern School of Business, described a pattern they called organizational silence. In many organizations, employees know about serious problems and still choose to say nothing, and Morrison and Milliken argued that this silence is a shared state, something the whole organization settles into together.

It starts at the top. When leaders are uncomfortable hearing bad news, and quietly believe that they know best or that disagreement means something’s wrong with the team, those beliefs shape how decisions get made and how dissent gets received. Employees notice, and they compare notes. Over time, a shared belief forms that speaking up is pointless at best and risky at worst, and people stop doing it, even when they can see a problem clearly.

The cost is information. The organization loses what it would need to catch its own mistakes, and leaders often don’t realize anything is missing, because silence can look a lot like agreement from the top.

Morrison and Milliken were writing about established organizations with layers of management. A startup has fewer layers, and I’d argue the effect can be stronger there, because the team is small and nearly everyone reports to the founder.

What Happens to the Person Who Speaks Up

James Westphal and Poonam Khanna found something similar among corporate directors, in a study of how boards keep their own members in line. Directors who took part in governance changes that cut against top management’s interests at one company were then socially distanced by fellow directors on other boards they served on. They were invited to fewer informal meetings, and their advice was sought less often. The distancing worked. Directors who’d recently experienced it were less likely to support similar changes afterward.

Founders aren’t sitting on the boards of the largest public companies, and the lesson still travels. The people around a founder watch closely what happens to whoever pushed back last.

Founder-Friendly and What It Can Leave Out

Investor culture has made “founder-friendly” one of its highest compliments. Much of that is deserved, because founders need room to build. It has also come to mean lighter diligence and governance that waits until a later round. Investors like to say they bet on the founder, which is meant as support, and it also puts the whole weight of a company on one person’s judgment with fewer people checking it.

Inside the company, the people who joined early are often the most loyal, and loyalty makes for a poor early warning system. A team that wants the founder to succeed will often protect the founder from bad news. Updates start going only to the people who’ll be impressed by them, which is how isolation and vanity feed each other.

Build Mentorship Into the Operating System

Mentorship cannot be something you hope appears when you need it. Choose one or two people and make the relationship explicit. Tell them what you want from them, what you expect of yourself, and how often you’ll meet. A standing monthly call is better than a vague promise to grab coffee sometime.

Put the check-in on a schedule and protect it, especially when the numbers are bad. Send the real numbers in advance, including the ones you least want to discuss. Give the meeting three simple questions: What changed? What is not working? What decision are you avoiding? The point is not to perform progress for a mentor. It is to make reality discussable before pressure turns it into a story.

A good check-in is not a performance review. It is a place to bring the thing you have not figured out yet. If all you bring is good news, you have found another audience, not a mentor.

That is also the difference between a network and a support system. A network gives you people to call. A support system tells you when you will speak, what you will bring, and who is allowed to challenge you. Build the second one deliberately.

Give those people permission to be direct. Ask them to challenge your assumptions, your market research, and the neat answer the model just gave you. Thank them when they do. If every conversation ends with you explaining why they are wrong, you have built another room where nobody can help you.

Keep some contact with people outside the company too. A founder group, a co-working day, or a standing walk can catch the thing you would never think to put on an agenda. Set up those relationships while things are calm, so they are already there when you need them.

I did not choose isolation, and I doubt most founders do either. It can happen one skipped call at a time. It can also start with a workflow that never required another person in the first place. I drifted into it, and keeping the right people close was my job.

The right people do not just believe in you. They stay close enough to the facts to disagree with you, and they keep showing up on the schedule you set. That consistency is what makes honesty normal instead of something you reach for in a crisis. It is how bad news stays information.