One Bad Quarter

I ran a company for twelve years. It was the hardest thing I've ever done and I wouldn't trade a day of it, not because of how it ended but because of what the difficult parts cost me and what that cost eventually turned into. I'm not sure I'm a better person for it, I'd leave that to the people who had to work with me, but I came out the other side with a clearer sense of what I'm capable of and what I'm not, which is probably the most useful thing you can take from twelve years of anything.

I'm writing this because I think a lot of people are closer to starting something than they realise, and because the conditions for doing it right now are genuinely different from what they were a few years ago and from what they'll be a few years from now. That window has a specific shape and I want to try and describe it.

Paul called me this week. He lives on the ninth floor and runs a company that's been building a voice AI ordering system for a restaurant group with thirty stores opening Friday. The dev team had gone quiet in that particular way dev teams go quiet when they know they've shipped something that doesn't work, and he wanted to know where to find someone who could come in and fix it quickly and cheaply.

I told him it was like trying to fix a tunnel where the two sides didn't meet. On the surface it sounds straightforward, it's only one meter off and most of the work is already done, but the meter is load-bearing, the original team is gone, and whoever comes in now has to inherit every decision those people made without having been there when they made them. Someone will fix it eventually but it won't be quick and it won't be cheap and most people I know wouldn't go near it.

He said he's writing the client off and starting again.

The people who built that product were probably doing everything right by the measures they were given. Tickets closed, sprints completed, standups attended. Nobody owned the outcome because the system they were working inside was never built for anyone to own it, and I think that's worth sitting with for a moment because it's not a story about bad engineers or a bad company, it's a story about what happens when you optimise hard enough for process that accountability gets distributed so evenly across tools and hierarchy and ceremony that when something finally fails there's genuinely nobody left holding it. The system didn't break. It worked exactly as designed, and this is what that looks like.

I started thinking about who I could recommend to Paul, good engineers I know with the right skills and the right instincts, people who could own something like this and actually fix it. And then I realised I was running through the same list I'd been running through for six months, people I think are good enough to build something of their own, and the conversation I keep having with them about why they haven't.

I messaged Alistair last week about helping a journalist set up a Patreon, do a few updates to a website, and post a bit on social media to help build an audience. Two or three hours a week at most, skills I know he has but has never really had the chance to use because his current role keeps him in a narrow lane.

He said he was going for senior next year and his job was his main priority right now. Probably also partly because the project wasn't exciting to him, which is a fair reason. He gave me permission to write about it but disagreed with the broader point, said his situation is personal rather than systemic and probably less common than I'm making out. He might be right about his own reasons. I think he's wrong about how common it is.

I've been having a lot of these conversations over the last six months and what I've noticed, slowly, is that more people are actually moving than weren't moving before. The tide has already started to turn. The ones who haven't started yet will eventually have no choice, and the difference between starting now and starting when that moment arrives is mostly the difference between doing it because you chose to and doing it because everything else ran out.

Andy lost his job last year and spent about three months looking, here in London where the market is genuinely harsh and the gap between roles feels longer than it used to. He found a new role and took it. Three months of uncertainty is a long time and the job was there. The visible risk always wins against the invisible one, and the invisible one doesn't disappear just because you stopped looking at it.

Oliver has done everything right. Good company, senior role, respected, the kind of engineer you want at the other end of a phone at 2am when something has gone wrong and nobody knows why. He's at the top of the ladder he was given and he's stopped enjoying it, which I think is what happens when you get there and realise the ladder was leaning against the wrong wall. We've talked a few times about whether he should start something of his own. He's thinking about it and I think he'll get there.

Nina has been more deliberate about starting a company than most people I know. She's spent time building what she calls a cushion, enough financial runway to think clearly about what she wants to build rather than jumping at the first thing out of desperation. She's still working out what she wants to build, which is the right problem to be working on before you start.

Andy waiting for the right job, Alistair waiting for the promotion, Oliver waiting to figure out his next move, Nina waiting until she knows what to build. Different stages, different reasons, different lives. But they're all waiting, and I keep wondering what they're waiting for.

These are just the examples I've written about. I've had versions of this conversation with more people than I can count over the last six months and the through line is always the same thing, the timing isn't right, the market is too harsh, the mortgage is real, things will be clearer in a few months. The timing never feels right because the careers most of us built were designed, deliberately and rationally from a company's perspective, to make the cost of leaving feel larger than the cost of staying. Promotion tracks, vesting schedules, performance cycles, all of it is architecture for keeping people inside and it works, not because companies are malicious but because it's good design for their purposes. The feeling that now isn't the right time is the system doing its job.

Dobre was our very first employee and he's starting a charity to rescue dogs. He's already built the full CMS and everything the charity needs operationally using AI, moving faster than most professional teams would have managed, and right now he's working through the legal setup which is slow and unglamorous and not the part anyone enjoys but the thing actually exists, he built it, and the gap between having an idea and having a working system that used to take months and a team of people he closed in a few weeks on his own.

QTT worked with us a long time ago and has since built serious experience across a lot of different companies and problems. She spent years being deliberate about it, saving carefully, and she's now at the point where she has roughly a year's runway without needing a salary and she's starting something. Not because anyone pushed her into it but because she spent years quietly building the conditions that made it possible.

Both of them got there differently and they're building very different things but neither of them waited for the conditions to be perfect, they just got to a point where not starting felt worse than starting.

The standard line is that the best time to start was yesterday and the second best time is today, which is true as far as it goes but doesn't really capture what feels different about right now, so let me just describe what I've actually been doing.

While I was travelling earlier this year I ended up building four websites for people I met along the way, a dive school, a photographer, a journalist building a membership platform, a neurotech company I'd invested in that needed a web presence. All of them free, all of them running off my home server, all of them built and live within about thirty minutes and another hour of feedback and small changes. None of these people had budgets or teams or any expectation that something real would exist by the end of the conversation. The dive school instructor was surprised it was done before he'd finished his coffee.

That kind of thing wasn't possible a few years ago, not on that timescale, not by one person with a laptop and a bit of downtime between dives. I'm not saying this to suggest I did something impressive, I didn't, that's actually the point. The barrier between having a problem and having something working that real people can use has quietly collapsed and most people haven't tried it yet so they don't quite believe it. You don't need a team, you don't need a budget, you need a problem worth solving and a few hours of genuine attention.

A few years from now the early advantage will be gone and the market will have filled in, and the people who moved in this window will have something the people who waited won't have and can't buy later. The window is real.

The deal sold to anyone who built a career in tech over the last few decades was that the abstraction was the point, that process was maturity, that titles meant something, that a well-managed career inside a well-managed company was the destination, and for a while the economy was growing fast enough that the gap between that promise and the reality underneath it stayed invisible and nobody had much reason to look too closely at it.

The gap is still there. The growth that papered over it isn't.

Paul's thirty stores are the loud version, a visible failure with a deadline and a client watching it happen. Most of it is much quieter than that: the senior engineer who's been inside the same abstraction layer for five years and doesn't know what he's lost, the product that ships but doesn't actually solve anything, the promotion that arrives inside a structure that's already quietly contracting around it.

Do it inside your company and you might get recognised for it. Do it in your own startup and you give yourself a real shot at something that actually compounds. Either way, the outcomes you were promised are one bad quarter away from being scrapped, and a lot of companies are having bad quarters.