The startup I shut down, and the team I had to let go

The customers rejected the product. That was the line on the slide. What the slide did not say was that the product was three years of my team’s life, that I had personally recruited most of them with a story about where we were all going, and that in a few weeks I would be the one telling them it was over.

My son Divit was three years old when I shut down the division. I remember that detail more clearly than the financials. Because the financials are abstract — a chart bends the wrong way, a forecast turns red — but a three-year-old at home is a very specific reminder of what your decisions cost the people you led. Each of them had a Divit. Or an EMI. Or a parent in another city they sent money to every month.

I want to write about that honestly, because most of what gets said about closing a business is either a LinkedIn post about “learnings” or a war story polished smooth by hindsight. The actual experience is neither. It is small, sweaty, and humiliating, and it changes you.

The promise is the thing you break

When you start something, you don’t just sell a product. You sell a future, and you sell it hardest to the people you hire.

I told smart, capable people to leave stable jobs and bet on me. I described the trajectory, the market, the version of themselves they’d become two years in. I believed every word. That belief is the fuel — you cannot build anything without it. But it also means that when the thing fails, you have not just lost money or missed a number. You have broken a promise you made to a real human being who trusted you enough to reorganise their life around your conviction.

That is the part nobody prepares you for. The grief is not about the company. It is about the gap between what you promised and what you delivered.

I didn’t lose a business. I let down a team, some investors, and a community I had told I would serve. The balance sheet recovers faster than that does.

The decision you delay is the most expensive one

Here is my honest confession: I knew before I knew.

There were signals — client confidence eroding, cash flow tightening, the product landing softer than we’d modelled. Part of me had already done the math. But admitting it meant admitting failure, and a leader’s pride is very good at dressing up denial as “let’s give it one more quarter.”

That quarter is not free. Every week I delayed the decision was a week my team kept pouring themselves into something I suspected was already gone. Delaying the call did not protect them. It just moved the cost from my ego to their time — and time was the one thing they could never get back.

I have come to believe that the single hardest skill in leadership is not motivating people or raising money. It is looking at evidence that contradicts your story and acting on it before your pride is ready. The book I later wrote keeps circling one line: the challenge lies not in identifying what needs to change, but in implementing it. I lived the cost of that gap. Knowing it was over was easy. Doing something about it was the months-long fight.

Effort is not the same as progress

This is where the lens I now write about everywhere — moving from effort to effortless — first cut me badly.

My team was working hard. So was I. Long nights, weekend syncs, heroic pushes. And I mistook all that effort for progress, because effort feels like virtue. It looks like commitment. It earns you sympathy. But the market does not pay you for effort. It pays you for delivering something so much better than the alternative that customers switch and never look back. A jump big enough that going back feels absurd.

We never built that. We built something a little better, sometimes, for some people. And a small improvement, however much sweat went into it, is not enough to make anyone change. Customers stayed with what they had. They were not being unfair. They were being rational, the same way you are rational when you keep choosing the couch over the gym.

All our effort was real. It just wasn’t pointed at anything big enough. That is the most expensive lesson I have ever paid for: heroic effort aimed at a small improvement is still a small improvement. The valley of high effort is only worth crossing if there’s something genuinely better waiting on the far side — a place where the new thing becomes the obvious default and nobody wants the old one back. We were grinding through that valley toward a destination that was barely uphill of where everyone already stood.

The day itself

I won’t dramatise the conversations. They were quiet. Most people had sensed it coming — teams always do, before leaders admit it out loud, which is its own quiet indictment of how long I waited.

A few things stayed with me. Most of my team found new jobs within a couple of months; they were good, and the market knew it. But a few struggled longer. One or two sold things — a bike, a little gold — to bridge the gap. A couple left the city entirely and went back to their hometowns, and never came back. I think about them. The macro story is “the division was wound down.” The micro story is that a specific person packed up a specific life because a bet I led didn’t pay off.

I learned that you do not get to control the narrative of how a failure lands on other people. You only get to control whether you faced them honestly while it happened. I tried to. I was not always good at it. I was sometimes a coward who hid behind process when what people deserved was a direct human conversation.

What failure actually does to a leader

It does not make you wiser in some clean, montage-friendly way. First, it makes you smaller. There is a period where you are genuinely worse at your job — more cautious, more defensive, quicker to assume the worst. Failure is not automatically a teacher. Left alone, it is just damage.

What turned it into something useful was being forced to separate two things I had fused together: my identity and my outcome. For a long time, I was the venture. So when the venture failed, the only available conclusion was that I had failed — full stop, as a person. That is a trap. The event of failure is not what defines you; what you do next is. I had to learn to say “this thing I did failed” instead of “I am a failure,” and those are not the same sentence even though my gut insisted they were.

The other thing it did, eventually, was give me a different relationship with risk. I now genuinely operate as if today could be the last day of whatever I’m building — not from fear, but as planning. You prepare for the worst not because you expect it, but because preparing is the only thing that lets you act bravely when the evidence turns. Change is inevitable; suffering is optional — but the suffering only becomes optional if you’ve done the unglamorous work of being ready before you need to be.

If I could go back and say one thing to the version of me staring at that red forecast, it would be this: the kindest thing you can do for the people who trusted you is to stop being kind to your own pride. Make the call. Tell them straight. Then help them land somewhere good. Everything else — the story, the legacy, the version of yourself you were protecting — costs other people more than it’s worth.

I wrote a whole book partly to make sense of seasons like this one, and I’ve put the frameworks and tools that actually helped me recover over in the resources. If you want the longer arc of how this and a few other scars shaped how I think, that’s on the about page.

The team I let go taught me more than any product I shipped. I just wish the tuition hadn’t been paid by them.