There is an old idea that a cart pushed too fast loses its wheel. Not because the wheel is broken. Not because the cart is poorly built. But because the speed outpaced what the structure could handle.

The wheel was fine for the journey it was designed for. It just was not ready for that one.

I went to a book launch this week. A journalist who has spent years interviewing entrepreneurs about turning setbacks into breakthroughs. What struck me listening was how consistent the pattern was. Not that failure was inevitable. But that the founders who broke through were not the ones who avoided it. They were the ones who understood what it was telling them.

The wheel came off, and instead of replacing it and pushing harder in the same direction, they asked why.

I have done it. More than once. I want to tell you about two of those times, because the lessons did not arrive when the wheel came off. They arrived much later, and they were worth more than the failures cost.

The app that could not be sustained

In 2011, we built what I believe was the first compliance app in our sector.

The idea was genuinely good. Insurance brokers needed to evidence client meetings: when they happened, where, what was discussed. We built an app that captured all of it. GPS location, timestamped notes, voice recording, an auditable trail sent automatically to both broker and client.

The feedback when we launched was excellent. Our insurer partner backed it. Brokers who used it loved it.

Then we hit the wall.

The economics

App store economics in 2011 were nothing like they are today. There was no subscription model. You could not adjust your price upwards, only down. We either priced it at £19.99, which made adoption almost impossible, or 99p to be priced like a game, which made it commercially unsustainable. We made it free. Within a year, we could not keep up with the development costs to maintain updates and version control for a product generating no revenue.

Phone display advancement accelerated, and the development could not keep up. The app faded away.

Last year, fourteen years later, a colleague received a message from someone asking if we had ever built a compliance app. A broker had been talking about it. Asking if it still existed. Said it was an excellent product.

I sat with that for a moment when he told me.

Working with an external developer meant every small change needed a new quote. Every update took weeks to schedule. We could not iterate quickly, could not respond to user feedback, could not stay close to the product.

If we were going to innovate properly, we needed a developer in-house. That realisation came entirely from a product that did not work commercially. And it led directly to our first in-house development hire: a superstar who rebuilt our entire e-learning platform from the ground up, helped us reach 26% market share, and made us market leader in our sector.

The wheel came off the app. But it showed us exactly which part of the cart needed reinforcing before we pushed again.

Too early is its own kind of failure

A few years later, we took that learning platform beyond financial services. Same gap analysis model. Same approach to building competence rather than just logging course completions. But available to any business that wanted to develop their team properly, not just insurance professionals managing regulatory requirements.

The pitch meetings were almost universally positive. People understood the problem we were solving. They liked our approach. They asked intelligent questions. But the sales only dripped through.

We came close, repeatedly. A homelessness charity in Cardiff using the platform to help people return to work. A partnership with the South Wales Chambers of Commerce. Interest from schools, prisons, corporates. Organisations in Canada and Ireland genuinely excited about what we had built.

We came second in a major local authority tender we were certain was ours. The feedback when it came was almost comical: we had lost on a points-based scoring system because our courses did not have audio narration. A feature that would have taken a couple of weeks to add. We just had not known to look for it in the procurement criteria. All our additional features could not be scored.

The broader truth was this: the market was not ready. Organisations understood the problem. They liked our solution. But they were not ready to move away from traditional approaches and make the investment to change. We were too early. Just.

Then Covid arrived. Selling a new solution to organisations whose worlds had just been turned upside down became impossible. You cannot ask a business to invest in changing how it develops its people when it is trying to work out whether it will still exist in six months.

When the idea is wrong

Stop. The market has told you something fundamental about the fit between what you have built and what people will pay for. Listen to it.

When the timing is wrong

Learn what the market needs to see before it is ready to move, and build toward that instead. These are different problems with different lessons attached.

Sometimes the timing is not wrong. It is stolen. An external shock, a change nobody could plan for, a window that closes before you reach it. That is not a lesson about your judgement. It is a reminder that commercial structure has to be able to absorb shocks it did not see coming, because the ones that matter most are always the ones you cannot predict.

What failure actually costs

The businesses I work with are growing. They have built something that works. They have pushed the cart a reasonable distance. And then growth stalls, or slows, or starts to feel like it is costing more than it is returning.

When I ask what has been tried, the list is usually long. New marketing. A rebrand. Different pricing. An extra salesperson. A restructure. Sometimes two restructures. All of it activity. Some of it useful. Most of it treating the symptom rather than the cause.

The compliance app did not teach me that apps were a bad idea. It taught me that the right infrastructure, at the right pace, is the precondition for everything else. Today’s app economics and subscription-based pricing would suit the model we wanted to deliver in 2011. It just did not exist at that time.

The e-learning platform did not teach me that cross-sector expansion was a mistake. It taught me that the market’s readiness matters as much as your product’s quality, and that being too early is only a failure if you do not know what to do while you wait.

A wheel that falls off a cart moving in the wrong direction is just information. It is telling you something the founder did not want to hear before they spent money confirming it.

The question worth asking

When I work with founders on their proposition, one of the early conversations is always about the decisions that did not work out. Not to dwell on them, but because they are usually the clearest evidence of where the real problem is.

A pitch that failed because of price is a positioning problem. A client that churned is often an infrastructure and service problem. A product that nobody bought might be a market-timing problem. Or a messaging problem. Or a distribution problem. The failure itself is just the surface. What is underneath it is the useful part.

Most founders I talk to have learned something from their failures. What they often have not done is connected that learning to a deliberate change in how they are building the business. That gap, between knowing something and acting on it, is where most plateaus live.

The cart is fine. The wheel is fine. The question is whether the thing that came off is telling you about the road, or about the direction you are pushing in.