The Moment You Realise What Isn’t There

We won a piece of business we were not expecting to win. The revenue jump from our previous largest contract was significant enough to change the shape of the company. We were elated.

Thirty minutes later, someone looked at the calendar, and the elation gave way to something else entirely. We had committed to initial operating capability (‘IOC’), a military term I had carried with me from my time in the Royal Marines, within ninety days. We had sold something we did not yet have: no capability, no people, no technology, no process. Just a contract, a deadline, and the gap between them.

In startup jargon, this is sometimes called ‘jump and backfill.’ You commit, you move, and you build the capability behind you fast enough to honour what you have promised. I had done versions of it in uniform, and I understood instinctively why it worked. Dealing with unexpected, unplanned events is a trained and learned skill. The unfamiliar is not automatically a threat. It is a problem to be solved under pressure, and pressure was something I had been conditioned to work through rather than away from.

What I had not fully accounted for was how much of the infrastructure that made that instinct viable had simply ceased to exist.

The Scaffolding You Never Noticed

The technology gap we could manage. We could iterate, build as we went, procure the infrastructure we needed without facing dramatic lead times. The people gap was a different problem entirely.

We did not want contractors. The business case was clear: permanent hires build programme knowledge, carry institutional memory, and compound their value over time. Contractors do not. But the standard hiring cycle, from identifying a candidate to them being in the building and productive, was itself approximately ninety days. Finding people, recruiting them, and waiting while they worked out notice periods with existing employers. We were looking at a ninety-day IOC deadline against a ninety-day hiring lead time. There was no solution to that equation that left both constraints intact.

We brought in contractors. A specialist systems integrator who arrived with an experienced team in place. Junior roles supplemented with individual contractors. We hit IOC. The margin took the hit.

What I was reaching for, without being able to name it at the time, was the network of competence that elite institutions provide almost invisibly. At NASA, if you needed someone who could do a specific thing, they were already there, already filtered by the institution. At SpaceX, the same. In the Royal Marines, the person to your left and right had been through the same process you had. In a startup with eighteen months of history, that network does not exist. You have to buy it in from whoever will sell it, at whatever the market charges, in the timeframe you cannot extend.

The scaffolding was gone. What I had assumed was a capability I possessed was, in significant part, a capability the institutions had provided.

When You Become the System Itself

There is a transition point in moving from operating inside great institutions to founding your own that almost nobody describes honestly. In every institution I had been part of before, there was a way things worked that preceded me and would outlast me. I had been shaped by it, sometimes without knowing. When I started the company, I became responsible for creating it. And the early decisions I made, quickly, out of necessity, with incomplete information and no predecessor to consult, became the cultural foundation before I had thought about them in those terms.

One of the clearest examples is one that might sound trivial but was not. In the early months, I made the call to take on an office. The expense was questioned. We were a small team and the cash mattered. But I was fixed on it: training together, learning together, fighting together. I had seen what it produced in the Marines. I had felt its presence and absence in different ways at NASA and SpaceX. We called the office The Cauldron, because it was where we brewed the business.

We would never have made the early progress we did without being in the same space. Not proximity as an abstract principle, but the speed at which information moves when it travels at the pace of conversation rather than email.

That decision became cultural precedent before I had thought about it in those terms. The team drew a conclusion about what kind of organisation this was and what it would prioritise, without a single explicit conversation about values. Those early decisions, the ones that feel pragmatic and necessary at the time, are often the ones that turn out to have been the most consequential. The team is watching. They always are.

What Transferred and What Didn’t

The most useful thing my military background gave me as a founder was conceptual familiarity with the unexpected. Not the absence of difficulty, but the trained reflex of treating an unplanned situation as a problem to solve rather than an emergency to survive. The ‘jump and backfill’ instinct was not recklessness. It was a reflex built over years, operating through the two-speed decision framework I described in an earlier post in this series: move fast on reversible decisions, apply more rigour to the ones that cannot be undone.

What did not transfer cleanly was the expectation of excellence.

In a military context, imperfection has consequences that are sometimes irreversible. That standard gets conditioned in deeply, and it does not come out cleanly when you change contexts. Almost weekly, I found myself questioning the completeness of what we were building. Not because it was broken, but because it was not finished in the sense I understood finished to mean. The team was moving, the product was working, progress was happening, and the instinct kept reasserting itself regardless.

It took time to accept that success and perfection are different things. In a startup, chasing perfection can be as fatal as failing to deliver, because you run out of runway while the product that would have been good enough sits in another iteration cycle. The most dangerous version of this is that it looks like rigour from the inside. It took conscious effort to distinguish between the instinct that was protecting quality and the instinct that was impeding progress. That recalibration was not a single moment of insight. It was a recurring tension I had to consciously override, and it arrived with a regularity that surprised me.

What the Exit Actually Revealed

The company sold for a number that, at the time, validated a lot of decisions at once. But the valuation was not a referendum on the culture we had built, the office we had named, or the standards we had argued about. What the buyer was actually reaching for was a single insight we had arrived at through a different route entirely.

We had started as a business that offered customers the use of our hardware in our data centres. They brought the software; we provided the infrastructure. A reasonable model, and it worked.

But we were listening. The refrain from customers was becoming loud and consistent: if only somebody could run our system for us. Not the hardware. The application. The whole operation. Microsoft was offering its Business Productivity Online Suite (‘BPOS’) for productivity tools, but there was no practical solution for mid-tier organisations running line of business (‘LOB’) applications, the custom and specialist software that actually ran most of their operations. We pivoted to fill the gap.

By 2010, as BPOS was becoming Office 365 and it was clear that the managed services model was about to reshape the market, the buyer, a global IT services provider looking to accelerate its position in a rapidly changing competitive landscape, understood exactly what they were looking at. They were not buying our headcount or our culture. They were buying the concept, early, and the evidence that it worked.

The thing that produced the exit was not the principle I had invested the most energy defending. It was the willingness to listen to customers carefully enough to hear what they were actually asking for, and the willingness to rebuild the business around the answer once we heard it clearly. That is worth sitting with. The returns did not come from what I had been most certain about. They came from what the market told us, clearly and repeatedly, once we were paying the right kind of attention.

The Question Worth Sitting With

Every organisation has invisible scaffolding. Inherited processes, cultural momentum, trusted networks, implicit decision-making frameworks that nobody documented because they never needed to. Leaders who have been inside long enough often cannot see it, because it has been part of the background the whole time.

For a chief executive or a private equity (‘PE’) operating partner, the version of this worth sitting with is not abstract. Acquisitions regularly discover, too late, that what they were buying included invisible infrastructure that evaporates when the founder exits, the key team disperses, or the institutional memory walks out the door. The valuation assumed the scaffolding would transfer. It rarely does. It had never been on any asset register.

I did not notice most of mine until I had to build it from nothing. That is a slow and expensive way to find out what was there.

The question is this: if your organisation’s invisible scaffolding suddenly became visible, what would you recognise that you had been relying on without knowing it? And what would you discover, looking at it clearly for the first time, that you had never actually built at all?