Insights

A company arrived at a capital conversation certain they had everything they needed. A tight deck. Credible numbers. A Dropbox folder of supporting documents nobody had asked for. And a claim, stated with the kind of confidence that makes you want to believe it: their technology was superior to anything else available in the market for their intended application. They expected the money to follow. I was part of the team responsible for due diligence before they went to investors. I put the claim to the test. Multiple tools, different queries, the same question approached from different angles. ...

There is a role that accumulates quietly in founder-led companies. It has no job description. Nobody applies for it. The founder does not choose it deliberately. It forms in the gap between a growing organisation and the infrastructure that organisation needs to function — and by the time it is visible, it has been the operating reality for months or years. The role is Chief Escalation Officer. The job title says CEO. The job description, if you wrote it honestly from the calendar and the inbox and the pattern of decisions that arrive each day, says something different. It says: the person through whom every significant decision must pass before the organisation can move. ...

Most leaders who calculate it find the number sitting between 10 and 35% of annual revenue. The first reaction is always: that cannot be right. It is right. Not because the organisation is failing. The companies this applies to are growing, or holding, or moving in the right direction by most of the measures they track. The teams are capable. The founders are working harder than they have ever worked. The results are just not proportional to the effort. Somewhere between what the organisation should be producing and what it is actually producing, something is being lost. It can be felt. It cannot be found on a spreadsheet. ...

Some problems are not solved by better decisions. They are structured so that every available response makes the underlying issue worse. This is not a failure of judgment. It is not a management problem or a culture problem or a communication problem. It is an architectural problem — a structural condition that produces bad outcomes regardless of how capable or well-intentioned the people inside it are. The name for it is the Double Bind. ...

A client came to me with a specific problem. Their middle management layer wasn’t performing. Managers weren’t taking ownership. They weren’t leading their teams. They were still behaving like operators rather than leaders, which was trapping senior leadership in day-to-day decisions that should have been handled one level down. The presenting diagnosis was not unreasonable. The behaviour it described was real and observable. The solution it pointed toward was clear: develop the middle management layer. ...

In 1870, an Iowa farmer named Jesse Hiatt noticed a seedling growing in his orchard. He cut it down twice. It kept coming back. The third time, he let it grow. The apple it produced was genuinely unlike anything available. Firm. Sweet. Complex. He named it the Hawkeye. A nursery bought the rights, renamed it the Red Delicious, and began distributing it across the country. By the mid-twentieth century it was America’s best-selling apple. In its peak years, it held 75% of the domestic market. ...

Something is slowing your company down. You can feel it. You may not be able to find it on a spreadsheet. The company is growing, or holding, or moving in broadly the right direction. The team is capable. You are working harder than at any previous point in the company’s life. And the results are not proportional to the effort. There is a drag — on growth, on cash flow, on your own energy — that does not have a clear origin. ...

The leadership team had spent two days on strategy. Good people. Serious thinking. A real conversation about where the company was going and what mattered. On the third day, someone asked what they were actually working on that week. The room went quiet in a specific way. Not confused. Just suspended between the strategy they had just agreed and the work that was waiting for them when they got back to their desks. The gap between those two things had no name and no bridge. ...

The previous essay in this series established the Stagnation Tax — the quantifiable annual cost of structural dysfunction in a founder-led organisation, typically running between 10 and 35% of annual revenue. This essay breaks it into its three components and shows how to estimate each one. The three buckets are not equally visible. One leaves no trace at all. One hides inside what feels like ordinary friction. One is politically the hardest to close. Together they account for most of the gap between what an organisation should be producing and what it actually does. ...

Nobody joins an organisation intending to disengage. They arrive with energy, with ideas, with a genuine interest in doing good work. They want to contribute. They want to be trusted with meaningful decisions. They want to feel that what they do each day connects to something that matters. Six months later, some of them are doing the minimum. Not because they became less capable. Not because they stopped caring. Because the structure they are operating inside has taught them, one experience at a time, that caring actively costs more than it returns. ...