The first four essays in this series were all about the same thing, approached from different angles. A company with a claim that didn’t survive thirty minutes of research. A marketing agency writing posts for clients who refused to discuss strategy. An investor who said nothing, moved to the next meeting, and was never heard from again. An apple that looked perfect while the quality had already been irreversibly gone for thirty years. ...
The brief was straightforward. A LinkedIn post. Something that would show the market they were active, thinking, growing. Something polished and credible by the end of the week. I asked what they were trying to build. The conversation stopped. “We don’t want to talk about that. That’s not relevant. We just want the LinkedIn post.” This was not an unusual client. That sentence, or a version of it, is one of the most common things I heard in that period, working inside a marketing agency, helping companies communicate who they are to the markets they want to reach. ...
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. ...
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. ...
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. ...
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 meeting went well. At least, that is what the founder believed when they left the room. The investor had been engaged. Asked good questions. Stayed for the full session. Said something polite at the end about following up. They did not follow up. This is not a story about bad manners. It is a story about what investor silence actually is, and what founders systematically misread it to be. ...