The Observer's Notebook

  The Difference Between a Business Problem and an Orientation Problem Some problems look tactical. They aren’t. By the time founders reach me, they’ve already done what responsible operators do. They adjusted the offer. Reworked pricing. Rebuilt the funnel. Hired support. Tried the strategy everyone said should work. Nothing is obviously broken. And yet nothing fully holds. That’s usually when the conversation changes. Not because the business suddenly became complicated, but because the problem was misidentified from the start. What a Business Problem Actually Is A true business problem has a location. Conversion is low because the page isn’t carrying its weight. Revenue dipped because pipeline maintenance slipped. Positioning stopped resonating because the market moved and the message didn’t move with it. These problems are real. They respond to intervention. You find the break, you repair the break, forward motion resumes. Experienced founders are usually capable of solving the...

  Why Capable Founders Keep Starting Over The founders who end up in my work aren't struggling because they lack skill. Most of them are exceptionally capable. They can execute. They understand their market. They've built things before. They keep starting over anyway. This is the pattern I've watched repeat across service businesses at every stage: the person with the most evidence of capability is often the one rebuilding from scratch the most frequently. Not because they failed. Because something stopped compounding and they couldn't figure out why, so they started over. That's the part nobody talks about clearly. Starting over gets framed as pivoting. Or as evolution. Or as finally getting clear on what you really want to do. Sometimes those things are true. But in most of the cases I see, starting over is what happens when a capable person applies real effort to a business that has quietly lost its orientation, and the effort stops producing results that match t...