Outthinker

Listen to an AI audio recording of this newsletter Three months into 2026, one thing is clear: this is not a year that will reward certainty. The first quarter has been full of headlines. Tariffs. Elections. AI announcements. War. Market swings. A steady stream of predictions about what will happen next. But leaders do not […]

Listen to an AI audio recording of this newsletter Every March, something remarkable happens. Millions of people fill out brackets for the ​NCAA tournament​, March Madness, knowing full well that their predictions will almost certainly be wrong. In fact, the NCAA has long noted that the odds of picking a perfect bracket are roughly 1

Written by Kaihan Krippendorff and Nazanin Homayoun Jam At the very beginning of a business, there’s a moment that matters more than the product itself. It’s the moment when a founder realizes they can’t build it alone. An idea only becomes real when others are willing to believe in it, invest their energy in it, and help carry it forward. That

Listen to an AI audio recording of this newsletter I turned 55 a few weeks ago. Birthdays have a way of making time visible. I took a few days off to be with the people who matter most to me — my wife and my kids. We stayed near the ocean, and on the morning

Listen to an AI audio recording of this newsletter The energy in ​South by Southwest​ (SXSW) is hard to describe if you haven’t experienced it. Every March, Austin, Texas, turns into a living lab for ideas. Founders, technologists, filmmakers, investors, and musicians spill out of panel rooms into coffee shops and sidewalks, continuing conversations that

Written by Kaihan Krippendorff and Nazanin Homayoun Jam Scale has a way of revealing things leaders didn’t know they were relying on.  In the early days, that dependence is easy to miss. Small teams coordinate through instinct. Founders compensate for missing systems. Favorable market conditions can hide weak pricing, weak incentives, or weak discipline. But

Listen to an AI audio recording of this newsletter I’m writing this while preparing to speak with a group of marketing master’s students at ​Universidad Americana​ in Paraguay about strategy, growth, and how organizations decide where to place their bets. Just before noon, I step into the hotel van, and we wind our way through

Listen to an AI audio recording of this newsletter A few days ago in London, I walked into ​LHH​’s Executive Exchange Conference with a familiar feeling. Floor-to-ceiling windows overlooked the River Thames as it curved through the city, steady and continuous, a reminder that even the most established systems are always in motion. Inside the

Listen to an AI audio recording of this newsletter Last week, I spoke to a room full of independent roofing and siding distributors at ​NEMEON​. The conversation was candid, grounded, and far more hopeful than the headlines would suggest. Because yes, the construction and roofing industries are changing fast. Consolidation is accelerating. National players are

Listen to an AI audio recording of this newsletter Most new business ideas begin the same way. There is a flash of insight. A conversation that refuses to leave your head. A sketch on a napkin. A deck built late at night. For a brief moment, everything feels electric. Then the silence starts. Early excitement