Author name: Kaihan Krippendroff

Listen to an AI audio recording of this newsletter For years, we have talked about automation as if it were the destination. Install the software. Connect the systems. Eliminate the repetitive work. Free up time. All of that matters. But it is no longer enough. Lately I have been listening to a podcast called ​Automate […]

Listen to an AI audio recording of this newsletter At the recent Outthinker Summit in Miami, our coaches compared notes from the companies they advise, and a clear pattern emerged. The power of the Outthinker 9 Ps framework is not just that it gives leaders nine separate boxes to fill out. It expands the aperture

Written by Kaihan Krippendorff and Nazanin Homayoun Jam Not every scale story is led by the founder. Many brands begin with entrepreneurial spark, but the next chapter, turning a promising business into a global institution, often belongs to someone who didn’t start it. Scale requires a different kind of leadership, someone willing to step in,

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