Kaihan Krippendorff

Listen to an AI audio recording of this newsletter A few weeks ago, I was talking with my friend Jeff about how much of life and business runs on default. We like to imagine that we are constantly making thoughtful, intentional choices. But of course, we are not. We do not have the time, attention, […]

Listen to an AI audio recording of this newsletter At our next ​Outthinker Summit on May 28​, we will gather with a group of strategy and transformation leaders already asking one of the most urgent questions facing large organizations: How do we turn AI from a productivity tool into a growth engine? That question has

Listen to an AI audio recording of this newsletter Most companies do not lose because they lack data. They lose because they use data to arrive at the same conclusions as everyone else. Today, executive teams have access to more information than any generation of leaders before them. Dashboards update in real time. Customer data

Listen to an AI audio recording of this newsletter I was out in the Pacific Northwest speaking to the executive team of a fast-growing consumer products company. The company had brought together its leaders not just from the United States, but from Japan and Europe. It was only the second time leaders from the entire

Written by Kaihan Krippendorff and Nazanin Homayoun Jam Some founding stories begin where the personal and the professional can no longer be separated. For Dwayne Clark, that line dissolved when he was twelve years old, watching his grandmother — a woman who spoke three languages, ran her own business in the 1930s, and raised thirteen

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