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 […]
Why Scaling Gets Harder at $500 Million Read More »
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
From Personal Pain to a New Standard of Care Read More »
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
Automate the Process. Protect the Thinking. Read More »
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
Today’s Competitive Edge: People, Pricing, and Partnerships Read More »
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,
The Art and Discipline of Scaling Read More »
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
Five Signals From Q1 That Will Shape Q2 Read More »
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
From Customer to Fan: How Lifetime Value Becomes Exponential Read More »
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
Scaling What You Stand For Read More »
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
A Birthday, the Ocean, and a Lesson in Strategy Read More »
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
SXSW: When AI Gets Hands Read More »
