Insights

The Blog.

Essays and field notes for PE-backed CEOs navigating performance, transition, and reinvention.

Blog

Don’t Waste the Miss

Every CEO eventually gets a quarter that doesn't go the way the plan said it would. The best ones treat it as one of the most useful moments they'll get…

Landon Olsen Sep 28, 2026 3 min read
Blog

The Energy You Bring Is Part of the Plan

Every plan has the obvious inputs: the strategy, the budget, the team, the timeline. There's one more that rarely makes the list and quietly shapes all of them, and that's…

Landon Olsen Sep 21, 2026 3 min read
Blog

Start the Question Early

Most CEOs think their transition starts at the exit. The best ones started years earlier, with a single honest question.

Landon Olsen Sep 14, 2026 3 min read
Blog

Acknowledgement Isn’t Alignment

You leave a conversation with your board or your boss feeling like you got a yes. Everyone was pleasant, heads were nodding, no one pushed back. Then nothing happens. If…

Landon Olsen Sep 7, 2026 3 min read
Blog

Peace Is a Posture, Not a Destination

A lot of driven people quietly believe peace is waiting for them on the other side of the next milestone. It usually isn't, and that turns out to be good…

Landon Olsen Aug 31, 2026 2 min read
Blog

From AI Strategy to AI Advantage

Almost every board conversation right now includes some version of "what's our AI strategy?" It's the wrong question, and it quietly sends teams chasing tools instead of outcomes.

Landon Olsen Aug 24, 2026 3 min read
Blog

Clarity Comes From Distance

Ask leaders who stepped back from the seat what surprised them most, and a lot of them say the same thing: they could suddenly see the business, and their own…

Landon Olsen Aug 17, 2026 3 min read
Blog

Build the Team That Doesn’t Wait for You

There's a quiet sign that a leadership team has come to depend on you too much: every real decision finds its way back to your desk. Two leaders disagree, and…

Landon Olsen Aug 10, 2026 3 min read
Blog

Let Them Fly

There's a story worth sitting with. What happens to a butterfly when you put it in a box and close the lid? It suffocates.

Landon Olsen Aug 3, 2026 3 min read