AI compressed the timeline for everything. Everything except trust. Decisions that used to take a quarter now take a week. The people at the top are being asked to show up differently, faster, with less room to think. Every year, we bring our highest-growth founders to one place and ask them to stop running for a few days. This year, we took them to Portugal for our 2026 Endeavor Outliers Retreat. Javi Olivan, COO of Meta, set the tone on day one: scaling in the AI era isn’t a technical problem but a leadership one. When the company can move faster than you can think, the bottleneck isn’t the product, it’s you. From there, the conversations went everywhere they needed to go. C-suite readiness for AI. Whether now is the time to raise, to exit, or to hold. Board tensions. Moving your family across countries. Whether you’re still the right person in the seat… These guard down conversations turned 90 Endeavor Entrepreneurs that arrived as founders to leave as something closer to fr...