To catch that window, Gil offered a practical suggestion: pre-schedule a board meeting once or twice a year specifically to discuss exits. If it’s a standing calendar item, it drains the emotion out of the equation.

This matters more now than it might have a few years ago. A lot of AI startups exist partly because the foundation models haven’t expanded into their category yet. But as many founders — like Deel CEO Alex Bouaziz –have jokingly begun to acknowledge, that won’t last forever.

Oh great and powerful @DarioAmodei – builder of minds, father of Claude. I humbly request you leave payroll to us at Deel. We are but simple folk who process paystubs and chase compliance deadlines. But if you do come for us, call me first 🙏

As Gil put it: “As you see shift[s] in differentiation and defensibility and all the rest, it’s a good time to ask, ‘Hey, is this my moment? Are these next six months when I’m going to be the most valuable I’ll ever be?’”