12-month window | TechCrunch

On a recent episode of No Priors — the excellent podcast co-hosted by AI investors Sarah Jo and Elad Gil — Gil made a point about exit timing that is no doubt familiar to founders who have spent time with him, but seems especially useful in this moment of dealmaking.

For most companies, Gill says, there’s a period of about 12 months in which the business reaches its peak value, “and then it crashes” and the window closes. The companies that reap generational returns are often the ones where someone spies on the moment rather than assuming the good times will get better. Mark Cuban’s Lotus, AOL, and Broadcast.com sites were all sold at or near the top, and they are all held up by Gil as examples of fashion that foresaw what was coming and pulled the rip cord smartly.

To take advantage of that opportunity, Gill offered a practical suggestion: schedule a board meeting once or twice a year to specifically discuss exits. If it’s a fixed item on the calendar, it drains emotion from the equation.

This matters more now than it did a few years ago. There are a lot of AI startups out there, partly because the basic models haven’t expanded to their category…yet. As many (such as Dell CEO Alex Bouaziz) jokingly acknowledge, this won’t last forever.

As Jill puts it: “As you see the shifts in differentiation and defensibility and all the rest, it’s a good time to ask the question: ‘Is this my moment?’ Are these the next six months where I will become the most valuable ever?