In a recent episode of No Priors—an excellent podcast co-hosted by AI investors Sarah Guo and Elad Gil—Gil made a point about exit timing that’s no doubt familiar to founders who’ve spent time with it, but one that seems especially useful during back-and-forth deals.
Gil said that for most companies, there’s a period of about 12 months where the business peaks, “and then it crashes.” Companies that capture generational returns are often the ones where someone spies the moment rather than assuming that the good times will only get better. Lotus, AOL and Mark Cuban’s Broadcast.com are all trading at or near the top, and all are held up by Gil as forward-thinking and gracefully dwarf outfits.
To capture this window, Gil offered a practical suggestion: schedule a board meeting once or twice a year specifically to discuss exits. If it’s a permanent calendar item, it takes emotion out of the equation.
This is more important than it was a few years ago. Many AI startups exist in part because the foundational models haven’t yet entered their category. But many founders, like Alex Bouaziz, CEO of Deel, have begun to jokingly admit that it won’t last forever.
As Gil said: “As you see the difference and defensive ability change and everything else, it’s a good time to ask, ‘Hey, is this my moment?’ Are the next six months going to be the most valuable month I’ll ever have?”
