Post by Whitney Belmonte

I once texted the CEO of the public company I worked for at 7am on a Saturday. Like a maniac. 😂 It could’ve been one of my worst decisions, but that’s not how it turned out. Here’s what happened… I was leading product marketing at Chegg when AI suddenly became the topic of conversation—every meeting, every strategy doc, every hallway chat. It was clear this wasn’t just hype—it was going to change everything. I got curious. Then obsessed. I started playing with AI tools. Making Instagram reels about how to use AI in business. And then… things took off. A few of the videos went crazy viral—one was shared over 30,000 times. And that’s when the guilt hit. I was working at a company being disrupted by AI… while going viral for talking about how amazing AI was. 😬 So in a full-blown anxiety spiral, I did something UNHINGED: I texted the CEO. At 7am. On a Saturday. Not just any CEO—Dan Rosensweig. The CEO of a public company. Host of his own TV show. Board member of billion-dollar businesses. Like… a real CEO. He later told me he was shocked (and honestly kind of amused) that someone at my level had the guts—or the delusional confidence—to text him at sunrise on a weekend. But he took the call. And he was kind. Logical. Generous with his time. He asked thoughtful questions. Treated me like an equal. I already admired him, but that conversation changed how I thought about leadership. Fast forward two years: I leave corporate to run an AI consulting business full-time. I post about it. Dan reaches out to say congrats—again. 🌊 Then today, I post a random beach video from Montauk. Dan sees it. Messages me: “I’m in Montauk too. Want to meet?” So we grabbed coffee. Talked about AI. Reinvention. Risk. The art of building a life that actually feels good to live. And now I’ve got a new favorite full-circle story. Moral of the story? Share the thing you’re obsessed with. Be bold enough to act on it—even if it feels awkward or messy. 🤯Text your CEO (maybe wait till 9am). And trust that the right people will get it.