In this short conversation, Jason Lemkin describes an AI system that automatically generates highly personalized event invitation emails. The AI aggregates massive amounts of contextual data—identifying every attendee from a conference, mapping adjacent competitors, and crafting a narrative that makes the recipient feel compelled to attend. Lemkin used the tool to email CEOs of his portfolio companies, processing data on roughly 8,000 attendees and producing tailored recommendations for each recipient. The system outperforms existing event‑matching software, uncovering hidden competitive presences and even advising when attendance may not be worthwhile. While the AI delivers superior quality, each email requires 2–3 minutes of compute, highlighting a trade‑off between depth of personalization and processing time.
Chapters
from the— and maybe even it's all the accumulated context in the, in the chat, in the window. But, or maybe it's something Replit pushed out the hour before. I don't know. But it cropped— I mean, I really hate the term AGI, but when it writes a better email than any human could, it's like—
it's just OnShot on the back, right?
No, because the thing is, the reason it's so good is it's not just the quality of the email, which was undoable. It was the amount of hours it would take to find, okay, who— what's every single person from Blubbr coming? And then it assembled all the adjacent competitors for WrapUp. They're like, here are all the people coming to James and Bloomberg. You might want to go meet with all. And it assembled in a way that made it seem like James had to be there. He's like, you invested in the company, the half the company's here, the adjacent folks, the other players, the new players, the competitors are. How could you not be here, James? And it's like, how could you be not? Right. And then I had 10K write it to the CEOs of all the companies I invested in, and it went through all 8,000 people coming and assembled the best list for them to all meet. And it destroyed all the matching software we have here. Yeah. Destroyed it. Destroyed it. Now, it did take like 2 to 3 minutes per email. Mm-hmm. That's a lot of compute and going on. A lot of context. Yeah, a lot. But, and I sent it to one of my founders and it, and it uncovered that 8 of his competitors, 8 of the entire management team of his top competitor were coming and all the adjacent folks in his marketplace. And then it summarized why maybe it wasn't worth his time to come this year.
Oh. Yeah. No, it's very nice. He's like, he's like, you're—
No, he was like, your part of vertical SaaS is relatively lightly attended, but, but here are the 20 people you should meet. And he's like, that's the best marketing he email I've ever gotten too. I don't know, we got on that track, but that is, um, yeah, well, it's super powerful, right?
