James Gilbert

HubSpot acquired The Hustle off a single cold email

Kieran explains the deal originated internally at HubSpot, then a teammate named James Gilbert sent The Hustle a cold email to make first contact. That cold outreach is how the entire acquisition got connected.

“So we went and talked to some media companies and I think it was James, no it wasn't, it was someone internally and said, hey, have you thought about The Hustle? And I told James, who's on my team, hey, you go check out The Hustle, talk to The Hustle. And that's how we first got connected.”

Anatomy of a cold email that lands an acquisition

Sam reads the actual cold email from HubSpot's James Gilbert: a personalized opener acknowledging Sam's Lyme diagnosis, a clear ask about acquiring content businesses, and shared interests like self-storage and home ownership to build rapport.

“hey, Sam, I've been a longtime follower of you. Sorry to hear about your recent diagnosis of Lyme. I know it's pretty hectic, but hope you're okay. And I like that. So he goes, so we're looking to partner or even acquire content businesses where we think it'd be a right fit. And then basically he says, uh, is this something you would be interested in talking about? And he said, by the way, I'm also interested in self-storage and I think home ownership is not an investment, but a consumption point.”

Steal thisOpen a cold email with a genuinely personal note, then dangle a shared interest before making your ask.