Mailchimp

“The guidance was hands off, eyes on. And that was the biggest change for me, being, trying to be hands off, but eyes on.”

“We talked for a year, by the way, the whole thing was an entire year of due diligence and sort of courting each other you know, testing the waters here and there.”

“Once you get it to, like, 500 to a thousand employees, it's less of a startup or a company where everyone's kind of following the same mission. It's not, you know telepathic, where everyone knows what it is the leader wants. It's like you're the mayor of a rea…”

“There were times when I think we could have sold the business early. There were a lot of people, you know, a lot of suitors knocking on the door, a lot of investors knocking on the door. And I think I just sort of had this like stubbornness that I didn't need …”

“After a few years in MailChimp might have been making a few 100,000 dollars at the most. And our agency business was making a little bit, just barely more than that, but it was flat.”

“Because of my mother, I think I never called our customers small businesses. I never said small, I would say businesses, or I would talk about their dreams of becoming big, but I never like called it. It's useful, you know, internally to call it a category SMB…”

“Freemium was something that we kind of accidentally fell into, didn't really think much about it, and that turned out to be this thing that kind of, I think we were probably, you know, in tens of thousands or hundreds of thousands of users at the time, and the…”

“I still maintain that Mailchimp is really just the end of a series of pivots from grade school.”

“Sick and tired of the whole process, by the way, because it takes away six months of your innovation and your inner, you know, your momentum and stuff. It's distracting.”

“Mailchimp was making hundreds of millions of dollars and we were on the cusp of a billion ARR when the acquisition happened. So, I mean, we were already doing really, really well, highly profitable.”

“To me, that's high performance. It's sort of like looking at the roots of what's causing you to not be high performance and changing these core habits that are blocking you.”

“I think that event, you know, we ran some analytics on this, I think, you know, a while, while ago, and there was definitely there was a bump, but I think people were surprised at how much there was kind of already these big, huge tailwinds and that, you know,…”