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Ben Chestnut

Ben Chestnut

American internet entrepreneur and former CEO of MailChimp

Aug 12, 2026

14:10
What would more money actually do? But there was another reason, something deeper than the math.
14:15
What I noticed every time they came knocking, they would really just give me someone else's playbook.
14:21
They would say, take our money and then you can do what Constant Contact did.
14:24
They really just wanted me to be the next IPO.
14:27
And so I kind of, as an entrepreneur, I'm sure you all can relate, I wanted to build my own thing my way.
14:33
This was my baby, I was gonna do it Bruce Lee style.
14:37
This is the way, my way.
18:16
And Ben Chestnut was starting to feel different.
75:49
Yeah.
75:50
We learned a lot from that.
75:51
Um, and I, I am grateful for what we learned from it.
75:54
And, you know, in retrospect, I think we were always intentional about our culture at Mailchimp, right? I mean, we got people to help us codify it.
76:05
I mean, we hired a chief culture officer.
76:07
I, I would say that we were really good with our culture, and what can happen to a founder, you know, this is, this is my warning to other entrepreneurs out there, is when you're good at culture in the early years, sometimes you can kind of lull into like an autopilot, right? Like, we were good and we were attracting people because of our culture.
76:27
People were doing stories about our culture.
80:15
Are, are you a believer in luck? Or do you think that what happened really has to do with just how strategic and smart you guys were?
19:33
To raise money.
19:34
Yeah, pretty much.
19:35
It was a couple of things.
19:36
I. freemium was new so freemium the concept debuted in like a book by chris anderson from wired magazine i think the book is called freemium we had been working on a free plan at mailchimp for like about a year and we were ready to launch it and i had a blog post drafted something like mailchimp's free plan you know that was the title and the next morning i was going to publish it and the next morning i came in and there was a book lying on my desk and it said freemium And some employee of mine, he knew we were talking about this free plan and he got this book and he put it on my desk and I thought, oh, I'll just call it that freemium.
20:15
And so I changed my blog post title to, you know, MailChimp goes freemium.
20:19
I think that was my post.
20:21
And when I did that, a guy here, Hudson, Charles Hudson, I think it was his name.

28 MINS LATER

47:59
at that time.

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