Ben Chestnut: Why I Sold MailChimp; How My Kids Found Out I Was a Billionaire | E959

Ben, I am so excited for this. I had the most wonderful discussion with your sister beforehand. But thank you so much for joining me today.

Glad to be here. Thanks for inviting me.

I wanted to-

And I hope she didn't give you too much dirt.

Oh, she gave me so much dirt. But we're gonna get into that-

(laughs)

... later.

(laughs)

We were just chatting now, and you said to me that you're an accidental entrepreneur. And so talk to me, how did you come to found Mailchimp? And what was that aha moment for you?

Well, you know, I always wanted to be a designer, you know. I, I, I loved drawing when I was a kid. I had a couple of businesses, um, in grade school. You know, I, I used to sell... I would get those little 3M sticky pads and I would draw animations, li- little cartoon flip books, and I would sell those on the bus.

Wow.

Um, and, and, you know, that's how I got my taste of business. And I, you, you know, moved on to selling candy, comic books, m- uh, my own comic books that I would draw. Uh, and I, and I still maintain that Mailchimp is really just the end of a series of pivots from grade school. But I, I always wanted to be a car designer. You know, I went to industrial design school. I kinda, along the way, fell in love with web design. You know, I got an internship at an appliance company, and I learned how to design appliances. And I was really bad. I was good at designing things on the computer, but I was really bad with my hands. I didn't have the dexterity to kind of use that X-ACTO blade and cut foam models, uh, like you're supposed to do. You gotta... You have to do that with... when you design cars as well. I was really bad at it. And, you know, the mentors that I had at the time were like, "Yeah, you're... All of these refrigerators are lopsided." So one of them, you know, gently nudged me towards the, the Silicon Graphics machine and said, "You m- you might wanna try 3D rendering instead." (laughs) And so I, I, I fell in love with that machine. I fell in love with computers. I never went back. I learned web design that summer internship. Uh, and yeah, I got into that the next, the next semester and never went back.

You mentioned Mailchimp being kind of the result of a series of kind of continuous pivots. I love that description. When did you realize, "Oh, oh wow, this is a real thing"? Was it a millionaire or 10 millionaire or international offices? When was that, "Oh, this is real"?

It took me a long time to realize that. I mean, it was, it was an accidental kind of a business. We built it for just a couple of our customers who are having problems sending out email newsletters. Our real business was doing web design. And it was just sort of we built it on the side, and it kinda got annoying to log in and use it on behalf of our customers. So we just made it self-serve. We just said, "You log in, you use it, and pay with a credit card 'cause we're tired of cashing the checks as... or depositing all these little, you know, $50 checks." Um, I was driving to the bank too much. And so great problem to have, but it was also very, very annoying that way. And so anyways, we made it totally self-serve, and it just started to grow organically. But we never took it seriously. We just focused on our web design business. And I don't know, maybe three or four years went by, and we were so... We were exhausted from running an agency. I mean, the billable hours game, we... selling to clients, we were bad at it. And, um-