The Exchanges

Q the incredible relationship you have with your mother. Um, I do with mine. Um, and she mentioned that with her funeral, you bought kind of every flower in town or as much as you could buy. And I just wanted to ask you in terms of your relationship with your mother, How did she impact how you are as a father first and how you are as a leader second?

A You know, my mother, um, she was an entrepreneur. She, she ran a, um, a hair salon, uh, in the kitchen of our home. Uh, and so we always had customers, uh, in the house and I was always helping her out, emptying ashtrays, you know, organizing the hair rollers and that sort of thing. And I watched money exchange hands and I always joke, you know, to me, if I close my eyes and I think about business, There's a smell to business and the smell is hairspray and cigarettes. You know, that's what business smells like to me. Um, so she, she didn't really talk about entrepreneurialism or business. She treated it as it was a living. It was a way to make ends meet. It was a way to help pay for the bills, you know, and I, You know, she was from Thailand and to her business is just something you do to make a little extra money. To me being a little bit more, you know, I was born in here in the States. My father is born in the States. He thought about business differently. You know, he was always talking about how does this unlock? How does the scale, you know? And so I always dreamed of my mother just scaling out of the kitchen and she never really did. And I think there was a little bit of like disappointment in me that, you know, this wonderful thing that my mother did never really, um, Just turn into like the next Vidal Sassoon or something like that. Uh, and I think that's, that's, that…

AI assessment note: “that's kind of in the DNA of Mailchimp, this sort of like this, this understanding”

Q Ben, tell me final one. What are the next five years hold for you? What's your plan ahead?

A I've met many founders who've sold their business and then they, they go off and they want to do crazy adventures. And I, and I applaud them for that. And, and, you know, no judgments whatsoever, but some of them talk about, I've met one that wanted to explore the depths of the ocean. Uh, one wanted to explore space, right? Um, and I've told them all like, what do you want? And I said, well, I want to explore my own mind. I want to know why I think the way that I do. I want to know why I am the way that I am. And I think that's infinite. That's bigger than the universe inside here. Just getting to know that. And then I also say something that's really vexing, confusing and angering to a lot of people. Nobody really gets me when I say this, but what I want the most is to not want.

AI assessment note: “I want to explore my own mind. I want to know why I think”

Q Was that always beneficial? Do you think in hindsight, you know, if you think, you know, I'm sure the most and you could have taken a 100,000,500 million, a billion, um, like everyone wanted to give MailChimp money. I remember, I'm a VC for a living, Ben. Um, like, are there moments where you're like, actually, my stubbornness was not good?

A Who knows? I mean, there are probably some people out there who could look at it and say, Ben, if you'd just taken this money back then, you could have scaled even bigger, and maybe, right now, you would have sold for twenty billion. Who knows? Um, I don't know. Uh, there are some people who say, yeah, you would, you would have had, you know, a slice of the pie instead of the whole pie, but the pie would have been bigger. Um, there's no way to tell, but I do know that when I look back at my life and my business, I'm really proud to say I did it my way. Uh, and I'm really, really proud of that. You know, there's, there's sort of a Bruce Lee element of it. He did it his way. He came up with his own style and I came up with my own way of running this business. And, um, I'm, I'm really proud of that. And it wasn't, it was always collaborative. Okay. You know, I don't want to say that it was all me. We did it our way. Might be a better way of saying it, right? Like, I'm really proud of that.

AI assessment note: “there's no way to tell, but I do know that when I look back”

Q Oh, she gave me so much dirt, but we're gonna get into that dirt later. 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?

A 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 three M sticky pads, and I would draw animations, little cartoon flip books. And I would sell those on the bus. Um, and, and, you know, that's how I got my taste of business. And I, you know, moved on to selling candy, comic books, 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 kind of, 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 exacto blade and cut foam models, uh, like you're supposed to do. You're gonna, 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 might want to try three D rendering inste…

AI assessment note: “Mailchimp is really just the end of a series of pivots from grade school.”

Q the incredible relationship you have with your mother. Um, I do with mine. Um, and she mentioned that with her funeral, you bought kind of every flower in town or as much as you could buy. And I just wanted to ask you in terms of your relationship with your mother, How did she impact how you are as a father first and how you are as a leader second?

A You know, my mother, um, she was an entrepreneur. She, she ran a, um, a hair salon, uh, in the kitchen of our home. Uh, and so we always had customers, uh, in the house and I was always helping her out, emptying ashtrays, you know, organizing the hair rollers and that sort of thing. And I watched money exchange hands and I always joke, you know, to me, if I close my eyes and I think about business, There's a smell to business and the smell is hairspray and cigarettes. You know, that's what business smells like to me. Um, so she, she didn't really talk about entrepreneurialism or business. She treated it as it was a living. It was a way to make ends meet. It was a way to help pay for the bills, you know, and I, You know, she was from Thailand and to her business is just something you do to make a little extra money. To me being a little bit more, you know, I was born in here in the States. My father is born in the States. He thought about business differently. You know, he was always talking about how does this unlock? How does the scale, you know? And so I always dreamed of my mother just scaling out of the kitchen and she never really did. And I think there was a little bit of like disappointment in me that, you know, this wonderful thing that my mother did never really, um, Just turn into like the next Vidal Sassoon or something like that. Uh, and I think that's, that's, that…

AI assessment note: “that's kind of in the DNA of Mailchimp”

Q It's different from a venture funded business though, isn't it? Because in a venture funded business, It absolutely does. You sell and you get hit with like a billion overnight. And here it's like, you just progressed very nicely, but continuously.

A Like an oak tree with really deep, strong roots. I mean, it's just very, very slowly. And, and we had kids and that's, that's a very humbling experience to have children. My co-founder had two girls. I had two boys, roughly the same age. And I don't know, man, that just grounds you. And, uh, um, I, I always felt like, you know, I wanted my kids to see me You remember what your parents did, not always what they said, but what they did, and you become what they did, and I always wanted my kids to see me working on customers, and when they would ask, you know, Dad, what are you doing? I never said, you know, making money. I never said, you know, running my company. I always said helping customers. That's always my answer, and I just wanted them to be helpful watching me. So anyways, That relationship with money, I don't know. I, I was lucky that we eased into it, and I just sort of want us to have the right attitude of, of being helpful with it.

AI assessment note: “I was lucky that we eased into it”

Q Was that always beneficial? Do you think in hindsight, you know, if you think, you know, I'm sure the most and you could have taken a 100,000,500 million, a billion, um, like everyone wanted to give MailChimp money. I remember, I'm a VC for a living, Ben. Um, like, are there moments where you're like, actually, my stubbornness was not good?

A Who knows? I mean, there are probably some people out there who could look at it and say, Ben, if you'd just taken this money back then, you could have scaled even bigger, and maybe, right now, you would have sold for twenty billion. Who knows? Um, I don't know. Uh, there are some people who say, yeah, you would, you would have had, you know, a slice of the pie instead of the whole pie, but the pie would have been bigger. Um, there's no way to tell, but I do know that when I look back at my life and my business, I'm really proud to say I did it my way. Uh, and I'm really, really proud of that. You know, there's, there's sort of a Bruce Lee element of it. He did it his way. He came up with his own style and I came up with my own way of running this business. And, um, I'm, I'm really proud of that. And it wasn't, it was always collaborative. Okay. You know, I don't want to say that it was all me. We did it our way. Might be a better way of saying it, right? Like, I'm really proud of that.

AI assessment note: “there's no way to tell, but I do know that when I look back”