The Exchanges

Q It was gonna be like a, a streaming service?

A Yeah, yeah. And Dan was into music. Dan's, um, he's into, he was a DJ, he's a music producer, he's into electronic music, and so he interviewed for the job thinking he was interviewing, uh, to write content about music, and halfway through his interview with, he realized that I was interviewing him to be a coder, and he had no idea how to code HTML, and so he totally lied to Uh, totally lied to me and claimed that he, he knew how to code. Um, he took the job and then he bought HTML for dummies and he crammed for whatever it was, two weeks before his first day on the job. And in his first day he was scared to death and his desk was right next to mine and he, he thought he was going to get busted by me. Um, but he was an amazing coder. I, I used to come back and look at his code and I remember, you know, saying this is remarkable. It's just like the code that you would see in books, like no one codes this neatly. Now I know it's because he literally crammed from those books.

AI assessment note: “Yeah, yeah. And Dan was into music.”

Q It was gonna be like a, a streaming service?

A Yeah. Yeah. And Dan was into music. Dan's, um, he's into, he was a DJ. He's a music producer. He's into electronic music. And so he interviewed for the job thinking he was interviewing, uh, to write content about music. And halfway through his interview with, he realized that I was interviewing him to be a coder and he had no idea how to code HTML. And so he totally lied, uh, totally lied to me and claimed that he, he knew how to code. Um, he took the job. And then he bought HTML for dummies, and he crammed for whatever it was, two weeks before his first day on the job. And in his first day, he was scared to death, and his desk was right next to mine, and he, he thought he was gonna get busted by me. Um, but he was an amazing coder. I, I used to come back and look at his code. I remember, you know, saying, this is remarkable. It's just like, The code that you would see in books, like no one codes this neatly. Now I know it's because he literally crammed from those books.

AI assessment note: “Yeah. Yeah. And Dan was into music.”

Q Um, you were eventually transferred to Georgia Tech where you studied industrial design. And did you have sort of like a job in mind that you wanted to do when you graduated?

A Yeah. I mean, I just, I wanted to design cars. I'm a car nut. I love cars. Um, I thought that I would study this, um, and maybe move off to Detroit and be a car designer or something. Uh, that, that was the idea. Yeah. But I got an internship at an appliance company one summer. In, uh, Amana, Iowa. You know, my job as an intern was to scan about a thousand paint chips, and they're all variations of white. Eggshell white, cream white, off-white, glossy white, flat white. So that was my job, and I actually finished that in a couple weeks, and then I just started, they let me do prototypes. They let me build models of refrigerators and that sort of thing, and, um, I learned that I'm really, really bad at building models. And I guess I was, you know, in retrospect, so bad at that. Um, one of the, one of the designers in the studio took me aside and said, you know what, maybe, maybe this isn't for you. Um, you should look into this new thing. It's called web design. It's all the rage. Uh, look into that as a career. Uh, and that was, you know, life-changing advice. I went to the Cedar Rapids Barnes and Noble cause there's nothing else to do at that time. I found some, um, books on web design by, uh, Linda Weinman, lynda.com, and, uh, I learned all about web design.

AI assessment note: “Yeah. I mean, I just, I wanted to design cars.”

Q And, and you guys did like merch too, right? Like you made t-shirts. I mean, you're, you're the monkey mascot. Like all over the place.

A I had, you know, the typical kind of cafe press, you know, stick the logo in the upper left, you know, pocket area. And I had a designer said, you know, we can make this really, really cool. We can use these really designer t-shirts that feel really soft and comfortable and make it something that people would want to wear. And so he created these and then we decided, you know, what if we, um, what if we just had like a t-shirt giveaway and, um, it went viral. We did a t-shirt giveaway and it just went berserk on Twitter. And, you know, we always had really lucky breakthroughs, um, on new, new media, new channels, new networks, Twitter, Facebook, Instagram. It seems like since we were constantly tinkering, we were always there when those channels got big. I mean, I still remember the day, um, when someone told, one of our employees said, I listened to this thing called podcasts on my drive to work. And I think we should sponsor a podcast. Um, and I thought it was, you know, just a weird idea. I'd never heard a podcast, but I said, screw it. Here's some money and go, go sponsor podcasts. It was the Joe Rogan podcast. And so like, we were always like really on the early cutting edge of all of these new, new inventions at the time. Um, we eventually, we did get the budget to do things like TV and you know, they were okay, but they're not all they're cracked up to be.

AI assessment note: “We can use these really designer t-shirts... we did a t-shirt giveaway”

Q Did your mom ever get a brick and mortar salon?

A No, no, she never did that. She never scaled out of the kitchen. I would have loved to have seen her scale out of the kitchen because I was so proud of her, but that, I don't know that that was ever her intention, but she, she did inspire my, um, older sister to start her own salon that was, uh, a non-kitchen based one. Like you say, a brick and mortar one. Um, she opened up a real salon that was very successful and Uh, in the eighties. And, um, boy, she was just an inspiration for me, um, as well. And, and partly because, you know, she would come home every couple of weekends with toys, toys for me and money for my parents. And I, I, I just thought, you know, I want to run a business too when I grow up. Cause this is, this is good for the family. And I remember, um, I was too young to understand it at the time, but I, I pieced together the story afterwards, um, Talking to my dad and my sister, but she basically had a falling out with her business partners, and things got really ugly, and she had to file for bankruptcy, and that just ruined her life, to be blunt. I mean, it just, and that's the sort of thing that, you know, has, has kind of influenced me and, and Dan, my co-founder, um, his, his father ran a bakery, uh, when he was growing up, and he saw that business.

AI assessment note: “No, no, she never did that. She never scaled out of the kitchen.”

Q How were you, I mean, why would a, why would somebody go to a service like MailChimp when they could go to a much bigger competitor that probably, you know, had much bigger staffs, and maybe they were more sophisticated? What were you offering that they, that they weren't?

A Personality. When you're serving small businesses, you're talking about entrepreneurs with a dream, right? They, They're probably starting a business that's been started a million times before. Your ice cream parlor is not a new invention, but they have a dream. They have something unique. Theirs is going to be different because XYZ. There's something unique about them. And so MailChimp, you know, with the chimpanzee mascot, we were weird and offbeat and quirky, just like all entrepreneurs. So now we have this sort of internal, internal tagline that we, we, we say, um, we got you because we get you. So that's, I, I believe that that's why they came to us is because our unique brand, uh, showed that we understood what it was like to be an entrepreneur.

AI assessment note: “Personality. When you're serving small businesses, you're talking about entrepreneurs with a dream”

Q What did you do? You stood in front of them and said, and said what?

A Things are great. We're awesome. Who knows? You know, I, I barely remember, and, and, you know, are there any questions? And we had people The questions that, that were coming were, you know, totally unexpected. So, you know, we were talking about how successful things were growing, you know, we were on a tear, things were looking like up and to the right. It's amazing. And people were raising their hands saying, so, so what's the strategy? You know, and my answer, you know, as a startup founders, we don't need no stinking strategy. We've got this, you know, and half the audience would, would cheer and say, yeah, we don't need no strategy. And the other half would say, yeah, we do. And, and they were just I re I remember the person asking me that, you know, raising his hand and saying, why do you feel the need to keep it a secret? And I remember thinking, oh my God, there actually is no strategy. You know, you know what I remember? I remember looking out at this audience, and I remember half of it being kind of old guard, you know, sort of like the typical startup pirates, and the other half of people, like, being really concerned, like, what, why are you hiding things from us? Um, and so the whole meeting just completely flopped. It was, it was, it was an awful meeting, and I was just, um, shell-shocked from the whole thing, and I remember going back to my office, just sitting…

AI assessment note: “Things are great. We're awesome. Who knows? You know, I, I barely remember”

Q And so as you started to develop a so-called culture, did you also start to develop a strategy of what you wanted to be?

A Eventually. It took a few more years after that, actually. I mean, here's the thing about early years of a, of a startup. You, the, the idea of strategy just gets more sophisticated the older you get. So in the early years, yes, I think we did have a strategy. In retrospect, it was nothing but a product roadmap. It was just, we will build these three things this year. Um, so yeah, we did eventually have these strategies and we, we made a conscious effort to always keep it simple. No more than three themes. You know, it had to fit on a sticky note was always my philosophy. So many years later, I think, uh, 2018 is when things had to get way more sophisticated and we started to see that we needed to hire, uh, eventually what we have now, a chief strategy officer. Cause man, it is, it's a thing now. It's real. Uh, I can safely say we do have a strategy now.

AI assessment note: “Eventually. It took a few more years after that, actually.”

Q But you saw an opportunity there because most businesses in America are small businesses, right? And that most people I think in the, in the U S are employed by small businesses.

A We saw the opportunity. We saw the inspiration too. It just felt more fulfilling. I mean, we remember we had a taste of serving big business. We knew what that was like. We knew that it, uh, would fill the wallet, but, um, serving small businesses, serving the underdog was always our thing. And it, and it would, it just felt better. And yeah, the volume was there, you know, the, the idea of that long tail. We worked as an agency. We know what it's like when you lose a big client because of nine, 11 or a pandemic or something. Yeah. You lose a big anchor client. You can't pay your bills and you have to lay people off. It's horrible. You know, you have to depend on just a handful of customers with the long tail. You know, we're, we're serving, you know, thousands or millions of tiny customers who pay small amounts of money. You don't rely on anyone, uh, too much such that, you know, they're sort of too big to fail. We cannot survive without them. We, we, we're actually a very, very much more resilient company serving the long tail.

AI assessment note: “We saw the opportunity. We saw the inspiration too. It just felt more fulfilling.”

Q In those early days, from what I understand, you guys, um, 2007, you're full on and into MailChimp. And there was a huge 800 pound gorilla in this space called Constant Contact. They were big, right? They were already huge. And from what I understand, like, you guys started to attract investors, inquiries to, to fund and scale your business.

A Yeah. Yeah. I didn't understand really the whole investment world at all. You know, I was just focused on growing the business, surviving, and suddenly these, you know, fancy pants people from the West Coast started knocking on my door and, um, asking me to go out for lunch. And they would tell me, you know, there's this company called Constant Contact. They just IPO. They made a lot of money. We think, um, you could be the next IPO. And, you know, I talk about our business and I would tell them how we, um, we help small business and they say, well, that's That's cute. That's great. We can help you take our money and we can help you pivot and serve the enterprise because that's where the real business is. And, um, I just thought, you know, that was just, I could do it, but I, something about it just felt wrong to, um, to me and Dan. We just, we just wanted to stay. It just felt, it felt really good to serve small businesses. It was just in our DNA.

AI assessment note: “suddenly these, you know, fancy pants people from the West Coast started knocking”

Q So how did you start to change the culture of, of the company?

A Yeah. So we, what we cared about most was actually our employees who had been with us for so many years. We wanted them to become good managers and progress through leadership at Mailchimp. So we started to think about like, what would it be like if we had like a Mailchimp school or a Mailchimp Academy? We started to inquire about that, uh, talking to some local professors at Emory university. And they said, yeah, we can absolutely help you with that. But first we need to know something about your culture. You know, we were like, well, what's that? I don't, I don't know what that means. And they said, oh, well, you know, it's, it starts off with your core values. And we said, we don't, what is that? So yeah, that's, that's how the whole journey began. And we, you know, I hired a chief culture officer to kind of help us maintain that culture. That's how the whole process came to be.

AI assessment note: “I hired a chief culture officer to kind of help us maintain that culture.”

Q And who did you initially target? Like, who are your clients?

A The idea at the time was, um, it was something that we observed at Cox. You know, there was an engineering team, geniuses, just rocket scientists, working on, you know, the Cox servers, doing hard things. We were working in the marketing department, and marketers needed, they needed stuff too, but the engineers were always too busy. And engineers kind of didn't want to stoop so low to do marketing stuff as well. It was like, it was beneath them. And so our, our target market was marketing departments, um, where we would help them build little, uh, microsites, um, websites that basically they didn't have to go to their engineering department to ask for. I guess we were sort of like a rogue team, uh, for marketing departments.

AI assessment note: “our target market was marketing departments, um, where we would help them build little”

Q When you, um, the company today easily, if you wanted to, you could easily sell it and probably have been offered lots of money for it. I mean, you own half of it. Would you ever, um, consider doing that, selling it?

A I've had offers. Um, the thing is, I love what I do. And, um, I find that I am happiest when I have a really tough problem to solve. When my eyebrows are like, my, my forehead is all furrowed and wrinkled because I'm just like struggling to figure out, oh, this is a new challenge. How do I conquer this? Um, and that never ends when you run a business. I mean, it's just, it's never ending, uh, problems to solve. And so I just feel like every day, um, Um, I always have some new challenge, uh, and I love that. I really do. And I, and I just can't see myself retiring. I don't know. I, I, it's one of those things I, you know, you never, you learn over time after 20 years of running a business, you learn never say never, right? I think I have an open mind about it, but I can say really honestly and truly like having meaningful work, uh, is just the most important thing I think.

AI assessment note: “you learn never say never, right? I think I have an open mind about it”

Q How did you guys come up with a, with a name?

A There were lots of reasons. So first of all, my parents, uh, when they were in Thailand, they actually had a pet monkey. And they would always tell me stories about this pet monkey. And the moral of the story was always never, ever have a pet monkey. They're mischievous. They're awful. They make a mess. They get jealous when you leave them to go out on a date. Um, never, ever have a pet monkey, Ben. So I was always fascinated by them. Uh, you know, dreaming about what, how cool it would be to have a pet monkey. And then, um, there was a phase that I went through, um, my Jim Henson years where I really, really wanted to be a ventriloquist, and I got a monkey Muppet, and I carried that thing everywhere I went, and I had, like, little comedy shows for the family. Um, you could not separate me from my, my monkey. So, you know, I, I've always loved monkeys, and And I always brought them into my designs as well. So, you know, we had our e-greetings site, and I noticed, like, the one e-greetings that I had of a monkey was the most popular e-greeting that, you know, the few users that we had actually sent to their friends. Uh, even, like, whenever we designed websites for our clients, and we had three options to show them, the one that we loved, that we, that we always hoped that the client would choose, whenever we put stock photography in there, we would put monkeys in the one. And i…

AI assessment note: “I've always loved monkeys, and And I always brought them into my designs as well.”

Q How do they describe it? Like a leadership training?

A Yes. There was a lot of that kind of stuff, right? So talking about strategy, talking about culture and stuff like that. But, um, the most helpful stuff was like, they, they make you get out of this mode or it's all about me. And it's really all about the team. It's all of it. You know, it sounds cheesy, but you know, you have to understand like what's going through everyone's minds when they're talking to you. Is I am not good enough. That's like the self-conscious thing. That's this tape that's playing through everyone's mind. And you have to remember that as a leader and you've got to like shake that out of them, make them feel confident, make them work as a team. You know, it was, it was more psychological stuff like that, that kind of helped me get out of my rut and think about leadership in a different way.

AI assessment note: “Yes. There was a lot of that kind of stuff, right?”

Q What, what explains that? Did it become a more competitive Was that it? There was just more people doing that kind of work?

A You know, we would, we would get business, and then we would get busy doing their work, and while we were doing their work, nobody was pitching for new business, and so when we were done doing the work, there was no new business, and we, it would basically be like hitting the reset button. We'd have to go out and hunt for more business. So it's just like these constant ups and downs and ups and downs that, um, just kept us from, from really breaking through, and I'll never forget, it was like, 2000 five-ish, There was something that totally changed. I, um, I was working at home in my apartment, coding something for sure. And it was sometime in the afternoon, Teresa, she was a night shift pediatric nurse, right? So she was presumably supporting you guys or she was, she was, yeah, health insurance and everything from her really stabilized me, which, which, which allowed me to be an entrepreneur. So she's a pediatric nurse. She does the night shift to make extra money, works holidays. I barely see her, right? So she wakes up around noon, around lunchtime or so. So she flips on Oprah, and I'm coding, and I'm just like, oh great, Oprah, I've got to listen to this, um, roll my eyes, and there's some episode on with a guy named Robert Kiyosaki, and he's, and he has this book called Rich Dad, Poor Dad.

AI assessment note: “we would get busy doing their work, and while we were doing their work, nobody was pitching”