The Exchanges

Q I love that in terms of kind of how that impacted, you know, especially the smell. I also heard about your father and the fishing trips. Um, Lottie asked, what did you take away from those and how do you reflect on lessons from them?

A Well, my father, you know, the, the lake where we would go fishing was always about 45 minutes to an hour away. Uh, it was a really long drive. And whenever I drove with him, he always took the slow scenic route. The back country roads, you know, and it would frustrate me sometimes because I knew after a while I would start going fishing sometimes with my brother and we'd hop in his car and he would take the interstate and we'd get there in 15 minutes. So I knew there was always a faster path, but my father always took the scenic route and, and, you know, and I think That was a big lesson for me. You know, sometimes it's not always better to be faster. And when we went fishing, he also did not just like stop, get out of the car and start fishing. It was always like another mile or two mile hike to get to where we were fishing. Always. He always took the hard path. And, you know, I would, I would whine and complain all the time. And he would make me love, you know, the fishing poles, the minnow bucket, all of this equipment, the tackle box. And I would complain and complain and complain, and I would always wish that there was like a device or some kind of transportation, you know, like Star Trek, just beam us there. I would always talk about inventions to make it easier, uh, and, and just complain that my feet were hurting, whatever, and he never said anything. This is what I re…

AI assessment note: “That was a big lesson for me. You know, sometimes it's not always better”

Q the success that you've had. And actually, especially when the magazine covers were there, how did you retain your humility and not let your ego get inflated when the world is saying, wow, This CEO, he's a huge Silicon Valley and he's built the billion dollar business that no one else can build and blah, blah, blah. How did you retain your humility and not, and fight against ego inflation?

A The magazine covers only happened in the last few years. You know, I, I just genuinely did not care about publicity. I tried to get the publicity in the very early years of MailChimp. It always failed. Nobody cared. They were, you know, they were laughing at the chimpanzee mascot. Nobody cared about email. Nobody cared about sass at the time. I could never get any publicity and I realized You know, I'm, what I'm doing is I'm seeking that validation, right? Maybe as that misfit who was always, you know, pushed aside. I wanted that validation, damn it. Um, and that's what I wanted from the publicity. And then I realized, you know what? The only validation I need is a paying customer. When they open up that wallet and pay me with their credit card, that's validation. And so I rewired my brain to only care about that for many, many years. Didn't care too much about publicity. And then it was only in the final few years, you know, I, I got a chief comms officer who just said, You could use some publicity. Let's do it. It'll help us with hiring where we're at a scale, a thousand employees, you know, we're competing with some publicly held companies. We got to get the word out. And I've read about, you know, other privately held family businesses that were very, very stealthy and quiet. And then every few years they would open the doors. Mars Candy is one of them that I read about. Li…

AI assessment note: “I rewired my brain to only care about that for many, many years.”

Q I love that. Um, tell me lottery tickets. I don't know where to go with this one, but Lottie told me again. I had to ask it. What is up?

A Well, my, that's my wife and I, we're high school sweethearts. Okay. So we're in high school and we stop at the store and she wants lottery tickets. Uh, and my, my, my wife bought all these lottery tickets and she's, And I'm driving us home, and she's scratching them off, and you know, she's not a stickler for details, my wife. She doesn't necessarily always read these instructions, and she scratched off a ticket, and I think it was something like your numbers, your numbers had to match the winning number in order to win that prize, and she thought that your number had to be greater than the winning number to win, and so, you know, maybe the winning number was seven, and she scratched off And she said, oh my God, I won 25,000 dollars. And I was so excited. I almost crashed the car. And I was like, oh my God, this is so cool. We're rich. Um, and then she kept scratching and she said, oh my God, I won another 5000 dollars. And I was like, cool, but weird to win twice. And then she kept scratching and she said, I won another two dollars. And I was like, hold on. Lottery tickets don't work this way. He don't win 25,000 and then two dollars. So anyways, It was just this, we were, you know, like, so elated that we, we, we finally had money, you know, because we were pretty poor back then. Uh, we grew up in a pretty poor town. And that was like our ticket out, you know, and no, we, we…

AI assessment note: “we ended up not winning at all. And anyways, I continue to buy lottery tickets”

Q 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 a 10 millionaire or international offices? When was that? Ooh. This is real.

A 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 were 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 kind of 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 because we're tired of cashing the checks or depositing all these little You know, 50 dollar checks. Um, I was driving to the bank too much. It's a 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, you know, I, I, I, one day I, I caught this episode. I think my, my wife was watching Oprah. She, she is a night shift nurse. She came home, you know, she crashes on the couch and turns on Oprah and I'm working at home and, you know, I'm coding away at some website and there's a guest on Oprah. His name's Robert Kiyosaki. You should have him as a guest someday.…

AI assessment note: “It took me a long time to realize that.”

Q I love that in terms of kind of how that impacted, you know, especially the smell. I also heard about your father and the fishing trips. Um, Lottie asked, what did you take away from those and how do you reflect on lessons from them?

A Well, my father, you know, the, the lake where we would go fishing was always about 45 minutes to an hour away. Uh, it was a really long drive. And whenever I drove with him, he always took the slow scenic route. The back country roads, you know, and it would frustrate me sometimes because I knew after a while I would start going fishing sometimes with my brother and we'd hop in his car and he would take the interstate and we'd get there in 15 minutes. So I knew there was always a faster path, but my father always took the scenic route and, and, you know, and I think That was a big lesson for me. You know, sometimes it's not always better to be faster. And when we went fishing, he also did not just like stop, get out of the car and start fishing. It was always like another mile or two mile hike to get to where we were fishing. Always. He always took the hard path. And, you know, I would, I would whine and complain all the time. And he would make me love, you know, the fishing poles, the minnow bucket, all of this equipment, the tackle box. And I would complain and complain and complain, and I would always wish that there was like a device or some kind of transportation, you know, like Star Trek, just beam us there. I would always talk about inventions to make it easier, uh, and, and just complain that my feet were hurting, whatever, and he never said anything. This is what I re…

AI assessment note: “That was a big lesson for me. You know, sometimes it's not always better”

Q I think the most kind of prominent lessons are from kind of quite painful times. Um, you know, mine are probably mostly from being bullied at school too. Um, when you think about the most painful lesson that you've learned that you're also pleased to have learned, which is kind of a weird, uh, paradox, what would you say it would be?

A Just being a misfit was always this painful thing just throughout all of school for me. I mean, even through high school, even a little bit through college, Uh, but what I've learned in, in retrospect is that it, it made me think differently. It made me kind of, um, stubborn in some ways. It made me kind of, uh, stick to my guns. I think that that really gave me this focus to be an entrepreneur, a successful entrepreneur. You know, and I think that there were times when I think, um, 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 that. I didn't want it. I was going to do it myself and I was going to do it my way.

AI assessment note: “what I've learned in, in retrospect is that it, it made me think differently.”

Q A calm demeanor, that's leadership. I like that a lot. I also hear that you're a cyclist, and so I want to kind of bring them together and ask, what does high performance in business and leadership mean to you when I say those words?

A When I think about high performance at Mailchimp, the way that I ran the business, I, I never really thought about it as setting a high goal and telling people to crush it at all costs. Um, I would set the high goal And then think about what habits do we need to get there? So, you know, when I started getting back into fitness, I got really overweight in the first 15 years running the company. It was only very recently when I had my first child that I said, oh my god, I gotta lose this weight. I gotta I really started to think about it. I couldn't even run a mile. And I was like, what are my habits that are preventing me from doing that? And it was kind of like staying up too late watching TV. So I just like unplugged the TV. No more TV for me. And I would go to bed earlier. 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. Not really chasing after running that mile. Like, I would, I tried. I couldn't do it. It wasn't until I slept better, ate better, drank better, then I could run a little bit better. Anyways, it's about getting to the core of the problem, uh, and I guess deleting habits more than anything else.

AI assessment note: “To me, that's high performance. It's sort of like looking at the roots”

Q intelligence too. And I spoke to Lottie again, and you said before the show that she's, you know, A brilliantly gifted business leader. She told me that you were world class when it came to emotional intelligence, EQ. How do you feel when you hear that? And what makes you think that you're so good at, what do you think she sees in you about how brilliant your EQ is?

A I don't know. I'm conflicted about it. I, I know that I can be pretty insightful about people's feelings. Uh, I was, I was a really quiet loner in school. Uh, I was, You know, I went to a rural country town school, and I was one of like three Asians, you know, in the whole school. So we were, we were, I was kind of a misfit, um, and a lot of misfits flocked to me. They, I don't know why, but I was leader of the misfits always, and I think MailChimp is like the island of misfit toys sometimes, and I think those early years of kind of listening and learning from a lot of these people who would come and talk to me, It kind of really helped me like tune into the way people were feeling and what they were going through. But then again, the reason why I'm conflicted about is I also have this flip side of me as a leader, right? So I talked about my father, like being this really friendly guy, but when it's time to lead the troops, you can, you can be kind of cold or harsh on the surface, right? You got to do what you got to do. To me, I think that most people probably see that side of me. So anyways, I could be, I, I do, I have been told many times I have a high level of self-awareness and a high amount of EQ Uh, but I'm also told I can be kind of cold and robotic, uh, cause I'm pretty logical and I would just say what, what's gotta be done. I may be in a more overly stoic way. I don'…

AI assessment note: “I'm conflicted about it. I, I know that I can be pretty insightful”

Q again, do you know what I mean? Um, I, I, I, I've got two more questions and then I promise to let you roll, but the first that I have to ask is, like, in terms of the sale, why did you decide that then was the right time, having gone, oh, this guy's crazy, when he was advising you, to, oh, I might sell now. What was that transition?

A Never really had a desire to sell, but I always felt it was my duty to listen to people when they wanted to buy, right? I would always learn something along the way. So anyways, we had, we had a couple of companies come knocking a couple of years ago, and you know, I listened to them, I opened the door, and it went a little further than normal, um, because they were pretty compelling offers, and I had a senior team that you have to get your senior team involved. Right? Uh, and once they get involved, it's almost like, um, they get a taste of blood. They're like sharks that, that are, they're on the scent. Right? And, um, and they want to win. This is, this is what like high performance senior leaders do. They want to win. And we got to the end of that process and the, the offers weren't there for me. Uh, and we ultimately said, no, we didn't, we didn't do anything. And that's a huge letdown for the senior team. That's, that's like, you're coming from this high of, like, and remember, these are people who also did not want to sell. They joined because we were a bootstrapped company, but we had all kind of mentally switched and said, all right, we're ready. It is time to do this.

AI assessment note: “we had all kind of mentally switched and said, all right, we're ready.”

Q Help me out. You're wise and, you know, seasoned, as you delightfully put it earlier. Um, what's the secret to a happy marriage?

A Oh my gosh. Um, I, Ah, I, I have been, I'm very lucky. My wife was a nurse, and she became friends with a lot of nurses who were older, and so we used to go out to dinner with a lot of these older couples, and what I noticed was the happiest couples had husbands who just kept their damn mouths shut. And I just, I just kind of thought, Okay, so they are repressing themselves. That's the key. And I think I've learned that they're not repressing themselves. They just learned that they've humbled down and learned that they're not always right. And it's not always about winning. And that's not, that's not everything is winning. And I just sort of let go and, and just learn to just shut up and maybe listen a little bit harder, not just at what they're saying, but why are they saying it? And when you listen that deep and try to just focus on why are they saying the things that they're saying? I don't know that it helps a lot. It just, it does help me shut up.

AI assessment note: “happiest couples had husbands who just kept their damn mouths shut”

Q I think the most kind of prominent lessons are from kind of quite painful times. Um, you know, mine are probably mostly from being bullied at school too. Um, when you think about the most painful lesson that you've learned that you're also pleased to have learned, which is kind of a weird, uh, paradox, what would you say it would be?

A Just being a misfit was always this painful thing just throughout all of school for me. I mean, even through high school, even a little bit through college, Uh, but what I've learned in, in retrospect is that it, it made me think differently. It made me kind of, um, stubborn in some ways. It made me kind of, uh, stick to my guns. I think that that really gave me this focus to be an entrepreneur, a successful entrepreneur. You know, and I think that there were times when I think, um, 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 that. I didn't want it. I was going to do it myself and I was going to do it my way.

AI assessment note: “Just being a misfit was always this painful thing... made me think differently.”

Q again, do you know what I mean? Um, I, I, I, I've got two more questions and then I promise to let you roll, but the first that I have to ask is, like, in terms of the sale, why did you decide that then was the right time, having gone, oh, this guy's crazy, when he was advising you, to, oh, I might sell now. What was that transition?

A Never really had a desire to sell, but I always felt it was my duty to listen to people when they wanted to buy, right? I would always learn something along the way. So anyways, we had, we had a couple of companies come knocking a couple of years ago, and you know, I listened to them, I opened the door, and it went a little further than normal, um, because they were pretty compelling offers, and I had a senior team that you have to get your senior team involved. Right? Uh, and once they get involved, it's almost like, um, they get a taste of blood. They're like sharks that, that are, they're on the scent. Right? And, um, and they want to win. This is, this is what like high performance senior leaders do. They want to win. And we got to the end of that process and the, the offers weren't there for me. Uh, and we ultimately said, no, we didn't, we didn't do anything. And that's a huge letdown for the senior team. That's, that's like, you're coming from this high of, like, and remember, these are people who also did not want to sell. They joined because we were a bootstrapped company, but we had all kind of mentally switched and said, all right, we're ready. It is time to do this.

AI assessment note: “we had all kind of mentally switched and said, all right, we're ready.”

Q Help me out. You're wise and, you know, seasoned, as you delightfully put it earlier. Um, what's the secret to a happy marriage?

A Oh my gosh. Um, I, Ah, I, I have been, I'm very lucky. My wife was a nurse, and she became friends with a lot of nurses who were older, and so we used to go out to dinner with a lot of these older couples, and what I noticed was the happiest couples had husbands who just kept their damn mouths shut. And I just, I just kind of thought, Okay, so they are repressing themselves. That's the key. And I think I've learned that they're not repressing themselves. They just learned that they've humbled down and learned that they're not always right. And it's not always about winning. And that's not, that's not everything is winning. And I just sort of let go and, and just learn to just shut up and maybe listen a little bit harder, not just at what they're saying, but why are they saying it? And when you listen that deep and try to just focus on why are they saying the things that they're saying? I don't know that it helps a lot. It just, it does help me shut up.

AI assessment note: “the happiest couples had husbands who just kept their damn mouths shut.”

Q A calm demeanor, that's leadership. I like that a lot. I also hear that you're a cyclist, and so I want to kind of bring them together and ask, what does high performance in business and leadership mean to you when I say those words?

A When I think about high performance at Mailchimp, the way that I ran the business, I, I never really thought about it as setting a high goal and telling people to crush it at all costs. Um, I would set the high goal And then think about what habits do we need to get there? So, you know, when I started getting back into fitness, I got really overweight in the first 15 years running the company. It was only very recently when I had my first child that I said, oh my god, I gotta lose this weight. I gotta I really started to think about it. I couldn't even run a mile. And I was like, what are my habits that are preventing me from doing that? And it was kind of like staying up too late watching TV. So I just like unplugged the TV. No more TV for me. And I would go to bed earlier. 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. Not really chasing after running that mile. Like, I would, I tried. I couldn't do it. It wasn't until I slept better, ate better, drank better, then I could run a little bit better. Anyways, it's about getting to the core of the problem, uh, and I guess deleting habits more than anything else.

AI assessment note: “It's sort of like looking at the roots of what's causing you to not be high performance”

Q think my biggest problem is I have the savior complex, which is you bring me your problems, and I ingest them as my own. I've reflected on that recently. When you reflect, and it's really interesting now, you're, You know, you stepped away from the role of CEO. When you reflect on your own CEO-ship and style of leadership, how would you describe it, and did it change over time?

A Yeah, it did. I mean, and, and maybe in the very early startup years, I didn't have this kind of a stay in your lane. I know my lane kind of an attitude. You do just absorb everyone's problems because it's a life or death situation to a startup. So, you know, I just want to be fair to startup leaders out there listening to this. Sometimes you got to take all that on. Like I said, I'm an old fart. I'm almost 50. This is something that happens as you age. Maybe a little older, maybe a little wiser. Um, I, I think that, you know, in the very early years of MailChimp, creativity was everything to me. Uh, and, and I was, you might describe me as, you know, bring on really talented, creative people and just be very hands-off. And I really do think that helped me in those early years. Um, and I, and I think that my co-founder, Dan, really helped vet to make sure not only were they creative, but they had a good work ethic too. So without Dan, I don't know that this would have worked, but You know, I just brought in the best, smartest, creative people and stayed out of their way, and that was always my attitude. But I think 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, it's not, you know, um, telepathic, where everyone knows what it is the leader wants. It's like you're the mayor of a…

AI assessment note: “Yeah, it did. I mean, and, and maybe in the very early startup years”

Q intelligence too. And I spoke to Lottie again, and you said before the show that she's, you know, A brilliantly gifted business leader. She told me that you were world class when it came to emotional intelligence, EQ. How do you feel when you hear that? And what makes you think that you're so good at, what do you think she sees in you about how brilliant your EQ is?

A I don't know. I'm conflicted about it. I, I know that I can be pretty insightful about people's feelings. Uh, I was, I was a really quiet loner in school. Uh, I was, You know, I went to a rural country town school, and I was one of like three Asians, you know, in the whole school. So we were, we were, I was kind of a misfit, um, and a lot of misfits flocked to me. They, I don't know why, but I was leader of the misfits always, and I think MailChimp is like the island of misfit toys sometimes, and I think those early years of kind of listening and learning from a lot of these people who would come and talk to me, It kind of really helped me like tune into the way people were feeling and what they were going through. But then again, the reason why I'm conflicted about is I also have this flip side of me as a leader, right? So I talked about my father, like being this really friendly guy, but when it's time to lead the troops, you can, you can be kind of cold or harsh on the surface, right? You got to do what you got to do. To me, I think that most people probably see that side of me. So anyways, I could be, I, I do, I have been told many times I have a high level of self-awareness and a high amount of EQ Uh, but I'm also told I can be kind of cold and robotic, uh, cause I'm pretty logical and I would just say what, what's gotta be done. I may be in a more overly stoic way. I don'…

AI assessment note: “I'm conflicted about it. I, I know that I can be pretty insightful”

Q it made me actually not great in business in one way, being I always want to people please, even when it's not the right decision, because I, I want friends, which sounds really Not sad when it's hit like that, but like, that's a really negative trait that I've taken from being a misfit. Do you think there are any negative traits you've taken from maybe being a misfit yourself?

A Now we're getting into some really deep psychological stuff here. Um, I, I think that for me, being a misfit meant that I was bullied quite a lot, and I was discounted and disrespected quite a lot, uh, through my childhood years. Not at home. I lived in a very loving home, you know. Thank god I had that kind of Shield around me. But when I went to school, you know, it was like fists up, get ready. Um, so I, I was always ready for a fight. So I was ready to defend myself. And I think it made me want to prove that I was a valuable person. And I think that that probably gave me this drive to be a great successful entrepreneur. It just, it just pushed me. I had to prove it. So on the one hand, that's, that's really, really good. Probably on the other hand, it You know, if I feel like people are trying to push me in one direction, that sort of like, oh no, that, that old instinct of, oh, I'm being bullied pops up again, and I will push back, and I'll be very cold about it too, because I, I, I give no, I won't give any kind of, uh, you know, no apologies, man. You know, it's just like, this is what we got to do, we got to do it, and I will not be swayed or pushed again, never again. And so, what, what that means is, I think, you know, Sometimes you have to go with the politics and understand politics a little bit better. Uh, and I understand it. I get it. I really do. Uh, I do have t…

AI assessment note: “if I feel like people are trying to push me... I will push back”

Q the success that you've had. And actually, especially when the magazine covers were there, how did you retain your humility and not let your ego get inflated when the world is saying, wow, This CEO, he's a huge Silicon Valley and he's built the billion dollar business that no one else can build and blah, blah, blah. How did you retain your humility and not, and fight against ego inflation?

A The magazine covers only happened in the last few years. You know, I, I just genuinely did not care about publicity. I tried to get the publicity in the very early years of MailChimp. It always failed. Nobody cared. They were, you know, they were laughing at the chimpanzee mascot. Nobody cared about email. Nobody cared about sass at the time. I could never get any publicity and I realized You know, I'm, what I'm doing is I'm seeking that validation, right? Maybe as that misfit who was always, you know, pushed aside. I wanted that validation, damn it. Um, and that's what I wanted from the publicity. And then I realized, you know what? The only validation I need is a paying customer. When they open up that wallet and pay me with their credit card, that's validation. And so I rewired my brain to only care about that for many, many years. Didn't care too much about publicity. And then it was only in the final few years, you know, I, I got a chief comms officer who just said, You could use some publicity. Let's do it. It'll help us with hiring where we're at a scale, a thousand employees, you know, we're competing with some publicly held companies. We got to get the word out. And I've read about, you know, other privately held family businesses that were very, very stealthy and quiet. And then every few years they would open the doors. Mars Candy is one of them that I read about. Li…

AI assessment note: “I rewired my brain to only care about that for many, many years.”

Q How do you think about bringing your, you know, two boys up, um, in, bluntly, much more fortunate environments than, you know, you were brought up in yourself. How do you retain hustle and ambition and hunger when very different financial situation?

A Well, I mean, I used to worry about that a lot, um, and then I realized the heart of that was that it was because I wanted them to be an entrepreneur like me, and that's an unfair thing for a parent, uh, to, to, um, want in a child. I mean, the child, he's, they're gonna grow up to be what they want to be. That's, that's what I want to have for them, some freedom and independence for them to decide. So I had to let go of that expectation of them. So that, that was one big thing. Um, I, I also really didn't talk about money that much and they never really knew that MailChimp was that successful. They just knew that I was maybe a nice, helpful guy to customers. It was their classmates. Uh, one day, one of their classmates brought a magazine with my face on the cover. Uh, cause I guess her dad had given it to her and say, Hey, take this to your friend. Um, and that was when they said, is it true that, you know, MailChimp is this worth this much worth that much? You know, and I had lots of conversations with them. It never really, intellectually, they got it, but it never really registered for them, because then, you know, they would say funny things like, you know, oh, there's this kid at school. His dad has a Porsche. They must be rich, Dad. When will we be rich? You know, and I was, you know, so they kind of intellectually got it when they were young, but not really, because we …

AI assessment note: “I had to let go of that expectation of them. So that, that was one big thing.”

Q Can I ask Ben, did you enjoy that? You are an incredibly creative, emotive, effusive person, kind of running process on individual little squadrons. It's not where I get energy from, and I don't think, it doesn't feel like it's where you got energy from.

A To me, it was about the transformation of Ben. You know, and I, and I, over the years, I watched a lot of founders You know, they would, they would evolve and they would say, I'm more of a creative guy. I'm going to step back from this and let somebody else take over. And I would always think, you know, that's kind of a cop out. I'm not going to be like that. I'm going to evolve. It's your job to get older, wiser, change your way. You can't be creative. You can't just sit there and code all your life. You can't be the designer all your life. And so I'm going to evolve and do this other opera operational in air quotes. I'm going to be more operational in my life. And I, and I really think that I, I got pretty darn far with that. Uh, and I'm proud of how far I got with that, and I was, I was willing to keep on going, and I think it's just, it's also important to be self-aware and learn when you're not so good at it. And I think that's the thing. So, so Harry, I think I could have kept on going and evolving and trying. And one day I just realized I had enough people just kind of say, you're, you're not great at this operational stuff, Ben. And then I, and I just kind of realized, you know what? The only reason I'm still doing this is because no one can fire me. So that's why I've been going at it so long. So I started to lean more on operational people on the senior leadership tea…

AI assessment note: “The only reason I'm still doing this is because no one can fire me.”

Q Can I ask, ah, you said about him not praising you there, or, you know, waiting for you, but silently. Did he tell you he loved you?

A Yeah. Yeah, he did. Uh, there were times when he would say that, and there were times when he would, you know, say that he was proud of me. It was usually after me, you know, going through some struggle myself. You know, he would see me just improve myself in some way, and those were when he would reserve that praise. But other times, like if he saw me struggling or stressed about something, he would say, that's the norm. That stress Is the norm. If, if you're not stressed, you're insane. Yeah, I remember him saying that. He was like, you know, people who are just completely calm all the time, and they never get phased, um, like even, he would, you have a calm demeanor, that's leadership, but inside you can be really, really, it can feel chaotic and stressed, but you don't show it, right? But people who don't even feel that stress inside, he would say there's something wrong with them. So anyways, anyways, he would never like appease me or give me that kind of like, oh, you poor thing kind of a stuff. He would just very silently, you know, and he would help me get through stuff, but it was if I prevailed, that was when he kind of reserved that praise.

AI assessment note: “Yeah. Yeah, he did. Uh, there were times when he would say that”

Q think my biggest problem is I have the savior complex, which is you bring me your problems, and I ingest them as my own. I've reflected on that recently. When you reflect, and it's really interesting now, you're, You know, you stepped away from the role of CEO. When you reflect on your own CEO-ship and style of leadership, how would you describe it, and did it change over time?

A Yeah, it did. I mean, and, and maybe in the very early startup years, I didn't have this kind of a stay in your lane. I know my lane kind of an attitude. You do just absorb everyone's problems because it's a life or death situation to a startup. So, you know, I just want to be fair to startup leaders out there listening to this. Sometimes you got to take all that on. Like I said, I'm an old fart. I'm almost 50. This is something that happens as you age. Maybe a little older, maybe a little wiser. Um, I, I think that, you know, in the very early years of MailChimp, creativity was everything to me. Uh, and, and I was, you might describe me as, you know, bring on really talented, creative people and just be very hands-off. And I really do think that helped me in those early years. Um, and I, and I think that my co-founder, Dan, really helped vet to make sure not only were they creative, but they had a good work ethic too. So without Dan, I don't know that this would have worked, but You know, I just brought in the best, smartest, creative people and stayed out of their way, and that was always my attitude. But I think 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, it's not, you know, um, telepathic, where everyone knows what it is the leader wants. It's like you're the mayor of a…

AI assessment note: “Yeah, it did. I mean, and, and maybe in the very early startup years”

Q it made me actually not great in business in one way, being I always want to people please, even when it's not the right decision, because I, I want friends, which sounds really Not sad when it's hit like that, but like, that's a really negative trait that I've taken from being a misfit. Do you think there are any negative traits you've taken from maybe being a misfit yourself?

A Now we're getting into some really deep psychological stuff here. Um, I, I think that for me, being a misfit meant that I was bullied quite a lot, and I was discounted and disrespected quite a lot, uh, through my childhood years. Not at home. I lived in a very loving home, you know. Thank god I had that kind of Shield around me. But when I went to school, you know, it was like fists up, get ready. Um, so I, I was always ready for a fight. So I was ready to defend myself. And I think it made me want to prove that I was a valuable person. And I think that that probably gave me this drive to be a great successful entrepreneur. It just, it just pushed me. I had to prove it. So on the one hand, that's, that's really, really good. Probably on the other hand, it You know, if I feel like people are trying to push me in one direction, that sort of like, oh no, that, that old instinct of, oh, I'm being bullied pops up again, and I will push back, and I'll be very cold about it too, because I, I, I give no, I won't give any kind of, uh, you know, no apologies, man. You know, it's just like, this is what we got to do, we got to do it, and I will not be swayed or pushed again, never again. And so, what, what that means is, I think, you know, Sometimes you have to go with the politics and understand politics a little bit better. Uh, and I understand it. I get it. I really do. Uh, I do have t…

AI assessment note: “I will push back, and I'll be very cold about it too”

Q Can I ask, ah, you said about him not praising you there, or, you know, waiting for you, but silently. Did he tell you he loved you?

A Yeah. Yeah, he did. Uh, there were times when he would say that, and there were times when he would, you know, say that he was proud of me. It was usually after me, you know, going through some struggle myself. You know, he would see me just improve myself in some way, and those were when he would reserve that praise. But other times, like if he saw me struggling or stressed about something, he would say, that's the norm. That stress Is the norm. If, if you're not stressed, you're insane. Yeah, I remember him saying that. He was like, you know, people who are just completely calm all the time, and they never get phased, um, like even, he would, you have a calm demeanor, that's leadership, but inside you can be really, really, it can feel chaotic and stressed, but you don't show it, right? But people who don't even feel that stress inside, he would say there's something wrong with them. So anyways, anyways, he would never like appease me or give me that kind of like, oh, you poor thing kind of a stuff. He would just very silently, you know, and he would help me get through stuff, but it was if I prevailed, that was when he kind of reserved that praise.

AI assessment note: “Yeah. Yeah, he did. Uh, there were times when he would say that”

Q Can I ask Ben, did you enjoy that? You are an incredibly creative, emotive, effusive person, kind of running process on individual little squadrons. It's not where I get energy from, and I don't think, it doesn't feel like it's where you got energy from.

A To me, it was about the transformation of Ben. You know, and I, and I, over the years, I watched a lot of founders You know, they would, they would evolve and they would say, I'm more of a creative guy. I'm going to step back from this and let somebody else take over. And I would always think, you know, that's kind of a cop out. I'm not going to be like that. I'm going to evolve. It's your job to get older, wiser, change your way. You can't be creative. You can't just sit there and code all your life. You can't be the designer all your life. And so I'm going to evolve and do this other opera operational in air quotes. I'm going to be more operational in my life. And I, and I really think that I, I got pretty darn far with that. Uh, and I'm proud of how far I got with that, and I was, I was willing to keep on going, and I think it's just, it's also important to be self-aware and learn when you're not so good at it. And I think that's the thing. So, so Harry, I think I could have kept on going and evolving and trying. And one day I just realized I had enough people just kind of say, you're, you're not great at this operational stuff, Ben. And then I, and I just kind of realized, you know what? The only reason I'm still doing this is because no one can fire me. So that's why I've been going at it so long. So I started to lean more on operational people on the senior leadership tea…

AI assessment note: “after that, I started to think, yeah, I don't, I don't get a lot of energy”

Q other founders? Say you're advising me, we're in a coffee shop, and I'm thinking about, you know, a new trait, habit, style of leadership. How would you advise me on, hey, Harry, Just push through it. Like, keep going. Don't be a cop out. Versus, no, listen to your team. Step back, Harry. You're not meant for this. How do you advise them on whether to listen to which one?

A I mean, that actually happens all the time, Harry. Like, I meet with founders. I don't invest. I don't do any kind of angel investing. They just come to me kind of as a therapist. They sort of sit on my couch, and they just tell me all their problems. I really don't give them a lot of advice, to tell you the truth. I say, Oh yeah, that happened to me. Yeah, that happened to me, and this is what happened. Boy, I had it worse than you, man. Here's how I effed it up worse. Uh, and this is what I did to get through it. Uh, but you might have to do something different, but that's what I did. And most of them are just relieved that they're not the only one suffering through this. Um, and I remember myself, I didn't have a lot of founders to talk to, uh, in the early days. In Atlanta, there wasn't much of a startup ecosystem. And so I didn't have that. And, and I thought I was just The only one stupid enough to make the stupid mistakes that I was making. Um, so to me, my goal when I talk to founders is just sort of say, Hey, no, man, we, we all make that mistake. All of us.

AI assessment note: “I really don't give them a lot of advice, to tell you the truth.”

Q other founders? Say you're advising me, we're in a coffee shop, and I'm thinking about, you know, a new trait, habit, style of leadership. How would you advise me on, hey, Harry, Just push through it. Like, keep going. Don't be a cop out. Versus, no, listen to your team. Step back, Harry. You're not meant for this. How do you advise them on whether to listen to which one?

A I mean, that actually happens all the time, Harry. Like, I meet with founders. I don't invest. I don't do any kind of angel investing. They just come to me kind of as a therapist. They sort of sit on my couch, and they just tell me all their problems. I really don't give them a lot of advice, to tell you the truth. I say, Oh yeah, that happened to me. Yeah, that happened to me, and this is what happened. Boy, I had it worse than you, man. Here's how I effed it up worse. Uh, and this is what I did to get through it. Uh, but you might have to do something different, but that's what I did. And most of them are just relieved that they're not the only one suffering through this. Um, and I remember myself, I didn't have a lot of founders to talk to, uh, in the early days. In Atlanta, there wasn't much of a startup ecosystem. And so I didn't have that. And, and I thought I was just The only one stupid enough to make the stupid mistakes that I was making. Um, so to me, my goal when I talk to founders is just sort of say, Hey, no, man, we, we all make that mistake. All of us.

AI assessment note: “I really don't give them a lot of advice, to tell you the truth.”

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: “Like an oak tree with really deep, strong roots. I mean, it's just very, very slowly.”

Q 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 a 10 millionaire or international offices? When was that? Ooh. This is real.

A 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 were 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 kind of 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 because we're tired of cashing the checks or depositing all these little You know, 50 dollar checks. Um, I was driving to the bank too much. It's a 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, you know, I, I, I, one day I, I caught this episode. I think my, my wife was watching Oprah. She, she is a night shift nurse. She came home, you know, she crashes on the couch and turns on Oprah and I'm working at home and, you know, I'm coding away at some website and there's a guest on Oprah. His name's Robert Kiyosaki. You should have him as a guest someday.…

AI assessment note: “It took me a long time to realize that.”

Q How do you think about bringing your, you know, two boys up, um, in, bluntly, much more fortunate environments than, you know, you were brought up in yourself. How do you retain hustle and ambition and hunger when very different financial situation?

A Well, I mean, I used to worry about that a lot, um, and then I realized the heart of that was that it was because I wanted them to be an entrepreneur like me, and that's an unfair thing for a parent, uh, to, to, um, want in a child. I mean, the child, he's, they're gonna grow up to be what they want to be. That's, that's what I want to have for them, some freedom and independence for them to decide. So I had to let go of that expectation of them. So that, that was one big thing. Um, I, I also really didn't talk about money that much and they never really knew that MailChimp was that successful. They just knew that I was maybe a nice, helpful guy to customers. It was their classmates. Uh, one day, one of their classmates brought a magazine with my face on the cover. Uh, cause I guess her dad had given it to her and say, Hey, take this to your friend. Um, and that was when they said, is it true that, you know, MailChimp is this worth this much worth that much? You know, and I had lots of conversations with them. It never really, intellectually, they got it, but it never really registered for them, because then, you know, they would say funny things like, you know, oh, there's this kid at school. His dad has a Porsche. They must be rich, Dad. When will we be rich? You know, and I was, you know, so they kind of intellectually got it when they were young, but not really, because we …

AI assessment note: “I had to let go of that expectation of them.”