Transcript

[Harry] 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.

[Ben] Glad to be here. Thanks for inviting me. And I hope she didn't give you too much dirt.

[Harry] Oh, she gave me so much dirt, but we can get into that later. We were just chatting now and you said to me that you're an accidental entrepreneur. And so how did you come to found MailChimp and what was that aha moment for you?

[Ben] I always wanted to be a designer. I loved drawing when I was a kid. I had a couple of businesses in grade school. I would get those little 3M sticky pads and I would draw animations, little cartoon flip books, and I would sell those on the bus. And that's how I got my taste of business. And I moved on to selling candy, my own comic books that I would draw. And I still maintained that MailChimp is really just the end of a series of pivots from grade school. I always wanted to be a car designer. I went to industrial design school. I kind of along the way fell in love with web design. I got an internship at an appliance company and I learned how to design appliances. And I was good at designing things on the computer, but I was really bad with my hands. I didn't have the dexterity to use that exacto blade and cut foam models like you're supposed to do. You have to do that when you design cars as well. I was really bad at it. And the mentors that I had at the time were like, yeah, all of these refrigerators are lopsided. So one of them gently nudged me towards the silicon graphics machine and said, you might want to try 3D rendering instead. And so I fell in love with that machine. I fell in love with computers. I never went back. I learned web design that summer internship. I got into that the next semester and never went back.

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

[Ben] Oh, this is real. It took me a long time to realize that 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 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 $50 checks. It was driving to the bank too much. 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. We were exhausted from running an agency, the billable hours game selling to clients. We were bad at it. One day I caught this episode. My wife was watching Oprah. She's a night shift nurse. She came home and she crashes on the couch and turns on Oprah and I'm working at home and 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. He's up there and he's talking about passive income, recurring revenue and all that kind of stuff. And it was the first time I had ever heard about anything like that. And so I stopped coding and I listened and I said, this guy's onto something. And I bought all of his books, read about it. And I just started thinking, should I get into real estate? What kind of recurring revenue business can I do? Meanwhile, MailChimp's sitting here making recurring revenue by the way. I'm like, what should I do? What could be the next business? And then it hit us, wait, we've got this MailChimp thing on the side and we took its revenue and we separated it from our agency revenue for the first time. We used Excel. We drew graphs for the first time in our lives. We were like, this Excel thing is pretty cool. We color coded the revenue for MailChimp versus the revenue from our agency and MailChimp was growing and our agency was flat and declining. That was all we needed to say, let's stop the agency business and let's focus on MailChimp as a software company. What sort of level revenue was it then? Was it like a million, 10 million, 5 million? After a few years in, MailChimp might've been making a few hundred thousand dollars at the most. Our agency business was making just barely more than that, but it was flat. You have to remember this was after the dotcom crash. It was slim pickings in Atlanta, Georgia, getting website business. We were making a hundred thousand errors at the time, not even close to millionaires.

[Harry] I get it, but being that that stage three years in, it's not like rocket ship growth. My question is when was that inflection point where it went actually very much stratospheric?

[Ben] It was a sort of another accidental thing. We fell into freemium. That was it. Five years of chasing after silver bullets, just, Oh, this is going to be the unlock. And it wasn't the unlock. Let's launch this feature. That'll be the unlock. And it wasn't the unlock. Let's do this PR. That'll be the unlock. Never. And freemium was something that we fell into. Didn't really think much about it. And that turned out to be this thing. I think we were tens of thousands or hundreds of thousands of users at the time. And then within one year it was a million users. Within another year it had doubled again and it just kept doubling for a few years after that, just thanks to freemium.

[Harry] It's always what you don't expect. We mentioned your sister at the beginning. I do want to touch on a couple of fascinating elements I discussed with her. I hope it's okay for me to ask, but she mentioned the incredible relationship you have with your mother. I do with mine. She mentioned that with her funeral, you bought 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?

[Ben] Yeah, she was an entrepreneur. She ran a hair salon in the kitchen of our home. We always had customers in the house and I was always helping her out, emptying ashtrays, organizing the hair rollers and that sort of thing. And I watched money exchange hands. And I always joke, 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. And that's what business smells like to me. 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. She was from Thailand. And to her, business is just something you do to make a little extra money. To me, being born in here in the States, my father is born in the States, he thought about business differently. He was always talking about how does this unlock? How does this scale? 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 disappointment in me that this wonderful thing that my mother did never really just turned into like the next Vidal Sassoon or something like that. And I think that's been the DNA of MailChimp, this understanding that small business entrepreneurs, they might start small, but they're dreaming big, they want it to be something big. Because of my mother, I think I never called our customers small businesses, I would say businesses, or I would talk about their dreams of becoming big. It's useful internally to call it a category SMB category, internal reference only. That's what I would tell my writers and marketers. But outward facing, I really hated to use the word small business because they have big ambitions.

[Harry] I love that in terms of how that impacted especially the smell. I also heard about your father and the fishing trips. A lot of you asked, what did you take away from those and how do you reflect on lessons from them?

[Ben] The lake where we would go fishing was always about 45 minutes to an hour away. It was a really long drive. Whenever I drove with him, he always took the slow scenic route, the backcountry roads. 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, he would take the interstate and we'd get there in 15 minutes. So I knew there was always a bastard path, but my father always took the scenic route. That was a big lesson for me. Sometimes it's not always better to be faster. When we went fishing, he also did not just 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. I would whine and complain all the time. And he would make me lug the fishing poles, the minnow bucket, all of this equipment, the tackle box. I would complain and complain. And I would always wish that there was a device or some kind of transportation like Star Trek, just be there. I would always talk about inventions to make it easier and just complain that my feet were hurting, whatever. He never said anything. This is what I remember most. He never turned around and said, hurry up, stop complaining. He never praised me either. In other words, he was very stoic and he would be walking ahead of me and I would be whining and complaining. He would stop, turn around and quietly wait until I caught up. And then when I caught up to him, he never said a word. He turned back around and started hiking again. And that was it. I think I learned stuff's going to be hard. It's not worth complaining. Just keep hiking. When stuff's really hard, look at your feet and just keep marching one foot at a time. Left, right, left. That's it. He was also in the military. I remember one day they were coming back from some kind of training mission. It was families reuniting with all of the soldiers. And I had no idea that my father was this head of this platoon squad. I don't know the terminology. I had no idea he was the leader. My father was just a kind, quiet, stoic kind of guy to me. I got to watch him lead this big troop, all these troops. And he would turn hot. And then these soldiers would jump up in formation. And they would turn and obey his every order. And I'd never seen my father act that way. To me, it was really violent or loud. He'd never acted that way. He made them do what they did. And then he put them at ease. And then he was just a very personable kind of a guy. Everyone came up, hugged him, shook his hand. So I could see that there are two sides. If you're a leader, you do what you got to do to lead the troops. You don't have to be harsh and vicious all the time. You can also be friendly on the other side.

[Harry] You said about him not praising you there or waiting for you silently. Did he tell you he loved you?

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

[Harry] I like that a lot. I also hear that you're a cyclist. So I want to bring them together and ask, what does high performance in business and leadership mean to you when I say those words?

[Ben] When I think about high performance at MailChimp, the way that I ran the business, I never really thought about it as setting a high goal and telling people to crush it at all costs. I would set the high goal and then think about what habits do we need to get there. 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 got to lose this weight. 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 staying up too late watching TV. So I just unplugged the TV, no more TV for me. And I would go to bed earlier. To me, that's high performance. So 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. 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. It's about getting to the core of the problem. I guess deleting habits more than anything else.

[Harry] What do you say to people who struggle with the discipline? I agree with you totally. Often it's too much alcohol. Often it's not going to the gym, watching TV. And they go, oh, but it's a long day. I need my gin and tonic, whatever it is. What do you say to them who say, I don't have the discipline. Oh, I'm tired. I've got kids.

[Ben] I don't talk to them. I'm a little bit like my dad. It's like, if you want it, you'll do it. If people want something bad enough, they figure out that discipline. They just must not want it. I'm close to 50. I'm an old fart now. You sort of learn to just stay in your lane. The key to happiness is staying in your lane and knowing when people need to be in their lane. Don't get in their lane and don't let them get in your lane. To me, if somebody is just not disciplined to take control of their lives and be successful, they must not want it. And I'm not going to bother with it.

[Harry] What do you mean stay in your lane? I'm too interested.

[Ben] Everybody has problems. You got problems. I got problems. You bring those problems to my table. Hey Harry, good for you, man. I'm not going to make it my problem. I'll give you some advice. I'll probably try to get down to the core. If you really want advice, I'll give it to you. But I'm not going to be attached to making sure you follow that advice. Take it or leave it. It's up to you.

[Harry] But we have like 40 or 45 people across our companies now. And I 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 reflected on that recently. When you reflect, and it's really interesting now that you stepped away from the role as CEO, when you reflect on your own CEO ship and style of leadership, how would you describe it? And did it change over time?

[Ben] Yeah, maybe in the very early startup years, I didn't have this kind of 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. 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. I think that when the very early years of MailChimp, creativity was everything to me. And you might describe me as bring on really talented, creative people and just be very hands-off. And I really do think that helped me in those early years. 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. 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 not telepathic where everyone knows what it is the leader wants. It's like you're the mayor of a really big city and their pockets and neighbourhoods of that are just out of control sometimes, or they're just doing their own thing. But I was told that I got some coaching around two, 300 employees. And they said that my leadership style was a little bit hands-off, which can be good, but it was also eyes-off. And they told me the guidance was hands-off, eyes-on. And that was the biggest change for me being trying to be hands-off, but eyes-on.

[Harry] How did you change as a result of that?

[Ben] I used to just give grand big picture vision. I could rely on a small team to be telepathic and just get it done. No, what you had to change is be a lot more explicit about the goal, maybe some KPIs, maybe talk about what happens if you don't meet the goals. You have to rely a lot more on senior managers and lower level managers to actually manage people and hold people accountable. That's hard to do when you're a startup that's just sort of used to having a bunch of free-range creatives do what they want.

[Harry] Did you enjoy that? You are an incredibly creative, emotive, effusive person running process on individual little squadrons.

[Ben] 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. To me, it was about the transformation of Ben. Over the years, I watched a lot of founders. 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 that's 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 operational in air quotes. I'm going to be more operational in my life. And I really think that I got pretty darn far with that. And I'm proud of how far I got with that. I was willing to keep on going. And I think 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 Harry, I could have kept on going and evolving and trying. And one day I just realized I had enough people just say, you're not great at this operation stuff, Ben. And I just 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. I started to lean more on operational people on the senior leadership team. And I was self-aware enough to step back in some areas. And after that, I started to think, yeah, I don't get a lot of energy from that. I really don't. I'm much better when it's sort of connecting the dots for a lot of creatives in the room.

[Harry] How would you advise other founders? Say you're advising me, we're in a coffee shop and I'm thinking about a new trait, habit, style of leadership. How would you advise me on, Hey, Harry, just push through it. Keep going. Don't be a cop-out versus 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?

[Ben] That actually happens all the time, Harry. I meet with founders. I don't invest. I don't do any kind of angel investing. They just come to me 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. And this is what I did to get through it. But you might have to do something different. That's what I did. Most of them are just relieved that they're not the only ones suffering through this. I remember myself, I didn't have a lot of founders to talk to. In the early days in Atlanta, there wasn't much of a startup ecosystem. And I thought I was just the only one stupid enough to make the stupid mistakes that I was making. So to me, my goal when I talked to founders was just sort of say, Hey, no, man, we all make that mistake. So I don't really give a lot of straight up advice. I just relate to them. I think it goes back to relationships, which is like, there's times where most people just want to be heard. And actually saying, Yeah, I feel you. I had that too, is exactly what you need. But it takes emotional intelligence too.

[Harry] And I spoke to Lottie again, you said before the show that she's 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? What do you think she sees in you about how brilliant your EQ is?

[Ben] I'm conflicted about it. I know that I can be pretty insightful about people's feelings. I was a really quiet loner in school. I went to a rural country town school that I was one of like three Asians in the whole school. So I was kind of a misfit. And a lot of misfits flocked to me. 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 don't know those early years of listening and learning from a lot of these people who would come and talk to me, it really helped me tune into the way people were feeling and what they were going through. The reason why I'm conflicted about is I also have this flip side of me as a leader. So I talked about my father like being this really friendly guy. But when it's time to lead the troops, you could be cold or harsh on the surface, you got to do what you got to do. Most people probably see that side of me. So anyways, I have been told many times I have a high level of self awareness and a high amount of EQ. But I'm also told I can be cold and robotic because I'm pretty logical. And I would just say what's got to be done. I may be in a more overly stoic way.

[Harry] I had Drew Houston on the show recently, and he said something brilliant, which was there's no nice way to deliver a grenade. And I think to that option, which is like, you know, well, then you're fired. Say it nicely, then all night, you're still fired. It sucks. I totally get you. You said about being leader of the misfit set. And again, the joy of doing the show is I can change the schedule. I was a misfit too, Ben, and I didn't have any friends for most of school. And it made me actually not great in business in one way being I. always want to people please. 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?

[Ben] Now we're getting into some really deep psychological stuff here. 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 through my childhood years. Not at home. I lived in a very loving home. Thank God, I had that kind of shield around me. But when I went to school, it was like fists up, get ready. So 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. I think that gave me this drive to be a great successful entrepreneur. It just pushed me, I had to prove it. On the one hand, that's really good. Probably on the other hand, if I feel people are trying to push me in one direction, 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. No apologies, man. This is what we got to do. We got to do it. And I will not be swayed or pushed again, never again. Sometimes you have to go with the politics and understand politics a little bit better. And I understand it, I get it. I do have that EQ to get it. But sometimes you just have that sort of angst from your childhood. And you just sort of say, if it's illogical, I'm not going to concede or deal with that. When you talk about bad habits. I think that's probably what I inherited from my environment. I think the most kind of prominent lessons are from quite painful times.

[Harry] What do you think about the most painful lesson that you've learned that you're also pleased to have learned, which is a weird paradox? What would you say it would be?

[Ben] Being a misfit was always this painful thing throughout all of school for me, even through high school, even a little bit through college. But what I've learned in retrospect is that it made me think differently. It made me stubborn in some ways. It made me stick to my guns. I think that really gave me this focus to be an entrepreneur, a successful entrepreneur. And I think there were times when I think we could have sold the business early, there were a lot of people, a lot of suitors knocking on the door, a lot of investors knocking on the door. I just sort of had this 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.

[Harry] Was that always beneficial? Do you think in hindsight, if you think you know, I'm sure the moment you could have taken 100 million, 500 million, a billion, everyone wanted to give MailChimp money. Are there moments where you're like, actually, my stubbornness was not good?

[Ben] Who knows, there are probably some people out there who could look at it and say, Ben, if you've just taken this money back then, you could have scaled even bigger, and maybe right now you'd have sold for 20 billion, who knows. There are some people who say, yeah, you would have had a slice of the pie instead of the whole pie, but the pie would have been bigger. There's no way to tell. But I do know that when I look back on my life, I'm really proud to say I did it my way. And I'm really proud of that. 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. I'm really proud of that.

[Harry] The thing that I also think about is MailChimp, was it a 17 year journey, an 18 year journey?

[Ben] 21, not that I'm counting.

[Harry] Anyone, not that you're counting. It is such an ingrained part of your identity, actually, as my business is mine. I hate going on holiday, Ben, because I lose my identity. I'm not working, and then I don't know who the fuck I am. My question to you is, when you stepped away from CEO, how did you handle that loss of identity and losing something that was so ingrained in who you were?

[Ben] One company, one great, amazing leader tried to buy our company many years ago. Out of a sense of duty, I heard them out. And ultimately, I said no. And he told me, hey, you're going to change. And when you do, when you change your mind, can you give me first dibs? That kind of annoyed me. Why do you think I'm going to change my mind? Why are you so sure that I'm going to change my mind? And he said, you're going to think about life differently. Right now, you are defined as your business. It is everything to you. But as you get older, you're going to realize that your business is just something that you created and something that you do, but it is not you. And then you will be ready to sell. And I said, yeah, whatever. Thank you. I was nice about it. But I just secretly was like, that guy's nuts, hung off the phone and forgot about it. Maybe I was in my early 30s at that time. Lo and behold, 10 years later, I'm in my 40s, mid 40s. Something happens when you're in your mid 40s. All right. It happens to everybody. Their friends and their families start to die. You start to reflect on life. It's one of those things where it's like, you're just chugging along with your business. You're not really thinking about this, but friends your own age, people you knew start to pass away and heart attacks, whatever it might be. Family starts to pass away. You start to think about life and you start to think about, well, my life is not my business and that's just a job. It's just something that hits you. There was never a desire to take investment or to sell the company. And it's just one of those things that just happens many years later to you. When that started to happen, it goes away. This attachment that you have, it goes away. It did to me at least, but I know a lot of people that can't seem to shake it. Like they sell a business and they keep on going and they start more and more. I just can't imagine why anybody would want to do that.

[Harry] Did you find the transition hard?

[Ben] First of all, I don't know that I transitioned that hard. I'm still in the middle of this. I'm still at MailChimp. I haven't stepped away from it, but I am focusing a little bit more on innovative projects, being an advisor in that capacity. One of the guys that we ended up using a company called Catalyst to be our broker. You know the guys at Catalyst?

[Harry] I know them well, fantastic.

[Ben] Yeah, they're great. So the guy that reached out to me, it was about 10 years ago, he reached out to me and I was like, I'm not selling my business, go away. And he was just very nice. He kept a relationship with me. He was very calm and patient. He's very Zen and philosophical. And we just built a friendship over the years. And he was actually a practicing Buddhist. When the time came to sell the business, he was probably finally Jesus is 10, 10 years sales pipeline here. I'm going to close this. Anyways, he went through the deal with me before it was over. He said, Hey, I want to talk to you about this. I've seen a lot of founders go through this process. And what you're going to learn is your entire life, your career, your ideas of CEO is composed of nothing but a whole bunch of habits. And these habits are driving you and these habits are making you do everything that you're doing. These habits are making you think about everything that you think about. And those habits are going to start to die off, you're not going to be called into meetings anymore. The emails are going to stop coming in the calendar, invites are going to stop. And it's going to feel weird what it is habits are being deleted. And maybe you'll develop some new habits. But think about it that way. That was the guidance that I got from and I thought that was a little bit crazy, maybe. But I have seen this start to happen. I've talked to other founders too. They said, did you wake up one morning and notice that there were no emails on fire in your inbox? And I said, yeah, that happened to me today. And she was like, yeah, that's happening to me now. Anyways, you really do start to realize, wow, it's nothing but habits. You wake up, you check your phone, you do this, you do that. They're good habits that make you a great leader, but they are just habits. Other thing I'll say here is MailChimp's success came very organically and slowly. So I have seen founders maybe that they were maybe overnight successes. And I think that going from poor to rich can really do a number on your brain. And I think my co-founder Dan and I were so lucky that we just sort of really gradually grew and we could stay grounded. We kept some level of humility if I'm allowed to say so myself. But the transition hasn't been too hard on us.

[Harry] That was going to be my question. We were going to get to relationship with money, but you've been on the front cover of many magazines lauded for the success and efficiency of the business. And you joke about being wise and older. You're still pretty young to have 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 issued 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 fight against ego inflation?

[Ben] The magazine covers only happened in the last few years. 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 laughing at the chimpanzee mascot. Nobody cared about email. Nobody cared about sass at the time. I could never get any publicity. What I'm doing is I'm seeking that validation. Maybe as that misfit who was always pushed aside, I wanted that validation, damn it. And that's what I wanted from the publicity. And then I realized the only validation I need is a paying customer. When they open up that wallet and pay me with their credit card, that's a validation. I rewired my brain to only care about that for many, many years, didn't care too much about publicity. And it was only the final few years I got a chief comms officer who just said, you could use some publicity, let's do it. It'll help us with hiring. We're at a scale of a thousand employees. We're competing with some publicly held companies. We got to get the word out. And I had read about other privately held family businesses that were very stealthy and quiet. And then every few years they would open the doors. Mars Candy is one of them that I read about. They would open the doors a little bit, reveal a little bit in order to recruit. They would need to bring in fresh employees, fresh blood, and then they shut the doors again. That was really why I opened up the doors. I just said, all right, let's do this. Let's get some magazine covers. That's fine by me. And then, yeah, it happened. But I think the fact that I had already been jaded on publicity, that's probably what might've kept me a little bit grounded there. And also during the entire time, I would send regular communications to employees, just saying all of this stuff that the magazines are celebrating, they're celebrating everything we accomplished in the past, but in the future, we've got to reinvent MailChimp. We were turning from just an email point solution to this multi-channel platform. That's where we're heading. We are going to fail miserably at that for many years. And people are going to make fun of us and all of this glory that we had in the past. We're going to lose it. These magazines, they're talking about that glory back there. You better get used to hard times ahead. I kept saying stuff like that. The first time we got the magazine cover, actually, the comms team bought a big stack of them, put them around the office. They were so proud of it, but I always teach our employees to be humble. That's one of our core values is humility. They could make fun of me. I didn't care. We had that kind of environment. I remember somebody drew a moustache on my face on the magazine cover and they drew a moustache on everybody's face. Actually, I laugh so hard and I was so proud that we have this culture that could just be brave enough to poke a little fun. I took a picture of it, posted on Slack, and I said, this is hilarious, more please. And somebody in the company, Sean Cook, he started an art gallery where we encouraged everyone to deface my face. And there was like a contest. It was like a brilliant art show of everybody gluing googly eyes on my face, just doing all kinds of things to make fun and just humble us all back down again.

[Harry] It slightly reminds me of Willy Wonka opening the doors to Charlie Chocolate Fashion and then shutting them again. In terms of the sale, why did you decide that them 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?

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

[Harry] You see your number and you're like, ah, yeah, I would.

[Ben] Yeah. And then you take it away. So I had this conundrum and I was sick and tired of the whole process, by the way, because it takes away six months of your innovation and your momentum and stuff. It's distracting. So I was at this point where I was telling everybody, I was ready to tell them never again. I'm not going through this process. We're going to stay bootstrapped, self-funded. If you don't like that, it's time to go. Cause I'm drawing a line. Never again. I was days away from sending that memo to my senior leaders and I got that call from catalyst and they said, this one's different. You need to listen to this. And I said, sure, fine. And it was into it. And I listened to Alex Chris. He knew small business. He had built a startup before that serves small business. He runs a small business self-employed group at Intuit. He talked about small business in a way no other leader had talked to me about it before. He knew the same stuff that Dan and I knew. And that's very rare. He talked about it with a passion that I'd never heard before. We talked about what it would be like to combine forces. And I felt like MailChimp was at a place where it needed to go to the next level. I needed to hire another leader to get us there or I could join forces with Intuit. And it could be like, you know, Intuit was like this big jet, the ones that refuel the small fighter jets. And I felt like this is like a refuelling moment for us. We can just connect, get pumped full of fuel and then take off with our mission and continue getting MailChimp to its big act too. So it was very compelling. We talked for a year, by the way. The whole thing was an entire year of due diligence and courting each other, testing the waters here and there. I was really hesitant about the whole thing the entire time. It was just too compelling to say no.

[Harry] I had Ryan Smith on the show from Qualtrics and he talked about his relationship to money when he sold Qualtrics and became a billionaire. And I asked him, what is your relationship to money? You know, you move very quickly into different astronauts of wealth. How do you reflect on your own relationship to money? And how do you think about that today?

[Ben] We didn't move that quickly. MailChimp was making hundreds of millions of dollars and we were on the cusp of a billion ARR when the acquisition happened. We were already doing really well, highly profitable. So I don't know that my money profile changed overnight. Like I said, it's a venture funded business though, isn't it?

[Harry] 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.

[Ben] Like an oak tree with really deep, strong roots. It's just very slowly. And we had kids. That's a very humbling experience to have children. My co-founder had two girls. I had two boys, roughly the same age. I don't know, man. That just grounds you. 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, dad, what are you doing? I never said, making money. I never said running a company. I always said, helping customers, always my answer. I just wanted them to be helpful watching me. So anyways, that relationship with money. I don't know. I was lucky that we eased into it and I just sort of want us to have the right attitude of being helpful with it.

[Harry] How do you think about bringing your two boys up in bluntly much more fortunate environments than you were brought up in yourself? How do you retain hustle and ambition and hunger when very different financial situations?

[Ben] I used to worry about that a lot. And then I realised 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 to want in a child. The child, they're going to grow up to be what they want to be. 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. That was one big thing. 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. One day, one of their classmates brought a magazine with my face on the cover because I guess her dad had given it to her. And that was when they said, is it true that Mailchimp is this worth this much worth that much? But I had lots of conversations with them. Intellectually, they got it, but it never really registered for them because then they would say funny things like, oh, there's this kid at school. His dad has a Porsche. They must be rich, dad. When will we be rich? So that they intellectually got it when they were young, but not really, because we never really acted that way. I am told by many people who've worked on home offices with super wealthy families. It's really just about how you live, not really what you teach or what you say to them. It's really how you act. And all I could do is say, I hope that they learn by watching us that we just tried to be earnest and try to be helpful. And that's it.

[Harry] If you save up, you could buy that Porsche one day. One day you could buy that Porsche. I love that. That's so sweet. I want to move into a quick fire band. So I say a short statement and you give me your immediate thoughts. Does that sound okay?

[Ben] Can I tell you something about Porsches though? Yeah. They sell a lot of cars. You can edit this out if it's too long.

[Harry] I'd love to. Go for it.

[Ben] I'm a car guy. I love cars. I don't have 20 cars or anything like that, but I do have a nice car. I have an R8 and I love that R8. My son, he's like, dad, there's this kid in school. His dad has a super car. And secretly I'm like, I have a super car. I have Iron Man's super car for Pete's sake, but they don't think of it that way. I don't treat it that way. I guess I don't talk about it that way, but they have no idea that we have this damn... They know it. They know the car. They ride in it with me sometimes, but they just don't think about it that way. There's something about that. I don't treat it that way. I love it because it's a very powerful, very fast, probably the last normally aspirated V10 of its kind. And it's an everyday driver. I love it for those reasons. It's not a possession that I need to flaunt.

[Harry] Is that your most lavish purchase?

[Ben] Not even close, but we will talk about those things. I like nice things now. I'm a designer and I love things that are well designed. And a lot of times those things are luxuries.

[Harry] I totally get it. That Gulf Stream is not cheap, but I do want to move into a quick fire round. So I say a short statement. You give me your immediate thoughts. Does that sound okay?

[Ben] All right, let's do it.

[Harry] So Lottie told me on this one, ask what books are capturing your heart these days.

[Ben] Can I say not business books?

[Harry] Yeah, of course. I've read like a thousand business books.

[Ben] I had this library down in my basement. I had a flood recently and it destroyed almost all of them. And it was really cathartic to throw them all away. And now the only books that are remaining are sort of philosophical ones, stuff about life. I'm reading stuff from Thich Nhat Hanh. He's a Vietnamese Zen Buddhist monk. And the peace, peace is every step is one that I'm listening to and loving right now. He's also got another one that I just finished called Art of Power, the Art of Power. I think I'm loving them because it's probably therapeutic and helping me unlearn some of those habits we talked about.

[Harry] Ben, what does a day look like for you? Is there like a typical routine to the day if you would have generalized?

[Ben] I never had a typical routine ever, even with the business. I was forced into it, but I never really kept to a schedule. Right now, these days, it's more like dealing with no routine. I just got a dog. You know, I step back. I'm more of an advisor. I should be able to sleep late, but I'm not. I'm waking up at five thirty like I always did, taking this dog out. The dog is keeping me busy.

[Harry] What was the secret to the weight loss? What worked?

[Ben] A lot of riding and a lot of walking. Walking is way more effective than people think it is. And I've lost five pounds just walking this darn dog every day. But the riding, I think, was a very big deal and stopping soda. Why are we talking about weight loss?

[Harry] We're talking about anything I want. It's my fault. Okay. All right. Sugar water. Get rid of all sugar water. The truth is, I was like an obese fat kid when I was young. And so I'm always fascinated by people's weight loss journeys.

[Ben] Can I tell you, I visited my great uncle Clarence down in Miami one day, and he was in his 90s. And he's a funny guy. He used to be a truck driver for a dairy company. And I wanted to visit him with my wife. And I said, What advice do you have? And he was like, really, he was skinny, like a skeleton. And he was diabetic. He was quite unhealthy because of that. And he said, he told me no sugar, no sugar. He said he used to wake up for his morning shift and fill up his thermos with heavy cream to save time and get in more miles and make more money. And he would just drink from that thermos all day. And he said that's what gave him diabetes. He regrets it. And he told me no sugar, drop soda, don't put sugar in your coffee, just drop. And he was like a skeleton. I love that man. He was such a good inspiration for me, but he was a skeleton. He was like, no sugar, and it scared the shit out of me. So Harry, that's how I lost my weight. I just, it got scared out of me.

[Harry] I love that. Tell me lottery tickets. I don't know where to go with this one. But Lottie told me again, I had to ask it.

[Ben] What is all that my wife and I were high school sweethearts. Okay, so we're in high school, and we stop at the store and she wants lottery tickets. My wife bought all these lottery tickets, and I'm driving us home and she's scratching them off. And she's not a stickler for details. My wife, she doesn't necessarily always read these instructions. She scratched off a ticket. And I think it was something like 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 maybe the winning number was seven, and she scratched off a 10. And she said, Oh, my God, I won $25,000. And I was so excited. I almost crashed the car. And I was like, Oh, my God, this is so cool. We're rich. And then she kept scratching. And she said, Oh, my God, I want another $5,000. And I was like, cool, but weird to win twice. And then she kept scratching. And she said, I won another $2. And I was like, hold on, lottery tickets don't work this way. He don't win $25,000 and then $2. So anyways, we were so elated that we finally had money because we were pretty poor back then. We grew up in a pretty poor town. That was like our ticket out. And no, we ended up not winning at all. And anyways, I continue to buy lottery tickets. And we joke about it to this day. We still have a lot.

[Harry] That is the most like realizing depressing shit. But hey, when you're like, Oh, bugger, roll.

[Ben] That really is. And she still makes the mistake. Sometimes she'll get a lottery ticket as a job for a birthday. And she'll say, Oh, my God, I won. I won.

[Harry] And they're like, Welcome to a day of male chimps.

[Ben] Nevermind the 21 years of building up this great billion dollar business. So you won. You think you won the lottery?

[Harry] So help me out. You're wise seasoned, as you delightfully put it earlier. What's the secret to a happy marriage?

[Ben] Oh, my gosh, I'm very lucky. My wife was a nurse, and she became friends with a lot of nurses who are older. And so we used to go out to dinner with a lot of these older couples. What I noticed was the happiest couples had husbands who just kept their damn mouth shut. I just Okay, so they are repressing themselves. That's the key. And I think I've learned they're not repressing themselves. They just learned that they've humbled down to learn that they're not always right. And it's not always about winning. And that's not everything is winning. I just sort of let go 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 does help me shut one.

[Harry] You're just ultimately repressed to the point where you're reasonably rationalizing that.

[Ben] It could be that it could be that. Yes. But also, also, if I keep my mouth shut and follow her advice, things really are happening.

[Harry] What three traits would you most like your children to have?

[Ben] So I have an acronym floating in my head at all times that I thought would be my guidance on raising children. It was bliss. It stands for balance, love, independence, and self sufficiency four traits, maybe self improvement and self awareness. Like I want them to just sort of understand it's about slowly incrementally improving yourself and overcoming challenges. Is it adaptability, perseverance, grit?

[Harry] What would you most like to change about the world of startups?

[Ben] I think it's happening, actually. I would love it to not be located only in Silicon Valley in New York. I would love it to just be able to, like with MailChimp, it happened in Atlanta. It happened in our homes. I'd love it to just be everywhere as tech startups to not have to be in those two locations.

[Harry] Ben, tell me final one. What are the next five years hold for you?

[Ben] I've met many founders who've sold their business and then they go off and they want to do crazy adventures. And I applaud them for that. One wanted to explore space. And I've told them all, what do you want? And I said, I want to explore my own mind. I want to know why I think the way they 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 her to want to not want. And I think that What does that mean?

[Harry] What does that mean to not want you? Surely you don't want now you don't want for anything. You can buy anything.

[Ben] Yeah, I don't feel a desire to. I think it means learning to be content with what you got.

[Harry] Are you there now?

[Ben] And so I met one founder who said that when he sold his business, he bought a yacht and he went to Greece and he dropped anchor. And he was like, I have made it. And then a bigger yacht dropped anchor next to him the next day, a much bigger yacht. And he was like, Oh, I haven't worked hard enough. He said he was so happy when he got that yacht. And then as soon as he saw someone with a bigger yacht, he became unhappy just like that.

[Harry] Why? Why?

[Ben] And I think it's preventing that. That's what I'm having.

[Harry] Have you got that now though?

[Ben] I don't know. I think time will tell you said five years. Why? Why are you pushing me now? You said over the next five years? Give me time here.

[Harry] And I'm a VC. I'm here to push you your timeline.

[Ben] My timeline.

[Harry] That's why you didn't take VC money. Listen, Ben, I've loved this. You are a star. Thank you so much for my incredibly prying questions, but you've been amazing. So thank you.

[Ben] Thank you, Harry. Thanks for having me. This was a lot of fun. I absolutely loved doing that show.