The Twenty Minute VCBen Chestnut: Why I Sold MailChimp; How My Kids Found Out I Was a Billionaire | E959
EVERY SPOKEN WORD
120 min read · 24,188 words- 0:00 – 5:08
Origin Story of Mailchimp
- HSHarry Stebbings
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.
- BCBen Chestnut
Glad to be here. Thanks for inviting me.
- HSHarry Stebbings
I wanted to-
- BCBen Chestnut
And I hope she didn't give you too much dirt.
- HSHarry Stebbings
Oh, she gave me so much dirt. But we're gonna get into that-
- BCBen Chestnut
(laughs)
- HSHarry Stebbings
... later.
- BCBen Chestnut
(laughs)
- HSHarry Stebbings
We were just chatting now, and you said to me that you're an accidental entrepreneur. And so talk to me, how did you come to found Mailchimp? And what was that aha moment for you?
- BCBen Chestnut
Well, you know, I always wanted to be a designer, you know. I, I, I loved drawing when I was a kid. I had a couple of businesses, um, in grade school. You know, I, I used to sell... I would get those little 3M sticky pads and I would draw animations, li- little cartoon flip books, and I would sell those on the bus.
- HSHarry Stebbings
Wow.
- BCBen Chestnut
Um, and, and, you know, that's how I got my taste of business. And I, you, you know, moved on to selling candy, comic books, m- uh, my own comic books that I would draw. Uh, and I, and I still maintain that Mailchimp is really just the end of a series of pivots from grade school. But I, I always wanted to be a car designer. You know, I went to industrial design school. I kinda, along the way, fell in love with web design. You know, I got an internship at an appliance company, and I learned how to design appliances. And I was really bad. I was good at designing things on the computer, but I was really bad with my hands. I didn't have the dexterity to kind of use that X-ACTO blade and cut foam models, uh, like you're supposed to do. You gotta... You have to do that with... when you design cars as well. I was really bad at it. And, you know, the mentors that I had at the time were like, "Yeah, you're... All of these refrigerators are lopsided." So one of them, you know, gently nudged me towards the, the Silicon Graphics machine and said, "You m- you might wanna try 3D rendering instead." (laughs) And so I, I, I fell in love with that machine. I fell in love with computers. I never went back. I learned web design that summer internship. Uh, and yeah, I got into that the next, the next semester and never went back.
- HSHarry Stebbings
You mentioned Mailchimp being kind of the result of a series of kind of continuous pivots. I love that description. When did you realize, "Oh, oh wow, this is a real thing"? Was it a millionaire or 10 millionaire or international offices? When was that, "Oh, this is real"?
- BCBen Chestnut
It took me a long time to realize that. I mean, it was, it was an accidental kind of a business. We built it for just a couple of our customers who are having problems sending out email newsletters. Our real business was doing web design. And it was just sort of we built it on the side, and it kinda got annoying to log in and use it on behalf of our customers. So we just made it self-serve. We just said, "You log in, you use it, and pay with a credit card 'cause we're tired of cashing the checks as... or depositing all these little, you know, $50 checks." Um, I was driving to the bank too much. And so great problem to have, but it was also very, very annoying that way. And so anyways, we made it totally self-serve, and it just started to grow organically. But we never took it seriously. We just focused on our web design business. And I don't know, maybe three or four years went by, and we were so... We were exhausted from running an agency. I mean, the billable hours game, we... selling to clients, we were bad at it. And, um-
- HSHarry Stebbings
(sighs)
- BCBen Chestnut
... you know, I, I, I... One day, I, I caught this episode. I think my, my wife was watching Oprah. (laughs) She, she's a night shift nurse. She came home, you know, she crashes on the couch and turns on Oprah. And I'm working at home, I'm, 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. (bell dinging) 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, you know, "Hmm, 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?" (laughs) And then, and then, duh, it hit us, "Wait, we've got this Mailchimp thing on the side." And we, we took its revenue, and we separated it from our agency revenue for the first time. We, like we used Excel, we drew graphs for the first time in our lives. We were like, "This Excel thing is pretty cool." And we, you know, we, we color-coded the revenue for Mailchimp versus the revenue from our agency. And Mailchimp was growing, and our agency was flat or, and kind of declining. And so that was all we needed to say, "Let's stop the agency business, and let's focus on Mailchimp as a software company."
- HSHarry Stebbings
Can I ask, what, what sort of level revenue was it then? Was it like a million, 10 million, 5 million?
- BCBen Chestnut
Oh my gosh, man. It was, you know, after a few years in, Mailchimp might have been making a few hundred thousand dollars at the most. And our agency business-
- HSHarry Stebbings
Oh, my God.
- BCBen Chestnut
... was making a little bit, just barely more than that, but it was flat. I mean, you-
- HSHarry Stebbings
Whoa.
- BCBen Chestnut
... have to remember this was after the dot-com crash. So it was slim pickings in Atlanta, Georgia getting website business. And so we were making, you know... We were hundred-thousandaires at the time. (laughs) Not even close to millionaires.
- HSHarry Stebbings
I, I get it. But like, you know, being like at that stage three years in,
- 5:08 – 6:17
Freemium Pricing Model
- HSHarry Stebbings
respectfully, it's, it's not like rocket ship growth. Do you know what I mean? And so I guess my question is like, when was that inflection point where it went actually very, very much stratospheric? Was there a moment where, between years, it really-
- BCBen Chestnut
Yeah.
- HSHarry Stebbings
... moved up a niche?
- BCBen Chestnut
Yeah. Well, it was a sort of another accidental thing, you know. We kind of fell into freemium. Um, it... I, I talk about this quite a lot. I don't know if you want me to dive into it. But we, we kind of fell into the freemium pricing model.
- HSHarry Stebbings
And that was the unlock for you?
- BCBen Chestnut
That was it. I mean, and, and keep in mind, you know, it was like five years of chasing after silver bullets. Just, "Oh, this is gonna be the unlock," and it wasn't the unlock. "Let's launch this feature. That will be the unlock," and it wasn't the unlock. "Let's do this PR. That'll be the unlock." Never. And, you know, freemium was something that we kind of accidentally fell into, didn't really think much about it, and that turned out to be this thing that kinda... I think we were probably, you know, in tens of thousands or hundreds of thousands of, of users at the time.... and then within one year, it was a million users. Uh, and then within another year, it had doubled again. And it just kept doubling for a few years after that, just thanks to freemium.
- 6:17 – 8:52
How Ben’s Mother Impacted His Life
- BCBen Chestnut
- HSHarry Stebbings
Wow. I mean, it's always what you don't expect. We mentioned your sister at the beginning. I do wanna touch on a couple of really, um, kind of fascinating elements I discussed with her. Um-
- BCBen Chestnut
Oh, boy. Here we go.
- HSHarry Stebbings
Well, I mean, I- I- I hope it's okay for me to ask, but she mentioned, you know, the incredible relationship you have with your mother. Um, I do with mine. Um, and she mentioned that with her funeral, you bought kind of every flower in town or as much as you could buy. Um, 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?
- BCBen Chestnut
You know, my mother, um, she was an entrepreneur. She, she ran a, um, a hair salon, uh, in the kitchen of our home. Uh, and so we always had customers, uh, in the house. And I was always helping her out, emptying ashtrays, you know, organizing the hair rollers and that sort of thing. And I watched money exchange hands. And I always joke, you know, to me, if I close my eyes and I think about business, there's a smell to business. And the smell is hairspray and cigarettes. You know, that's what business (laughs) smells like to me. Um, so she, she didn't really talk about entrepreneurial-ism or business. She treated it as it was a living. It was a way to make ends meet. It was a way to help pay for the bills, you know? And I, you know, she was from Thailand. And to her, business is just something you do to make a little extra money. To me, being a little bit more, you know, I was born here in the States. My father was born in the States. He thought about business differently, you know? He was always talking about, "How does this unlock? How does this scale?" You know? And so I always dreamed of my mother just scaling out of the kitchen. Uh, and she never really did. Uh, and I think there was a little bit of, like, disappointment in me that, you know, this wonderful thing that my mother did never really, um, just turn into, like, the next Vidal Sassoon or something like that.
- HSHarry Stebbings
Right.
- BCBen Chestnut
Uh, and I think that's-
- HSHarry Stebbings
(laughs) .
- BCBen Chestnut
... uh, that's- that's kind of in the DNA of Mailchimp, this sort of like, this- this understanding that small business entrepreneurs, you know, they might start small, but they're dreaming big. They want it to be something big. And I don't know, I- because of my mother, I think I never, I never called our customers small businesses. I never said small b- ... I would say businesses, or I would talk about their dreams of becoming big. But I never, like, called it ... It's useful, you know, internally to call it a category, SMB category, right?
- HSHarry Stebbings
Sure.
- BCBen Chestnut
Like in internal reference only, that's what I would tell my, uh, writers and marketers. But outward-facing, I- I really, really hated to use the word small business 'cause they have big, big ambitions.
- 8:52 – 13:38
What Ben Learned From His Father
- BCBen Chestnut
- HSHarry Stebbings
I love that in terms of kind of how that impacted, you know, (laughs) e- especially the smell. I also heard about your father and the fishing trips.
- BCBen Chestnut
Yeah.
- HSHarry Stebbings
Um, what ... L- a lot of us, what did you take away from those? And how do you reflect on lessons from them?
- BCBen Chestnut
Well, my father, uh, you know, with 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 backcountry roads, you know?
- HSHarry Stebbings
Mm-hmm.
- BCBen Chestnut
And it- 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.
- HSHarry Stebbings
Huh.
- BCBen Chestnut
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 lug, 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 (laughs) like Star Trek, just beam us there. I would always talk about inventions to make it easier. Uh, and c- and just complain that my feet were hurting, whatever. And he never said anything. This is what I remember most. He never turned around and said, "Hurry up. Stop complaining." Uh, he never praised me either. He was, in other words, he was very stoic. And he would be walking ahead of me, and I would be whining and complain. He would stop, turn around, and quietly wait and- until I caught up. And then when I caught up to him, he never said a word. He'd turn back around and started hiking again. And that was it. And I don't know, I think I kinda learned stuff's gonna be hard, it's not worth complaining. (laughs)
- HSHarry Stebbings
(laughs)
- BCBen Chestnut
Just keep hiking. When stuff's really, really hard, look at your feet and just keep marching one foot at a time. Left, right, left. That's it. You know? He was also in the military. Um, I remember one day, um, I don't know. He, th- they were coming back from some kind of training mission and th- it was families reuniting with, with all of the soldiers. And I had no idea that my father was, um, this, this head of this, I don't know, I don't know, the platoon squad? I don't know the terminology. But I had no idea he was the leader. You know, my father was just a kind, quiet, stoic kind of guy to me. And I got to watch him lead this big troop, all these troops. And you know, he would, "Ten-hut!" You know? And then these s- soldiers would just like jump up in formation and they would turn and do, obey his every order. And I'd never seen my father act that way. To me, it was like really violent or loud. I'd never, he'd never acted that way. And then, you know, 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, you know? I could see that there are two sides when, you know, if you're a leader, you do what you gotta do to lead the troops. But you don't have to be harsh and vicious all the time. You can also be friendly on the other side.
- HSHarry Stebbings
Can I ask, uh... You said about him not praising you there or, uh, you know, waiting for you but silently. Did he tell you he loved you?
- BCBen Chestnut
Yeah. Yeah, he did.
- HSHarry Stebbings
Good.
- BCBen Chestnut
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." (laughs) You know, I remember him saying that. He was like, "You know, people who are just completely calm all the time and they never get fazed..." Um, like even... He would s-... "You have a calm demeanor. That's leadership. But, uh, 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." Uh, 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
- 13:38 – 16:38
High Performance in Business & Leadership
- BCBen Chestnut
reserved that praise.
- HSHarry Stebbings
A calm demeanor that asks leadership. I like that a lot. I also hear that you're a cyclist. And so I wanna...
- BCBen Chestnut
Mm-hmm.
- HSHarry Stebbings
... kind of bring them together and ask, what does high performance in business and leadership mean to you when I say those words?
- BCBen Chestnut
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, uh, 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. (laughs) I gotta..." I, 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. It... 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. (laughs) 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.
- HSHarry Stebbings
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 too much TV. And they go, "Oh, but it's, it's a long day, I need my gin and tonic," whatever it is. (laughs) Um, what do you say to them who say, "I don't have the discipline? Ugh, I'm tired. I've got kids."
- BCBen Chestnut
(laughs) I don't. I don't talk to them. I'm k-... A little bit like my dad. It's like, if you want it, you'll do it. If, if people want something bad enough, they figure out that discipline. They just must not want it. That's... And, and, and, and I'm, and I'm a 48... Am I 48 or 49? I forget. I'm, I'm close to 50. I'm... You know, I'm an old fart now. And you, you sort of learn to just stay in your lane. The key to happiness is staying in your lane and know- knowing when people need to be in their lane. And don't get in their lane and don't let them get in your lane. So, so 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 gonna bother with it.
- HSHarry Stebbings
What do you mean stay in your lane? I'm too interested.
- BCBen Chestnut
Oh, you know, people... Everybody has problems. You got problems. I got problems. You bring those problems to my table. Hey, Harry, good for you, man. (laughs) I'm not gonna take it... I'm not gonna make it my problem. I'm not gonna give you... I'm not gonna... I'll, I'll give you some advice, you know. I'll probably try to get down to the core. If, if you really want advice, I'll give it to you. But I'm not gonna be attached to making sure you follow that advice. Take it or leave it.
- 16:38 – 21:21
How would you describe your style of leadership?
- BCBen Chestnut
It's up to you.
- HSHarry Stebbings
Well, you know, w- uh, 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've reflected on that recently. When you reflect... And it's really interesting now you're... You know, 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?
- BCBen Chestnut
Yeah, it did. I mean, and in a... 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 wanna be fair to startup leaders out there listening to this. Sometimes you gotta take all that on. Uh, like I said, I'm an old fart. I'm almost 50.
- HSHarry Stebbings
(laughs)
- BCBen Chestnut
This, this is something that happens as you age. (laughs) Uh, 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... Uh, 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 1,000 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 really, really big city, and there are pockets and neighborhoods of, that are just out of control sometimes, or (stutters) just doing their own thing. And (laughs) , and so, you know, I was told that my, I, I, I got some coaching, you know, around f- 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, you know, m- you know, the, uh, the, uh, the guidance was, "Hands off, eyes on." And that was the biggest change for me, being, trying to be hands-off but eyes-on. And I wasn't used to that.
- HSHarry Stebbings
How did you change as a result of that?
- BCBen Chestnut
Uh, you know, uh, I used to just give kind of, like, grand, big-picture vision, and I could rely on a small team to be that sort of telepathic and just get it done. Um, no, what you had to change is, like, be a lot more explicit about the goals, um, maybe some KPIs, maybe (laughs) talk about, you know, what happens if you don't meet the goals. Um, you have to rely a lot more on senior managers and, 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.
- HSHarry Stebbings
C- can I ask, Ben, did you enjoy that? You are an incredibly creative, emotive, effusive person. Kind of running process on individual little squadrons-
- BCBen Chestnut
Yeah.
- HSHarry Stebbings
... 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.
- BCBen Chestnut
To me, it was about the transformation of Ben, you know?
- HSHarry Stebbings
Mm-hmm.
- BCBen Chestnut
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, I'm gonna 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 gonna be like that. I'm gonna 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. Uh, you can't be the designer all your life, and so I'm gonna evolve and, and do this other oper- "operational," in air quotes. I'm gonna 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-
- HSHarry Stebbings
(laughs)
- BCBen Chestnut
... I was willing to keep on going, and I think it's just, you, it's, it's also important to be self-aware and learn when you're not so good at it (laughs) , and I think that's the thing. I, so, so Harry, I think I could have kept on going and evolving and trying, and one day, I just realized s- I, I had enough people just kind of say, "You, 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 'cause no one can fire me." So (laughs) -
- HSHarry Stebbings
(laughs)
- BCBen Chestnut
... that's why I've been going at it so long. So I started to lean more on operational people, on the senior leadership team, and, you know, I was self-aware enough to kind of, like, step back in some areas, a- and then, and then after that, I started to think, "Yeah, I don't, I don't get a lot of energy from that. I really don't." (laughs) I'm, I'm much better when it's sort of connecting the dots for
- 21:21 – 23:00
Advice to Founders
- BCBen Chestnut
a lot of creatives in the room.
- HSHarry Stebbings
How would you advise 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."
- BCBen Chestnut
(laughs)
- HSHarry Stebbings
Versus, "No. Listen to your team. Step back, Harry. You, you're not meant for this." How do you advise them on whether to listen to which one?
- BCBen Chestnut
The, I mean, this, that actually happens all the time, Harry. Like, uh, I meet with founders. I don't invest. I don't do any kind of angel investing. It, it ... 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 f- 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, and I thought I was just the only one stupid enough to make the stupid mistakes that I was making.
- HSHarry Stebbings
(laughs)
- BCBen Chestnut
Um, so to me, my goal when I talk to founders was, is to just sort of say, "Hey, no, man. We, we all make that mistake, all of us."
- HSHarry Stebbings
I think it goes back to relationships, which is like there's times when most people just want to be heard-
- BCBen Chestnut
Mm-hmm.
- HSHarry Stebbings
... and actually-
- BCBen Chestnut
Yes.
- HSHarry Stebbings
... saying, "Yeah, I feel you. I had that too," is exactly what you need.
- BCBen Chestnut
Yeah.
- HSHarry Stebbings
Um, so I, I get you. But it takes emotional intelligence too, and I spoke to Lottie again. And you said before the show that she's, you know,
- 23:00 – 25:00
Emotional Intelligence
- HSHarry Stebbings
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 ... Or what, what do you think she sees in you about how brilliant your EQ is?
- BCBen Chestnut
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, uh, you know, I, I went to a rural country town school, and I was one of, like, three Asians, y- 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, uh, and learning from a lot of these people who would come and talk to me, it kind of really helped me, you know, like, tune into the way people were feeling and what they were going through. But then again, the reason why I'm conflicted about it 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, you're c- you can be kind of cold or harsh on the surface, right? You gotta do what you gotta 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 will just say what's, what's gotta be done, uh, maybe in a more overly stoic way. I don't know. But, uh, you know... So, I don't know. I- I'm k- I'm kind of conflicted about that, but...
- HSHarry Stebbings
I mean, I had Drew Houston on the show recently, and he said something brilliant, which was, "There's no nice way to deliver a grenade." Um, (laughs) -
- BCBen Chestnut
(laughs)
- HSHarry Stebbings
... and I think to that often, which is like, "You know what, Ben? You're fired." So like- (laughs)
- BCBen Chestnut
(laughs)
- HSHarry Stebbings
... say it nicely or say it not nicely, you're still fired. It sucks.
- 25:00 – 28:19
Lessons From Being a Misfit
- HSHarry Stebbings
Um, but I totally get you. You said about kind of being the leader of the misfit set, and again, the joy of doing this show is I can change the schedule. Um, 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, even when it's not the right decision, because I, I want friends, (laughs) which sounds really s- sad when I say it 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?
- BCBen Chestnut
Ooh, 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? And 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, I was always ready for a fight. Was always 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, 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 will be very cold about it too, 'cause I, I, I, I give no... (laughs) I won't give any kind of, uh, you know, no apologies, man. You know, it's just like, "This is what we gotta do. We gotta do it." Uh, 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 that EQ to get it. But some of the... Sometimes you just have that sort of angst from your childhood, and you just sort of say, "No, I'm not... If, if it's illogical, I'm not gonna, I'm not gonna concede or deal with that." So, you know, i- it... When you talk about bad habits, I think, probably, that's probably what I inherited from, from my environment.
- HSHarry Stebbings
I think the mo- most kind of prominent lessons are from kind of qu- quite painful times. Um, you know, I- 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?
- BCBen Chestnut
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've sold the business early. There were a lot of people s- 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 th- that I didn't need that. I didn't want
- 28:19 – 32:16
Do you wish you took VC money?
- BCBen Chestnut
it. I was gonna do it myself, and I was gonna do it my way.
- HSHarry Stebbings
Was that always beneficial, do you think, in hindsight? You know, if you think... You know, I'm sure there were moments when you could've taken a hundred million, 500 million, a billion. Um, like everyone wanted to give Mailchimp money. I remember. I, I'm a VC for a living, Ben. (laughs)
- BCBen Chestnut
Yeah.
- HSHarry Stebbings
Um, like are there moments where you were like, "Actually, my stubbornness was not good"?
- BCBen Chestnut
Who knows? I mean, there are probably some people out there who could look at it and say, "Ben, if you'd just taken this money back then, you could've scaled even bigger, and maybe right now you, you would've sold for 20 billion." Who knows? Um... I don't know. Uh, there are some people who say, "Yeah, you would, you would've had, you know, a, a slice of the pie instead of the whole pie, but the pie would've been bigger." Um, there's no way to tell, but I do know that, uh, when I look back at my life and my business, I'm really proud to say I did it my way. Uh, and I'm really, really proud of that. You know, there's, there's sort of a Bruce Lee element of it. He did it his way. He came up with his own style, and, and I came up with my own way of running this business. And, um, I'm, I'm really proud of that. And, and it wasn't... It was always collaborative, okay? You know? I don't wanna say that it was all me. We did it our way, mi- might be a better way of saying it, right? Like, I'm really proud of that.
- HSHarry Stebbings
I totally get you. The thing that I also think about is, you know, Mailchimp was, was it a 17-year journey, an 18-year journey?
- BCBen Chestnut
21, not that I'm counting. (laughs)
- HSHarry Stebbings
21, 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, 'cause I lose my identity. I'm not working, and then I don't know who the fuck I am.
- BCBen Chestnut
Yeah.
- HSHarry Stebbings
So 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 are?
- BCBen Chestnut
So one company, one great, amazing leader tried to buy our company many years ago. And, you know, o- out of a sense of duty, I heard them out, and then ultimately I said no. And he told me, "Hey, you're gonna change, and when you do, when you change your mind, can you give me first dibs?"And that, that kind of annoyed me. I was like, "Why do you think I'm gonna change my mind? Why are you so sure that I'm going to change my mind?" Um, and he said, "You know, you're gonna think about life differently. Like, right now, you are defined as your business. It is everything to you. But as you get older, you're gonna 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," you know? "Thank you." I was nice about it, but I just secretly was like, "That guy is nuts."
- HSHarry Stebbings
(laughs)
- BCBen Chestnut
Hung up the phone and, you know, forgot about it. Uh, and this was, you know, maybe I was in my early 30s at that time. Low and behold, 10 years later, you know, I'm in my 40s, mid-40s, and something happens when you're in your f- mid-40s. All right? And it happens to everybody. (laughs) Um, their friends and their families start to die, and you start to reflect on life when you're, when you're in your 40s. It is, and it's really, it's one of those things where it's like, you're just chugging along at your business, you're not really thinking about this, but friends your own age, people you knew, start to pass away, they have heart attacks, whatever it might be. Family starts to pass away. You start to think about life, uh, and you start to think about h- whoa, whoa, my life is not my business. Uh, that's just a job. Uh, it, it's just something that hits you. Like, 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, many later, many years later to y- to you. So, so, you know, I... When that started to happen, it goes away. This attachment that you have, it goes away. It, it, it just happens to you. 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 and more. Like, I, I just can't imagine why
- 32:16 – 35:26
On Selling Mailchimp
- BCBen Chestnut
anybody would want to do that. (laughs)
- HSHarry Stebbings
Did you find the transi- did you find the transition hard?
- BCBen Chestnut
Um, s- first of all, I don't know that I transitioned that hard. Uh, I, I, but I'm still in the middle of this, right? I'm still at Mailchimp, uh, I haven't stepped away from it, but I am focusing a little bit more on innovative projects, uh, and kind of being an advisor in that capacity. But, but I, I was, I was lucky. I think, um, we ended up using a company called Catalyst to be our broker. Um-
- HSHarry Stebbings
Yeah, yeah, yeah.
- BCBen Chestnut
And... You, you know the guys at Catalyst?
- HSHarry Stebbings
I know them well. They're fantastic. They're, like, the best in the business.
- BCBen Chestnut
About 10 years ago he reached out to me, you know? And I was like, "I'm not selling my business, go away." And he was just very nice, and, um, and he kept a relationship with me. He was very calm and patient, and he's very, very zen and philosophical. And we just b- built a friendship over the years. And he was actually a practicing Buddhist. When the time came to sell the business, like, he was, he was probably like, "Finally, Jesus, this 10, 10-year sales pipeline here. I'm gonna close this."
- HSHarry Stebbings
(laughs)
- BCBen Chestnut
Anyway (laughs) , anyways, he, he, he, he went through the deal with me, um, and before it was over, he said, "Hey, I wanna talk to you about this. I've, I've seen a lot of founders go through this process, and what you're gonna learn is your entire life, your career, your, your ideas of CEO is composed of nothing but a whole bunch of habits."
- HSHarry Stebbings
Huh.
- BCBen Chestnut
"And these habits are driving you, and those 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 gonna start to die off. You're not gonna be called into meetings anymore. The emails are gonna stop coming in. The calendar invites are gonna stop. And it's gonna feel weird. Uh, but what it is is habits are d- being deleted, and maybe you'll develop some new habits, but think about it that way." That was the guidance that I got from him, and I thought that was a little bit crazy, maybe. (laughs)
- HSHarry Stebbings
(laughs)
- BCBen Chestnut
But I have seen this start to happen. I've talked to other founders too, that said, "Did you wake up one morning and, 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." And so, 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. And, and they're good habits, you know, uh, that, that make you a great leader, but they are just habits. Uh, uh, another thing I'll say, Harry-
- HSHarry Stebbings
Mm-hmm.
- BCBen Chestnut
... is, you know, Mailchimp's success came very organically and slowly. So, I, I have seen founders, you know, maybe that they were maybe overnight successes-
- HSHarry Stebbings
Sure.
- BCBen Chestnut
... uh, and I think that, you know, going from poor to rich, uh, can really do a number on your brain. Uh, I, and I think, you know, my co-founder Dan and I were so lucky that we just sort of really gradually grew and we could stay grounded. Uh, so I think that just, you know, we, we kept some level of humility, if I, if I'm allowed to say so myself, and I think that's kind of helped us not, you know, go through... Uh, uh, the transition hasn't been too hard on us.
- HSHarry Stebbings
That was gonna be my question. W- we're gonna get to relationships with money, but you've been on the front page, you know, front cover of many magazines, um,
- 35:26 – 39:35
How did you retain your humility?
- HSHarry Stebbings
lauded for the success and efficiency of the business. And, you know, you joke about, you know, 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 eschewed Silicon Valley and he's built a 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?
- BCBen Chestnut
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 SaaS 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, s- 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. We're, we're at a scale, a thousand employees. You know, we're competing with some publicly held companies. We gotta get the word out. And I'd 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. Like, they would open the doors a little bit, reveal a little bit in order to recruit. They would (laughs) need to bring in fresh, fresh employees, fresh blood, and then they'd shut the doors again. So 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." Uh, and then yeah, i- it happened and, um, but I think the fact that I had already been jaded on publicity, that's probably what might have kept me a little bit grounded there. And also during the entire time, I told, you know, 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. So I was like, "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. Um, and all of this glory that we had in the past, we're gonna lose it, but these magazines, they're talking about that glory back there. You better get used to hard times ahead." I kept saying stuff like that. Um, the first time we got maga- a magazine cover actually, you know, 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. And, um, they can make fun of me. I didn't care. Uh, we had that kind of environment. And I remember somebody drew a mustache on my face on the magazine cover, uh, and they threw a mu- thr- threw a m- drew a mustache on everybody's face actually. And I saw that, and I laughed so hard, and I was so proud that, you know, we have this culture that could just be brave enough to poke a little fun, you know? Uh, and so I, I took a picture of it, posted it on Slack, and I said, "This is hilarious. More please." And somebody in the company, uh, Sean Cook, he actually had... He, he started an art gallery where we encouraged everyone to deface my face. Uh, and, and there was, like, a contest. And, like we had... It was like a brilliant art show of everybody, you know, gluing googly eyes on my face (laughs) , you know, just doing all kinds of things to kind of make fun and just humble us all back down again.
- HSHarry Stebbings
I totally get you. It slightly reminds me of Willy Wonka kind of opening the doors to Charlie Chocolate Factory-
- BCBen Chestnut
(laughs)
- HSHarry Stebbings
... and then shutting them again. Do you know what
- 39:35 – 43:27
Why did you decide to sell when you did?
- HSHarry Stebbings
I mean? (laughs)
- BCBen Chestnut
Yeah.
- HSHarry Stebbings
Um, I, I do... 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?
- BCBen Chestnut
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... 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?
- HSHarry Stebbings
Mm-hmm.
- BCBen Chestnut
Uh, and once they get involved, it's almost like, um, (smacks lips) they get a taste of blood. They're like sharks that, that are, that are on the scent, right? And, um, and they wanna win. This is, this is what, like, high performance senior leaders do. They wanna 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-
- HSHarry Stebbings
Yeah.
- BCBen Chestnut
That's like you're coming from this high of, oh... 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 got mentally switched and said, "All right, we're ready. It is time to do this." And then, no.
- HSHarry Stebbings
And you see your number. You see your number and you're like, "Ah, I would..."
- BCBen Chestnut
Yeah, yeah. A- a- a- and, and, and then, and then you take it away. And then so, so I had this conundrum. I was, I was like, um... And I was sick and tired of the whole process, by the way, 'cause it takes away y- y- six months of your innovation and your inner- you know, your momentum and stuff. It's dis- it's distracting. And so I was at this point where I was, I was telling everybody... I was ready to tell them, "Never. Never again. I'm not going through this process. I'm... We're gonna stay bootstrapped, self-funded. If you don't like that, it's time to go, right?" 'Cause the... I'm drawing, I'm drawing a line. Never again. And I was like days away from s- sending that memo to my senior leaders, and I got that call, uh, from Catalyst and they said, "This one's different. You need to listen to this." And, um, I said, "Sure, fine." Uh, and, and it was Intuit and I listened to Alex Chris, and he knew small business. He had built a, a startup before that served small business. He, you know, he runs a small business, um, 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, you know, Dan and I knew. And that's very, very rare. Um, and he talked about it with a passion that I'd never heard before. And we talked about, you know, what, what it would be like to combine forces, and I kind of felt like, you know, Mailchimp was at a place where it needed to go to the next level. I needed to hire another leader to get us there, um, or I could join forces with Intuit and it could be like...... you know, into, it was, like, this big, this, this big jet. You know, the, the ones that refuel the small fighter jets? And I kind of felt like, this is like a refueling moment for us. We can just, like, connect, get pumped full of fuel, and then take off, uh, with our mission and continue, you know, getting Mailchimp to its, to its big act two. So it was very compelling. We talked for a year, by the way. The whole thing was an, an entire year of due diligence and sort of courting each other, um, you know, testing the waters here and there. Um, so I, I, I don't know. I, I don't know-
- HSHarry Stebbings
Would-
- BCBen Chestnut
... I don't know that there was any one thing that said, "This is it. Now is the time." It w- I was really, like, hesitant about the whole thing the entire time, but it was really just, I guess, this compelling... It was just too
- 43:27 – 45:22
Relationship to Money
- BCBen Chestnut
compelling to say no.
- HSHarry Stebbings
I had Ryan Smith on the show from Qualtrics, and he, he talked about his relationship to money when he sold Qualtrics and, you know, became a billionaire. (laughs) Um, and, and I asked him, like, "O- o- what is your relationship to money?" And I, I ask you the same thing, which is like, you know, you move very quickly into different echelons of wealth. How do you reflect on your own relationship to money? And, and how do you think about that today?
- BCBen Chestnut
Uh, I... We didn't move that quickly. I mean, Mailchimp was making hundreds of millions of dollars, and we were on the cusp of a billion ARR when the acquisition happened. So I mean, we were already doing really, really well. Highly profitable. So I don't know that my, my money profile changed overnight, really. Um, so I don't, I, like I said-
- HSHarry Stebbings
It's fun- it's funny, isn't it?
- BCBen Chestnut
... when we were at our peak-
- HSHarry Stebbings
It's different from a venture-funded business though, isn't it? Because like in a venture-funded business, it absolutely does. You sell and you get hit-
- BCBen Chestnut
Yeah.
- HSHarry Stebbings
... with, like, a billion overnight.
- BCBen Chestnut
Yes.
- HSHarry Stebbings
And here, it's like, you just progressed very nicely, but continuously.
- BCBen Chestnut
Like an oak tree with really deep, strong roots. I mean, it's, it's just very, very slowly. And, and we had kids, and that was, 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, "Be- Dad, what are you doing?" I never said, you know, "Making money." I never said, "Running my company." Uh, I always said, "Helping customers." That's always my answer. And I, I just wanted them to be helpful, uh, watching me. So anyways, that relationship with money, I don't know. I, I, I was lucky that we eased into it, and I just sort of want us to have the
- 45:22 – 47:37
How do you raise your children?
- BCBen Chestnut
right attitude of, of being helpful with it.
- HSHarry Stebbings
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?
- BCBen Chestnut
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, 'cause then, you know, they would say funny things like, you know, "Oh, there's this kid at school. His pa- his dad has a Porsche. They must be rich, Dad. When will we be rich?" (laughs) You know? And I was... You know, so they, they kind of intellectually got it when they were young, but not really, because we never really acted that way. You know? Uh, and so it's, it's... I don't know. I, I am told by many people, um, who've, who've worked on home offices with super wealthy families, you know, it's, 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 can do is say I, I hope that they learned by watching us that we just try to, to be earnest and try to be helpful. Um, and that's it.
- HSHarry Stebbings
And if you save up, you could buy that Porsche one day. One day-
- BCBen Chestnut
(laughs)
- HSHarry Stebbings
... you could buy that Porsche. (laughs)
- BCBen Chestnut
(laughs)
- HSHarry Stebbings
I love that. That's so sweet. Um, I want to move into a quick fire, Ben. So I say a
- 47:37 – 48:34
Favorite books
- HSHarry Stebbings
short statement and you give me your immediate thoughts. Does that sound okay?
- BCBen Chestnut
All right. Let's do it.
- HSHarry Stebbings
So Lottie told me on this one, "Ask what books are capturing your heart these days."
- BCBen Chestnut
Oh my God. I'm, uh, can I say not business books?
- HSHarry Stebbings
Yeah, of course.
- BCBen Chestnut
(laughs) 'Cause I have read, like... I've read, like, a thousand business books. Uh, I had this library down in my basement, and I've, I had a flood recently, and it destroyed almost all of them, and it was really cathartic to throw them all away. (laughs)
- HSHarry Stebbings
(laughs)
- BCBen Chestnut
And now, the only books that are remaining are sort of philosophical ones, stuff about life. I'm reading stuff from, um, Thich Nhat Hanh. He's a Vietnamese, uh, Zen Buddhist monk. And, uh, Peace, Peace Is Every Step is one that I'm listening to and loving right now. Uh, he's also got-
- HSHarry Stebbings
Nice.
- BCBen Chestnut
... another one that I just finished called Art of Power, The Art of Power.
- HSHarry Stebbings
Mm.
- BCBen Chestnut
Uh, and, uh, it's, I think it's... I think I'm loving them because it's probably therapeutic in
- 48:34 – 49:10
A Day In The Life
- BCBen Chestnut
helping me unlearn some of those habits we talked about.
- HSHarry Stebbings
Ben, what does a day look like for you? Is there, like, a typical routine to the day, if you were to kind of generalize?
- BCBen Chestnut
I never had a typical routine, ever, even with the business. I mean, uh, I was forced into it, but I never really, like, kept to a schedule. Um-... no. Right now, these days, um, it's, it's more like dealing with no routine. Uh, I, I just got a dog. (laughs) So, so, uh, you know, being in my, 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 5:30, like I always did, taking this
- 49:10 – 51:04
Weight Loss Tips
- BCBen Chestnut
dog out. I mean ... (laughs) The dog is keeping me busy. Um-
- HSHarry Stebbings
What was the secret to the, what was the secret to the weight loss? What worked?
- BCBen Chestnut
(sighs) Uh, a lot of riding and a lot of walking.
- HSHarry Stebbings
Hm.
- BCBen Chestnut
Walking is way more effective than people think it is.
- HSHarry Stebbings
Yeah.
- BCBen Chestnut
Uh, and I've lost five pounds just walking this darn dog every day.
- HSHarry Stebbings
(laughs)
- BCBen Chestnut
Uh, but, but the riding, I think, was a, was a very big deal, and, um, stopping soda. Why are we talking about weight loss? (laughs)
- HSHarry Stebbings
We can talk about anything I want. It's my podcast. (laughs)
- BCBen Chestnut
Okay. All right. (laughs) Soda, sugar water, get rid of all sugar water.
- HSHarry Stebbings
Because I, I know, 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. Um, and so yeah-
- BCBen Chestnut
I, I went ... I'll tell, can I tell you? I, I visited my, um, Great Uncle Clarence down in Miami one day, and he was in his 90s. Um, and he's a funny guy, and he, he used to be a, a, a truck driver for a dairy company.
- HSHarry Stebbings
(laughs)
- BCBen Chestnut
And I went to visit him with my wife, and, you know, I said, "What advice do you have?" And he, and he was, like, really, he was skinny, like a skeleton. Uh, and he was diabetic. He was, he was quite unhealthy because of that. And he said, he told me, "No sugar. No sugar." He said he used to, when he, he'd 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, drop it." And, you know, he was like a skeleton. I loved that man. He was such, such a good inspiration for me. But he was a skeleton, and he was like, "No sugar!"
- HSHarry Stebbings
(laughs)
- BCBen Chestnut
And it scared the shit out of me. (laughs) So Harry, that's how I, that's how I lost my weight. I just ... (laughs)
- 51:04 – 53:19
Why Ben Buys Lottery Tickets
- BCBen Chestnut
It got scared out of me. (laughs)
- HSHarry Stebbings
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 with lotto?
- BCBen Chestnut
Oh. (laughs) Well, my, it, that's ... My wife and I, we're high school sweethearts. Okay? So we're in high school, and we stop at this 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, 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." Um, and then she kept scratching, and she said, "Oh my God, I won another $5,000." And I was like, "Cool, but weird to win twice." And then she kept scratching-
- HSHarry Stebbings
(laughs)
- BCBen Chestnut
... and she said, "I won another $2." And I was like, "Hold on. Lottery tickets don't work this way. You don't win 25,000-"
- HSHarry Stebbings
(laughs)
- BCBen Chestnut
"... and then $2." (laughs) So anyways, it was just this ... So we, we were s- you know, like, so elated that we, we f- we finally had money, you know, 'cause 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 ended up not winning at all. And anyways, I continue to buy lottery tickets. Uh, and we joke about it to this day. (laughs)
- HSHarry Stebbings
That, that is the mo- that is the most, like, realizing depressing shit though, when you're like, "Oh, bugger. Wrong."
- BCBen Chestnut
(laughs) It really is. And she still makes the mistake. Sometimes, she'll ... I'll get her a lottery ticket as a joke, maybe for a birthday, and she'll s- and she'll say, "Oh my God, I won, I won!" Uh, you know, and it's, and it's-
- HSHarry Stebbings
You're like, you're like, "Welcome to a day of Mailchimp's revenue." (laughs)
- BCBen Chestnut
(laughs) Yeah. I was like, "Nevermind the 21 years of building up this great billion-dollar business. Uh, you won. You think you won," (laughs) "the lottery."
- HSHarry Stebbings
Dan-
- BCBen Chestnut
(laughs)
- HSHarry Stebbings
Dan, Dan, help, help me out. You're
- 53:19 – 54:55
Secret to Marriage
- HSHarry Stebbings
wise, and you know, seasoned, as you delightfully put it earlier. Um, uh, what's the secret to a happy marriage?
- BCBen Chestnut
(laughs) Oh my gosh. Um, I ... (sighs) I, I have been ... I, 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.
- HSHarry Stebbings
(laughs)
- BCBen Chestnut
And, and then I, I just, I just kind of thought, "Okay, so they are repressing themselves. That's the key." And I think I've learned-
- HSHarry Stebbings
(laughs)
- BCBen Chestnut
... they, 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 learned 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. (laughs)
- HSHarry Stebbings
(laughs) You are just ultimately repressed to the point where you're reasonably rationalizing it. (laughs)
- BCBen Chestnut
(laughs) It could be that. It could be that.
- HSHarry Stebbings
(laughs)
- BCBen Chestnut
Yes. But I, but, but also-
- HSHarry Stebbings
You know, intellectually.
- BCBen Chestnut
Also, if I keep my mouth shut and follow her advice, things really are happier. (laughs)
- HSHarry Stebbings
You might even get laid. (laughs)
- BCBen Chestnut
Maybe that's more important. I don't know. (laughs)
- NANarrator
(laughs)
- HSHarry Stebbings
That is
- 54:55 – 56:10
Ben’s Guidance to Raising Children
- HSHarry Stebbings
brilliant. Uh, tell me, um, speaking of kind of a, that, but like, what three traits would you most like your children to have?
- BCBen Chestnut
Uh, I, I would want them ... So, I, I kind of have a- an acronym floating in my head at all times that I, I thought would be, like, my, my guidance on, on raising children. And, and it was bl- It was, uh, BLISS. So it stands for balance, love, independence, and self-sufficiency. So what is that? One, two, three, four. Four, four traits. So I, I, it's, it's really that. And I don't know. I, I, I ... Maybe, maybe self-improvement and self-awareness. Like, I want them-
- HSHarry Stebbings
Yeah.
- BCBen Chestnut
... to just sort of understand, you know, it's about slowly, incrementally improving yourself and, and overcoming challenges. Is it adaptability? Perseverance? Grit? I don't know.
- HSHarry Stebbings
Yeah.
- BCBen Chestnut
I don't know.
- HSHarry Stebbings
What, what would you most like to change about the world of startups?
- BCBen Chestnut
I think it's happening actually. Um, I would love it to not be located only in Silicon Valley and New York.
- HSHarry Stebbings
Yeah.
- BCBen Chestnut
I would love it to just be able to ... Like, with Mailchimp, it happened in Atlanta, it happened in our homes. You know, I'd love it to be, just be everywhere,
- 56:10 – 58:37
Ben’s Next Five Years
- BCBen Chestnut
as, you know, tech startups, um, to not have to be in those two, two locations.
- HSHarry Stebbings
Ben, tell me. Final one. What do the next five years hold for you? What's your plan ahead?
- BCBen Chestnut
I've met many founders who've sold their business and then they, they go off and they wanna do crazy adventures. And I, and I applaud them for that, and, and, you know, no judgments whatsoever. But some of them talk about ... I met one that wanted to explore the depths of the ocean. Uh, one wanted-
- HSHarry Stebbings
Wow.
- BCBen Chestnut
... to explore space, right? Um, and I've told them all, like, "What do you want?" And I said, "Well, I wanna explore my own mind. I wanna know why I think the way that I do. I wanna 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.
- HSHarry Stebbings
Huh.
- BCBen Chestnut
Just want to not want. And I think that'll ...
- HSHarry Stebbings
What does that mean? What does that mean, to not want? You ... Surely you don't want now. You don't want for anything. You can buy anything.
- BCBen Chestnut
Yeah, I, I don't feel a desire to. I, I, I feel e- if I ... I think it means learning to be content with what you got.
- HSHarry Stebbings
Are you there now?
- BCBen Chestnut
And, and so I, I, I met one founder who said that when he sold his business, he bought a yacht, and he went to, you know, 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, "Ugh! I haven't worked hard enough." (laughs) He was, he said he was, he was, you know, 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. "Why? Why?" And I think it's preventing that. That's what I mean.
- HSHarry Stebbings
Have you, have you, have you got there now though?
- BCBen Chestnut
I don't know. I think time will tell. You said five years. Why are you t- why are you pushing me now? You said over the next five years.
- HSHarry Stebbings
(laughs)
- BCBen Chestnut
Give me time, Harry.
- HSHarry Stebbings
Ben, Ben, I'm a VC. I'm here to push you. Your timeline? My timeline.
- BCBen Chestnut
(laughs)
- HSHarry Stebbings
That's why you didn't take VC money. Um, listen, Ben, I've loved this. You are a star. Thank you so much for my incredibly prying questions.
- BCBen Chestnut
(laughs)
- HSHarry Stebbings
But you've been amazing, so thank you.
- BCBen Chestnut
Thank you, Harry. Thanks for having me. This was a lot of fun.
Episode duration: 58:37
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