Bootstrapped to $12B: Mailchimp’s Ben Chestnut on Life After the Exit

26:19You hit your late 40s, friends start to die. And you start thinking about life a little bit differently. Your priorities shift. And up until then, my business was my life. It was me. It defined me. and I could never even fathom separating myself from the business. But, you know, my mother passed away. My father passed away. Actually, I had like a three-year run where a lot of family passed away. While you were running the business. Yeah, it was just timing. It wasn't like one little thing. It wasn't COVID. It was just a lot of random stuff happening. When that happens, you just sort of say, really what happened was I thought, okay, my business, I love it, but it's not my life.

26:59I could still do it for many years. But it's not my life. It's not me. It's a great accomplishment, but it's not me. And once you make that separation, then when people come knocking, you're more open to it. And so we had a round of companies come knocking. And I was like, okay, let me hear what you've got. This was, you know, my executive. I'm telling you the thing that caused this, that made me cross. So this first round was just my curiosity. Just me saying, all right, I've never really actively pursued this. I never thought I would, but all right, you guys let me know. Oh, see how it goes.

27:33So we went through the whole due diligence process. And this was shocking to my executive team. Like they were MailChimp lifers and I was never going to sell. So suddenly here I am open to the idea. And I'm like, I'm just open to the idea. Let's just go through this. And you get your whole executive team to get on board, to do all of these presentations. It's like sharks smelling blood. They want to win. They want this to happen at this point. The execs. The execs. Yeah. And they had never like really gone through the numbers and presented like this, like why you want to buy this company. And they went through all of this and, you know, timing wasn't right.

28:11The market wasn't right. The numbers just didn't work out for me. And I just said no. And then I was ready to just like go back to normal. Hey, guys, let's let's just forget that ever happened. But I could see it. I could see it in their eyes. Like it was real disappointment. And it's very hard to put the toothpaste back in the tube once they get a taste of that. So, you know, I was, I actually had a letter, an email written up to tell my whole executive team, sorry, that didn't work out. I won't do that again. I'm going to run this company till I die now. That's it. So if you don't want to stay on board, I understand.

28:47Now's the time. Now's the time for you to leave. I had this all written out. And I remember I got a call from Brian Kane from Catalyst. He said, hey, I think there's one more company that's looking you might want to consider. It's Intuit. And I said, oh, do I really want to open the door again? And I thought about it for a second. And I just, I remembered, you know, all my executives, the looks in their eyes. And I said, yeah, I think we have to go through with this. I think we have to try. I figure there's no going back to, you know, privately held. Also, by this time, we had already implemented a phantom equity program.

29:22So everybody had this taste of equity, you know. So it was tough. It would be tough to go back and revert back to quiet little founder run company. I wanted to, but that was the real reason that we sold. And so we went into this process with Intuit. I had always, you know, admired Scott Cook and what he had accomplished. And I always thought, yes, absolute legend. And I had actually had a phone call with him prior, a strategic question that I had. I interrupted him over lunch. He still took the call. He's smacking on his food. He's like, yeah, you want to do this, this and this. I was like, it was, it was genius advice.

29:59And I implemented it to him. It was like five minutes of out of his lunch. so I had a lot of admiration for the company and I had been told many times you know Intuit and Mailchimp are the only two really big well-known brands focused strictly on small business so I took the call and that's what it led to when I had Scott on the show the hair on my arms was up for the entire 90 minutes he's right incredible he's really really smart really good yeah um did the idea of going public not exist no no no i couldn't think of a greater hell uh than being a publicly held company why never i did not want to answer to the market i wanted to run my company my way you didn't even want to answer to vcs let alone the market damn right i didn't have a board either no board no i was actually going to ask bing gordon to be an advisor at one point i actually had a letter written up for a minute for whatever reason i never mailed it.

30:58I figured he'd never check his mail, but he was the only person I ever thought. I actually appreciate his advice, but no, I never actually created a, I had mentors. I bounced around different people asking them for advice, but I never had a formal board. And Ben, even during the time where in your late, mid to late forties, a bunch of people in your life, your parents included are passing away. Yeah. And you went through the dog and pony show of acquisitions. It fell apart. People close to you are, they're leaving, they're passing. You were still ready to go on and do this forever. Yes, I was.

31:44I was, but things got hard when the pandemic hit now. That was another really, really bad moment for me. I had a COO who was a great COO for many years and she took the company to new levels and it was all good, but the time had come for her. It was mutual. She wanted to go ahead and leave. And, you know, this was 2019. We worked together for many, many months to kind of wind down, say goodbye. We had a big celebration in late December 2019. And I figured, okay, she's going to leave. That's my COO. And I loved her. She was my COs work like the president of the company. That's how I run. So she did a lot.

32:24But I figured I can do some of her work. I can manage this for, you know, three, four months. I'll search for another CEO. I had a couple of people lined up that I that I was interested in bringing on board. I said, no big deal. So she leaves in the December. We get into January. This thing called COVID-19 hits and all hell breaks loose. I have no COO and I have to run the company directly through this pandemic. And we have to learn how to do this work from home thing, et cetera, et cetera. So it got, and then, you know, there was a whole cultural upheaval across America, right? That was taxing.

33:03That was definitely taxing. I took it like, you know, I was, I took it like a trooper. I was ready to fight through it, get past it, keep running the company if I needed to. But by then, Intuit was knocking. We were talking about things and I could have gone both ways, actually. I could have run it. I was always ready for Intuit to just walk away. And then I would just happily take the reins. It would have sucked with no COO and, you know, an executive team probably ready to walk away because, like I said, it's really hard once they taste blood. Yeah, but don't you think that willingness to walk is what ultimately gave you leverage to do the deal that you wanted with Intuit?

33:37Maybe. Because you were genuinely okay with continuing on. I was. And I think that they knew that I had a record of just walking away from stuff and not primarily being money motivated or anything like that. I think that I was just a very strange creature to a lot of to a lot of companies that that knocked. And did any of them try to keep you after the acquisition? Could that even be? I wouldn't want to stay. And, you know, and they were very, really thoughtful during the due diligence. They said, you know, what kind of founder are you? Are you going to you're going to want to stay and manage it day to day?

34:10Like we can support that. Are you the kind of guy that kind of want to walk off into the sunset? And I said, yeah, sunset guy. I'm a sunset guy. So, um, yeah, no, I think I was satiated. I think I'm not going to sell this thing until I've I'm done. You know, if I'm not done, I'm going to stick to it. So just the act of selling it to me is just why, why would I hang? Why would I try to run it? I always felt, you know, a duty to help through a transition, of course, you know, But I told them I wanted it to be a very fast transition and I want to walk away into the sunset. And I help anybody that you deem to be the next CEO, get them on board.

34:50Was your co-founder as on board as you were for all of these decisions, whether staying or leaving? Yeah, Dan's great. I mean, we never had - You two were tied to the hip on this. Absolutely. And we were never - And he said, hey, if you want to go, let's keep going. And if you want to sell, let's sell. Yeah. Actually, during the due diligence, by that time, Dan was like, you take the lead on it. And every night I would call him and just give him the download on everything that happened. Everything that this person said versus this. He had an update at the end of every day. And so it was just maintaining that trust.

35:21And, you know, I would tell him we might have to walk away after this. And he, yeah, he was, he understood. He was supportive. Couldn't have a better partner. What about at home? Were you getting pressure from, are you married? Married to kids. Kids? Yeah. Was your partner, what was that like at home during these times? My wife, Teresa's unbelievably supportive through the whole thing. And she was like, hey, Ben. Do it or don't. If you want to keep going, keep going. Yes, but 52, 48, 52%, she felt like you're probably, you should probably sell to relax a little bit because I had been going for so long.

36:02And it was stressful. I felt like the stress was good for me. I was solving tough problems, but she saw the stress that I was dealing with and she felt sorry for me. I think we never really talked about it openly, but I could tell she was leaning a little bit towards you ought to sell this thing. So in hindsight, do you feel like the stress was good for you still? Yeah. So, so remember I said in the early days we were solving tough problems and that was, I love those problems. Like it's building a better product as it grew. And I, I was not a founder anymore. I was a CEO. We had a thousand employees at the end.

36:38I w it was more like solving organizational problems, managerial organizational. I hated that, but I, I felt like it was a duty. I did it anyway. I had read so many stories of founders, you know, bailing because things got hard and they needed to hire somebody else to be the CEO. I felt like I'm not going to jump ship. I'm going to learn what it takes to be a good CEO and hell, no one's going to fire me. If we had a board, if we were funded, I would probably have been fired. But I was able to like - Do you think so? I think so. I needed to learn my way into the role of CEO. And I bet you a lot of investors would have been impatient and they would have probably seen all of that money and just booted me out because they've seen so much potential, you know?

37:25Can I ask you like a pretty personal question and feel free to not answer if you don't want to. when your parents passed away and you were still running the business, did you feel like maybe if you weren't working, you would have been able to spend more time with them during the end of their life? Oh, no. I knew that this was coming many years prior. Yeah. I said, they're getting old. They're going to pass away. And so I made it every two weeks. We drove a little road trip and visited my parents every two weeks. How far away did they live? Not too far. Two and a half hours. Okay. Yeah. So I moved them from our childhood home.

38:02I bought them a lake home that made it a lot nicer to go visit them. We stayed in the little guest house in the back and, um, you know, I took the kids there. They would go fishing with dad, grandpa, and, um, we had a lot of family reunions there. So we, I knew that this was coming and I said, I don't want to live with a regret that, you know, I could have spent more time with mom. So I spent as much time as I could with them. I specifically asked, you know, mom, daddy, any regrets, any advice for me? My mother was a Buddhist. A few years after that, she got diagnosed with cancer. She didn't want to go through surgery.

38:34She was ready to just, you know, she was okay with death. So we definitely knew that was coming after that. And we just made sure we visited every two weeks. And my mother-in-law was also kind of nearby. So we would visit her as well. I guess money as a tool in this scenario is very helpful. making money as you go to be able to do things like this. Yeah. Right? Move them, buy a house, go to a place where you have space. That's right. Where you're comfortable. Yeah. It's your home. They're living in it. Like it's, you know. No regrets. Yeah. Yeah. Do you feel listless now? I feel good now. How long did it take before you stopped checking your email in the morning?

39:17Oh, that took a while. That took a while. How long? Six months to a year, probably. You know, I was really lucky to get to know Brian Cain from Catalyst Partners. You should bring him on someday. Anyways, he started a relationship with me back in 2015. And he said, someday, if you ever want to sell MailChimp, call me. And, you know, he was the only guy that I ever really stayed connected with. And very thoughtful guy, very Zed. And when we sold, he said, hey, I need to talk to you about something. You're going to find out that your entire life is built on habits and you're not even aware of them.

39:57And the business will be gone, but you'll be checking the mail. There'll be going to be all of these sort of leftover habits and you're going to have to just let them shed off of you before you do anything else. So I thought that was weird, but he was absolutely right. They were just checking the mail, checking social, whatever, you know, needing that meeting to get an update. That was all gone. Did you have to fill it with something else? Did you find? No. So crazy enough, I got a dog. It was a complete accident. I don't like dogs. My son wanted a dog. He pestered me through the pandemic. He promised he would clean up after the dog.

40:34And so I caved and we got a rescue dog. And after the acquisition, that's all I do. I walk the dog and the dog was good therapy. It was like, I was walking two, three miles in the morning, two, three miles in the afternoon with this dog and talking to it. I thought my neighbors would think I was crazy, but he was a good therapist. No judgments from a dog. And do you, you see that tweet from that guy, I forget his name, but he tweeted about making all these millions after selling his company. And he did all of these other things because he, and he wish he knew to just kind of chill for a while.

41:11It was a very viral tweet. Vinay from Loom? Yeah, maybe. And I felt like replying and saying, dude, get a dog. Was he living in Hawaii? I think he had like even did a stint with the government. He tried all kinds of things. I think so. Yeah, it's actually - You know him? That was our portfolio. We led the series A of Loom. Oh, cool. Tell him to get a dog. We had his co-founder and CEO, Joe, on both before and then more recently after the acquisition. Cool. You know Joe lives in Atlanta, the CEO of Loom. Oh, neat. oh neat i used loom for a little bit there yeah it was it was new and then i sold and i i can't remember the title of the article but it was something catchy yeah yeah basically the premise of it was this whole time i thought i was gonna make a lot of money and sell this company and then i was gonna be fulfilled and i've never felt yeah less fulfilled yes my entire life like i'm traveling around the world.

42:04I have more money than anything. I tried to do a tour of duty in the government with Doge to find purpose to fill this hole. Yeah. Yeah. You would have just said, get a dog, get a dog because it just kind of makes you sit for a while. Get okay with the voices in your head, you know, relax a little bit before you go off and do something else. Do the voices in your head, are those gone too now? Yes, yes. And I just mean, you know, a lot of people, oh God, there's a quote out there. It goes something like all the wars would be gone if men would just be okay sitting down quietly and listening to the voices in their head.

42:41If they could just be okay with that, we wouldn't have so many problems in this world. That's what I mean. Like there's just a lot of people who just, they don't want to hear what they have to say. They don't want to listen to themselves and they have to go do something. They have to be busy or they have to stir shit up. Those people are the worst to be around. And it's just so they don't have to sit on the couch in a quiet room and listen to their. But don't you think the problem, Ben, is that the voices in your head are the things that catalyze you forward into positive motion? all the things that were productive for you and channeled in building a company now sitting idle are all the things that are exhausting you no i think the chatter is what i'm talking about there's like a surface level chatter of random shit that goes through your brain noise and then you kind of have your real self sitting further back listening to the voices and that's the side of you that has to interpret the chatter, ignore the chatter.

43:48The chatter is like, is there a tiger behind that bush that's going to kill me? Is that going to kill me? Like the chatter is necessary for survival, but you also have this deeper voice that has reason that can tell you, don't, don't do that shit. Calm down. There's no tiger here. Plan accordingly. You know what I mean? Does that make any sense? It does make sense. But did you, did you not, were you able to be so Zen about the chatter when you were building the company? Yes. You really were. Yes. Cause I know I don't, I didn't consciously think about that, but I, I, my COO would always say, why are you so f***ing Zen?

44:27How can you be so f***ing Zen through this? And I always had that. Like if, if there was any kind of emergency or a problem going on, the world slowed down for me. And I thought more clearly. I'm just good in crisis. Were you the opposite too? When things were peaceful, did it freak you out? Yeah, I think so. I think so. And that's dangerous too. You want to stir shit up a little bit. Like you wanted to create some chaos. Yeah. Or I didn't, I don't like chaos, but maybe come up with a new idea for the business. That's what a founder can do if they don't control that voice. And why do you think you would do that?

45:01To have something, a new problem to solve. That's the habit. You're stuck in these habit loops. And I'm only valuable to the company if I'm solving a problem or inventing something new. So let me keep inventing new, new things. And that just wreaks havoc on the team. And I'm guilty of doing that, but I think I controlled it decently well through my COO. Yeah. She was my buffer. When did you get the COO? I had a COO. My first one was a guy named Neil, 2007, I think. About seven years in, five years in. Yeah. I was working at a.com. He was brought on board as the CMO. We had a couple of lunches.

45:43He was trying to get a lay of the land of this company that he was about to lead. And then we all got laid off. So he and I stayed connected and I had done a few websites for him and the new company that he was working for. Then he tried to be an entrepreneur a few times. He did a few little startups. And then by 2007, I convinced him to join me. And what year did the Serial podcast come out? I don't remember. Everything is a blur to me. I remember. I remember. It was 2015, 2014 and 2015. Yeah. I was still at the old office. I know that because I was listening to, that was the first time I heard about MailChimp.

46:19I was taking the Caltrain. I was riding my bike over Potrero Hill in a suit because I wanted to be a professional so bad. Well, I was making cold calls in an entry-level job. In a suit on her bike? Yeah, because I crashed my car and just couldn't afford a new one. And then take it to the Caltrain. And then I would start sending out cold emails while I was on the Caltrain down to Mountain View listening to Serial, which was always introduced by MailChimp. Yeah. Boy, did that podcast. That was the first, maybe that was the first podcast that I even ever listened to. Oh, wow. I can't remember, but that really hit the zeitgeist of, I just hit the zeitgeist.

47:04Yeah. Pure luck. I mean, we had sponsored a podcast prior that failed. Okay. And I think we had paid in so much. They said, you got first dibs on the next podcast. And they liked our ads. We had some funky ads. What was the ad? The ad was, um, you know, MailChimp for email marketing and hats for cats and dogs. We had these monkey hats that people were putting on their dogs. And then our customers who had cats were mad. No, we started with cat hats. I might have to back up a little bit here. I had a distant relative in Thailand knitting these funky little animal hats. And I told her, make me some monkeys.

47:46And she made me a whole bunch of these. I mean, we got hundreds of them. And then we started to take them to trade shows, conferences, and they were just a smash hit. I mean, they went viral on Flickr at that time. And so we knew we had something really fun. And so we made baby sizes and then people started to put them on their animals. And I made a little teeny tiny one for cats because I thought that was just so ridiculous. And so she knitted these tiny little monkey cat hats. And we had customers posting pictures. And these are angry cats. They don't like hats. Cats really, really hate hats.

48:22But they were just the most viral, hilarious pictures. And then people started demanding dog hats. Anyways, so this was crazy and viral. And then so we did these ads saying email marketing plus hats for your cats and dogs. And then a little noise of a monkey. Maybe. Maybe we had that at that time. But the podcast, the producer said that they actually got lots of phone calls asking for the hats. Where do I get the hats? And they said, no, it's just a joke. But they got so much of a reaction from that ad that they loved us as an advertiser. They thought that we were very creative. And so they said, sorry, this podcast was a flop.

49:03You get dibs on the next one. And that happened to be cereal. And so we said, all right. It's us. It was kind of like, ah, it's all a flop. It was a failure. and then, you know, serial came out. We were like, okay, whatever. They did the audio where they interviewed people on the street to, you know, trying to say this ad, we wrote this, you know, MailChimp for your email marketing. And then they, they got this young woman, this random young woman who totally mispronounced it as MailChimp and they sent it, you know, my director of marketing brought it to me and said, okay, you're not going to like this, but I think it's kind of funny and endearing.

49:37And I listened to this young lady mispronounce it and I just said, yeah, screw it, run it. What's the big deal? It's just a cheap podcast anyway. And we were getting, it was free, you know, podcasting to us. We were always, our whole philosophy was experiment with everything while it's cheap. And so podcast advertising, we were doing that all over the place. And that podcast just happened to take off. We don't know why, but it took off. And that ad, the MailChimp mispronunciation really took off. And that was a moment for us. That was like, wait a minute. We are now branching out from just the tech world.

50:11We had like grandmas asking what MailChimp was. Like Saturday Night Live did a skit about Serial and MailChimp. I mean, it was like going mainstream. And I said, wait, this is a really, really interesting moment. let's call some ad agencies and see if we can get a big ad campaign to make us more you know maybe global i don't know and so we reached out to a bunch of agencies none of them responded until droga five droga five reached out and said we'll do it and they did the craziest ad campaign for us what they do so cool well they played on the mispronunciation so like mail camp and they so they said okay what other kind of mispronunciations could there be they did mail shrimp and that was a hilarious ad and they hired like famous musicians to come up with the jingle and it was awesome and they played them in movie theaters.

51:03We had whale synth, we had fail chips and that was potato chips. We found a vendor who could make potato chips where all of them were crushed. You know, the crushed chips at the bottom, they taste really good. Yeah, yeah. Those are the best part. So what if the whole bag was just crushed chips? And so we gave those away. Anyways, it was an amazing campaign. And that really, really, really kind of put our brand. I mean, it was at the Cannes Film Festival. Like our team flew out there to accept an award for that. Like I have the lion. Wow. Yeah. Were there any other experiments, cheap experiments that you ran that came even close to the success of this?

51:45No, not to that success. But we were always running cheap experiments that did pay off in the end. but that one was, that one was crazy. That was an anomaly that still remained on our charts, our revenue charts, our traffic charts. Did that revenue sustain? Sort of. It was a crazy blip. What I mean is that thing ran in the fall. Every fall since then looks like a failure compared to the previous fall because that one was just so big. So it was this anomaly that became this kind of, we rolled our eyes at it. Damn you, cereal. But I think it paid off, you know, because it was just so cheap for us.

52:21What it did was it put our brand on the map. Then we knew that we kind of needed to redesign the logo, kind of make it more consistent, more scalable. And it was really easy to find a great brand agency because they had seen the ad campaign from Droga. After that, it was so easy to get publicity, to get anything we wanted. Employees knew who we were. We didn't have to convince them that we were a profitable company. like everybody knew us at that point. And I do think ultimately it helped the brand look way more valuable to acquirers. So it paid off big time in the end, just that little accidental campaign.

53:00Can you talk about how you have a hard time conducting interviews in an office? Is that true? Be more specific. The quote that I read again, I don't know if this is true or not, But it said that you typically do interviews over dinner. Oh, like hiring interviews. Yes. Yeah. Yeah, I don't have a hard time in the office, but I would rather meet out where it's very noisy and distracting. And I think it's easier to play mind games with the candidate and just kind of keep them on their toes. And I would always, I would want to see if they could maintain focus in the noise. So if a waitress dropped their stuff or somebody dropped a plate, for some reason, a pet peeve of mine is when people just completely lose all focus and they just go to that.

53:45Or an attractive waitress, their eyes go. You can't maintain focus in a conversation? That's a big deal to me. I know that sounds silly and minor, but that is big to me. I would have failed your interview. I don't know. You're maintaining really intense eye contact. Here I can, but in the real world, this is like make-believe world for me. In the real world, I have very happy eyes. I constantly am scanning everything around me. But I'm looking ahead. If I'm with an executive, a senior VP or something, and we're having our weekly one-on-one, it's going to be in my office and we need to pay really close attention to each other.

54:26Anyways, that's a thing that I always look for. But I don't know. It was always easier to get into their heads. And I would play like what? Dumb. Like I played like, you know, everybody kind of knew me. Executives would come in, kind of know that I was it was a privately held company, no formal investors, no board or anything. and it was easy to kind of think of me as some country bumpkin who just lucked into the business so I would go to these dinners with them and you know say well you know like with my general counsel when I was interviewing him I would ask him about legal advice and stuff and I would just act dumb and say well explain that to me again I don't understand why wouldn't you just do this you know and I would look for how they responded to me like if they were disdainful or arrogant about it and say, no, you can't do it that way.

55:19My best executives, the best people that I had interviews with, they would be intrigued. They would say, well, maybe I could have done it that way. And they were sort of intellectually curious about my ridiculous ideas. And that to me showed signs of expertise, mastery. Like they knew their shit so good. They weren't defensive about it. They would allow you to poke it from different angles and challenge it. And they would just see that as like, you know, wrestling. Like it was intellectual wrestling with you and they would have fun with it. I would look for that kind of thing. It didn't always have to be at a restaurant.

55:58But that was the sort of thing that I, I never had like a formula or set questions that I would ask interviewees. I would just try to learn everything I could about what their area of expertise was. And then sort of just test their humility is what I, I would have said at the time. I don't know that I would describe it that way now. I would just test their willingness to explain it and their ability to explain it in simple words that like a child could understand because that would indicate mastery. I always used to say that it was also useful because we serve millions of small businesses and they are not all business degree, business school graduates.

56:37You know, these are just salt of the earth working on Main Street. They're not going to listen to some executive explains it. Like you got to put it in simple terms when you're working with small business. So that was my MO talking to these people. What else would you test for? Anything else? That was the main thing. How would you describe it now if not humility? Mastery? Mastery. Yeah. I call it humility because could they bring themselves down to my level that I was faking? Usually I would know what they did and what they had accomplished and all of that. But I would just act dumb. what do you do now?

57:15Like with my free time? Yeah. I walk the dog a lot. Are you being serious? Yeah, I walk the dog a lot. It's very peaceful. I run a family foundation with my wife. That kind of, you know, that's a meeting every now and then, every quarter. No, but like really, like what did you do? Like what do you do in a day? Like, okay, you walk the dog for an hour a day? Yeah. Okay. You know, twice. I got to do that twice. That's two hours. Okay. Yeah, yeah. Wake up at seven? Take the kid to school. Chop the kids off? Mm-hmm. Go to their track meets, go to their sports events in the afternoon. Okay, but that's like seven.

57:49There's still a gap from like, call it 8.30, 9 after you cook and breakfast to four. I was doing Pilates for a while with my wife. That was fun. And then we'd go to lunch afterwards, grocery shopping. You're like living a retired. You're living a retired. I'm a retired old bastard. And do you feel old? No. I mean, I know I'm old, but I don't, I don't feel old. I exercise. I spend a lot of time exercising. I get on the bike. I get on the treadmill, try to do a little bit of weights. So I try to stay healthy. Were you exercising when you were building the company? Yeah. You were? Mm-hmm. I love biking.

58:24Often. Mountain biking, road biking. Yeah. Anything with pedals. And then I would kind of balance it with some running. And I suck at running, but I do it anyway. How did you eat when you were building the company? I ate fine. I ate... So you think you were pretty physically healthy when you were doing MailChimp? Yeah. I think I rode harder. You're on stage when you're the CEO. I tell people, you're not faking it. You shouldn't fake it. You should be authentic, but you are an exaggerated version of yourself. So I like cycling, but I probably pushed it way harder than I needed to while I was running the business because I had a lot of cyclist employees.

59:01You want to show up for them a little bit. Yeah, we were pushing each other on Strava. It was just kind of fun that way. You're a role model, basically. And then you sell the company, lights are off, curtains close, you're off stage. You have no audience. You have zero audience. Yeah. Nothing. And so if you have nobody to prove anything to anymore, what do you do? Like, what do you do? I think that was your original point. Like, what do you do? Isn't it interesting, though, that... I still ride, but not as much. You're right. Like you constantly are being observed. Yes. And you are constantly on stage.

59:40Yes. And so everything that you do is being examined. It's being judged. They're reading between the lines to see what you really meant, even if you meant nothing. Yes. And now it's like lights off. When did you realize that that was happening? You probably hated that. No, I didn't. So so I had already observed that this happened. So I knew CEOs who exited, who would have like a huge social media following and they could tweet this dumbest shit and it would get retweeted a million times. And then as soon as they sold or retired, zero, like crickets chirping. And so I was like, I knew that I would become irrelevant as soon as I sold.

1:00:20Part of me actually really relished that, like to not have to be a role model, not have to be on shift. Like it was a good part of my life to do that. It made me better. I really do appreciate that. I'm grateful for that period of my life. But to not have that burden anymore and just do things only because I want to do them, I much prefer this. So I did not hate it. I kind of laughed at it. I could probably post some really offensive shit now and nobody would know. What are some other like the Strava one and your team being on Strava with you and going on bike rides with you is a good one. And what are some other like practical ones at work that you felt like you were on stage or that you had to lead and felt like a burden?

1:01:01I mean, you would just have to post on LinkedIn every once in a while. Like, what's my reading list? Right. Who gives a shit what my reading list is? I mean, I guess some people would be curious, but yeah, it's things like that. Yeah. Or a world event happening. What's your take on it? You're like a public figure. Yeah. I don't want to. My take is private. What about the like showing up first, leaving last? Like, did you feel any burden there? Man, 20 years in, you're not doing that as much. Yeah. And especially the way that I, my COOs were like the president. They were doing that, you know? So no, I don't, everything I kind of weaned off very gently.

1:01:40Everything. There was not like a harsh cutoff when I sold. Mentally. When you see this new era of technology that's engulfing us right now. I'm so glad I'm not in business. Are you? Yeah. That's very atypical from what I hear. Really? Because AI is disrupting everything. And as soon as there's an AI disrupting something, it gets disrupted. Early on in MailChimp, I realized in the tech industry, we needed to reinvent ourselves every three years. Customers' tastes change and their technology needs changed every three years. I had to keep MailChimp very nimble. I would never commit to anything that would take longer than let's say one year because then I couldn't be able to turn on a dime so that worked for like the first 10 years and then like you're at year 15 it's like it's accelerating I can feel it accelerating and my company's getting bigger and harder to turn I have to start making bets and these are not big bets these are just you know medium-sized bets for what I can afford and then now with it accelerating even faster I don't see how you could, how you can keep up with that.

1:02:49And this is coming from a guy we invest, we invested in AI very early, big data, all of that stuff using NVIDIA, like 2008. We were, we were very early in that world because we were processing abuse data, email data, spam data, right? We needed to protect our server. So we were, we were doing it for abuse prevention. And then we, you We got into like email design, copywriting with AI, and then I sold. And now I look back and just say, oh my God, I'm so glad I'm not a CEO of a tech company anymore. I was with the founder of one of our portfolio companies called Glean last night. We were the first investor and it was their 100 million ARR party.

1:03:32Took them three years to get there. Pretty good. Three and a half years. That's amazing. Amazing. Jeez. Kids these days. And if there was an eye of this AI hurricane, they're in the dead center of it. So he was a celebrity last night. And so I just cornered him for a second just to tell him how happy I am for him. And still a long road ahead, but I just wanted to say, this is pretty cool. There's a lot of people here. This is insane. He was telling me, so he started a company called Rubrik before this one. Rubrik is a cybersecurity company, now public. he was saying you know jubin when we were at rubric we would have to reinvent the company every three to four years that was just the state of the industry and three to four years was like the cycle of innovation set similar to what you're kind of describing yeah that was like upheaval internally like it was like a new founding every three to four years and he was like that was really hard right now it's about every six months oh my god we have to reinvent the company yeah And this is a company that just went from zero to 100 in three, three and a half years.

1:04:38How many employees? They just doubled to probably 700. That's a lot of people to change. Exactly. Yeah. It just dawned on me last night. That is insane. Yeah, man. Talk about my timing. Insane. Yeah. Yeah. I mean, the techie in me loves it. I'm nerding out by all of the cool stuff that you can do now. But then I think about, you know, I put my CEO hat on and I'm like, I am so glad I'm not dealing with this. Well, I saw a tweet went viral yesterday about somebody making like a flight simulator game after a couple of hours. Yeah. Prompting AI. Yeah. What the hell? If I was running a gaming company, I'd be scared shitless right now.

1:05:23Yeah. Yeah. I know there's not much bravado there, but like intellectually, think about retooling your company and pivoting. You know how hard it is to get all of your soldiers marching in one direction and believing in one strategy. It's unbelievably difficult, especially with more than 100 employees. 700, I had 1 ,000. Company has multiple thousands every six months to retool it. Oh, my God. How? How is that even possible? yeah i'm walking the dog taking pilates exercising i'm studying philosophy on the side taking online courses i'm so glad are you hanging out with founders still some founders come to me just seeking some advice and war stories and i'm very happy to do it until they give me like a pitch deck and then i i'm like no i'm not no investing for you but like if they need if they're going through really tough times, like the kind that quote, you know, just when things couldn't get worse, they get even worse.

1:06:25They come to me and I talk them through it. I enjoy that a lot. When do you think was the time that you thought nothing could get worse and then it got worse? Jesus Christ. It was always the servers, man. Servers crashing. That was... It would be an elated day because you'd have so much demand because this... After customers already were angry about something else, a bug that we would launch that would like take the whole app down. And then, you know, later that night, the servers would go down. There was one where we upgraded every one of our servers to industrial grade SSDs. And we paid the money for this and it was going to be faster, more performant.

1:07:01And we did that. And then like a few months after, we thought we were getting hacked because a server went down. We had like a cluster of 10 or something at that time. Server went down and a few hours later, another one would go down, another one would go down. You know, my engineers are calling me like something. We've never seen this before in our lives. We don't know what's going on. And in like every few hours, another one would go down. And like, I was like, oh my God, we're so dead. What's going on here? Like, I remember at the playground, pushing my boy on the swing, listening. Like, what, what, is it a hacker?

1:07:32What's going on? Long story short, it was a defect in SSD drives. It was a particular brand that died after so many hours. They just all kaput. They just went kaput. And these servers were installed, you know, one after another, and they just died. So that was a... Entrepreneurs now... We learned that we were sold consumer-grade SSDs, not the industrial grade that we paid for. Entrepreneurs now don't even... They've never even thought about this problem. Right, right. What do they do? They just kind of send it out to the cloud. Spin it up on AWS. Yeah, yeah. You say AWS. Remember Mechanical Turk when Amazon did that?

1:08:07We were using... We were paying Mechanical Turk... Turkers, I think they called them. to grade the design of emails, to train our system to design beautiful emails automatically. And they revolted against us. It was almost like they unionized or something and revolted against what we were paying them. We refused to pay the ones that were cheating. So anyways, you ask, you know, things that can go wrong. Like it was just constant. But that's business. I appreciate you doing this. And I think you're living a good retired life. And I believe that you got it all out of your system and that you are fully satiated.

1:08:46And that you won't see me starting up another business soon. No, no. And if for everybody listening, all you VCs out there, dibs. No, just kidding. No, I appreciate you doing this. And I it's just cool to I appreciate you sharing everything so honestly. And it's cool to see you just like chilling and enjoying enjoying kind of just puttering around. Yeah. Thank you. Yeah. Get a dog, guys. Get a dog. When you hear the word grit, what do you think of? Yeah, you ask people this. I think of fishing. So I would go fishing with my dad every weekend. And he would park in the worst places. Never just where we fish.

1:09:30It would always be a mile or two away. And he would make me, I'm a little kid hauling fishing poles, buckets, all this stuff. and we would have to walk through stupid terrain to get there. And I would whine, bitch and moan the whole way. He would never placate me. He would never say shut up or anything. He would just stop, wait for me to catch up. And as soon as I caught up, he'd start walking again. And he did that every weekend. And after a while I learned, after many years I learned, there's no sense complaining. Just do it. We'll make it there. Just do it. Just march. One foot in front of the other.

1:10:06Just get through it. That's what he taught me. And I think that is what gave me grit. So anytime there was a hardship at the company, I had that baked into my brain. Like, no sense complaining. Just one foot in front of the other. It'll be over soon. Just get through it. That to me is grit. What a story. Ben, thank you. Thanks for having me. This is fun, right? Maybe this is like closure for me.

1:10:35That's it. Thanks for listening. If you liked the episode, please tell a friend and check back every Monday morning for a new guest or go back into the archives where we've done more than 200 episodes with some fantastic folks. This podcast is a Kleiner Perkins production and was edited by Eric Johnson from Lightning Quad. Thank you.

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