Pod Insights The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch 20VC: Mailchimp's Ben Chestnut on The Biggest Leadership Lessons Scaling to a $12Bn Acquisition and $1BN+ ARR, The Secret to Happiness, Being a Great Husband and Father & Why 2021 was the Right Time To Sell to Intuit About this episode Ben Chestnut is the Co-Founder of Mailchimp, the all-in-one marketing platform for small businesses. Last year, in Sept 2021 it was announced that Intuit would acquire Mailchimp for a reported $12BN. There are so many things to love about the Mailchimp journey to this point. First, Mailchimp was founded as the result of a side project of a design agency Ben and his co-founder, Dan, used to run. Second, Mailchimp is and has always been based in Atalanta, eschewing the notion you have to be in SF or NYC to build a massive business. Then third, they never raised venture funding for the business all the way until their $12BN acquisition. Ben led Mailchimp to over 1,200 employees and millions of global users. In Today's Episode with Ben Chestnut We Discuss: 1. From Mama's Kitchen to the Smell of Business and Founding Mailchimp: How did Ben turn a mediocre agency into the founding of Mailchimp? What was the a-ha moment? At what stage of the business did Ben quit the agency and go all in on Mailchimp? What sign did he need that Mailchimp had true product-market fit? When Ben's mother died, he bought every flower in the local town to commemorate her. How did Ben's mother impact the type of father and husband he is today? How did she impact the way that he led Mailchimp as CEO? Ben's fishing trips with his father played a big role in his early years, what were the single biggest lessons for Ben from his fishing trips with his father? 2. Ben Chestnut: The Leader: How does Ben define the term "high performance" in leadership? What does Ben mean when he says "the secret to happiness is to stay in your lane"? Why would Ben describe himself as the "leader of the misfits"? How did that early experience and labeling impact both the people he hired and the culture he created at Mailchimp? What does Ben mean when he says he used to have a "hands off, eyes off" leadership style? What have been the single biggest drivers in his development as a leader? 3. Ben Chestnut: The Person: Relationship to Money: How does Ben reflect on his relationship to money? How has it changed over time? Why does Ben still to this day buy lottery tickets with his wife? Conquering Fatherhood: What does being a great father to Ben mean? How does Ben attempt to instil the same work ethic and drive when his children are born into immense wealth? The secret to Marriage: What does Ben believe is the core to a successful and thriving marriage? How does Ben view his role in the marriage? How has it changed over time? Potential Lost Identity: A founder's identity is so closely tied to their company, how did Ben manage the challenge of selling his company but retaining his identity? What did Ben learn about himself through many different acquisition processes? 4. Mailchimp: The Business: Why did Ben never raise venture money in the 21 year journey of Mailchimp? Why did Ben never accept any of the acquisition offers that came before Intuit? How did Ben motivate his team after they knew each acquisition offer was being turned down? Why did Ben decide the acquisition by Intuit was the right decision for the company? How does Ben view his role in the company now and moving forward?
Transcript 11,213 words · 4 speakers
Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:00 Speaker 00 The key to happiness is staying in your lane and knowing when people need to be in their lane. Don't get in their lane and don't let them get in your lane. To me, if somebody is just not disciplined to take control of their lives and be successful, they must not want it, and I'm not going to bother with it.
0:13 Harry Stebbings? This is 20 VC with me, Harry Stebbings, and I've wanted to do this show for many years because there's so many things that I just love about this guest's story. First, they did not build their business from San Francisco or New York, but Atlanta, proving that massive companies can be built from anywhere. Second, they did it with no venture capital at all, despite every venture investor wanting to invest. And then finally, our guest today scaled the company as CEO until they reported $12 billion acquisition by Intuit in 2021. If you haven't guessed it already, I'm so excited to welcome to the hot seat Ben Chestnut, co-founder at Mailchimp, the all-in-one marketing platform for small businesses. I also want to say a huge thank you to Ben's sister, Lottie, who gave me some amazing question suggestions pre the episode, and it made such a difference.
0:58 Harry Stebbings? But before we dive into the show's day, 20 VC is supported by First Republic Bank. When private equity and venture capital firms are funding the innovations of tomorrow, speed is of the essence. That's why at First Republic, you'll be paired with your own banker, who will remain dedicated to helping your team through all market cycles and will be ready to respond quickly to your requests. As a First Republic client myself, having a direct relationship with a personal banker, who I can really depend on to help me make the right decision, matters a lot. In fact, your banker will serve as your single point of contact by phone, email, or First Republic's secure app. Visit firstrepublic.com today to learn more. That's firstrepublic.com, member FDIC and equal housing lender.
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2:50 Speaker 02 representing both early stage and late stage financings, handling more than 1,300 private financings every year with an equal split of investor and company clients. So to learn more about the number one most active law firm representing VC backed companies going public, head over to Cooley.com and also check out Cooleygo.com. Cooley's award winning free legal resource for entrepreneurs. But now I'm so excited to hand over to the one and only Ben Chestnut, co-founder at Mailchimp.
3:23 Speaker 03 You have now arrived at your destination.
3:26 Speaker 02 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.
3:33 Speaker 00 Glad to be here. Thanks for inviting me and I don't hope I can give you too much dirt.
3:37 Speaker 02 Oh, she gave me so much dirt, but we're gonna get into that later. We were just chatting now and you said to me that you're an accidental entrepreneur. And so how did you come to found Mailchimp and what was that aha moment for you?
3:49 Speaker 00 I always wanted to be a designer. I loved drawing when I was a kid. I had a couple of businesses in grade school. I would get those little 3M sticky pads and I would draw animations, little cartoon flip books. And I would sell those on the bus and that's how I got my taste of business. And I moved on to selling candy, my own comic books that I would draw. And I still maintain that Mailchimp is really just the end of a series of pivots from grade school. I always wanted to be a car designer. I went to industrial design school. I kinda along the way fell in love with web design. I got an internship at an appliance company and I learned how to design appliances and I was good at designing things on the computer but I was really bad with my hands. I didn't have the dexterity to use that X-acto blade and cut foam models like you're supposed to do. You have to do
4:32 Speaker 00 that with when you design cars as well. I was really bad at it and the mentors that I had at the time were like, "Yeah, you're, all of these refrigerators are lopsided." So one of them gently nudged me towards the silicon graphics machine and said, "You might want to try 3D rendering instead." And so I fell in love with that machine. I fell in love with computers. I never went back. I learned web design that summer internship. I got into that the next semester and never went back.
4:58 Harry Stebbings? You mentioned Mailchimp being the result of a series of kind of continuous pivots. I love that description. When did you realize, "Oh, wow, this is a real thing"? Was it a millionaire or 10 millionaire or international offices? When was that, "Ooh, this is real"?
5:12 Speaker 00 It took me a long time to realize that. It was an accidental kind of a business. We built it for just a couple of our customers who were having problems sending out email newsletters. Our real business was doing web design and it was just sort of, we built it on the side and it got annoying to log in and use it on behalf of our customers. So we just made it self-serve. We just said, "You log in, you use it and pay with a credit card" because we're tired of cashing the checks or depositing all these $50 checks. I was driving to the bank too much. Anyways, we made it totally self-serve and it just started to grow organically, but we never took it seriously. We just focused on our web design business and I don't know, maybe three or four years went by. We were exhausted from running an agency. The billable hours game, selling to clients, we were bad at
5:56 Speaker 00 it. One day I caught this episode. My wife was watching Oprah. She's a night shift nurse. She came home, she crashes on the couch and turns on Oprah and I'm working at home and I'm coding away at some website and there's a guest on Oprah. His name's Robert Kiyosaki. You should have him as a guest someday. He's up there and he's talking about passive income, recurring revenue and all that kind of stuff. And it was the first time I had ever heard about anything like that. And so I stopped coding and I listened and I said, "This guy's on to something." And I bought all of his books, read about it and I just started thinking, "Should I get into real estate? What kind of recurring revenue business can I do?" Meanwhile, Mailchimp's sitting here making recurring revenue, by the way. I'm like, "What should I do? What could be the next business?" And then duh, it hit us. Wait, we've got this MailChimp thing on the side.
6:38 Speaker 00 We took its revenue and we separated it from our agency revenue for the first time. We used Excel, we drew graphs for the first time in our lives. We were like, this Excel thing's pretty cool. We color-coded the revenue from MailChimp versus the revenue from our agency, and MailChimp was growing and our agency was flat or in declining. That was all we needed to say. Let's stop the agency business and let's focus on MailChimp as a software company.
7:01 Harry Stebbings? What sort of level revenue was it then? Was it like a million, 10 million, 5 million?
7:06 Speaker 00 After a few years in, MailChimp might have been making a few hundred thousand dollars at the most. Our agency business was making just barely more than that, but it was flat. You have to remember, this was after the dot-com crash. It was Slim Pickens in Atlanta, Georgia, getting website business. We were making, we were 100,000 airs at the time. Not even close to millionaires.
7:28 Harry Stebbings? I get it, but being that that says three years in, it's not like rocket ship growth. My question is, when was that inflection point where it went actually very much stratospheric?
7:38 Speaker 00 It was a sort of another accidental thing. We fell into freemium. That was it. Five years of chasing after silver bullets, just, oh, this is gonna be the unlock. And it wasn't the unlock. Let's launch this feature. That'll be the unlock. And it wasn't the unlock. Let's do this PR. That'll be the unlock. Never. And freemium was something that we fell into, didn't really think much about it. And that turned out to be this thing. I think we were tens of thousands or hundreds of thousands of users at the time. And then within one year, it was a million users. Within another year, it had doubled again. And it just kept doubling for a few years after that, just thanks to freemium.
8:12 Harry Stebbings? It's always what you don't expect. We mentioned your sister at the beginning. I do wanna touch on a couple of fascinating elements I discussed with her.
8:18 Speaker 00 Here we go.
8:18 Harry Stebbings? I hope it's okay for me to ask, but she mentioned the incredible relationship you have with your mother. I do with mine. She mentioned that with her funeral, you bought every flower in town or as much as you could buy. And I just wanted to ask you, in terms of your relationship with your mother, how did she impact how you are as a father first? And how you are as a leader second?
8:38 Speaker 00 Yeah, she was an entrepreneur. She ran a hair salon in the kitchen of our home. We always had customers in the house. And I was always helping her out, emptying ashtrays, organizing the hair rollers and that sort of thing. And I watched money exchange hands. And I always joke, to me, if I close my eyes and I think about business, there's a smell to business and the smell is hairspray and cigarettes. And that's what business smells like to me. She didn't really talk about entrepreneurialism or business. She treated it as it was a living. It was a way to make ends meet. It was a way to help pay for the bills. She was from Thailand and to her, business is just something you do to make a little extra money. To me, being born here in the States, my father is born in the States, he thought about business differently. He was always talking about, how does this unlock? How does this scale?
9:22 Speaker 00 I always dreamed of my mother just scaling out of the kitchen and she never really did. And I think there was a little bit of disappointment in me that this wonderful thing that my mother did never really just turned into like the next Vidal Sassoon or something like that. And I think that's been the DNA of MailChimp, this understanding that small business entrepreneurs, they might start small, but they're dreaming big. They want it to be something big. Because of my mother, I think I never called our customers small businesses. I would say businesses or I would talk about their dreams of becoming big. It's useful internally to call it a category, SMB category, internal reference only. That's what I would tell my writers and marketers, but outward facing, I really hated to use the word small business because they have big ambitions.
10:04 Harry Stebbings? I love that in terms of how that impacted, especially the smell. I also heard about your father and the fishing trips. A lot of you asked, what did you take away from those and how do you reflect on lessons from them?
10:14 Speaker 00 The lake where we would go fishing was always about 45 minutes to an hour away. It was a really long drive. And whenever I drove with him, he always took the slow scenic route, the back country roads. It would frustrate me sometimes because I knew after a while, I would start going fishing sometimes with my brother and we'd hop in his car. He would take the interstate and we'd get there in 15 minutes. So I knew there was always a faster path, but my father always took the scenic route. That was a big lesson for me. Sometimes it's not always better to be faster. When we went fishing, he also did not just stop, get out of the car, start fishing. It was always like another mile or two mile hike to get to where we were fishing, always. I would stick the hard path. I would whine and complain all the time.
10:58 Speaker 00 And he would make me love the fishing poles, the minnow bucket, all of this equipment, the tackle box. I would complain and complain, and I would always wish that there was a device or some kind of transportation like Star Trek. Just beam us there. I would always talk about inventions to make it easier and just complain that my feet were hurting, whatever. He never said anything. This is what I remember most. He never turned around and said, hurry up, stop complaining. He never praised me either. In other words, he was very stoic and he would be walking ahead of me and I would be whining and complaining. He would stop, turn around and quietly wait until I caught up. And then when I caught up to him, he never said a word. He turned back around and started hiking again. And that was it. I think I learned stuff's gonna be hard. It's not worth complaining. Just keep hiking.
11:43 Speaker 00 When stuff's really hard, look at your feet and just keep marching one foot at a time, left, right, left. That's it. He was also in the military. I remember one day they were coming back from some kind of training mission. It was families reuniting with all of the soldiers. And I had no idea that my father was this head of this platoon squad. I don't know the terminology. I had no idea he was the leader. My father was just a kind, quiet, stoic kind of guy to me. I got to watch him lead this big troop, all these troops. And he would, ten hut! And then these soldiers would like jump up in formation and they would turn and obey his every order. And I'd never seen my father act that way. To me, it was like really violent or loud. I'd never, he'd never acted that way. He made them do what they did and then he put them at ease.
12:27 Speaker 00 And then he was just a very personable kind of a guy. Everyone came up, hugged him, shook his hand. So I could see that there are two sides. If you're a leader, you do what you gotta do to lead the troops. You don't have to be harsh and vicious all the time. You can also be friendly on the other side.
12:43 Harry Stebbings? You said about him not praising you there or waiting for you silently. Did he tell you he loved you?
12:48 Speaker 00 Yeah, he did. There were times when he would say that and there were times when he would say that he was proud of me. It was usually after me going through some struggle myself. He would see me just improve myself in some way. And those were when he would reserve that praise. But other times, if he saw me struggling or stressed about something, he would say, that's the norm. That stress is the norm. If you're not stressed, you're insane.
13:15 Speaker 00 I remember him saying that. He was like, people who are just completely calm all the time and they never get phased. You have a calm demeanor, that's leadership, but inside you can be really, it can feel chaotic and stressed, but you don't show it. People who don't even feel that stress inside, he would say there's something wrong with them. He would never like appease me or give me that, oh, you poor thing kind of a stuff. He would just very silently, and he would help me get through stuff. It was if I prevailed, that was when he reserved that praise.
13:43 Harry Stebbings? Calm demeanor, that's leadership. I like that a lot. I also hear that you're a psychist. So I want to bring them together and ask, what does high performance in business and leadership mean to you when I say those words?
13:56 Speaker 00 When I think about high performance at Mailchimp, the way that I ran the business, I never really thought about it as setting a high goal and telling people to crush it at all costs. I would set the high goal and then think about what habits do we need to get there. When I started getting back into fitness, I got really overweight in the first 15 years running the company. It was only very recently when I had my first child that I said, oh, my God, I gotta lose this weight. I really started to think about it. I couldn't even run a mile. And I was like, what are my habits that are preventing me from doing that? And it was staying up too late, watching TV. So I just unplugged the TV, no more TV for me. And I would go to bed earlier. To me, that's high performance. It's looking at the roots of what's causing you to not be high performance and changing these core
14:40 Speaker 00 habits that are blocking you, not really chasing after running that mile. I tried, I couldn't do it. It wasn't until I slept better, ate better, drank better, then I could run a little bit better. It's about getting to the core of the problem. I guess deleting habits more than anything else?
14:57 Harry 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 a long day. I need my gin and tonic, whatever it is. What do you say to them who say, I don't have the discipline. Oh, I'm tired, I've got...
15:13 Speaker 00 I don't talk to them. I'm a little bit like my dad. It's like, if you want it, you'll do it. If people want something bad enough, they figure out that discipline. They just must not want it. I'm close to 50. An old fart now, you sort of learn to just stay in your lane. The key to happiness is staying in your lane and knowing when people need to be in their lane. Don't get in their lane and don't let them get in your lane. To me, if somebody is just not disciplined to take control of their lives and be successful, they must not want it, and I'm not going to bother with it.
15:41 Harry Stebbings? What do you mean stay in your lane? I'm too interested.
15:44 Speaker 00 Everybody has problems. You got problems, I got problems. You bring those problems to my table. Hey, Harry, good for you, man. I'm not going to make it my problem. I'll give you some advice. I'll probably try to get down to the core. If you really want advice, I'll give it to you. But I'm not going to be attached to making sure you follow that advice. Take it or leave it. It's up to you.
16:04 Harry Stebbings? We have like forty or forty-five people across our companies now. And I think my biggest problem is I have the savior complex, which is you bring me your problems and I ingest them as my own. I reflected on that recently. When you reflect, and it's really interesting now that you stepped away from the role as CEO. When you reflect on your own CEO ship and style of leadership, how would you describe it and did it change over time?
16:25 Speaker 00 Yeah, maybe in the very early startup years, I didn't have this kind of stay in your lane, I know my lane kind of an attitude. You do just absorb everyone's problems because it's a life or death situation to a startup. I just want to be fair to startup leaders out there listening to this. Sometimes you gotta take all that on. Like I said, I'm an old fart. I'm almost fifty, which is something that happens as you age. Maybe a little older, maybe a little wiser. I think that when the very early years of MailChimp, creativity was everything to me. And you might describe me as bring on really talented, creative people and just be very hands-on. And I really do think that helped me in those early years. My co-founder, Dan, really helped vet to make sure not only were they creative, but they had a good work ethic too. So without Dan, I don't know that this would have worked.
17:08 Speaker 00 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 five hundred to a thousand employees, it's less of a startup or a company where everyone's kind of following the same mission. It's not telepathic where everyone knows what it is the leader wants. It's like you're the mayor of a really big city and their pockets and neighborhoods of that are just out of control sometimes or just doing their own thing. I got some coaching around two, three hundred employees and they said that my leadership style was a little bit hands off, which can be good, but it was also eyes off. And they told me the guidance was hands off, eyes on. And that was the biggest change for me, being trying to be hands off, but eyes on.
17:52 Harry Stebbings? How did you change as a result of that?
17:54 Speaker 00 I used to just give grand big picture vision. I could rely on a small team to be telepathic and just get it done. No, what you had to change is be a lot more explicit about the goal, maybe some KPIs, maybe talk about what happens if you don't meet the goals. You have to rely a lot more on senior managers and lower level managers to actually manage people and hold people accountable. That's hard to do when you're a startup that's just sort of used to having a bunch of free range creatives do what they want.
18:23 Harry Stebbings? Did you enjoy that? You are an incredibly creative, emotive, effusive person, running process on individual little squadrons. It's not where I get energy from and I don't think, it doesn't feel like it's where you got energy from.
18:36 Speaker 00 To me, it was about the transformation of Ben. Over the years, I watched a lot of founders, they would evolve and they would say, I'm more of a creative guy, I'm going to step back from this and let somebody else take over. And I would always think, that's a cop out. I'm not going to be like that, I'm going to evolve. It's your job to get older, wiser, change your way. You can't be creative, you can't just sit there and code all your life. You can't be the designer all your life. And so I'm going to evolve and do this other operational in air quotes. I'm going to be more operational in my life. And I really think that I got pretty darn far with that and I'm proud of how far I got with that. I was willing to keep on going and I think it's also important to be self-aware and learn when you're not so good at it. And I think that's the thing, so Harry, I could have kept on going and evolving and trying.
19:19 Speaker 00 And one day I just realized, I had enough people just say, you're not great at this operation stuff, Ben. And I just realized, you know what, the only reason I'm still doing this is because no one can fire me. So that's why I've been going at it so long. I started to lean more on operational people on the senior leadership team and I was self-aware enough to step back in some areas. And after that, I started to think, yeah, I don't get a lot of energy from that. I really don't. I'm much better when it's sort of connecting. The dots for a lot of creatives in the room.
19:47 Harry Stebbings? How would you advise other founders? Say you're advising me, we're in a coffee shop and I'm thinking about a new trait, habit, style of leadership. How would you advise me on, hey, Harry, just push through it. Keep going. Don't be a cop out versus listen to your team. Step back, Harry. You're not meant for this. How do you advise them on whether to listen to which one?
20:06 Speaker 00 That actually happens all the time, Harry. I meet with founders. I don't invest. I don't do any kind of angel investing. They just come to me as a therapist. They sort of sit on my couch and they just tell me all their problems. I really don't give them a lot of advice, to tell you the truth. I say, oh yeah, that happened to me. Yeah, that happened to me and this is what happened. Boy, I had it worse than you, man. Here's how I effed it up worse. And this is what I did to get through it. But you might have to do something different. That's what I did. Most of them are just relieved that they're not the only one suffering through this. I remember myself, I didn't have a lot of founders to talk to in the early days. In Atlanta, there wasn't much of a startup ecosystem. And I thought I was just the only one stupid enough to make the stupid mistakes that I was making. So to me, my goal when I talk to founders was is to sort of say, hey, no, man, we all make that mistake.
20:51 Speaker 00 So I don't really give a lot of straight up advice. I just relate to them.
20:54 Harry Stebbings? I think it goes back to relationships, which is like, there's times when most people just want to be heard. And actually saying, yeah, I feel you. I had that too, is exactly what you need. But it takes emotional intelligence too. And I spoke to Lottie again. You said before the show that she's a brilliantly gifted business leader. She told me that you were world class when it came to emotional intelligence, EQ. How do you feel when you hear that? What do you think she sees in you about how brilliant your EQ is?
21:20 Speaker 00 I'm conflicted about it. I know that I could be pretty insightful about people's feelings. I was a really quiet loner in school. I went to a rural country town school and I was one of like three Asians in the whole school. So I was kind of a misfit and a lot of misfits flocked to me. I don't know why, but I was leader of the misfits always. And I think Mailchimp is like the island of misfit toys sometimes. And I don't know. Those early years of listening and learning from a lot of these people who would come and talk to me, it really helped me tune in to the way people were feeling and what they were going through. Why I'm conflicted about is I also have this flip side of me as a leader. So I talked about my father, like being this really friendly guy. But when it's time to lead the troops, you could be cold or harsh on the surface.
22:05 Speaker 00 You gotta do what you gotta do. Most people probably see that side of me. So anyways, I have been told many times I have a high level of self-awareness and a high amount of EQ. But I'm also told I can be cold and robotic because I'm pretty logical and I would just say what's gotta be done. I may be in a more overly stoic way.
22:22 Harry Stebbings? I had Drew Houston on the show recently and he said something brilliant, which was there's no nice way to deliver a grenade. And I think to that option, which is like, you know what, Ben, you're fired. Say it nicely, say it not nicely, you're still fired, it sucks. I totally get you. You said about being leader of the misfits then. Again, the joy of doing the show is I can change the schedule. I was a misfit too, Ben, and I didn't have any friends to most of school. And it made me actually not great in business in one way being I always want to people please. That's a really negative trait that I've taken from being a misfit. Do you think there are any negative traits you've taken from maybe being a misfit yourself?
22:55 Speaker 00 Now we're getting into some really deep psychological stuff here. I think that for me, being a misfit meant that I was bullied quite a lot. And I was discounted and disrespected quite a lot through my childhood years. Not at home, I lived in a very loving home. Thank God I had that kind of shield around me. But when I went to school, it was like fists up, get ready. So I was always ready for a fight. So I was ready to defend myself. And I think it made me want to prove that I was a valuable person. I think that gave me this drive to be a great, successful entrepreneur. It just pushed me, I had to prove it. On the one hand, that's really good. Probably on the other hand, if I feel people are trying to push me in one direction,
23:36 Speaker 00 that old instinct of, oh, I'm being bullied pops up again and I will push back and I'll be very cold about it too. No apologies, man. This is what we gotta do, we gotta do it. And I will not be swayed or pushed again, never again. Sometimes you have to go with the politics and understand politics a little bit better. And I understand it, I get it. I do have that EQ to get it. But sometimes you just have that sort of angst from your childhood and you just sort of say, if it's illogical, I'm not going to concede or deal with that. When you talk about bad habits, I think that's probably. What I inherited from my environment.
24:06 Harry Stebbings? I think the most prominent lessons are from quite painful times. When you think about the most painful lesson that you've learned, that you're also pleased to have learned, which is a weird paradox. What would you say it would be?
24:18 Speaker 00 Being a misfit was always this painful thing throughout all of school for me, even through high school, even a little bit through college. But what I've learned in retrospect is that it made me think differently. It made me stubborn in some ways. It made me stick to my guns. I think that really gave me this focus to be an entrepreneur, a successful entrepreneur. And I think there were times when I think we could have sold the business early. There were a lot of people, a lot of suitors knocking on the door, a lot of investors knocking on the door. I just sort of had this stubbornness that I didn't need that. I didn't want it. I was going to do it myself and I was going to do it my way.
24:51 Harry Stebbings? Was that always beneficial, do you think, in hindsight? If you're thinking, I'm sure there are moments when you could have taken a hundred million, 500 million, a billion. Everyone wanted to give MailChimp money. Are there moments where you're like, actually, my stubbornness was not good?
25:03 Speaker 00 Who knows? 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 have scaled even bigger. And maybe right now you'd have sold for 20 billion. Who knows? There are some people who say, yeah, you would have had a slice of the pie instead of the whole pie, but the pie would have been bigger. There's no way to tell, but I do know that when I look back at my life, I'm really proud to say I did it my way and I'm really proud of that. There's sort of a Bruce Lee element of it. He did it his way. He came up with his own style and I came up with my own way of running this business. I'm really proud of that.
25:33 Harry Stebbings? The thing that I also think about is MailChimp, was it a 17 year journey, an 18 year journey?
25:38 Speaker 00 21, not that I'm counting.
25:40 Harry Stebbings? Anyone, not that you're counting. It is such an ingrained part of your identity, actually, as my business is mine. I hate going on holiday, Ben, because I lose my identity. I'm not working and then I don't know who the fuck I am. My question to you is, when you stepped away from CEO, how did you handle that loss of identity and losing something that was so ingrained in who you were?
26:02 Speaker 00 One company, one great, amazing leader tried to buy our company many years ago. Out of a sense of duty, I heard them out and ultimately I said no. And he told me, hey, you're going to change. And when you do, when you change your mind, can you give me? First dibs that kind of annoyed me. Why do you think I'm going to change my mind? Why are you so sure that I'm going to change my mind? And he said, you're going to think about life differently. Right now, you are defined as your business. It is everything to you. But as you get older, you're going to realize that your business is just something that you created and something that you do, but it is not you. And then you will be ready to sell. And I said, yeah, whatever. Thank you. I was nice about it, but I just secretly was like, that guy's nuts. Hung up the phone and forgot about it. Maybe I was in my early 30s at that time.
26:46 Speaker 00 Lo and behold, 10 years later, I'm in my 40s, mid 40s. Something happens when you're in your mid 40s. All right, it happens to everybody. Their friends and their families start to die. You start to reflect on life. It's one of those things where it's like, you're just chugging along with your business. You're not really thinking about this, but friends your own age, people you knew, start to pass away. They have heart attacks, whatever it might be. Family starts to pass away. You start to think about life and you start to think about, whoa, my life is not my business. And that's just a job. It's just something that hits you. There was never a desire to take investment or to sell the company. And it's just one of those things that just happens many years later to you. When that started to happen, it goes away. This attachment that you have, it goes away. It did to me at least, but I know a lot of people that can't seem to shake it.
27:31 Speaker 00 Like they sell a business and they keep on going and they start more and more. Like, I just can't imagine why anybody would want to do that. Did you find the transition hard? First of all, I don't know that I transitioned that hard. I'm still in the middle of this. I'm still at Mailchimp. I haven't stepped away from it, but I am focusing a little bit more on innovative projects, being an advisor in that capacity. One of the guys that we ended up using a company called Catalyst to be our broker. Yeah, yeah. You know, the guys at Catalyst? I know them well, they're fantastic. Yeah, they're great. So the guy that reached out to me, it was about 10 years ago. He reached out to me and I was like, I'm not selling my business, go away. And he was just very nice and he kept a relationship with me. He was very calm and patient. He's very zen and philosophical and we just built a friendship over the years. And he was actually a practicing Buddhist.
28:15 Speaker 00 When the time came to sell the business, he was probably finally, Jesus is 10, 10 year sales pipeline here, I'm going to close this. Anyways, he went through the deal with me. Before it was over, he said, hey, I want to talk to you about this. I've seen a lot of founders go through this process. And what you're going to learn is your entire life, your career, your idea as a CEO is composed of nothing but a whole bunch of habits. And these habits are driving you and these habits are making you do everything that you're doing. These habits are making you think about everything that you think about. And those habits are going to start to die off. You're not going to be called into meetings anymore. The emails are going to stop coming in. The calendar invites are going to stop. And it's going to feel weird what it is habits are being deleted and maybe you'll develop
28:58 Speaker 00 some new habits, but think about it that way. That was the guidance that I got from her. And I thought that was a little bit crazy, maybe. But I have seen this start to happen. I've talked to other founders too that said, did you wake up one morning and notice that there were no emails on fire in your inbox? And I said, yeah, that happened to me today. And she was like, yeah, that's happening to me now. Anyways, you really do start to realize, wow, it's nothing but habits. You wake up, you check your phone, you do this, you do that. They're good habits that make you a great leader, but they are just habits. Other thing I'll say, Harry, is MailChimp's success came very organically and slowly. So I have seen founders, maybe that they were maybe overnight successes. And I think that going from poor to rich can really do a number on your brain. And I think my co-founder,
29:42 Speaker 00 Dan and I, were so lucky that we just sort of really gradually grew and we could stay grounded. We kept some level of humility, if I'm allowed to say so myself. The transition hasn't been too hard on us.
29:53 Harry Stebbings? That was going to be my question. We're going to get to relationships, money, but you've been on the front cover of many magazines lauded for the success and efficiency of the business. And you joke about being wise and older. You're still pretty young to have the success that you've had. And actually, especially when the magazine covers were there, how did you retain your humility and not let your ego get inflated when the world is saying, wow, this CEO, he's a shooed Silicon Valley and he's built the billion dollar business that no one else can build and blah, blah, blah. How did you retain your humility and fight against ego inflation?
30:25 Speaker 00 The magazine covers only happened in the last few years. I just genuinely did not care about publicity. I tried to get the publicity in the very early years of MailChimp. It always failed. Nobody cared. They were laughing at the chimpanzee mascot. Nobody cared about email. Nobody cared about SaaS at the time. I could never get any publicity. What I'm doing is I'm seeking that validation. Maybe as that misfit who was always pushed aside, I wanted that validation, damn it. And that's what I wanted from the publicity. And then I realized the only validation I need is a paying customer. When they open up that wallet and pay me with their credit card, that's a validation. I rewired my brain to only care about that for many, many years, didn't care too much about publicity. Then it was only in the final few years, I got a chief comms officer who just said, you could use some publicity. Let's do it. It'll help us with hiring. We're at a scale, a thousand employees.
31:09 Speaker 00 We're competing with some publicly held companies. We gotta get the word out. And I had read about other privately held family businesses that were very stealthy and quiet. And then every few years, they would open the doors, Mars Candy is one of them that I read about. They would open the doors a little bit, reveal a little bit in order to recruit. They would need to bring in fresh employees, fresh blood, and then they shut the doors again. That was really why I opened up the doors. I just said, all right, let's do this. Let's get some magazine covers. That's fine by me. And then, yeah, it happened. But I think the fact that I had already been jaded on publicity, that's probably what might have kept me a little bit grounded there. And also during the entire time, I would send regular communications to employees just saying,
31:51 Speaker 00 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 Milt. We were turning from just an email point solution to this multi-channel platform. That's where we're heading. We are going to fail miserably at that for many years. And people are going to make fun of us and all of this glory that we had in the past. We're gonna lose it. These magazines, they're talking about that glory back there. You better get used to hard times ahead. I kept saying stuff like that. The first time we got the magazine cover, actually, the comms team bought a big stack of them, put them around the office. They were so proud of it. But I always teach our employees to be humble. That's one of our core values is humility. They could make fun of me. I didn't care. We had that kind of environment.
32:35 Speaker 00 I remember somebody drew a mustache on my face on the magazine cover. And they threw, drew a mustache on everybody's face, actually. I laughed so hard and I was so proud that we have this culture that could just be brave enough to poke a little fun. I took a picture of it, posted on Slack, and I said, this is hilarious. More, please. And somebody in the company, Sean Cook, he started an art gallery. Where we encouraged everyone to deface my face. And there was like a contest. It was like a brilliant art show of everybody gluing googly eyes on my face. Just doing all kinds of things to make fun and just humble us all back down again.
33:11 Harry Stebbings? It slightly reminds me of Willy Wonka opening the doors to Charlie's chocolate factory and then shutting them again. 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?
33:26 Speaker 00 I never really had a desire to sell, but I always felt it was my duty to listen to people when they wanted to buy. Now, I would always learn something. We had a couple of companies come knocking a couple of years ago. I listened to them, I opened the door and it went a little further than normal because they were pretty compelling offers. You have to get your senior team involved. Once they get involved, they get a taste of blood. They're like sharks, they're on the scent and they want to win. This is what higher performance senior leaders do, they want to win. We got to the end of that process and the offers weren't there for me. And we ultimately said, no, we didn't do anything. And that's a huge letdown for the senior team. That's like you're coming for this high. And remember, these are people who also did not want to sell. They joined because we were a bootstrapped company.
34:10 Speaker 00 We had all mentally switched and said, all right, we're ready. It is time to do this.
34:15 Harry Stebbings? You see your number and you're like, ah.
34:17 Speaker 00 Yeah.
34:17 Harry Stebbings? I would.
34:18 Speaker 00 Yeah. And then you take it away. So I had this conundrum and I was sick and tired of the whole process, by the way, because it takes away six months of your innovation and your momentum and stuff. It's distracting. So I was at this point where I was telling everybody, I was ready to tell them, never again, I'm not going through this process. We're going to stay bootstrapped, self-funded. If you don't like that, it's time to go because I'm drawing the line, never again. I was days away from sending that memo to my senior leaders. And I got that call from Catalyst and he said, this one's different. You need to listen to this. And I said, sure, fine. And it was Intuit and I listened to Alex Chris. He knew small business. He had built a startup before that served small business. He runs a small business, self-employed group at Intuit.
35:01 Speaker 00 He talked about small business in a way no other leader had talked to me about it before. He knew the same stuff that Dan and I knew and that's very. Very rare. He talked about it with a passion that I'd never heard before. We talked about what it would be like to combine forces. And I felt like MailChimp was at a place where it needed to go to the next level. I needed to hire another leader to get us there. Or I could join forces with Intuit and it could be like, you know, Intuit was like this big jet, the ones that refuel the small fighter jets. And I felt like this is like a refueling moment for us. We could just connect, get pumped full of fuel and then take off with our mission and continue getting MailChimp to its big act two. So it was very compelling. We talked for a year, by the way, the whole thing was an entire year of due diligence and courting each other, testing the waters here and there.
35:45 Speaker 00 I was really hesitant about the whole thing, the entire time. It was just too compelling to say no.
35:50 Harry Stebbings? I had Ryan Smith on the show from Qualtrics and he talked about his relationship to money when he sold Qualtrics and became a billionaire. And I asked him, what is your relationship to money? You know, you move very quickly into different echelons of wealth. How do you reflect on your own relationship to money and how you think about that today?
36:06 Speaker 00 We didn't move that quickly and MailChimp was making hundreds of millions of dollars and we were on the cusp of a billion ARR when the acquisition happened. We were already doing really well, highly profitable. So I don't know that my money profile changed overnight. Like I said.
36:19 Harry Stebbings? Funny, isn't it? It's a venture funded business though, isn't it? Because in a venture funded business, it absolutely does. You sell and you get hit with like a billion overnight. And here it's like you just progressed very nicely, but continuously.
36:31 Speaker 00 Like an oak tree with really deep, strong roots. It's just very slowly. And we had kids. That's a very humbling experience to have children. My co-founder had two girls. I had two boys, roughly the same age. I don't know, man, that just grounds you. I wanted my kids to see me, you remember what your parents did, not always what they said, but what they did. And you become what they did. And I always wanted my kids to see me working on customers. And when they would ask, Dad, what are you doing? I never said, making money. I never said, running my company. I always said, helping customers, always my answer. I just wanted them to be helpful watching me. So anyways, that relationship with money, I don't know. I was lucky that we eased into it and I just sort of want us to have the right attitude of being helpful with it.
37:13 Harry Stebbings? How do you think about bringing your two boys up in bluntly much more fortunate environment? And you were brought up in yourself. How do you retain hustle and ambition and hunger when very different financial situation?
37:24 Speaker 00 I used to worry about that a lot. 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 to want in a child. The child, they're going to grow up to be what they want to be. That's what I want to have for them, some freedom and independence for them to decide. So I had to let go of that expectation of them. That was one big thing. I also really didn't talk about money that much and they never really knew that Mailchimp was that successful. They just knew that I was maybe a nice, helpful guy to customers. It was their classmates. One day, one of their classmates brought a magazine with my face on the cover. Cause I guess her dad had given it to her. And that was when they said, is it true that Mailchimp is this worth this much, worth that much? But I had lots of conversations with them.
38:07 Speaker 00 Intellectually, they got it, but it never really registered for them. Cause then they would say funny things like, oh, there's this kid at school. His dad has a Porsche. They must be rich, dad. When will we be rich? So they intellectually got it when they were young, but not really, because we never really acted that way. I am told by many people who've worked on home offices with super wealthy families. It's really just about how you live, not really what you teach or what you say to them. It's really how you act. And all I could do is say, I hope that they learn by watching us that we just try to be earnest and try to be helpful. And that's it.
38:40 Harry Stebbings? If you save up, you could buy that Porsche one day. One day you could buy that Porsche.
38:46 Harry Stebbings? I love that. That's so sweet. Well, I want to move into a quick fire band. So I say a short statement and you give me your immediate thoughts. Does that sound okay?
38:53 Speaker 00 Can I tell you something about Porsches though?
38:55 Harry Stebbings? Yeah.
38:55 Speaker 00 They sell a lot of cars. You can edit this out if it's too long.
38:58 Harry Stebbings? I'd love to. Go for it.
38:59 Speaker 00 I'm a car guy. I love cars. I don't have 20 cars or anything like that, but I do have a nice car. I have an R8 and I love that R8. My son, he's like, dad, there's this kid in school. His dad has a supercar. And secretly I'm like, I have a supercar. I have Iron Man's supercar for Pete's sake. But they don't think of it that way. I don't treat it that way. I guess I don't talk about it that way, but they have no idea that we have this damn. They know it. They know the car. They ride it. It with me sometimes, but they just don't think about it that way. There's something about that. I don't treat it that way. I love it because it's a very powerful, very fast, probably the last normally aspirated V10 of its kind, and it's an everyday driver. I love it for those reasons. It's not a possession that I need to flaunt.
39:44 Speaker 00 Is that your most lavish purchase? Not even close, but we will talk about those things. I like nice things now. I'm a designer and I love things that are well-designed. And a lot of times those things are luxuries.
39:56 Speaker 00 I totally get it. That Gulfstream is not cheap, but I do want to move into a quick fire round. So I say a short statement, you give me your immediate thoughts. Does that sound okay? All right, let's do it. So Lottie told me on this one, ask what books are capturing your heart these days? Can I say not business books? Yeah, of course. I've read like a thousand business books. I had this library down in my basement. I had a flood recently and it destroyed almost all of them and it was really cathartic to throw them all away.
40:24 Speaker 00 And now the only books that are remaining are sort of philosophical ones, stuff about life. I'm reading stuff from Thich Nhat Hanh. He's a Vietnamese, a Zen Buddhist monk. And the peace, peace is every step is one that I'm listening to and loving right now. He's also got another one that I just finished called Art of Power, The Art of Power. I think I'm loving them because it's probably therapeutic and helping me unlearn some of those habits we talked about. Ben, what does a day look like for you? Is there like a typical routine to the day, if you would have generalized? I never had a typical routine ever, even with the business. I was forced into it, but I never really kept it to a schedule. Right now, these days, it's more like dealing with no routine. I just got a dog. You know, I step back, I'm more of an advisor. I should be able to sleep late, but I'm not.
41:07 Speaker 00 I'm waking up at 5:30 like I always did, taking this dog out. The dog is keeping me busy. What was the secret to the weight loss? What worked? A lot of riding and a lot of walking. Walking is way more effective than people think it is. And I've lost five pounds just walking this darn dog every day. But the riding, I think, was a very big deal and stopping soda. Why are we talking about weight loss?
41:27 Harry Stebbings? We're talking about anything I want, it's my
41:29 Speaker 00 Okay, alright. Oh yeah, sugar water, get rid of all sugar water.
41:33 Harry Stebbings? 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.
41:39 Speaker 00 Can I tell you, I visited my great uncle Clarence down in Miami one day and he was in his nineties and he's a funny guy. He used to be a truck driver for a dairy company. And I went to visit him with my wife and I said, what advice do you have? And he was like, really, he was skinny like a skeleton and he was diabetic. He was quite unhealthy because of that. And he said, he told me, no sugar, no sugar. He said he used to, when 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. And he was like a skeleton. I love that man. He was such a good inspiration for me, but he was a skeleton.
42:23 Speaker 00 He was like, no sugar! And it just scared the shit out of me.
42:31 Speaker 00 So Harry, that's how I lost my weight. I just, it got scared out of me.
42:36 Harry Stebbings? I love that. Tell me, lottery tickets. I don't know where to go with this one, but Lottie told me again, I had to ask it. What is all?
42:44 Speaker 00 My wife and I were high school sweethearts. Okay, so we're in high school and we stop at the store and she wants lottery tickets. My wife bought all these lottery tickets and I'm driving us home and she's scratching them off. And she's not a stickler for details, my wife. She doesn't necessarily always read these instructions. She scratched off a ticket and I think it was something like, your numbers had to match the winning number in order to win that prize. And she thought that your number had to be greater than the winning number to win. And so maybe the, the winning number was seven and she scratched off a 10. And she said, oh my God, I won $25,000. And I was so excited, I almost crashed the car. And I was like, oh my God, this is so cool, we're rich. And then she kept scratching and she said, oh my God, I want another $5,000.
43:27 Speaker 00 And I was like, cool, but weird to win twice. And then she kept scratching and she said, I want another $2. And I was like, hold on, lottery tickets don't work this way. You don't win $25,000 and then $2.
43:40 Speaker 00 So anyways, we were so elated that we finally had money because we were pretty poor back then. We grew up in a pretty poor town. That was like our ticket out. And no, we ended up not winning at all. And anyways, I continue to buy lottery tickets and we joke about it to this day. We still have a lot.
43:57 Harry Stebbings? That is the most like realizing depressing shit. When you're like, oh, bugger.
44:01 Speaker 00 That really is. And she still makes the mistake. Sometimes she'll, I'll get her a lottery ticket as a jobbie for a birthday and she'll say, oh, I want, I want.
44:08 Harry Stebbings? You're like, welcome to a day of male chimps around you.
44:13 Speaker 00 Yeah. Never mind the 21 years of building up this great billion dollar business. You won. You think you won. The lottery.
44:21 Harry Stebbings? Now, help me out. You're wise and seasoned, as you delightfully put it earlier. What's the secret to a happy marriage?
44:28 Speaker 00 Oh my gosh. 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. What I noticed was the happiest couples had husbands who just kept their damn mouths shut.
44:47 Speaker 00 I just, okay, so they are repressing themselves. That's the key. And I think I've learned, they're not repressing themselves. They just learned that they've humbled down and learned that they're not always right. And it's not always about winning. And that's not everything is winning. I just sort of let go and just learn to just shut up and maybe listen a little bit harder, not just at what they're saying, but why are they saying it? And when you listen that deep and try to just focus on why are they saying the things that they're saying? I don't know that it helps a lot. It does help me shut one.
45:17 Harry Stebbings? You're just ultimately repressed to the point where you're reasonably rationalizing.
45:22 Speaker 00 It could be that. It could be that. Yes. But I, but also, also if I keep my mouth shut and follow her advice, things really are happening. What three traits would you most like your children to have? So I have an acronym floating in my head at all times that I thought would be my guidance on raising children. It was bliss. It stands for balance, love, independence, and self-sufficiency. Four traits, maybe self-improvement and self-awareness. Like, I want them to just sort of understand it's about slowly incrementally improving yourself and overcoming challenges. Is it adaptability, perseverance, grit? What would you most like to change about the world of startups?
46:07 Speaker 00 I think it's happening, actually. I would love it to not be located only in Silicon Valley in New York. I would love it to just be able to, like with MailChimp, it happened in Atlanta. It happened in our homes. I'd love it to just be everywhere as tech startups, to not have to be in those two locations. Ben, tell me, final one. What do the next five years hold for you? I've met many founders who've sold their business and then they go off and they want to do crazy adventures. And I applaud them for that. One wanted to explore space. And I've told them all, what do you want? And I said, I want to explore my own mind. I want to know why I think the way that I do. I want to know why I am the way that I am. And I think that's infinite. That's bigger than the universe inside here, just getting to know that. And then I also say something that's really vexing, confusing, and angering to a lot of people.
46:52 Speaker 00 Nobody really gets me when I say this, but what I want the most is to not want. Huh. Just want to not want. And I think that- What does that mean? What does that mean to not want? Surely you don't want now. You don't want for anything. You can buy anything. Yeah, I don't feel a desire to. I think it means learning to be content with what you got. Are you there now? And so I met one founder who said that when he sold his business, he bought a yacht. And he went to Greece and he dropped anchor. And he was like, I have made it. And then a bigger yacht dropped anchor next to him the next day, a much bigger yacht. And he was like, oh, I haven't worked hard enough. He said he was so happy when he got that yacht. And then as soon as he saw someone with a bigger yacht, he became unhappy, just like that.
47:35 Speaker 00 Why? Why? And I think it's preventing that. That's what I mean. Have you got there now, though? I don't know. I think time will tell. You said five years. Why are you pushing me now? You said over the next five years. Give me time, Eric.
47:47 Harry Stebbings? Ben, I'm a VC. I'm here to push you. Your timeline, my timeline. That's why you didn't take VC money. Listen, Ben, I've loved this. You are a star. Thank you so much for my incredibly prying questions, but you've been amazing, so thank you.
48:00 Speaker 00 Thank you, Harry. Thanks for having me. This was a lot of fun.
48:05 Harry Stebbings? I absolutely love doing that show. As you could tell, we had so much fun. Ben was incredibly accommodating with my wayward questions. Would love to see more of you. You can find us on YouTube at 20VC. You can also find us on 20vc.com. But before we leave you today, 20VC is supported by First Republic Bank. When private equity and venture capital firms are funding the innovations of tomorrow, speed is of the essence. That's why at First Republic, you'll be paired with your own banker who will remain dedicated to helping your team through all market cycles and will be ready to respond quickly to your requests. As a First Republic client myself, having a direct relationship with a personal banker who I can really depend on to help me make the right decision matters a lot.
48:47 Harry Stebbings? In fact, your banker will serve as your single point of contact by phone, email, or First Republic's secure app. Visit firstrepublic.com today to learn more. That's firstrepublic.com, member FDIC and equal housing lender. And speaking of amazing partners with First Republic there, if you're a venture capitalist or corporate strategist, I want to tell you about Tegus. Tegus is the only company in the world that aggregates qualitative information on private companies from seed stage to pre-IPO. With Tegus, you can access other VCs and founders' expert call transcripts from previous rounds to help source fast-growing companies, create compelling emails to really get a founder to respond and be excited to speak, and to diligence companies when a round is moving fast.
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49:52 Speaker 02 Over to tigus.co/growth for your free trial. And speaking of incredible resources like TIGUS there, I've always been a massive history fan. And so I want to talk about Cooley, the global law firm built around startups and venture capital. Since forming the first venture fund in Silicon Valley, Cooley is one of the most active law firms, representing both early-stage and late-stage financings, handling more than 1,300 private financings every year, with an equal split of investor and company clients. So to learn more about the number one most active law firm, representing VC-backed companies going public, head over to Cooley.com and also check out Cooleygo.com, Cooley's award-winning free legal resource for entrepreneurs.
50:32 Harry Stebbings? As always, I so appreciate your support and I can't wait to bring you an incredible 20 Sales episode on Wednesday with Maggie Hott, Director of Sales at Webflow.
Previous 20VC: The Story of Turning Around MTV, AOL and Time Warner | How To Be Effective When Making Hard Decisions | Tactics vs Strategy and Why Plans Are BS with Bob Pittman, CEO @ iHeartMedia Next 20 Sales: Webflow's Maggie Hott on When to Start and How to Scale the Best Outbound Sales Team, Why Founders Should Not Hire a Head of Sales First, The Must Ask Questions When Hiring Sales Reps and How To Structure the Process Page updated September 29, 2026 · transcript and summary are machine-generated