Everything that Breaks on the Way to $1B ARR with @mailchimp Co-Founder Ben Chestnut

I just saw entrepreneurialism as breathing, you know, it's just a thing you do in life. Only the Mailchimp brand can get away with the kind of content that we're publishing. Most people think of us as just sort of a software company, but we're here to empower. We're here to empower small businesses. They have a story to tell. They've got some cool idea for their brand, and when they log in, I don't want them to have to worry about how to make it work. I just want them to go in and tell their story. You're gonna have mistakes and setbacks. Everybody does. Nobody's smarter. Nobody knows what they're doing. That's actually tremendously frightening. Comforting and scary at the same time, but it's the truth. Prepare for many long nights. Just when you think it couldn't get worse, it's gonna get worse. It's gonna be like a storm and you're gonna be at the front of the ship just holding on for survival. Too much order is really horrible. I think my job is to find ways to create chaos. If you build a successful brand, it's because it's different. By definition, no playbook. First, I dream, I look into the future, and what are the goals? Our brand has sort of won the permission of small businesses to expand into more.

So I am so pleased to have Ben here. I did not know until we did our prep call that Back in the day, I was the ICP for Mailchimp. We'll talk about it, but we all have our hero apps. And I remember back in the day when first I was a SaaS founder, two things happened. I had no marketing help and I wanted to do a blog and an email list. So I had to figure out what blogging software to use. And I'm like, I had over 100 people on my list from a trade show and I wanted to email them. And I don't know how I found Mailchimp. We'll talk about it, but I loved it. And then I had this moment as a founder. This is a while ago where I'm like, God, this SaaS stuff's hard. Will it ever get big? And I'm driving on 101 and there's that Mailchimp billboard with just like the— I know I'm colorblind— the green or the yellow, was it one on the 101?

Yeah, it was like a little blue.

Yeah. Yeah, and I was like, oh my God, how much does that cost, a billboard? That must be like half a million dollars. Mailchimp must be huge. But it inspired me that, hey, like, this SaaS stuff could be pretty big. So it was very inspirational. And fast forward today, we were acquired last year for how much? I can't remember.

12 billion.

12 billion dollars. So pretty crazy journey, but not only is it crazy, it's a company that was fully bootstrapped and pretty consistent to its original vision from the beginning, right? So we're going to dig all of it, but it's definitely a hero story. And again, Ben was kind enough to do us digitally during, um, during the craziness, and we asked him every year, but he, he came this year. So, um, I do feel, I do feel blessed. So Well, I wanna dig into a bunch of things, especially some things I learned about Mailchimp that are not obvious from SMBs, 'cause I think it's super interesting. And then we do have a little time at the end because there's not another session on this, so if folks wanna leave after half an hour to go to another session, I don't know if Ben will be insulted, I won't be, but we can stay for a few minutes of questions, so think if you have a few, we have a little more time than I thought. But first, just deal stuff. M&A's so nichey, but this was interesting. To me. Tell us how, how long the deal took to happen.

Oh, the, the Intuit deal took a little more than a year to happen.

A year. A year from first date.

Yes. Okay.

And so what— what— as much as you can tell us about— I think some of it's public, but how did it happen? Did you get a random email or a DM or how did— how does this process happen for $12 billion? How did they get started?

We had been through sort of a little bit of an informal round with another couple of potential buyers. Yeah. And, you know, it, it didn't end with a good, a good deal. So we walked away from it and I I had sworn I would never listen to another offer again. I was done with it. I was going to move on and just run my company for the rest of my life. And then, you know, maybe within a couple of days I got a call from Catalyst, actually. I'd been working with them for many years. And they said, just take one more call. You're going to like this one. Oh, interesting. So I took a call with Alex Chris, my new boss. And I mean, we hit it off immediately. He's a small business entrepreneur. He'd been with Intuit for 17 years by then, but he had run a business, got acquired, and he knew the passion required to manage small business companies, and he knew the pain that they suffered from, and he knew what drove us at Mailchimp, and we just got along really well. But they are also a very careful company. They care about culture fit, and they did a lot of culture diligence, and that all, which I loved. I loved that they cared that much, but that did mean 1 year of kind of wooing each other.

So you want, there's a couple interesting things in this. We could spend all the time on this, but You went through another deal that didn't happen. That took months and months and months of distraction. It didn't happen, which is so frustrating. For whatever reason, it's so frustrating.

Right.

And then another year to complete this, a full year to complete this, of getting to know each other, right?

Yes.

And you didn't actually— usually I find these relationships, these come out of a relationship, right? And you hear of something, but this wasn't a preexisting relationship.

Not at all.

So you had to build it after that initial meeting?

Lots and lots of Zoom calls, phone calls, and text messages between me and Alex.

And it was during like peak craziness too, right?

It absolutely was, yeah.

Was that better in some ways?

It actually kind of helped me. I'm a little bit of an introvert, and so not having to meet him in person kind of helped in the early days. Yeah. So it was kind of nice, and you know, I got to talk to Sasan, the CEO, and also the founder, Scott Cook, who had given me some great advice many years ago about how to evolve Mailchimp to the next level, and it was just kind of weird and full circle for them to come back around and think about acquiring us.

—and they knew— so a year and you didn't know him, but of course everyone knew about Mailchimp. How did they think about Mailchimp? Obviously it's an iconic brand, but what was in their head? What got them excited since they didn't know you personally?

We both kind of hit it off very fast, Alex and I, and the common vision that we had was to have one great platform for small businesses. And we would both— we're talking to our customers and noticing that they were using so many different SaaS applications, paying so many different fees, and we just thought, you know, I had always dreamed of maybe we We handled the front office very well at Mailchimp, but what if we could build back office solutions? And the same thing happens over there at QuickBooks. They manage that back office very well for 38+ years, and they wanted to help their customers grow their audiences with the front office. And so it was sort of a match made in heaven.

Now with— and I'll admit, I'm a long-time Intuit customer, but I don't know all the products. But maybe being marketers being less their core focus, right? Is there a DNA challenge? Did they have to get to know marketers better? A non-issue, or how does having a similar but adjacent buyer work out?

I think it's still very early days, and they're very open to learning from us, and teaching them the ways of being weird. I think it's all a matter of teaching them how to embrace the kookiness and weirdness of the Mailchimp brand. That's what's appealing to marketers and brand managers out there. They love that weirdness, whereas I think if you're running back office and you're doing taxes, you have to be like, I mean, they have personality and character, but I mean, different. I think, I think creativity is frowned upon in accounting, uh, so they, they're having to learn a little bit there.

Yeah. So that's an evolution, embracing the weird.

Yeah, it's a journey. Cool.

And then, and so one last thing on this is just at Mailchimp scale, right, we, we passed a billion, although you notice it was right after the acquisition, right? Yeah. You don't really need to integrate the apps, do you? You just need it to thrive. Integration is not a huge deal at your scale, is it? It's not a top priority.

They've really made it a mandate to make sure that we keep our independence. Yeah. And so far, so good. You know, on the whole keeping it weird thing, can I just say we've got a campaign going on now with like a dancing rug and weird rolls, and I actually didn't lead that campaign. I'm usually at the heart of a lot of the weirdness, and to their credit, this one was straight from Intuit and our new CMO, Michelle. And I'm sort of looking at it as half spectator, just saying, I'm like, damn, Mailchimp's weird. Now I see what everybody else sees. I'm like, this is weird. What's the rug thing? Like, it's kind of kooky. So they are learning fast, I'll say.

Is the weirdness bar gone up now that we see more weird? I think it might have.

I don't know. It could just be that, you know, I've stepped back as CEO and now I'm looking at it with a fresh set of eyes. And I am, I'm walking around the halls. And when you're CEO, you just focus on day-to-day, thinking about next step and 10 steps from now. It's like a game of chess. I've stepped back as CEO and sort of, I'm walking the halls and looking at some of the fun stuff we've done over the years, and I'm like, wow, we are weird.

Yeah, it's kind of cool. So, I mean, you have a background as a designer. We didn't have a— but this weird thing is interesting. Yeah, what— how did you come to weird? Like, I remember in the old days of eSignatures, my co-founder wanted us to be the bad boys of eSignatures, and I'm like, I don't think that's going to work. Like, this is a product, yeah, 99% of the world doesn't trust, and I know you're a great marketer, but this is too edgy for back in the day, right? So how did— what, what did you want What did you want to get out of Weird? What was your vision here?

I mean, it was really probably coming from our small business customers. My co-founder Dan and I just believed in, really we didn't try to strategize that much or come up with all the answers ourselves. We just went out to the customers. And when we talked to them, they were kind of kooky themselves. I mean, whatever small business it is that you're trying to run, it's probably been done before. But each founder thinks, I'm going to do it better, I'm going to do it my way. And that's their personal brand. And I don't know, that was the first couple of iterations of our brand. They were a little bit weird and funny in a kind of a monkey kind of way. That was really the theme. And they just loved it, and we just sort of rolled from there. And, you know, I think one of our teammates kind of encapsulated perfectly. I think she came up with, "We got you because we get you." I think that's the appeal of our brand. For small business owners, we get them. Look at us. We're weird like you, or we're kooky and unique like you. And it's just worked for 21 years.

It is. I want to go on, but one interesting thing you brought up on the acquisition was that for the first time you added a CS team, right? In terms of customers.

Is that right? Am I simplifying?

We've never had any kind of sales or customer success ever. And what did you learn from that? What did you learn? I mean, you made it pretty far without a CS team with small businesses. What did you learn from that?

I mean, we started to— I mean, we just did so well with smaller businesses, and then we noticed as they grew, And, you know, maybe they would hire VPs of sales or VPs of marketing, and they would start to use Mailchimp. Their needs changed. Suddenly, it wasn't the founder who loved our unique and kooky small business brand, it was a new person, and they treated us differently. And so I would go out and visit some of them, and, you know, I would say, "What do you think of our brand? Where does our brand, you know, rest in your brain with other brands? Are we next to Nike? Are we next to Apple?" And I remember one marketer told me, No, your brand lies next to my microwave oven. And I said, you know, it kind of broke my heart a little bit. And I said, well, what do you mean your microwave oven? He said, you know, my founder liked you, he loved the brand, but I've got to grow this business and I need you to be reliable. And if it doesn't cook my food in a minute, I want someone to call and answer my questions and just get it running again. I don't want to have to read KB articles, blah, blah, blah, blah. So, you know, that told me, gosh, we've got to like spool up a customer success team of some sort. And it's been a long journey. We've got some great new executive leaders that are— and Intuit's got a lot of experience with this, and they're going to take it to another level.

But we talked— let's jump into that, because it was so interesting when we talked before of where the breakpoint is for your brand and product. And we talked about this breakpoint when marketing comes in, when a VP of marketing comes in, and whether you want to retain them always as a— do you always want to retain them as a customer?

It's tough. It's tough. It's really— it kind of requires a different culture, you know? I mean, for 21 years, we built one culture very well for the self-serve SMB market. And when you start to serve a completely different kind of customer set, you have to learn some new tricks. And we used to get very comfortable saying, well, I mean, if we're not right for you, then sorry, you'll have to find a new provider. And then we learned that we were letting a lot of customers down. They really wanted us to grow with them. It is a tough challenge. I feel like, you know, if they get started with your small business brand and they love the little chimpanzee, you know, and then the founder hands the keys to a VP of marketing, they really, their job is to take it to the next level. They want almost a different brand, you know, and I've struggled over the years, many years, to try to build that sort of Mailchimp Pro, that second level Mailchimp. It's tough. It's tough. It's tough to build one great iconic brand. To try to build two, I don't know. I don't have enough years.

Well, it's your own version of champion change, right? Yeah. We talk a lot about champion change, but really it's founder to VP. The VP, they might like a worse product, right? But they probably have some different, different experience, right? And does the founder want to use— does they— do they want to use their chip to stay with their favorite app when the VP maybe is using something else, right? Right. That's right. Yeah. And so this, going back to this Mailchimp Pro thing, so you never did build it. Would you, could you see in the data, like I could imagine, I mean Mailchimp, you can use it a lot, but I could imagine around $5,000, $1,000 a month, you might guess that there could be risk, right, in the account. Did you look at signals or anything like that?

We didn't look at those kinds of signals because we could, when you serve some of these small businesses, especially with e-commerce, if they're in that industry, you could have a small business with 2 or 3 employees, but their database is in the millions. It was really wacky to try to look at the data points. What we looked at was, um, if the founder set up a subaccount, you know, would send a username and password to their VP, you're basically making a copy of the keys for a VP. That was the potential breaking point. Got it. That was our red flag. If a new VP comes on, they're not going to read the instruction manual like the founder did. Got it.

So another admin, another core user, that was the signal right there.

That's right. And they're starting over with a fresh set of eyes, and competitors are there ready to talk to them and do the sales pitch, and we're like, RTFM, read the manual.

Not a great experience. But mostly you, and wildly successfully, you stuck doggedly to SMB, right? That was where our hearts were. That's what I want to talk about just for a minute. Is it just your DNA? Yeah. Your DNA as founders? Because those are, when you, we talked about, I think you said Uber was like a big account you lost, right? And that hurts us all as founders, right? But you didn't change Mailchimp. You didn't radically change, you didn't bang your, maybe you did, I don't think you banged your shoe on the desk and said, we're not gonna lose another massive customer, did you?

I felt like we, it was a technical challenge to me to just stay true to our roots and our brand, but make Mailchimp more performant. For those larger customers. So yeah, I kind of flipped the boat. Kind of did. Yeah, a little bit. I mean, it was, I remember it was like 6 figures a month was the revenue that we were getting. It's a lot. Now, you don't just sort of brush that off. I mean, that's a learning lesson for any founder. But I just, I kept challenging my team to like just make it more performant for those really large databases. And they really did. It was a great kind of constraint or technical challenge that made Mailchimp, it ended up making Mailchimp better for like the millions and millions of small businesses. And as for the larger customers, it's sort of a rite of passage. You know, if you go through high school and college and you have your Honda Civic and you graduate and you get a great paying job, do you upgrade to the Honda Accord? Or do you get your Beamer or Tesla or something new? And we saw that rite of passage. And we also saw that if we stayed true to ourselves and kept improving, after a few more years, they realized that darn Beamer is hard to maintain. And they come right back to us. And they kind of use the backdoor, they use the Mailchimp API, and that's where really, really massive businesses still use Mailchimp.

Were you able to track like word of mouth in terms of, and related in terms of customer acquisition and boomerangs, did you have a sense of how much came from word of mouth?

You know what, we were so, we didn't have a team that would track that sort of thing. We were so, with freemium we were getting, you know, I remember 10,000 signups a day from new customers, we were so busy trying to control that flood of new users and trying to prevent server outages, I don't know that we ever really had the time to look at retention.

Yeah, it's interesting on that one, we chat about it, what's super interesting to me and maybe to folks in the audience is that because of that top line growth in torrent, yeah, NRR, even—

I don't know what that's for.

Churn were not important to you, as long as you hit the top line number, right? Yes. You didn't, I mean, we're all talking about lighthouse metrics, like SMB, how can we get to 100% NRR, like, Enterprise 130 and measuring GRR in every metric, but this was never a lighthouse metric for Mailchimp.

I don't know, and I never had investors, so I never had to do reports.

That could be a part of it.

No business plan. I had a monthly bank statement, and I said, "What's the starting balance, and what's the ending balance? Ending should be bigger." Yeah. And it always was bigger. I still—

And even as you approached a billion, as you brought in more more, and we can talk, maybe we'll talk next about a couple great hires. They didn't push you more on this stuff as you brought in more DNA? You were this hyper-SMB DNA for so long.

They probably got tired of trying to teach me it, and they just gave up on me. I got it. They did it quietly somewhere. Got it. But I'm not aware of it.

Well, let's talk about, let's come back to the team, but let's talk about bootstrapping for a minute. Maybe we'll just use one more slide as a prop. We probably don't need them. Right. But it is different, right? And before we get there, just because on the internet and with founders, there's so much discussion of bootstrapping versus venture-backed, but I don't think it's usually a choice. Was it a choice for you for a long time? Did you, when you were an agency in the beginning or starting, did you turn away $10 million in seed funding? It wasn't a choice, was it?

Nobody really visited us. Yeah. Yeah, we were in Atlanta, Georgia, and nobody bothered to fly over until one of our competitors, Constant Contact, went public in '07. And then suddenly people in suits started to show up at our door. And I just didn't understand it. You know, I'm a product of the dot-com days. I was laid off in April 2000 during the dot-com bust, and there was a lot of distrust for a lot of that sort of, like, the VC world. It was a movement to do more pragmatic programming, yada yada yada. So we kind of avoided that for many years, and then they started showing up around '07, and I always invited them in, let them buy me lunch, and just try to learn as much as I could. But Mailchimp kept growing and growing, and we never really needed money. They would offer it and I would try to figure out what would I spend it on. And we just made plenty. And we ultimately never, never needed any kind of investment. Yeah.

So we were the other, you know, one of the other iconic bootstrap companies. I mean, there's a few, but is Atlassian. And we were talking before, Michael Cannon-Brookes, when he was at Saastr, said years ago, he said, I probably couldn't do Atlassian the same way today because I had 4 years to go really slowly when we're bootstrapped. Right. And I think Atlassian probably started in 2000. Right. Could you have done as great a hero story as the bootstrapping side? Could you have done it the same way now, or is the world too fast?

I could do it again. No, I think at that time, so they started in 2000, we started in 2000, that was a different time. Cloud was new. That was a new word. SaaS hadn't really even been invented just yet. I mean, everything was so new. It was a time of, it was like an unbundling. Who was that? Who's that guy, Barksdale? Yeah. He wants— somebody asked him for the secret to tech, running a tech company, Jim Barksdale, and he said, "It's cycles, bundling and then unbundling." And that was kind of a joke he gave, but it's true. It's really true. And so, like, at that time, 2000, everything was unbundling from desktops and mainframes or whatever we were using back then, PCs, and going to the cloud. And there was like, you needed a marketing cloud, you needed sales and CRM. Everybody was willing to pay for all of these different unbundled point solutions. And now I think that we're at a different time when people want it bundled back together again, and the cycle is just going to keep continuing. I think right now, I don't know that you could do what we did. Yeah, I think there— it will happen when there is a great unbundling again.

And what is, for MailChimp, what— I mean, this bundling, unbundling is interesting, right? Because we get busy, we have a trusted vendor, we want to buy more from them, but innovation happens, right? Maybe that's part of of the gym. What does bundling mean at Mailchimp today? What is a core, what does that mean versus 4 or 5 years ago?

Well, for us right now, it's sort of this hypothesis with Intuit that we had that small businesses— Oh, that's the super bundle. Yes, small businesses really want one platform where they can manage their business with QuickBooks and then grow their business with Mailchimp. Got it.

Well, that'll be a big experiment, right? It's the big— It's gonna be big. Related to that, we chatted before, about product expansion. I learned some interesting stuff from you, but what works and what doesn't, right? And what worked for you? I think we talked about landing pages being a surprise, right? And e-commerce being harder than you expected to expand in, right?

Yeah, e-commerce was a bit— it's a challenge to break into that world, but— and we built all kinds of things for our small businesses. Landing pages was one that we built I kind of thought they were boring, not really a big deal, and it was probably one of our most popular features over the last, in recent years. I mean, it just took off and sold like hotcakes, and I still to this day can't explain it. I'm just thankful that we had this culture at Mailchimp to constantly, not, we didn't even use the word innovate as far as I can remember. I always just said tinker. I said just keep tinkering with code and just keep trying little make small bets. I didn't want moonshots. They were too expensive. I just said make little small bets and fail fast and then just kind of like recalibrate. And landing pages is one of those little tinkering experiments someone did. Who knew? I mean, it just took off.

Well, that's— there's a little bit of non— it's interesting, there's a little non-standard of like as you get bigger, the bets have to be bigger, right? They have to be material. But maybe that wasn't how you thought about it. You still wanted to try it. Maybe it's the bootstrapping mentality. But landing pages turned out to be much larger than you thought. It wasn't planned on a whiteboard. That's right.

I don't know if they need to be all that. I guess they do need to be bigger, like if you're a public company and you have to care about Wall Street. I mean, but I think you need a lot of those little things baking in the oven, because you never know which one is really going to take off. It's tremendously hard to kind of manage that and then also run your business at the same time. That's tough.

Yeah, I just— as we're learning, I mean, back in the day we had Jeff Lawson from Twilio come once, and just after IPO, and he's like, I'm gonna do 100 experiments. I'm gonna do this type of SMS and M&Fs, and we're gonna see what sticks. And the next time he's like, well, I'm gonna buy SendGrid and Segment, 'cause I gotta get scale. Like, the experiments have to be really big. And then we had Peter Gassner from Viva who said, your experiment has to be bigger. Because you're gonna, if Mailchimp's coming up at a billion, and I wanna do 2 billion, my experiment better not do 50 million.

Yeah, you're right. You get to a size and maybe you just don't have the expertise in-house. You have to acquire the talent and bring it in. Yeah, I get it. Yeah.

But you said, but the landing page, you said one of the reasons it took off, and I think it's a learning we've all figured it out, is it's the same buyer, right? Versus e-commerce maybe is more complicated to sell to?

Yeah, I think with landing pages, what we overlooked, and we went back and talked to small businesses, they had their e-commerce solution and they loved it, and they had Mailchimp, which they use for the email marketing, But, you know, the marketer is different. They have different needs. They need to move fast. When they want to modify their commerce, when their shopping cart, they've got to ask for technical help from an engineer, and those two worlds tend not to like to talk to each other very much. And so marketers really wanted their own little solution that they could use without talking to any engineers. And they love the ability to spawn up really quick landing pages inside of Mailchimp that connected to their carts through the API and sell their stuff. So, yeah, that was the insight that we had.

And the— it was obvious to me when you said it, but the core ICP is the same today at a billion, which is someone who wants to get marketing going without any engineering resources, right? That's the designer background. Was that the ICP you intentionally, or someone intentionally went after, and it scaled, right? What's ICP? Well, the target buyer, user of your product.

Yeah, yeah, I mean, I mean, with—

for the very small business, your own company to a billion, you don't need to know any of these things. MRR, ICP, they don't, they don't matter. Just the top line.

Target buyer then. Yeah, why do we say ICP? Jason, come on, come on, marketing mumbo-jumbo. Yeah, it's the marketer. It's really the small business founder who You know, when you start a small business, I don't know, I don't think that you're thinking about your CMS or your CRM or anything. I think you're thinking marketing first. How do I sell my stuff? That's the first thing you're thinking of. So we're thinking about that. We're thinking about that founder.

Cool. And going back to one that we skipped around a little bit, but it's always interesting. Now that you can reflect a little bit, right? Yeah. Did I laugh too loud?

I'm sorry. It's sort of like erasing old CEO habits is what I'm trying to do.

But yes, reflect, let's call it reflect. 2 or 3 top game-changing hires, 2 or 3 top game changers on the journey.

My gosh, in the early years we had an engineer, a lead engineer named Chad. We called him the Chad because he never slept. He, I mean, really, he never slept. Left, and he was constantly building stuff. He was amazing. He was the one— we hired him to turn Mailchimp into two products, to take our old code, divide it into two, make one of them the list building for your blog, and the other one, if you wanted to send emails, that's when we charge you money. That's when I get ya. And he worked on that, and he was a machine, and after a year he said, "It's impossible. Your code sucks so bad. Let me just keep it one product and just make it free up to a point. And really, that's where freemium came from. Yeah. So he was amazing. Aaron Walter, our first designer, he was the first person I hired to take over my job as designer. He really cared about the brand and the UX and kind of melding that into one great customer experience. Man, that was transformational. And I've had two COOs prior to Intuit. Neil Bainton was our first COO, and he was sort kind of at that time our adult supervision, like Eric Schmidt managing Larry Page and Sergey at Google. He was their adult supervision, and Neil was my adult supervision. And he was an amazing COO that I think, I don't know, if you're a founder like me, you can be pretty abrasive, and I know you're obsessed over the product, and kind of in that weird Steve Jobsian kind of a way. And Neil was a really good buffer from me. So a lot of people just went to Neil instead of me, and I could really push Neil to make the product better. And then Farah, our next COO, was also just that buffer. Neil got us from like $0 to $300 million. Farah got us $300 to $700 million. And when did you—

we all want this magical COO that can hide our warts and issues, right? Yeah. When did you— the first one, when did you decide you needed him?

How'd you find him? Well, I mean, with Neil, he was really more adult supervision. He was a mentor. To be honest.

But your VCs didn't force him in?

There wasn't any— No, there was no forcing. I think, I just think that he was just a good balance. I mean, he knew, we knew our boundaries, our roles and responsibilities, I think they say now. But we knew he was really good at the operational stuff, and he was very senior to me. You know, he was in his late 40s, I was in my late 20s at the time. And I needed that experience in-house, and a lot of people really liked talking to him. He was like our father. So I mean, he was just a really— it was a sort of a yin-yang thing. Did you go recruit him?

Did you hunt him? Or how did you— what was the decision process?

He basically joined our dot-com right before we were all laid off together. Oh, so you knew him already. Yeah, yeah, we sort of kept the relationship. I gave him a lot of branding advice, he gave me a lot of marketing advice, and then eventually our paths crossed again and he joined.

Okay, we'll take some questions, but I want to hit two other things. One, a fun one on acronyms. Do you think there's such thing as PLG? What? Well, I mean, Mailchimp is so interesting for freemium, one, because it's successful, but two, because you decided later, right? 2 to 3 years into the journey, that was the big accelerant, right? Was going freemium, right? 9 years into the journey. 9 years into the journey. Okay, we should chat about that. We chat about— but half this audience wants to know about PLG. They want product-led growth. They want a magical product that when I get my little chimp in my email or I open it up, or something happens on the page, all this is, this is half the marketers in this room want to inject PLG into the product, but it doesn't sound like even today that's a top acronym at Mailchimp.

A product-led growth? Yeah. I mean, that was everything to us was, I mean, innovation, new features was marketing for us. Yeah.

I could not— So nothing new. PLG is nothing new in your book, right?

Yeah, no, no, that just, that's like common sense to me. We didn't call it PLG, we just called it building stuff.

Well, we didn't used to call it SaaS or cloud, but we kind of have to go in with these acronyms, don't we? Building stuff, yeah, it's become a holy grail. Alright, one last thing I want to hit, and we'll do some questions, but a billion ARR, right? A couple things. First of all, did you think 22 years ago Mailchimp would get there? Did you think you'd get to a billion?

I had no limits. I had hoped that we would get massive. I'd studied the the art of it, though. And I learned from a lot of CEOs and founders out there that you could probably get up to $800 million, and that last $200 million is the hardest you'll ever get. And that was absolutely true.

Yeah. Yeah. What was so hard? Just—

pandemic didn't help. What's that?

The pandemic did not help. No, it didn't help.

No, it didn't. No, it helped with half of our customer base that were e-commerce. Yeah. Yes. But we had a lot of, uh, bricks and mortars. Oh yeah, we really suffered bad.

One side or the other. Yeah, yeah, yeah. And so it's, it seemed, it didn't, so it didn't seem crazy to you. Is there a ceiling? I mean, I know you can't speak so much on behalf of Intuit, but can, can Mailchimp do $10 billion? Can all these products do $10 billion? Is it gonna do more? Like, is there any ceiling for this stuff?

I don't see why there should be. I mean, I think if we just keep that PLG mentality, PLG mentality, and just keep innovating and listening to small businesses and understanding what they need and pivoting fast and building for them, I don't see why there there's, there needs to be any limit. I used to think a trillion-dollar market cap, there's no way, and then now it's happening left and right, it seems like.

It is left and right.

So I mean, that was a theoretical limit before a company would implode, and it's not. I don't see them imploding.

So even Intuit, I should know, but I— tell me how much revenue Intuit's doing, but I think they grew over 30% last quarter, right? I mean, MailChimp helped, right? It's crazy, isn't it?

It's crazy, crazy, right?

At that scale, that a company of Intuit Yes.

I mean, you know me, I don't track numbers, so I don't even know.

But it's a lot of growth, right? So they've done well. Last one on this and then we can take some questions. So please ask them. But the enduring side of SaaS in 2042, is Mailchimp still around? Is it a brand and a product and is it similar to today? I absolutely see it still around.

Yeah. Yeah. Yeah. I see it really baked into QuickBooks. And I think that we're really just getting started with this. It's still very early days, and I just see customers managing their lists, managing their customer base in QuickBooks, paying their bills, and then saying, you know, when you look at that invoice that's been paid, you say, damn, that's a really great customer. How do I find more customers like them? Yeah, that's a button they can push, and then Mailchimp will take care of that. Let me find similar customers just like that. We have the data to do it. I see that really being sort of the next step where we go with that.

You're thinking like 21, 42, 22 24, when the last internet is used, it's an email? I mean, it was like, it could be the last. I think it's like the first thing on the internet. I think it may be the last thing we do on the internet too, is send an email, right? I mean, it's an amazing protocol, isn't it?

People have been telling me for 21 years email's dead.

And it's stronger than ever, right?

Going just fine. All right. Yeah.

All right, we may need some help, but any of you guys have some, come on up and ask a question. Hey, Rob.

Hey, Ben, congrats. I never see you in Atlanta. We have to come all the way out here to see each other.

Austin, Texas. That's what SaaS is for, get everyone together, right? So Ben, for founders who might think they don't ever want to be acquired, what advice would you give them, and maybe what was persuasive to you along the way?

Wow, Rob, that one's— that's a long one. If you don't ever want to get acquired, never open the door to anyone. Because here's really, honestly, if you open the door and let one in, you have to bring your executive team in with you eventually. And once everyone gets in on that, it's very tough to back down after that. When you say, "Well, that one didn't work. Let's forget about it altogether and go back to running our business." People— [Speaker:JASON M. LEMKIN] It is tough, right? [Speaker:CHRIS GILMORE] You can't put that toothpaste back in the tube. So if that's what you really want, never do that. But then I would warn you, like, you should never say never. And, you know, there are going to come these weird times, these cycles in the market where, my gosh, it's going to seem like every one of your competitors is getting way more funding. They can print equity in lieu of actual cash. Like, I've never understood that. And then it starts to get more attractive for people to join those companies, and you start to wonder, should I do that? Should I do that? And, you know, my advice would be like, maybe wait. Maybe wait a little bit, and you'll see the cycle turn again. But I think all of those factors started to make us think about doing it, and it helped— it convinced us to open the door. And then once that's open, it's hard to put that genie back in the bottle. So thanks for that question.

Hey Ben, big fan. Atlanta founder as well. Cool. So I can imagine you can relate in the fact that one of the biggest problems in Atlanta right now, it's not access to talent at Georgia Tech, Emory, etc. It's not it's not a lack of founders being there because you walk around, got ATV, ATDC, a lot of hubs. I would say it's access to capital. Um, so I'm curious, founders like yourself, Tope, Cobb Porter exiting recently, do you think that having that into the Atlanta ecosystem is actually going to change that capital flow into the ecosystem to get more founders funded?

Um, what— you're a founder in Atlanta, what's your Arkom.

We do churn mitigation for credit card processors or merchant acquirers.

Gotta give them some airtime.

Yeah, I, you know, it's a good question. I don't know much about creating access to capital. I never had it, never cared for it very much. I remember reading something about how ecosystems, startup ecosystems, get started, and a lot of it comes from acquisitions and talented people finally leaving your company to start their own. And I remember reading that many years ago and thinking, wow, there's so many talented people at Mailchimp and they won't leave, because it was such a great place. We made it such a great company, you know, and I think after an acquisition happens, people, they get transaction bonuses, they want to go out and start their own thing like I did, and I think that's the best sort of stimulant. So I hope that Mailchimp helps Atlanta in that way. Thank you. But I think if you want access to capital, if you want We want investors to come to the city. I think they finally learned that Atlanta is a great city to come to. And I think it's really on founders to build great businesses worth, worth the flight over. And we've got a lot of those in Atlanta now.

It's much flatter too than it used to be, right? I mean, I invested in Salesloft pre-revenue, so I've known Kyle and I introduced him to all his VCs because no one would go to Atlanta. That's right. I introduced him to Emergent. I've invested too in Emergence and Insight. But today everyone gets it. So I just think COVID makes it easier. Here. Yes, because everyone's— it's not that it's— it's still easier to be here, don't get me wrong. You can walk around and meet 500 VCs, but every investor is hunting, if not globally, across the US. So it's not— I think it's the talent. It's actually the talent's the big thing. The capital has become a little bit— a lot more flat than it was before.

But, but, you know, if you're going to start a B2B enterprise company, California is absolutely the best place to be. B2C, like a consumer brand, You can't beat Atlanta. We've got Coca-Cola, Home Depot, UPS, Delta Airlines, Chick-fil-A. Like, top, top brands are all right there in Atlanta.

Thanks for the question. Thank you. Thank you.

Hi, Ben. Hi, my name is Jerry, and like you, we are also building a bootstrapped company. And my question to you is, as you thought about building your company bootstrapped, how did you think about profitability and thinking about investing in the right areas? As did you always try to maintain X percentage of profitability? How did you think about that? I mostly, yeah, I talked about looking at the bank statements for one, but that was maybe, I guess, the trailing indicator or something. What I really cared about most was, here's some acronyms, the LTV. LTV. And CAC, I cared about that.

You did care about LTV.

That was the only thing I cared about, and it was really because my first COO, he made me listen to to some of the investor calls of our competitors, and they talked about their customer acquisition costs and their lifetime value. And I knew our lifetime value from a typical small business customer, I knew how much that was, and the trick was don't spend more than that. Yeah. I like it. Oh, and like, the lifetime value, I knew how long it took me to get that, you know, and you try to shorten that get that as short a time as you can, recoup that cost ASAP. That was really all I cared about. I would watch for that like once a quarter. Gotcha. Thank you. Yep. Good luck on the bootstrapping.

Hey man, so my founder also bootstrapped from Argentina. We're about 100 people, $10 million in ARR. We're doing well. Wow. But, yeah, but we are We're having a problem now with our tech and something about what you said yesterday. So the tech is built in a way that's not like— we didn't go and hire the best developers at the very first start. So it's a lot of old code that we're needing to redo. And so we're plateauing a bit because we can't scale the tech right now. How did you manage that as CEO, not being from a technical background? Because you're not a CEO that comes from the tech side, and that's my my challenge as well. How did you manage that, and did you ever have that?

I actually think if you don't come from the tech side, it's an advantage because you stay the hell out of the engineers' way. I mean, if you look over their shoulder and say, "You coded that wrong," I mean, it's just not going to help anything. So I had— I tried to hire the craziest and the best, and I just gave them cool toys, really powerful computers, and as big monitors as I could find at the time, and just left them alone. And I bought them snacks. And I mean, in the early days, I mean, I'm, yes, I'm trying to be funny, but in the early days when you have pirates, I mean, that's all that matters is they want to build great stuff. So we talked about the purpose, the mission, and they were just passionate about it. And they, and, and I just tried to stay out of their way. And, and I think v3 is pivotal for almost like every product. Like there's something about about V3. After V3, you're real. That's product market fit, maybe. And V3, maybe you're at V3. Our V3 was like that. It took a year to get it done.

We're at B4, actually, and that's, yeah, but.

Yes, it's around that area, around that time. But yeah, I mean, it's gonna hurt, and I don't know what to say, but this is a massive one. And then hopefully if you do this one right, then it's gonna be like nothing but iterations until maybe like V8. That was the next one.

We've all been through it, right? Yeah. But if you get the best talent, that's the only way to solve it. Whether it's a VPN, you're better people. We've all— everyone in this room has been through some version of it. Yeah. But you got to do it only once, right? Or it destroys you, right? That's right.

And the best talent doesn't always mean the best pedigree at the best university. Sometimes it's just some scrappy, really weird— like, we hired one that would look like an axe murderer, and I was afraid to be at the office late with him, but he was amazing. He built our entire API. I mean, he was just awesome. Awesome. So it's like, like, cast a broad net. The broader the net.

Yeah. All right, thanks for the question. Congrats to getting your $10 million.

Yes, man.

Thanks. I'm bootstrapping again also. Awesome. And I hadn't thought about this till I heard you talk about future Mailchimp, but is there a way we could use future Mailchimp to draw visibility to the whole environment, social governance and impact on the climate of the apps that we all use?

Gosh, that's a deep question.

I've been in it for 40 years. I've had time to think about it.

I don't know. You know, I have no idea. I don't— I'm a designer, and my product has a chimpanzee as its mascot. I don't— I'm probably the worst person to ask. But like, crazy is good, so I'd love to brainstorm with you about it. Yeah, that'd be great. Thank you.

All right, we'll take one more question and then give Ben a break, but thank you.

Hey, so it was mentioned earlier that Atlanta is becoming more and more of a tech city, and my question is, during the early days being in Atlanta, how were you able to attract top talent and retain that top talent without massive funding as you're bootstrapping over the years?

Not having the massive funding was in retrospect an asset because it attracted people who truly cared about the cause, not to get that money and the equity for it. So it's not that much of a weakness, to be honest with you. But when you're in the moment, it's hell, I know. But in retrospect, I'm so thankful we didn't have that massive funding. We tried everything. We tried to post jobs everywhere. What ultimately helped was we just said, forget it, just stop trying to hire people and iterate and launch cool stuff. And so we started to launch some stuff that was kind of innovative at the time, and that started to attract engineers. They would notice that stuff, and that's how we got our call from the Chad, and he came over. He was amazed by it. And then, you know, he was, I think, kind of jaded at his current startup. They weren't really listening to him, and he felt like he wanted to go to a place where people would listen to him. And so that's why he joined us. And I think that the one that looked like an axe murderer, he had a heart of gold. He was so kind. But he said that he joined us because all of my screenshots, my username, the fake username was Roger Waters. I was a Pink Floyd fan, and he was a Pink Floyd fan, and he said that's why he joined us. So I mean, in the early days when it's pirates, man, you just, you have no idea. You have no idea. I mean, just keep trying, and I would say really launch cool stuff. Just try to do cool stuff and publish it as much as you can, and that'll attract the talent.

So you got mission— I sometimes call them missionaries. They're folks that get— yes, yeah, they could make more money. You got to pay them enough to survive, but there are— if you're— if you're— most folks here are charismatic founder, they wouldn't be here. You can find a couple missionaries, including engineers, that will— not, not all of them. Like, I mean, Google pays better, Intuit pays better, but there are The stories are missionaries, so if you're struggling, be that, find your own charisma, and there's always a missionary story, right?

I paid them more than I paid myself in those early years too, by the way. You have to pay them. You don't have that massive funding. They want the cash. Sometimes I just didn't pay myself.

And then it sounds like, and then we'll wrap from that, but it's an interesting story, and then you got the missionaries, but then you created a center of excellence. So you got, the missionaries got you a few good engineers, and then people wanted to work on cool problems. Right? So you're able to get the expert, or—

and the rest. Gravity.

And that's how you get this flywheel going in engineering hiring. Like, find the missionaries that are great, and then people will be attracted to working with them. And then it's never easy, but any great founder, someone's got— some great engineer is going to want— some romantic engineer is going to want to work for you. Someone that believes in your mission, right?