The Ledger
Every statement that passed quotation and attribution checks. Mix any filter with any other: certainty 1/5, debate potential 5/5, or both at once.
why aren't all 41 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 0 checkable ones are still open, waiting for their date. predictions held up or didn't; assertions are supported or contradicted. on every card: ▮▮▮▮▮ certainty · ▮▮▮▮▮ debate potential. speakers are clickable
Chestnut: Serving the long tail makes a company much more resilient
“You know, you have to depend on just a handful of customers with the long tail. You know, we're serving You know, thousands or millions of tiny customers who pay small amounts of money. You don't rely on anyone too much such that, you know, they're sort of too…”
Mailchimp's Freemium Pipeline Spanned Up to Ten Years as Entrepreneurs Rebounded
“And it would take them quite a while to convert. I don't think most businesses would have the patience to wait for these customers because you'd see them come in and start a business, set up a MailChimp account, try to do something with a business. They would …”
Chestnut: Early VCs Relied on Identical Scare Tactics to Push Funding
“And then by the 10th one, I realized they were all saying the same thing. They were all using the same playbook. And it was always a scare tactic. Like, if you don't take our money, you're just gonna peter out and die. And so we just, I guess, more stubbornly …”
Chestnut: Mailchimp rejected venture capital due to uniform scare-tactic pitches
“You know, for the first two, I started to think about it, because I really believed their pitches, and then by the 10th one, I realized they were all saying the same thing, they were all using the same playbook and it was always a scare tactic, like, if you do…”
Mailchimp rejected venture investors because internal cash flow was sufficient
“We were totally self-funded. Investors still came, and, you know, they would say, you know, take our money, and we'd say, we can't, we don't know why we would need it. We, we're making plenty.”
Chestnut: Mailchimp has had acquisition offers, keeps an open mind on selling
“I've had offers. The thing is, I love what I do, and I don't know, I, it's one of those things I, you know, you never, you learn over time, after 20 years of running a business, you learn, never say never, right? I think I have an open mind about it, but I can…”
Strategy should have max three themes and fit on a sticky note
“We made a conscious effort to always keep it simple. No more than three themes. You know, it had to fit on a sticky note was always my philosophy.”
Chestnut: Footer logos in free emails made Mailchimp go viral
“Importantly, you know, if you signed up and sent an email from the freemium plan, the catch was, you know, our logo was in the footer of your emails, and so it went viral. People would click on that and sign up as well.”
Chestnut: Mailchimp hit 1M users within one year of freemium
“So you're talking about having, you know, a few 100,000 customers at the time after six years of business. And then within one year of launching freemium, we ballooned to a million users and it just kept growing exponentially after that.”
Chestnut: Freemium models are rife with abuse without strong anti-spam algorithms
“My angle was how freemium is great, but it's Rife with abuse, and you better have some good anti-spam algorithms like MailChimp does.”
Mailchimp Co-Founder Dan Kurzius Faked HTML Skills to Secure His Job
“He interviewed for the job thinking he was interviewing to write content about music. And halfway through his interview with, he realized that I was interviewing him to be a coder and he had no idea how to code HTML. And so he totally lied totally lied to me a…”
Mailchimp Reached $200 Million in Revenue by 2014 While Completely Bootstrapped
“The minimum revenue had to be two million in revenue, and, you know, we were, like, maybe at two hundred million or something by this time”
Private Equity Suitors Asked Bootstrapper Ben Chestnut About His Health, Not Growth
“I get private equity companies coming in and they don't ask me to take their money and grow it. They, the first thing they ask me is how's your health? It feels like they're just waiting for me to keel over.”
Mailchimp Hit One Million Users Just One Year After Launching Freemium
“So you're talking about having, you know, a few 100,000 customers at the time after six years of business. And then within one year of launching freemium, we ballooned to a million users and it just kept growing exponentially after that.”
Chestnut: Serving the long tail creates a much more resilient company
“You know, you have to depend on just a handful of customers with the long tail. You know, we're serving, you know, thousands or millions of tiny customers who pay small amounts of money. You don't rely on anyone too much such that, you know, they're sort of to…”
Chestnut: Freemium email models require robust anti-spam algorithms to prevent abuse
“My angle was how freemium is great, but it's rife with abuse and you better have some good anti-spam algorithms like MailChimp does.”
Chestnut: Mailchimp revenue almost tripled overnight after going full-time
“When we finally worked up the courage to do it, MailChimp revenue, if I recall correctly, almost tripled overnight.”
Mailchimp co-founder Dan Kurzius lied about coding skills to get hired
“Dan's he's into, he was a DJ, he's a music producer, he's into electronic music, and so he interviewed for the job thinking he was interviewing to write content about music, and halfway through his interview with, he realized that I was interviewing him to be …”
Chestnut: Mailchimp was the first sponsor of the podcast Serial
“Yeah, and so we were the first sponsor.”
Mailchimp Was Built Repurposing Code From Failed E-Greetings Site
“And we just took the scrap code from the greetings website. Luckily we didn't delete it, and yeah, we used that to build MailChimp.”
Chestnut: Mailchimp made $25–$50 per transaction versus $20K–$35K per web project
“The web design projects are like 20,000 dollars by this time we had gotten pretty good at sales. And so it was a really hard thing to convince my co-founders like, Hey, let's abandon the web design business where we're making 20 grand, sometimes 35 grand a pop…”
Mailchimp Became SaaS Because Chestnut Ran Out of Check Deposit Slips
“I ran out of check deposit slip and I said, I do not want to go inside the bank. We've got to find a way to build our customers online. And that was how we actually installed the credit card system. And that was when Mailchimp became an official SAS business.”
Chestnut: Tech conferences treated early email marketing like internet's dark underbelly
“There was definitely a stigma to email marketing. If we went to tech conferences and told people what we did, you know, things would get quiet. They'd walk away. You know, we were, they sort of thought of us as sort of like the dark underbelly of the internet.…”
Ben Chestnut: Mailchimp was at ~$200M revenue when attending Ohio leadership school
“The minimum revenue had to be two million in revenue, and, you know, we were, like, maybe at two hundred million or something by this time, and so I didn't tell them that. I submitted the form, and I said, you know, Yes, I make two million in revenue”
Mailchimp reached one million users in 2010 despite severe server crashes
“2010 is when You know, we're at a million users growing to two million fast servers were dying constantly. We were having to constantly move from data center to data center just to keep things alive.”
Mailchimp was making probably $10M to $15M in revenue around 2010
“I wish I could remember the timeline. It's been 20 years, you know, it's all a blur now, but we were making probably 10,000,015 million at the time.”
Chestnut: Mailchimp's first podcast advertising buy was Joe Rogan's podcast
“I mean, I still remember the day when someone told, one of our employees said, I listened to this thing called podcasts on my drive to work, and I think we should sponsor a podcast. And I thought it was, you know, just a weird idea. I'd never heard a podcast, …”
Chestnut: Mailchimp's Serial sponsorship quarter created a hard-to-beat Q4 benchmark
“And I mean, to this day, we look at our quarter four results and, you know, it's just like a bummer because the cereal, the quarter where we sponsored cereal did so amazingly well. It's hard to beat it every year.”
Chestnut: Mailchimp really took off after introducing subscription pricing
“And it took us a whole year to decide to finally put in those subscription fees, and we did, and that's when business really, really took off for us, too.”
MailChimp co-founder Ben Chestnut offered to sponsor CreativeMornings four months in
“Four months into launching. So apparently he read my blog and he emailed me and says, hey, my team, like literally, It said my team would poop their pants if they saw us team up. So can I support you? And I remember sitting there going, I don't know. And I jus…”
Chestnut: Mailchimp revenue almost tripled overnight after fixing core bugs
“When we finally worked up the courage to do it, MailChimp revenue, if I recall correctly, almost tripled overnight.”
Chestnut Abandoned $20,000 Agency Projects to Chase $25 Mailchimp Transactions
“The web design projects are like 20,000 dollars by this time. We had gotten pretty good at sales. And so, it was a really hard thing to convince my co-founders. Like, hey, let's abandon the web design business where we're making 20 grand, sometimes 35 grand a …”
Mailchimp Pivoted to SaaS Because Chestnut Ran Out of Check Deposit Slips
“I ran out of check deposit slip, and I said, I do not want to go inside the bank. We've got to find a way to bill our customers online, and that was how we actually installed the credit card system, and that was when Mailchimp became an official SaaS business.”
Mailchimp Struggled for Years to Top its Unprecedented Serial Sponsorship Quarter
“And I mean, to this day, we look at our quarter four results and, you know, it, it's just like a bummer because the cereal, the quarter where we sponsored cereal did so amazingly well. It's hard to beat it every year. It's like, darn it, that's cereal. It just…”
Chestnut: Mailchimp made $10M to $15M around 2010 while self-funded
“It's all a blur now, but we were making probably 10,000,015 million at the time. We were doing really, really well.”
Ben Chestnut Built Mailchimp Using Scrap Code From a Failed E-Greetings Site
“We just took the scrap code from the greetings website. Luckily we didn't delete it, and yeah, we used that to build MailChimp.”
Raz: Intuit acquired Mailchimp in 2021 for $12 billion
“A few months after this episode first ran in 2021, the software giant Intuit announced it was acquiring MailChimp in a deal worth twelve billion dollars.”
Ben Chestnut: Mastering banner ad psychology was essential to building Mailchimp
“I ended up being really fascinated by the art, like to learn how it within like two seconds to convince someone on the internet to click something is, it became fascinating for me. And I, you know, that skill to like build, build something, an animation really…”
Chestnut: Mailchimp was originally named ChimpMail until finding domain taken
“And so we decided to call it chimp mail. And then of course the domain was taken.”
Mailchimp Was Originally Conceived as 'ChimpMail' Before Finding the Domain Taken
“And so we said, hey, how about chimp mail? And so we decided to call it chimp mail, and then, of course, the domain was taken.”
Famous 'MailKimp' Serial Ad Was Voiced by a 14-Year-Old Norwegian Tourist
“By the way, back in 2015, when people were still talking about their viral ad on Cereal, the podcast's producer, Julie Snyder, revealed the identity of the person behind MailChimp. It turned out to be a fourteen-year-old girl from Norway waiting in line outsid…”