Insight
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…”
Opinion
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 …”
Insight
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 …”
Disclosure
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…”
Disclosure
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.”
Disclosure
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…”
Insight
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.”
Assertion Supported
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.”
Assertion Contradicted
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.”
Insight
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.”
Assertion Not checkable as stated
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…”
Insight
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.”
Assertion Contradicted
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.”
Insight
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…”
Assertion Supported
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”
Disclosure
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.”
Assertion Not checkable as stated
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 …”
Assertion Not checkable as stated
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.”
Assertion Not checkable as stated
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.”
Assertion Not checkable as stated
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.…”
Assertion Not checkable as stated
Chestnut: Rocket Science Group's agency revenue peaked at $200K–$300K through 2005
“If I could, the best that I remember our agency business ever doing was something like between two and 300 grand a year. That was the best we had ever done. And that was through 2005 here, by the way.”
Assertion Not checkable as stated
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…”
Assertion Not checkable as stated
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.”
Assertion Not checkable as stated
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.”
Ben Chestnut