Jul 12, 2021 · 1h 22m · how-i-built-this
Mailchimp: Ben Chestnut
Ben Chestnut · 54m spoken Guy Raz · 18m spoken Serial Vox Pop Contributor · 4s spoken Sarah Koenig · 2s spoken Serial Vox Pop Voice · 1s spoken
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
Mailchimp co-founder Ben Chestnut recounts how he transformed a bootstrapped web design side project into a multi-billion-dollar marketing automation titan by rejecting venture capital, serving small businesses, and embracing quirky, viral branding.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Guy holds 25.7% of the talking time here. How this is scored →
Guy as informed peer 4.3 Guest teaching 1.9 Guest disagreement 1.1 Guy pushing back 1.6
speaking balance: gold is Guy, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 36:50 Pushing back against venture capital playbooks
Ben emphatically rejects the premises of Silicon Valley venture capitalists, describing their pitches as formulaic scare tactics intended to force enterprise pivots.
Hardest push from Guy ▶ 1:13:12 Direct challenge regarding toxic culture allegationsGuy Raz confronts Ben directly with published accounts of high-level female staff exits and allegations of discrimination and bullying within the company.
Biggest teaching moment ▶ 8:25 Clarifying how he actually met his wifeBen corrects Guy's stated assumption about meeting his wife in high school, clarifying that they met as students in a military base karate dojo.
Guy holds their own ▶ 54:30 Demonstrating insider knowledge on podcast ad pricingGuy brings industry insider knowledge to the conversation, highlighting how surprisingly cheap the early 'Serial' sponsorship deal was compared to its monumental reach.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Guy as informed peer | Guest teaching | Guest disagreement | Guy pushing back | Why |
|---|---|---|---|---|---|---|
| Early Childhood, Military Roots, and Kitchen Hair Salons | 4 | 1 | 1 | 1 | Guy Raz sets a warm, biographical tone, occasionally demonstrating background research such as knowing about Dan Kurzius's father's bakery in Albuquerque. Ben shares personal anecdotes about his father's military service and his mother's informal kitchen hair salon. | |
| Meeting Teresa and Formative Lessons in Etiquette | 4 | 3 | 1 | 1 | Ben politely corrects Guy's assumption that he met his wife in high school, explaining they actually met at a military base karate dojo. The tone remains humorous and collaborative as Ben describes meeting her family. | |
| From Industrial Design Struggles to Discovering Web Design | 4 | 2 | 1 | 2 | Guy playfully teases Ben about not moving very far from home when going to college and design school. Ben candidly discusses his poor early academic performance and his clumsy start with physical industrial design. | |
| Banner Ads, Meeting Dan Kurzius, and the Dot-Com Crash | 4 | 2 | 1 | 1 | Guy inquires about the dot-com era dynamics at Cox Media. Ben humorously details how he hired co-founder Dan Kurzius after Dan bluffed his way through an HTML coding interview. | |
| Founding Rocket Science Group and the Birth of Mailchimp | 4 | 2 | 1 | 1 | Ben explains how an initial failed e-greetings project provided the reusable codebase for what became Mailchimp. Guy tracks the timeline and the transition from custom web agency billing to software-driven microtransactions. | |
| Overcoming Spam Stigma and Shifting to Recurring Revenue | 4 | 2 | 1 | 1 | Ben recalls the negative perception of email marketing as spam during the mid-2000s. He recounts discovering the concept of recurring revenue through Robert Kiyosaki on Oprah, prompting the team to compare revenue graphs. | |
| Going All-In on Mailchimp and Rejecting Venture Capital | 5 | 2 | 2 | 3 | Guy presses Ben on the risk of turning down venture capital while competing against well-funded giants like Constant Contact. Ben explains his disdain for aggressive VC playbooks and fear tactics. | |
| The Freemium Pivot and Explosive Viral User Growth | 5 | 2 | 1 | 2 | Guy highlights the historical pitfalls of free business models in publishing and SaaS. Ben recounts how technical limitations forced a free tier compromise that accidentally aligned with the emerging freemium movement. | |
| Serving the Long Tail and Guerrilla Billboard Marketing | 4 | 2 | 1 | 1 | Ben breaks down Mailchimp's deliberate focus on small business resilience and creative guerrilla marketing, including the accidental viral success of their Moscone Center billboard in San Francisco. | |
| The 'Serial' Podcast Sponsorship and the 'Mailkimp' Phenomenon | 5 | 2 | 1 | 1 | Guy leverages his podcast industry knowledge regarding the immense impact and low initial ad rates of 'Serial'. Ben reflects on approving the quirky vox pop ad featuring the viral 'Mailkimp' mispronunciation. | |
| Scaling Pains and the Disastrous Halloween All-Hands Fiasco | 4 | 2 | 1 | 2 | Ben describes a disastrous 300-person Halloween all-hands meeting where employees pressed him for a corporate strategy. Guy explores the resulting identity crisis and Ben's subsequent realization of his leadership limitations. | |
| Executive Leadership Training in Dayton and Brand Expansion | 4 | 2 | 1 | 1 | Ben recounts seeking executive training at Clay Mathile's school in Dayton, Ohio, which reshaped his perspective on leadership and encouraged Mailchimp to expand beyond pure email delivery. | |
| Navigating Pandemic Challenges and the Workplace Culture Reset | 5 | 1 | 1 | 4 | Guy directly addresses public investigative reporting concerning senior female departures and allegations of workplace sexism at Mailchimp. Ben acknowledges the criticism as a wake-up call and details their public culture reset plan. | |
| Ownership Independence, Leadership Realities, and the Role of Luck | 4 | 2 | 1 | 2 | Guy and Ben discuss the philosophy of independence, succession possibilities, and the balance between luck and preparation. Ben concludes with the realization that even veteran corporate leaders are constantly experimenting. |
Statements from this episode (18)
Web Designers Made Easy Money in the 1990s Due to Rare Skills
“You could be a complete goof off, but make a lot of money doing it, because it was really, really a rare skill.”
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…”
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.”
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 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.”
Rocket Science Group agency revenue peaked at $200K-$300K through 2005
“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.”
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 …”
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: 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: 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.”
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.”
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: 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.”
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…”
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…”
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.”
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…”