Ben Chestnut

In this recap episode, we highlight the best moments from our 2025 interviews and reflect on the ideas that defined the year. Featuring: David Rubenstein (co-founder of Carlyle) Yamini Rangan (CEO of HubSpot) Ben Chestnut (co-founder of Mailchimp) Winston Weinberg (co-founder and CEO of Harvey) Garrett Lord (co-founder of Handshake) Aidan Gomez (co-founder and CEO of Cohere) Michelle Zatlyn (co-founder of Cloudflare) Evan Spiegel (co-founder and CEO of Snap) Connect with Joubin X: https://x.com/Joubinmir LinkedIn: https://www.linkedin.com/in/joubin-mirzadegan-66186854/ Email: grit@kleinerperkins.com Follow on LinkedIn: https://www.linkedin.com/company/kpgrit Follow on X: https://x.com/KPGrit ​Learn more about Kleiner Perkins: https://www.kleinerperkins.com/

David Rubenstein

Co-Founder

Carlyle Group

Yamini Rangan

CEO

HubSpotDropbox

Ben Chestnut

Co-Founder

Mailchimp

Winston Weinberg

Co-Founder and CEO

Harvey

Garrett Lord

Co-founder and CEO

Handshake

Aidan Gomez

Co-founder & CEO

Cohere

Michelle Zatlyn

Co-Founder and COO

Cloudflare

Evan Spiegel

Co-founder & CEO, Snap

Snap

In 2001, three web designers built a quirky email tool called Mailchimp. It wasn’t their main business. It wasn’t even meant to make real money. For years, Ben Chestnut and his partners survived on web-design gigs, while Mailchimp earned just enough to cover lunch. Then…one surprising spreadsheet changed everything. In this episode, Ben reveals: The decision that tripled their revenue overnight How a mispronunciation on the world's biggest podcast turned into a marketing masterstroke How a painful wake-up call about leadership reshaped the company’s culture Listen now to hear how guerrilla billboards, a monkey logo, and a string of improbable breaks built one of the most recognizable names in tech. Follow How I Built This: Instagram → @howibuiltthis X → @HowIBuiltThis Facebook → How I Built This Follow Guy Raz: Instagram → @guy.raz X → @guyraz Substack → guyraz.substack.com Website → guyraz.com See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Ben Chestnut

Co-Founder

Mailchimp

Guest: Ben Chestnut, Former CEO and Co-Founder of Mailchimp If you find yourself selling your startup, then Mailchimp co-founder Ben Chestnut has some important advice for you: Get a dog.  When Intuit bought Mailchimp in 2021 for $12 billion, the company asked Ben if he wanted to stay on as CEO, but he chose to “walk off into the sunset” and let the new owners take over.  After that, he estimates it took 6 to 12 months before he stopped checking his email, social media, and calendar with the same level of stress a CEO might have. Adopting a dog, he discovered, forces you to “get OK with the voices in your head." “After the acquisition, that's all I do, I walk the dog,” Ben says. “And the dog was good therapy ... No judgments from a dog.” Mentioned in this episode: Intuit, Wolt, DoorDash, LinkedIn, Dan Kurzius, Salesforce, ExactTarget, Pardot, Constant Contact, Rackspace, Free by Chris Anderson, Wired Magazine, Charles Hudson, the Freemium Summit, Drew Houston, Dropbox, Evernote, Phil Libin, TechCrunch, Brian Kane, Catalyst Partners, Georgia Pacific, Scott Cook, Bing Gordon, Vinay Hiremath, Loom, Joe Thomas, Caltrain, Flickr, Saturday Night Live, Droga5, Cannes Film Festival, Strava, Twitter, LinkedIn, Nvidia, Glean, Rubrik, Amazon AWS, and Mechnical Turk. Links: Connect with Ben LinkedIn Connect with Joubin Twitter LinkedIn Email: grit@kleinerperkins.com  Learn more about Kleiner Perkins

Ben Chestnut

Co-Founder

Mailchimp

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?

Ben Chestnut

Co-Founder

Mailchimp

Join Mailchimp Co-Founder Ben Chestnut and SaaStr CEO Jason Lemkin in a follow-up to their popular fireside chat held during SaaStr @ Home 2020. Ben and Jason will chat about the highlights–and the challenges–of scaling a company like Mailchimp to $1B ARR. Full video: https://youtu.be/5fx3qFD62ak Want to join the SaaStr community? We're the 🌎largest community for B2B software. Subscribe for weekly updates: https://www.saastr.com/subscribeform Twitter: https://twitter.com/saastr LinkedIn: https://www.linkedin.com/company/2724976 Quora Group: https://www.quora.com/q/cloud Facebook: https://www.facebook.com/SaaStr/ Instagram: https://www.instagram.com/saastr/ Our North American Event: https://bit.ly/2OXeAYh Our European Event: https://bit.ly/2OZTad8

Ben Chestnut

Co-Founder

Mailchimp

This week, we’re returning to an episode of Masters of Scale featuring Ben Chestnut, the co-founder and CEO of Mailchimp. The email marketing platform was acquired this year by Intuit in a multi-billion-dollar deal that closed this month. Hear how Chestnut used a DIY ethos to grow the company without ever raising a dollar of outside funding. The Mailchimp story is the exception to Reid's rule (always raise more money than you think you need!). The episode explores a range of options for those who don't fit the VC-funding mold. Cameo appearances: LeVar Burton (Star Trek, Reading Rainbow, LeVar Burton Reads), Don MacKinnon (Milq), Karen Cahn (iFundWomen). Read a transcript of this episode: https://mastersofscale.com Subscribe to the Masters of Scale weekly newsletter: https://mastersofscale.com/subscribe See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Ben Chestnut

Co-Founder

Mailchimp

In the late 1990s, Ben Chestnut was a struggling young designer interning at an appliance company, when somebody suggested that he try designing for the internet instead. A few years later, Ben and two co-founders launched a web design agency, only to discover that the service they'd included almost as an afterthought—email marketing—was taking off among their small-business clients. The founders named that service Mailchimp and pivoted to it full-time in 2007, choosing a winking monkey as their mascot, and stumbling onto the Freemium model before it became mainstream. But their most impeccable timing came in 2014, when they decided to sponsor a new podcast called Serial, a move that catapulted the winking monkey into popular culture. Over the years, despite management jitters and a public reckoning over office culture, Mailchimp has remained profitable and self-funded, with revenue of $800 million in 2020.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Ben Chestnut

Co-Founder

Mailchimp

It's no secret that businesses today are struggling with an unpredictable economy. In this session, Mailchimp Co-founder and CEO Ben Chestnut will share the story of Mailchimp's founding amidst—and despite—the dot-com bubble burst, and how the company navigated a number of inflection points in the first 10 years of its founding. This episode is an excerpt from Jason and Ben's session at SaaStr Annual @ Home. Full video: https://youtu.be/LfLZzakn2r0 Podcast transcript: https://www.saastr.com/saastr-podcasts-for-the-week-with-jennifer-tejada-ben-chestnut-and-jason-lemkin/

Ben Chestnut

Co-Founder

Mailchimp

You can bootstrap your business to scale, but you'll have to make your own luck. Nobody knows this better than Mailchimp's Ben Chestnut. He used a DIY ethos to grow a $600M company without ever raising a dollar of outside funding. The Mailchimp story is the exception to Reid's rule (always raise more money than you think you need!). The episode explores a range of options for those who don't fit the VC-funding mold. Cameo appearances: LeVar Burton (Star Trek, Reading Rainbow, LeVar Burton Reads), Don MacKinnon (Milq), Karen Cahn (iFundWomen). Read a transcript of this interview at: https://mastersofscale.com/ben-chestnut-the-case-for-bootstrapping/ Subscribe to the Masters of Scale weekly newsletter: https://mastersofscale.com/subscribe See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Ben Chestnut

Co-Founder

Mailchimp