(July 2021) Ben Chestnut: From Side Business to $12 Billion – The Accidental Triumph of Mailchimp
How I Built This with Guy Raz
Guy Raz | Wondery
4.8 • 31.1K Ratings
🗓️ 25 August 2025
⏱️ 83 minutes
🧾️ Download transcript
Summary
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.
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Transcript
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| 0:00.0 | Wondery Plus subscribers can listen to how I built this early and ad-free right now. |
| 0:05.7 | Join Wondery Plus in the Wondery app or on Apple Podcasts. |
| 0:10.3 | You just realized your business needed to hire someone yesterday. |
| 0:14.9 | How can you find amazing candidates fast? |
| 0:17.9 | Easy. Just use Indeed. |
| 0:20.2 | Stop struggling to get your job posts seen on other job sites. Indeed's fast. Easy. Just use Indeed. Stop struggling to get your job posts seen on other job sites. |
| 0:24.1 | Indeed's sponsor jobs helps you stand out and hire fast. I was looking to hire someone recently |
| 0:29.5 | and the process was amazing because I actually used Indeed. There's no need to wait any longer. |
| 0:35.5 | Speed up your hiring right now with Indeed. And listeners |
| 0:39.1 | of this show will get a 100 pound sponsor job credit to get your jobs more visibility at |
| 0:45.5 | Indeed.com slash how I built. Just go to indeed.com slash how I built right now and support our |
| 0:53.8 | show by saying you heard about Indeed on this podcast. |
| 0:57.2 | Indeed.com slash how I built. Terms and conditions apply. Hiring, Indeed is all you need. |
| 1:05.3 | AI might be the most important innovation ever. It's storming every industry, with literally billions being invested. |
| 1:12.0 | So buckle up. The problem is that AI needs the right data and a lot of speed and processing power. |
| 1:17.8 | So how do you compete without costs spiraling out of control? Time to upgrade to the next generation |
| 1:23.2 | of the cloud. Oracle Cloud Infrastructure or OCI. OCI is a single platform for your infrastructure, database and application development, with |
| 1:33.3 | AI embedded across it all, and Oracle's sovereign cloud helps you address your requirements |
| 1:38.3 | for location, access and data residency. |
| 1:41.3 | OCI provides blazing fast speeds for AI's demanding workloads. And in the cloud, |
| 1:46.8 | when you pay by the minute, speed matters. And of course, nobody does data better than Oracle. |
| 1:52.6 | If you want OCI to help you do more and spend less like Uber, the Premier League and Oracle Red Bull Racing, |
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