The case for bootstrapping, w/Mailchimp's Ben Chestnut
Masters of Scale
WaitWhat
4.6 • 4.4K Ratings
🗓️ 30 November 2021
⏱️ 50 minutes
🧾️ Download transcript
Summary
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.
Transcript
Click on a timestamp to play from that location
| 0:00.0 | Real leaders don't back down when the stakes are high. They innovate. They push forward, |
| 0:07.5 | and then they take the stage at the Masters of Scale Summit. |
| 0:11.6 | Join us in San Francisco, October 7th to 9th to hear from the CEO of the New York Times, |
| 0:17.1 | scientists using cutting-edge technology to find cures, the leader of crypto powerhouse |
| 0:22.0 | Coinbase, a retired four-star general, and many, many more. |
| 0:26.7 | Apply now at mastersofscale.com slash apply 25. |
| 0:31.7 | That's masters of scale.com slash apply 25. |
| 0:36.9 | Your company's data is everywhere in systems, in silos and across teams. But if your |
| 0:42.8 | AI can't reach it, then that data isn't working for you. Every business has unique data, |
| 0:48.0 | what really makes a difference is how you use it. IBM helps your AI access your data wherever |
| 0:53.4 | it lives to change how you do business. Let's create |
| 0:57.5 | smarter business, IBM. To be an artist has always required that you find a way to solve for the financial equation of the cost of producing your art. |
| 1:16.3 | In the old days, it was a sponsorship system, right? |
| 1:20.1 | In medieval times, which was one of the greatest explosions of art culture on the planet, |
| 1:25.0 | it was all about finding a rich patron to support you, right? |
| 1:32.5 | That dynamic has always been present in the creation of art and the stories that are so important to the advancement of culture. |
| 1:48.1 | Yeah. and the stories that are so important to the advancement of culture. If you grew up in the 80s or 90s, you probably recognize that voice. |
| 1:52.4 | From Star Trek, The Next Generation, or the kids show Reading Rainbow. |
| 1:57.4 | It's Lavar Burton. |
| 1:58.9 | Over the years, he's emerged as a steadfast champion of literature and the arts. |
| 2:03.6 | He has a podcast now called LaVar Burton Reeds and a company called LaVar Burton Kids. |
| 2:10.8 | He thinks a lot about the power of stories. |
... |
Please login to see the full transcript.
Disclaimer: The podcast and artwork embedded on this page are from WaitWhat, and are the property of its owner and not affiliated with or endorsed by Tapesearch.
Generated transcripts are the property of WaitWhat and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.
Copyright © Tapesearch 2026.