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.
1:30 - Intro
3:51 - Ben’s childhood
6:14 - Ben’s introduction to entrepreneurship
7:51 - Life in highschool
11:58 - A path to web design
15:23 - Meeting Dan Kurzius
17:33 - The dot-com boom and crash
18:26 - Forming a web design company
23:34 - Making money from emails
24:58 - Coming up with the name
25:53 - The customers
28:43 - Cashflow
32:04 - Pivoting away from web design
37:53 - Attracting investors
40:49 - Going Freemium
47:44 - Beating the competition
51:20 - Marketing
55:20 - Sponsoring Serial
59:55 - From 3 employees to 300
67:29 - Leadership training
71:42 - Changing the culture of the company
75:00 - Dealing with the pandemic
77:21 - Accusations of sexism
80:40 - Considering selling the company
82:53 - Luck vs. hard work
Mailchimp
Ben Chestnut
Hephzibah, Georgia
Cox Media Group
Dan Kurzius
HTML
Fast Company
Business 2.0
Dot-com crash
Rich Dad Poor Dad by Robert Kiyosaki
Constant Contact
Freemium
Free: The Future of a Radical Price by Chris Anderson
Charles Hudson
Mailchimp billboard
Serial Podcast
The Mailkimp ad
Article about complaints of sexism
