(July 2021) Ben Chestnut: From Side Business to $12 Billion – The Accidental Triumph of Mailchimp | How I Built This with Guy Raz

In this episode of "How I Built This," Guy Raz interviews Ben Chestnut, the co-founder of Mailchimp, exploring the company's journey from a web design business side project to a leading online marketing platform. Chestnut recounts Mailchimp's early days, bootstrapped beginnings, and the pivotal decision to focus on small businesses, which led to significant growth. He shares insights into their creative marketing strategies, including the iconic monkey logo and their early adoption of podcast advertising. Chestnut also discusses the challenges they faced, such as navigating the stigma of email marketing and dealing with internal cultural issues as the company scaled, and also touches on the company's eventual acquisition by Intuit for $12 billion.

Outlines

Sign in to continue reading, translating and more.

Continue

(July 2021) Ben Chestnut: From Side Business to $12 Billion – The Accidental Triumph of Mailchimp

How I Built This with Guy Raz

Introduction to Ben Chestnut and Mailchimp's Origin Story

Early Influences and Entrepreneurial Roots

High School, Karate, and Discovering Web Design

Early Career and Meeting Co-founder Dan Kurzius

The Dot-Com Bust and Launching Rocket Science Group

The Accidental Birth of Mailchimp

Early Struggles and the "Cockroach" Mentality

Going All-In on Mailchimp and Rejecting Outside Investment

Growth Challenges and the Freemium Model

Exponential Growth and Focusing on Small Businesses

Creative Marketing and the "Serial" Sponsorship

Growing Pains and an Identity Crisis

Seeking Help and a Leadership Transformation

Developing a Culture and Strategy

Addressing Workplace Issues and the Future

Luck, Strategy, and the Reality of "Winging It"

(July 2021) Ben Chestnut: From Side Business to $12 Billion – The Accidental Triumph of Mailchimp

How I Built This with Guy Raz

00:13Introduction to Ben Chestnut and Mailchimp's Origin Story

Introduction to Ben Chestnut and Mailchimp's Origin Story

04:46Early Influences and Entrepreneurial Roots

Early Influences and Entrepreneurial Roots

08:18High School, Karate, and Discovering Web Design

High School, Karate, and Discovering Web Design

13:36Early Career and Meeting Co-founder Dan Kurzius

Early Career and Meeting Co-founder Dan Kurzius

17:56The Dot-Com Bust and Launching Rocket Science Group

The Dot-Com Bust and Launching Rocket Science Group

23:10The Accidental Birth of Mailchimp

The Accidental Birth of Mailchimp

27:53Early Struggles and the "Cockroach" Mentality

Early Struggles and the "Cockroach" Mentality

32:22Going All-In on Mailchimp and Rejecting Outside Investment

Going All-In on Mailchimp and Rejecting Outside Investment

37:12Growth Challenges and the Freemium Model

Growth Challenges and the Freemium Model

43:32Exponential Growth and Focusing on Small Businesses

Exponential Growth and Focusing on Small Businesses

49:22Creative Marketing and the "Serial" Sponsorship

Creative Marketing and the "Serial" Sponsorship

57:58Growing Pains and an Identity Crisis

Growing Pains and an Identity Crisis

1:03:14Seeking Help and a Leadership Transformation

Seeking Help and a Leadership Transformation

1:08:04Developing a Culture and Strategy

Developing a Culture and Strategy

1:13:34Addressing Workplace Issues and the Future

Addressing Workplace Issues and the Future

1:18:14Luck, Strategy, and the Reality of "Winging It"

Luck, Strategy, and the Reality of "Winging It"