Masters of Scale The case for bootstrapping, w/Mailchimp's Ben Chestnut
May 21, 2019
Ben Chestnut, CEO of Mailchimp, shares his journey of bootstrapping the company to $600 million without external funding. He emphasizes the DIY ethos that fueled Mailchimp's growth and explains how storytelling and community support are vital for entrepreneurs. The conversation delves into the unique challenges of bootstrapping in the tech landscape, contrasting it with VC funding. Chestnut also discusses the significance of aligning investors with a founder’s vision and innovative strategies that foster growth, such as engaging customer feedback and enhancing employee appreciation.
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Early Entrepreneurial Roots
- Ben Chestnut's mother ran a hair salon in her kitchen, instilling an entrepreneurial spirit in him from a young age.
- He helped by sweeping hair, emptying ashtrays, and organizing rollers, associating the smell of business with "cigarette smoke and perm."
Flip Books and Candy
- Chestnut's first business was creating and selling flip book animations to kids on the school bus.
- He later pivoted to selling candy, a more scalable product.
Hustling for Clients
- After college, Chestnut worked as a banner ad designer and, upon learning of the company's impending closure, proactively sought clients with his business partner.
- They secured projects worth $13,000 and $32,000 before even obtaining a business license.
