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.

44:56

Episode guests

Ben Chestnut

AI Chapters

Episode notes

Intro

3min

Stories of Entrepreneurship and Bootstrapping

12min

Navigating Bootstrapping Challenges in a Volatile Tech Landscape

3min

Navigating Investment and the Challenges of Early-Stage Growth

4min

MailChimp's Journey: From Struggles to SaaS Success

12min

Bootstrapping Success: The Power of Passion and Planning

4min

Reviving Growth Through Innovation

11min

The Importance of Employee Appreciation in Business Success

3min

You can bootstrap your business to scale, but you'll have to make your own luck. Nobody knows this better than Mailchimp's Ben Chestnut. He used a DIY ethos to grow a $600M 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 interview at: https://mastersofscale.com/ben-chestnut-the-case-for-bootstrapping/

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