Masters of Scale

The case for bootstrapping, w/Mailchimp's Ben Chestnut

Nov 30, 2021

Ben Chestnut, co-founder and CEO of Mailchimp, shares his inspiring journey of building a multi-billion-dollar email marketing platform without outside funding. He discusses the power of bootstrapping and the DIY ethos, presenting an alternative to the common VC model. The transformation from an internal tool to a successful SaaS company showcases the importance of resilience, innovation, and community support in entrepreneurship. Chestnut also highlights the significance of employee appreciation through unique programs, enhancing brand loyalty along the way.

44:56

Episode guests

Ben Chestnut

AI Chapters

Episode notes

Intro

2min

Bootstrapping Brilliance

11min

The Challenges and Rewards of Bootstrapping a Startup

3min

Navigating Investment Challenges and Growth Strategies

3min

MailChimp's Transformative Journey

12min

Bootstrapping Success: Resilience and Innovation

4min

Scaling Challenges and Innovative Solutions

11min

The Importance of Employee Appreciation and Innovative Leave Programs

4min

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

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