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.
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ANECDOTE

LeVar Burton's Kickstarter Success

  • LeVar Burton, despite running a business, doesn't consider himself a businessman.
  • He successfully crowdfunded his Reading Rainbow app after Silicon Valley showed no interest.
ADVICE

Bootstrapping to Scale

  • Consider bootstrapping if blitzscaling isn't suitable.
  • Bootstrapping requires catching multiple waves of good fortune.
ANECDOTE

Ben Chestnut's Early Influences

  • Ben Chestnut's entrepreneurial roots trace back to his mother's hair salon and selling flipbooks.
  • These early experiences instilled a strong work ethic and business sense.
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