#234 From Bootstrapped to $12B: Mailchimp’s Ben Chestnut on Life After the Exit

This episode of the "Grit" podcast features an interview with Ben Chestnut, founder of Mailchimp, discussing his 20-year entrepreneurial journey culminating in the company's $12 billion acquisition by Intuit. The conversation covers the challenges of building a successful business, including the initial nine years of "pure hell," the strategic decision to adopt a freemium model, and the eventual sale. Chestnut emphasizes the importance of perseverance despite immense difficulties and shares his post-acquisition experience, highlighting the unexpected shift in priorities and the surprising therapeutic benefits of dog-walking. A key takeaway is his advice to aspiring entrepreneurs: while entrepreneurship is incredibly hard, the rewards can be immense if one perseveres.