Podcast Shownotes

A Builder At Heart

As a child in Georgia, Ben and his brother would tinker with Legos, deconstruct and solder electronics together, and always have a hand in a 60 in One Electronic Project Lab by RadioShack. His family was led by a father in the Army and a mother who ran a successful hair salon out of their kitchen while nannying on the side. By the time he transferred to Georgia Tech, he was sure he wanted to be an engineer product designer. After an internship at Amana, an appliance company in Iowa, Ben learned that he did not like appliance design. But all was not lost, his time spent in Cedar Rapid’s Barnes and Nobles store led him to read a few books on web design to pass the time. Ben began to fall in love with the subject and after returning to Georgia, he took a few classes on it and started a small freelance business building websites. Web design was still a relatively new field, which meant most of what Ben was learning was self-taught, lawless, and full of explorative potential.

Side Project Turned Startup

At the height of the .com days, Ben was working for Cox creating banner ads, watching as the market flooded with venture capital money. He decided to try his hand at creating a better E-greeting site to sell to investors. Though impressive, the website never took off and the economic crash in April 2000 led to his lay-off from Cox. Ben used the severance money to start his own website-building business, and over time noticed a need for efficient email marketing by his clients. His team quickly restructured the failed e-greeting site into an email marketing platform known as Mailchimp. The side hustle website fulfilled the marketing requests from the company’s clients, while Ben continued to grind away at more website design. Six years in, the lack of scalability without burnout was catching up to Ben and his business partners. They decided to take a closer look at their previous side project, and realized that Mailchimp had been scaling upwards on its own – a major opportunity for further investment.

Ben Chestnut | Do What You Love | CreativeMornings/ATL

The First Million

Dealing with copycat competitors and a small team was weighing on the Mailchimp team. Ben hired a COO and CEO who convinced them to invest in hiring, building, and launching new features to market to the audience to the point of annoyance. Mailchimp surpassed 1 million, 20 million, then 300 million in revenue. Venture capitalists caught wind and soon Ben was wrapped up in meetings with men who he was hesitant to trust(think back to the 2000 crash), and who lacked sensitivity towards small business – the exact customer base that Ben was supported by. The team decided to remain true to their personal vision and company mission, without VC funding.

Ben admits he never felt ready to be CEO, and couldn’t figure out the right ‘formula’ for getting through imposter syndrome. There’s no playbook for unique products. A few lessons that he did learn?

Hire slow, fire fast, and provide good severance packages.
Keep your customers (and their feedback) close
Build a brand worth working for

Mailchimp's Ben Chestnut on bootstrapping a startup to $700M in revenue | TechCrunch

Moving Forward

To be a leader in the technological space, Ben lives by the philosophy that there is no such thing as a mistake, but rather, a happy accident. Keep innovating and nothing will truly be a failure. In terms of the future of technology, Ben’s excited to watch the development of AI for business services. For now, he’s focused on enjoying life after 21 years of hustling, being a great father and husband, and continuing to do the dishes.

Billionaire co-founder of Mailchimp will share insights ahead of INNOVATE competition – Jagwire