Ben Chestnut at Mailchimp has never spoken at BoS

Congratulations to team and founder on Mailchimp’s acquisition to Intuit.

On Monday the news that Mailchimp has been acquired by Intuit for $12 billion in cash and shares got people talking.

Cue Flurry of VCs Congratulating Themselves.

The usual playbook on Twitter when these deals go down is a flurry of hot takes and congratulations to the founder and team from investors who by law have to include a line that somehow reflects well on the investors foresight, vision or investment thesis – even when they did not invest.

For this deal, there were certainly ‘hot takes’ but VCs were noticeably absent in their rush to congratulate the company and founder on the acquisition incorporating their personal reflected glory.

Mailchimp has been bootstrapped from a web design agency in 2001. It has not taken any professional external funding so there are no investors involved. So congratulations, and of course, some reflected glory…

Ben has declined to speak repeatedly

Ben Chestnut Mailchimp

Over the years, I’ve really wanted to have Ben to talk at Business of Software Conference. It’s not through lack of asking.

Often, Ben couldn’t even use the excuse of being too busy, elsewhere, with an important customer, flying into space at the time. I knew exactly where he would be on those dates. At Business of Software Conference.

Ben and some of the Mailchimp leadership have been regulars since it began in 2008 – and he still remembers the very first conference…

You can find those talks and plenty more here.

Don’t get too excited if you want to listen to Ben though. Maybe one day..

Listening and Speaking

Many smart entrepreneurs value getting together with other smart people, sharing ideas, problems, camaraderie and contestation. They also know the amount of work and time that goes into putting a great talk together. I’ve noticed over the years that some of the smartest, most successful and admired leaders, prioritize listening over speaking.


There are plenty of entrepreneurs and CEOs who have a second career as a conference speaker. Fewer of them just get their heads down, think and learn, deliver results.

Congratulations Ben!

The default mode at many events is, ‘transmit’, we make a conscious effort to make it, ‘receive’ at BoS Conference.

While they often spend huge amounts of time teaching and coaching, they value the opportunity to learn.

Shouldn’t you?

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