So we’re so grateful Ben Chestnut founder of Mailchimp did several great deep dives with us over the years, and a truly great one just after Intuit’s stunning $12 Billion+ acquisition of Mailchimp here:
Ben’s kept a low profile since but he joined Kleiner’s Grit podcast the other day and talk about what selling is really like.
He’s happier now … m weostly … but it’s a much quieter life.
And he noted when he sold — he knew he’d “quickly become irrelevant.”
Even after selling a bootstrapped start-up for $12 Billion.
That section here:
Per the pod:
“Breaking the Founder Habits
It took Ben nearly a year to stop habitually checking email each morning – a classic founder withdrawal symptom. The partnership with Brian Cayne from Catalyst Partners proved invaluable, as Brian had foreshadowed these challenges back in 2015, warning Ben about the habits he’d need to shed post-exit.
The toughest part? Letting go of those ingrained behaviors: constant email checking, social media monitoring, and the addiction to problem-solving that defines founder life.
The $12B Dog Walker
Ben’s solution was wonderfully simple: “Get a dog.” His pandemic rescue pup became both therapy and purpose, creating structure through twice-daily 2-3 mile walks. When fellow founders asked about post-exit life hacks, his advice remained consistent: “Just get a dog.”
This extends to his portfolio companies too. As an investor in Loom, he specifically advised CEO Joe to consider canine companionship – understanding that founders need something to care for beyond their companies.
The Money Paradox
Despite achieving what most founders dream of – a massive exit and financial freedom – Ben confesses he’s “never felt less fulfilled.” Global travel and financial security didn’t provide the expected satisfaction.”
It’s Complicated
It’s a topic that every founder that sells deals with, but it it’s under-discussed. M&A itself is under-discussed. Selling is tough itself, but the feeling of being out of it afterwards can be tough on many.
It hasn’t been for Ben. He’s liberated about not to having to worry about the servers going down, the threat and disruption from AI, etc. I think I’d probably feel the same.
But I also know personally I was lost each time after selling my start-ups. Many aren’t. But many are. It’s complicated. Maybe of founders are. It’s a large part of why they do another one, I think.
— Ben Chestnut (@benchestnut) March 17, 2025
And it’s why I started SaaStr.
Ben did know though, as he points out. He knew the moment he sold, he’d be out of the circle folks cared about. Folks though also wouldn’t watch his every move. Pros and cons. 🙂
If you are selling your company, it’s something to at least talk through before you sign that term sheet. I don’t think it’s a reason on its own not to sell. Life is a journey. But I think, like Ben, it’s best to really understand it first.
