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Ben Chestnut

15 statements across 3 episodes · 5 bullish · 1 bearish · 2 people on the record · first statement Sep 20, 2022 by Ben Chestnut · said 17 times in 5 episodes since 2022 · across every show →

On the record as a speaker too: Ben Chestnut's record, appearances and statements → this page counts the times other people say the name.

Mentions by year

brought up most by Jason Lemkin (16), Brian Halligan (1)

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0122022202320242025episodes it came up in
002.51522022202320242025episodesmentions per episode
2025 3 mentions in 1 episode
2024 1 mention in 1 episode
2023 4 mentions in 1 episode
2022 9 mentions in 2 episodes 5 per episode

every mention, scene by scene, with the transcript →

Everything said about Ben Chestnut, oldest first

Sep 20, 2022
Disclosure
Chestnut paid Mailchimp's early employees more cash than he paid himself
“I paid them more than I paid myself in those early years, too, by the way. You have to pay them. You don't have that massive funding. They want the cash. Sometimes I just didn't pay myself.”
Ben Chestnut Sep 20, 2022 ▶ 44:55 Everything that Breaks on the Way to $1B ARR with @mailchimp Co-Founder Ben Chestnut
Sep 20, 2022
Disclosure
Chestnut scaled Mailchimp purely by ensuring his monthly bank balance grew
“I never had investors, so I never had to do reports. No business plan. I never, I had a monthly bank statement, and I said, what's What's the starting balance, and what's the ending balance? Ending should be bigger. And it always was bigger.”
Ben Chestnut Sep 20, 2022 ▶ 17:37 Everything that Breaks on the Way to $1B ARR with @mailchimp Co-Founder Ben Chestnut
Sep 20, 2022
Insight
Founders giving sub-account keys to a new VP signals high churn risk
“What we looked at was if the founder set up a sub-account, You know, send a username and password to their VP. You're basically making a copy of the keys for a VP. That was the potential breaking point. That was our red flag. If a new VP comes on, they're not …”
Ben Chestnut Sep 20, 2022 ▶ 14:16 Everything that Breaks on the Way to $1B ARR with @mailchimp Co-Founder Ben Chestnut
Sep 20, 2022 neutral
Assertion Partly supported
Mailchimp scaled without any sales or customer success teams
“We've never had any kind of sales or customer success ever.”
Ben Chestnut Sep 20, 2022 ▶ 10:27 Everything that Breaks on the Way to $1B ARR with @mailchimp Co-Founder Ben Chestnut
Sep 20, 2022 negative
Insight
Entertaining M&A talks creates irreversible executive momentum to sell the company
“If you don't ever want to get acquired, never open the door to anyone. Because here's, really, honestly, if you open the door and let one in, you have to bring your executive team in with you eventually, and once everyone gets in on that, it's very tough to ba…”
Ben Chestnut Sep 20, 2022 ▶ 34:00 Everything that Breaks on the Way to $1B ARR with @mailchimp Co-Founder Ben Chestnut
Sep 20, 2022
Assertion Not checkable as stated
Intuit's $12 billion acquisition of Mailchimp took over a year to close
“Oh, the Intuit deal took, ah, a little more than a year to happen.”
Ben Chestnut Sep 20, 2022 ▶ 3:23 Everything that Breaks on the Way to $1B ARR with @mailchimp Co-Founder Ben Chestnut
Sep 20, 2022 positive
Insight
Non-technical CEOs have an advantage because they cannot micromanage software engineers
“I actually think if you don't come from the tech side, it's an advantage because you stay the hell out of the engineer's way.”
Ben Chestnut Sep 20, 2022 ▶ 39:58 Everything that Breaks on the Way to $1B ARR with @mailchimp Co-Founder Ben Chestnut
Sep 20, 2022
Assertion Not checkable as stated
Mailchimp's freemium model drove 10,000 new customer signups every day
“We were so, with Freemium, we were getting, you know, I remember, 10,000 signups a day from new customers.”
Ben Chestnut Sep 20, 2022 ▶ 16:52 Everything that Breaks on the Way to $1B ARR with @mailchimp Co-Founder Ben Chestnut
Sep 20, 2022 positive
Opinion
California wins B2B enterprise, but Atlanta is unmatched for consumer brands
“If you're gonna start a B-to-B enterprise company, California's absolutely the best place to be. B to C, like a consumer brand, you can't beat Atlanta. We've got Coca-Cola, Home Depot, UPS, Delta Airlines, Chick-fil-A, like top, top brands are all right there …”
Ben Chestnut Sep 20, 2022 ▶ 37:36 Everything that Breaks on the Way to $1B ARR with @mailchimp Co-Founder Ben Chestnut
Jun 11, 2024 bullish
Assertion Not checkable as stated
Chestnut: Mailchimp aggregated 4 billion email addresses and trillions of interactions
“What that has led to is millions of small businesses importing their lists, and that has led to four billion email addresses and trillions of interactions that those email addresses have.”
Ben Chestnut Jun 11, 2024 ▶ 33:17 Ben Chestnut: The Top 10 Learnings Scaling Mailchimp to $1B ARR
Jun 11, 2024
Insight
Chestnut: A second product act takes hold at 30% of revenue
“We'll still be looking act one for a long time until act two, except, you know, what, 30, at least 30% of our revenue is my philosophy. Then really act two has taken hold.”
Ben Chestnut Jun 11, 2024 ▶ 21:40 Ben Chestnut: The Top 10 Learnings Scaling Mailchimp to $1B ARR
Jun 11, 2024 bullish
Insight
Chestnut: Brand marketing is the most economical marketing founders can do
“It's actually the most economical marketing you do because it goes viral that people tell their friends about, and that's the cheapest marketing that you could pay for.”
Ben Chestnut Jun 11, 2024 ▶ 16:08 Ben Chestnut: The Top 10 Learnings Scaling Mailchimp to $1B ARR
Jun 11, 2024 positive
Insight
Chestnut: Digital brands need physical artifacts to make their brand feel real
“The thing about billboards and branding is one thing is I always wanted something tangible with our brand. I, everyone interacts digitally, but you need something to feel. So I always have like MailChimp toys, something that I want on your desk that you can fe…”
Ben Chestnut Jun 11, 2024 ▶ 13:17 Ben Chestnut: The Top 10 Learnings Scaling Mailchimp to $1B ARR
Jun 11, 2024 neutral
Assertion Not checkable as stated
Chestnut: Mailchimp bootstrapped because Atlanta funding was unavailable post-dot-com bust
“I couldn't get funding even if I wanted to after the dot com bust. I was in Atlanta, so don't use me as a hero.”
Ben Chestnut Jun 11, 2024 ▶ 28:06 Ben Chestnut: The Top 10 Learnings Scaling Mailchimp to $1B ARR
Mar 12, 2025 neutral
Assertion Not checkable as stated
Lemkin: Mailchimp suffered a failed year-long M&A deal before Intuit sale
“They sold MailChimp to twelve billion to Intuit. There are actually a lot of learnings, but one is they had a deal before that, that fell apart and it almost destroyed the team. He said, going to your point, it really resonated almost destroyed the team. They …”
Jason Lemkin Mar 12, 2025 ▶ 19:04 The 10-Point Checklist For When You Sell Your Company With Founder Collective's Dave Frankel
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