The Exchanges

Every argument clarity score on this site is built from rows on this page. Each question and answer was assessed with names hidden, the host's own answers included, on four things from 1 to 5: directness (does it answer the question asked), coherence (do the ideas follow), precision (concrete details and clear references), compression (says a lot per word). The weighted mix (30/30/25/15) is the exchange score. A person's published score averages their exchange scores on raw tape only, at least 8 of them, shrunk toward the cohort mean. Full method →

Ben Chestnut no published score: only 4 usable exchanges on raw tape, and a fair score needs 8+ · coarse estimate ≈4.0/5 from 4 raw tape exchanges record → ← everyone

Every exchange below was scored with names hidden, four dimensions each from 1 to 5. An exchange's score is 0.30·directness + 0.30·coherence + 0.25·precision + 0.15·compression. The published score averages the raw tape exchange scores and shrinks small samples toward the cohort mean, so five great answers can't beat twenty good ones. Produced feed rows count only toward coarse estimates, never toward a full score.

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Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q Okay. And so what, what, as much as you can tell us about, I think some of it's public, but how, how did it happen? Did you get a random email or a DM or how did, how does this process happen for twelve billion? How do they get started?

A We had been through sort of an, a little bit of an informal round with another couple of potential buyers. Uh, and you know, it, it, it didn't end with a, a good, a good deal. So we walked away from it and I was, I had sworn I would never listen to another offer again. I was done with it. I was going to move on and just run my company for the rest of my life, and then, you know, maybe within a couple of days, I got a call, uh, from Catalyst, actually. I'd been working with them for many years, and they said, just take one more call. You're going to like this one. Oh, interesting. So I took a call with Alex Chris, uh, my, my new boss, and, uh, I mean, we hit it off immediately. He's a small business entrepreneur. Uh, he'd been with Intuit for 17 years by then, but Uh, he had run a business, got acquired, and he knew the passion required to manage small business companies, and he knew the pain that they suffered from, and he knew what drove us at Mailchimp, and we just got along really well, but they are, they're also a very careful company. They care about, ah, culture fit, and they did a lot of culture diligence, and, ah, that all, which I loved. I loved that they cared that much, and, but, but that did mean one year of, ah, kind of wooing each other.

AI assessment note: “I got a call, uh, from Catalyst... So I took a call with Alex”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q And how did, what did you learn from that? What did you learn? I mean, you made, you made it pretty far without a CS team with small businesses. What did you learn from that?

A I mean, we, we started to, I mean, we, we just did so well with, with smaller businesses, and then we noticed as they grew, And, uh, you know, maybe they would hire VPs of sales or VPs of marketing, and they would start to use MailChimp. Their needs changed. Suddenly, it wasn't the founder who loved our unique and kooky small business brand. It was a new person, uh, and they were, they, they treated us differently. And so I would go out and visit some of them, and, you know, I would say, what do you think of our brand? Uh, where, where does our brand, you know, rest in your brain with other brands? Are we next to Nike? Are we next to Apple? And I remember one, one marketer told me, uh, uh, no, your brand lies next to my microwave oven. And I, you know, it kind of broke my heart a little bit. And I said, well, what do you mean your microwave oven? And he said, you know, my founder liked you and he loved the brand, but I've got to grow this business and I need you to be reliable. And if it doesn't cook my food in a minute, I want someone to call and answer my questions and just get it running again. I don't want to have to read KB articles, blah, blah, blah, blah. So, you know, that told me, gosh, we've got to, like, spool up a customer success team of some sort, and it was, it's been a long journey. Uh, we've got some great new executive leaders that are, and Intuit's got a lot …

AI assessment note: “that told me, gosh, we've got to, like, spool up a customer success team”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q days of eSignatures, my co-founder wanted us to be the bad boys of eSignatures, and I'm like, I don't think that's gonna work. Like, this is a product that 99% of the world doesn't trust, and I know you're a great marketer, but this is too edgy for back in the day, right? So how did, what did you want to get out of WEIRD? What was your vision here?

A Uh, I mean, it was really probably coming from our small business customers. Uh, my co-founder Dan and I just believed in, really, we didn't try to strategize that much or come up with all the answers ourselves. We just went out to the customers. And when we talked to them, they were kind of kooky themselves. I mean, whatever small business it is that you're trying to run, it's probably been done before. But each founder thinks, I'm going to do it better. I'm going to do it my way. And that's their personal brand. And I don't know, there was the first couple of iterations of our brand. They were a little bit weird and funny, um, in a kind of a monkey kind of way. That was really the theme. Uh, and they just loved it, and we just sort of rolled from there. And, you know, I think one of our, one of our teammates, uh, uh, kind of encapsulated perfectly. I think she came up with, uh, we got you because we get you. I think that's the appeal of our brand. For small business owners, we get them. Look at us. We're weird like you, or we're kooky and unique like you. And it just, it's just worked for 21 years.

AI assessment note: “For small business owners, we get them. Look at us. We're weird like you”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q Got it. Well, that'll be a big experiment, right? Um, it's, it's the big, Related to that, we chatted before, um, about product expansion. I learned some interesting stuff from you, but what works and what doesn't, right? And what worked for you, I think we talked about landing pages being a surprise, right? And e-commerce being harder than you expected to expand in, right?

A Yeah, e-commerce, e-commerce was a bit, it's, it's a challenge to break into that world, um, but, and, and we, we built all kinds of things for our small businesses, um, Landing pages was one that we built. I kind of thought they were boring, uh, not really a big deal, and it was probably one of our most popular features over the last, in recent years. I mean, it just took off and sold like hotcakes, and I still to this day can't explain it. I'm just thankful that we had this culture at Mailchimp to constantly not, we didn't even use the word innovate as far as I can remember. I always just said tinker. I said just keep tinkering with code and just keep trying little, make small bets. I didn't want moon shots. They were too expensive. I just said, make little small bets, and fail fast, and then just kind of, like, recalibrate, and landing pages was one of those little tinkering experiments someone did. Who knew? I mean, it just took off.

AI assessment note: “Landing pages was one that we built. I kind of thought they were boring”

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