Ben built a company around a strong simple service and a quirky brand that sees annual revenue of $600 million dollars – and he never raised a dollar of outside funding. [8:33]

My mother ran a hair salon in our kitchen, but the word "entrepreneur" wasn't being used. This was just a way of life. This was called "making money", "paying the bills”. The house was always full of customers. [8:47]

His first business was making flipbook animations with sticky notes: My marketplace was the school bus, and I would go on and I would show some kids and they just had to have it, and I would charge a dollar for each one. Highly unscalable business. [10:05]

I got a job as a banner ad designer actually, which was even more invigorating than web design, because it was so fast-paced and you got results fast. [11:05]

Ben decides to start a design company: My business partner and I went out, and we got clients by knocking on doors. We got paying projects. We got a $13,000 project and a $32,000 project before even getting a business license. . .We wanted to bootstrap it. We wanted to keep it simple and pragmatic. [12:01]

Where the idea for Mailchimp came from: We noticed every customer—big or small— asked for the same thing: email marketing, every one of them. [19:15]

For five years Mailchimp is just the side project running on its own. And the thing is the income we were getting from Mailchimp, we weren't watching it. [21:00]

My partner made an Excel spreadsheet for Mailchimp's revenue, and it was climbing up and to the right – and the consulting business was just flat and maybe even declining. He said, "That's it, have faith in the math. This is what we should focus on." [21:48]

Most investors pitched this idea like, "What you've done here is great, it's wonderful, it's cute. Let's invest and then we'll help you move to enterprise because that's where the real money is." I couldn't stand that. I thought about building something that would empower small businesses. [25:25]

We kind of fantasized about being able to eat at Fuddruckers, because they had these $8 hamburgers. We thought, “If Mailchimp could just make enough money every month to pay our lunch every day.” It sounds ridiculous now, but that was really all the expectation we had. [27:22]

Ben put a toll-free number on the Mailchimp website and asked customers to call in with their most-requested features: They started to call us and they gave us all the features that we lacked. [33:40]

Ben stumbled on a way of getting the word out to their most passionate users: Every time we launched a feature and I blogged about it and tweeted about it, we got retweets and comments and more sales. [34:32]

Ben: What are we going to do with marketing?

Neil: Well, what's working?

Ben: Well, we code and then we blog and then we tweet.

Neil: Well do that, do it again.

Ben: Everybody's sick of it by now.

Neil: No, they're not. Keep going until it stops working.

And that was the lesson he taught. Don't be afraid to beat a dead horse if it's working. Keep going and hire people to keep it going.

Any kind of channel that's new, you need to be there on the ground floor before everyone else crowds it up. [35:45]

Ben likes to keep analytics simple: How much money did we make this month? Is it growing? At what rate? That's all I really care about. I keep it pretty simple. [40:37]

Full podcast here: Ben Chestnut Co-founder and CEO, Mailchimp on Masters of Scale

Learn from founders who came before you. Every week I read a biography of a founder and tell you what I learned on Founders podcast.

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