Jan 28, 2015

For Cultivated Wit, Email is No Joke

All business is funny business for the people behind creative agency/software company/storytelling conglomeration Cultivated Wit. And email makes it possible.

“Email was the very first thing we did,” says Craig Cannon, co-founder and product director. “I made a one-pager website with a MailChimp signup for our email list, and that was the entire website. From the beginning it was like, ‘Welcome to Cultivated Wit, this is our email, please sign up.’ We were like, ‘We don’t know what matters, but we know if we have people’s emails, we can get stuff done.’”

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Cannon met Baratunde Thurston and Brian Janosch a few years ago when they were all on staff at The Onion. In 2012, the trio set off on their own. Cultivated Wit’s projects are wide-ranging, but everything they do is informed by a belief in the power of humor.

The right amount of funny at the right time

Working on campaigns for the SF Aids Foundation, the Open Society Foundation, Fight for the Future, and other causes has only reinforced their hunch that smart, funny content can bridge gaps in attention and empathy.

“It’s comedy as a Flintstone vitamin,” Cannon says. “You need the nutrients, and if you cover it in sugar, people are like, ‘Oh, OK, I can do this!’”

A similar spoonful of sugar approach informs Comedy Hack Day. The weekend-long event series brings together comedians and developers to solve problems while poking fun at the tech industry. (Incidentally, the next one happens on Feb. 8, and will feature hilarious judges Natasha Leggero, Scott Aukerman, Veronica Belmont, and Jonah Ray.) Attendance is growing, thanks in part to Cannon’s use of Mandrill to streamline the application process. Early on, more than half of the people who registered wouldn’t show up, so he wrote a few Python scripts to connect a Google form with the Mandrill API. Now, after potential attendees fill out the form, Cannon reviews their profiles and flags his picks in a spreadsheet, which triggers automated messages and reminders to the folks he’s selected.

“As soon as they have that human connection, they’re in,” he says. The drop-out rate is now between 5 and 10%. “I attribute a lot of that to personal email communication. Even if a lot of that is coming from a bot, it looks like it’s from me. People like it.”

Cultivated Wit uses MailChimp to send out more general updates about Comedy Hack Day and their other goings-on. The agency arm also does creative work for clients like AOL, Google, and Whole Foods.

Cannon says MailChimp helps their small team communicate with a big group of people. “When you’re a small company, you can’t have 200 clients,” he says. “Through MailChimp, we’re able to keep in touch with like 5,000 people. That allows us to have an outsized presence for the amount of people and the amount of work we can potentially create.”

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Above: 2014 Comedy Hack Day judges Reggie Watts and Sasheer Zamata

Forced isn’t funny

Cultivated Wit’s email content is a collaborative effort: Cannon and Janosch trade writing and editing duties, and Cannon (who once did Photoshop magic at The Onion) handles the GIFs. After a couple years on the job, they’ve got a few elements nailed down. For instance, they know they get better responses when they put their main call to action and most important links up top. But one thing that’s nearly impossible to peg down is how to guarantee laughs.

“We’re not outwardly trying very hard to be funny,” Cannon says. “If you were to meet us in person, we’re pretty similar to what the email feels like. So I think it’s more about being honest, being yourself. I feel like, if you have a community of people that’s into whatever your list is about, you can be funny within that community. I understand this little overlap between tech and comedy. I couldn’t be really funny about sewing—I don’t know anything about sewing. I think you can kind of just trust your gut. Just go for it. Assuming you’re not gonna go be super racist or something like that.”