Emmy Award-Winning Content Marketing

Credit: Davy Rothbart, Wealthsimple

A while ago I was scrolling through Facebook and saw a sponsored post with Anthony Bourdain’s face on it and the headline, “Anthony Bourdain Does Not Want to Owe Anybody Even a Single Dollar.” Being a Bourdain fan, I clicked on it.

What followed was a great article about Anthony’s financial situation growing up and his philosophies on saving—complete with trademark Bourdain humor and all.

At the start of the article, it said: “Wealthsimple is a whole new kind of investing service. This is the latest installment of our recurring series “Money Diaries,” in which interesting people tell the unvarnished truth about their financial lives. We believe being honest about money is always valuable, even if it isn’t always good investment advice.”

And so began my love affair with Wealthsimple’s content marketing strategy.

First off, kudos to Wealthsimple for hacking Hollywood like champs. Swear to God, someone over there poached Horace Slughorn from Hogwarts School of Witchcraft and Wizardry and made him their director of influencer marketing.

Take one look at their Money Diaries series, and you’ll see an impressive list of interviews with A-listers discussing their finances.

Anthony Bourdain.

Kim Kardashian.

Elijah Wood. Margaret Atwood. Gary Numan. Woody Harrelson. Kevin Bacon. Jon Hamm. Kylie Jenner. Spike Lee. Awkwafina. Maria Bamford. Abbi Jacobson. French Montana. Tegan and Sara. Paul Reiser. Iman Shumpert.

The list goes on.

And on.

And on.

How in the world did a fintech company manage to execute better influencer marketing than most agencies in a long, looong time? I reached out to Davy Rothbart, the producer of many (most? all?) of their Money Diaries posts to find out.

Davy Rothbart’s CV is extensive—although I didn’t know that when I emailed him out of the blue and asked to chat about Money Diaries. I had seen his name at the bottom of the articles and decided to drop him a line.

Turns out the guy is an Emmy-award-winning director, Wikipedia page and everything.

Further proof of my ignorance arrived when I asked one of our content marketing strategists to hop on the call with me, and he Slacked back with this:

Ok, Patrick. Calm down. We’ve got an interview to do.

Fast forward to the call.

Davy shows up to the Google Hangout with his fricking Emmy Award perched on his shoulder like a golden parrot. How cool is that?!?!

Anyhow, Davy is a great guy. We had something like twenty minutes blocked off, but I think he ended up giving us over an hour of his time.

He prefaced the call by saying, “I don’t know if any of this will help, but here’s what I do.” Turns out, there was tons of advice that marketers should hear.

For the sake of structure, I’ve broken it into three parts: recruiting A-list influencers, the process of interviewing, and the critical elements of storytelling.

Without further ado, here’s how an Emmy-award-winning filmmaker executes a powerful content marketing strategy.

How to recruit A-list influencers

You’d think that having Hollywood connections would help you with influencer marketing…

Well, it turns out it does.

Davy straight up said that a lot of the interviews he has done for Wealthsimple have been set up because—true to Hollywood fashion—he knows someone who knows someone who knows someone.

So yes, it helps to have connections.

BUT—and this is a big but—not knowing people has never stopped a hard-working chump from getting what he or she wants. And even though it helps to have Elijah Wood’s cell number kicking around, that doesn’t mean Mr. Wood’s publicist will say yes when push comes to shove.

In fact, Davy said when they started the Money Diaries series he had to approach publicists with little more than the promise that “this is going to be cool some day.”

“Riiight,” they probably thought. “I’ve heard that one before.”

But the wild thing is, they actually bought it. They bought the company’s vision.

“Exposure was enough,” Davy said. “I wasn’t asking for a lot of their time, and the upside was that they could get a lot of publicity through the company’s future campaigns.”

So as far as I know, Wealthsimple didn’t have to pay a single celebrity for their Money Diaries posts. They were happy to do it for the exposure.

And you know what? I’ve noticed a similar effect myself from producing podcasts.

There’s a weird imbalance right now regarding the perceived value of different marketing channels. If you ask an A-lister to talk at your conference, you’ll be spending God knows how much on their speaker fee and travel and hotel. But podcasts? Totally the opposite. If you say, “Hey Mr. XYZ – any interest in recording a quick podcast remotely? Only takes twenty minutes and we’ll promote the heck out of it.” They’ll usually reply faster than a dude on Tinder in a small town. Even better if they’ve got something new to promote.

People—especially influencers—don’t realize that their name is as valuable (maybe more) in the headline of a blog post as it is on a conference screen.

Here’s the other thing Davy said, though. It’s not all about celebrities. It’s about people who are interesting—about the story they tell—that can be powerful.

This part I sorta agree with.

On one hand, I hear what he’s saying. Wealthsimple has written great stories on the finances of nuns and sword swallowers and crack addicts. If you can tell engaging stories for your target market day and night, knock yourself out.

But here’s the thing…

Margie who runs the cupcake stand on your corner doesn’t have a following.

The Rock does.

And if you happen to get an interview with The Rock, you can use cross-interest targeting to promote that piece of content, for example, to CEOs who are fans of Dwayne Johnson and digital marketing.

My two cents? Swing for the fences. Seriously.

[Months later, I took my own advice and asked Rand Fishkin to appear on our company’s podcast, which he agreed to. I’m telling you, go big or go home.]

The other benefit of swinging for the fences is that if you interview someone well-known, other well-known people are more receptive to it.

Davy says, “If you get a big name up front, it’s soooooo much easier to get other big names. It’s also smart to hire a well-known documentarian or film person, because then a lot of people just want to work with that person.”

Moral of the story: don’t be shy. Leverage your current connections and friends of friends to secure your first big name, and if you can’t do it that way, start reaching out with cold emails that emphasize the exposure the influencer will get. Hire someone that influencers will want to work with, or go after the ones who have something to promote at the moment (new books, Netflix specials, etc.). Above all, get creative and don’t give up.

How to structure your interviews

Davy says he typically conducts interviews over the phone and then transcribes the results into a 6,000-ish word transcript. (Sidenote: If you need to do any transcribing, I recommend Speechpad.)

In terms of the interview itself, he prepares 10 pre-written questions and then tries to go with the flow of the conversation.

What are the best questions?

For Wealthsimple—given that they’re a finance platform—the questions are mostly (obviously) about money. “What was your first job? How much did that pay? How has your career evolved?”

Whatever your business is, follow the same formula. Run a marketing agency? Ask about the most desperate thing they’ve done to get a client. Building a SaaS product? Ask about the most costly software mistake they’ve ever made.

Davy said exact dollar figures are key.

Articles that specify how much people spend on X or how much they made doing Y outperform everything else, especially if you lead with those figures.

That’s good advice for all bloggers. Readers love data, and people are inherently interested in how much things cost or how much people make. Use it to your advantage.

If you have problems getting people to open up about such things, let the interviewee know what others have shared. That’ll get their gears going and make it more likely that they’ll share something similar. Follow your natural curiosity and don’t stick too rigorously to your pre-written questions.

Critical elements of storytelling

There are countless books on the elements of storytelling, but when it comes to creating a content marketing strategy, here are Davy’s three biggest tips:

  • Start your post with an engaging, notable, or funny excerpt that sets the tone.
  • Segue into something relatable. It could be the voice of the person—are they known for being funny, conversational, open?—or maybe a personal email from a friend or something on social media. Anything relatable to the reader’s life.
  • Get as specific as possible. Again, use as many dollar amounts as you can.

What about keyword research and subheadings and all the other technical stuff that SEOs and bloggers get caught up with? Sure it’s important, but story is king. Davy even admitted (somewhat bashfully) that he has no idea who Wealthsimple’s audience is. He just tells the damn story and doesn’t worry about selling.

“The audience matters,” Davy says, “but good storytelling is universal. Write what you’d want to hear, what you’d find compelling, and go from there.”


Devon Hennig

Devon Hennig is a published author with a background in lead generation, brand development, and event speaking. He lives in Toronto and works as VP of Demand Generation at Vendasta.

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