So what is it about the brand that people want to share with others? In other words, what tips do you give your own team members?

An example of a news summary you would find in The Hustle’s daily email.

I’m a self-trained copywriter, so copywriting is a big deal to me. With simple word changes you can make more money, make people smile, change someone’s attitude, and so many other things — so copywriting is a huge deal to us.

At first I wrote every email an article using my voice that I refined over a few years. Then I created a comprehensive writer’s guide that explained our voice and best practices. The guide is much better now, but here’s an early version: http://thehustle.co/hustle-content-guide

Next we hired smart people who understood our mission, then put them through education. And right now we only have 1 writer and 1 editor on the daily emails.

What is the main goal of The Hustle? Conferences? News? Both? How do you separate those or use them together to drive the business? How does your email strategy tie into that goal?

My personal goal is to employ 1,000 people, and I think we might get there with The Hustle. As a company our mission is to the the number one destination for ambitious millennials, whether that be for news or entertainment.

We started as a conference so we could bootstrap the media business. We are not a conference company but a media business with a conference. Conferences can be a $10m- or $20m-a-year business, but our mission is to be much bigger than that. And creating a content company is how we’ll get there. Thankfully though our conferences do a great job of paying the bills while we’re young and give us a way to meet our users and get new content.

Our first story ever where we became a best selling romance novelist in a week in order to prove how scammy and shady a lot of Kindle authors (specifically self-help and business authors) are. I also loved the article where we had a guy spend 14 days high on LSD.

How do you track engagement so you know what to write (or not write about) next in your emails?

What we cover is 50% editorial decision-making and 50% data driven. We have software that tells us what topics are trending or are about to go viral, so we will look at those topics and see what kind of spin we could put on them that our readers will love. Other times we completely make shit up, like we did with the Kindle article. We keep an eye on what people share.

Facebook is cool, but not as impactful as getting an email. You send friends an email; you don’t really post on their wall anymore.

So that could backfire too if you get it wrong?

Oh yeah. A list can decrease fast if you don’t a.) keep growing and b.) aren’t creating badass content. If 0.5% people unsubscribe for every send then you better grow 1% everyday.

So what was the biggest mistake you made for The Hustle? What did you learn from it?

Hmm. Let me think. Hiring people based on talent rather than personality. We hired a few top journalist from other publications because I thought that was the right thing. It’s not, at least for us. Instead we found people who we liked being around, knew how to capture people’s attention, and were hungry. Then we trained them how to write well.

However, I’ve learned that it’s impossible to make a bad writer a great writer. A good writer can become great, but a bad writer cannot become great. Storytelling is something you’re born with. Some can learn, but it’s very tough.

What do your investors think of the strategy?

The people we raised money from were all speakers at Hustle Con, so they knew we could execute on big things. When we pitched them on the The Hustle we told them we wanted to become the next CNN. CNN and Fox has a median viewership age of around 60 years old so it makes sense. And very few companies have captured the millennial audience, so that’s what we pitched them.

When we pitched them on email, it was more like we are only starting with email but we are not just an email newsletter. In the same way Ted Turner ran a billboard company before starting CNN, we’re starting with email…

But after we dominate the email game we’ll move to video, web, TV, and more.

However, I truly believed my co-founder and I could have pitched them on anything. A vacuum startup, a media company, or a hot dog stand. They would have done it. Great investors invest in the people.

- Lightening Round -

What was the most recent spam message you got in your spam box? What was the subject line?

Something like “Re: Your billing statement.” Dog, I know we’ve never talked before so don’t act like your message is a reply to another email.

What is your favorite book?

Titan, the biography of John D. Rockefellar.

Caffeinated beverage of choice: Coffee, Tea, Soda?

I’ve been caffeine and alcohol free for two years+! I drink a ton of decaf coffee though and I bet there’s a tiny bit of caffeine in there, so I guess that.

Which company that you subscribe to does email the best? Why?

Chubbies Shorts and Huckberry. Huckberry has lots of male oriented outdoors articles and Chubbies is hilarious.

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