Expert Interviews


How John Henry—Star of Hustle on Viceland—Approaches Content, Motivation, and Fear

By: brunchwork

How John Henry—Star of Hustle on Viceland—Approaches Content, Motivation, and Fear

When John Henry moved back to New York City after high school to pursue a career as a jazz musician, he started working as a doorman. And, with the help of one of the residents in the Brooklyn building he worked in, Henry launched an on-demand dry cleaning business that served TV and film sets. A few years later, at the age of 21, he sold the company for $1M.

Wanting to give back to his community, John Henry went on to launch Cofound Harlem, a non-profit incubator that aims to help startups in Harlem find success. Today, he serves as a chairman for Cofound Harlem, a Partner at Harlem Capital, and host of Hustle, a Viceland TV show that focuses on mentoring entrepreneurs. We asked Henry all about his process—from staying motivated, to producing content, to overcoming fear—and here’s what he had to say. 


How do you stay motivated?

For me, motivation is overrated. Instead, it’s all about whether you can do the work when you’re not motivated. Can you find that one thing that will be your north star and enable you to do the work all the time, with or without motivation? Figure out what that is for you. For me, it’s my mission of building wealth for myself and my communities. That’s the one thing I will absolutely never tap out for.

How do you deal with the fear of failure?

Over time, fear has become a familiar friend. It never goes away, you just get more comfortable with it. I use fear as an indication of how big of a risk I’m taking. For example, if I started another dry cleaning business today, I wouldn’t be scared. But that’s because it’s not  big risk for me—I know exactly what to do in order to succeed. But any time you’re doing something new, the fear will be there. So I’ve just learned to get more comfortable with it. I shifted my understanding from, “Oh, it’s not that I have to overcome fear. It’s just that I have to learn how to direct it.”

How has content played a role in your success?

Content is so incredibly important and powerful. It shapes our aspirations—it shapes who we think we can be. It has played a very big part in furthering my mission. My brother and I have been creating content since 2014. First, I started by putting local content out. Everything was terrible at first, but we put in the reps. You need to put in the reps and the audience will start responding. Eventually Gimlet Media reached out and asked me to be a podcast host. And now, I’m the host of Hustle. They both found me because of my content. The answer to everything is more content. Content, content, content, content. I put out a lot of content and I’m still not putting out enough.

When it comes to content, do you prioritize quality or quantity?

Quantity. I will sacrifice the quality for the quantity. Quantity leads to quality because, with the reps, you get much better over time. Like sometimes, my brother will send me a video and I know it could be incrementally better. But I know a plus or minus 2% difference isn’t as valuable as just putting it out there and gaining response.


How did you make your content stand out in a saturated market?

When I first started, I was running out of stuff to say and I was feeling the pressure. Then I realized I only have 10 basic truths, really, and I leaned into that. That’s all I lived pretty much over and over. I leaned into my own lane, drowned out the noise, and got over the fear of putting my stuff out there. And speed really helps, too. It helps you be less precious about the content you post. If you only put out one post a month, you’re going to need it to perform really well. But if you put out content every few hours, you don’t have to worry about it as much.


When should you stop hustling?

For me it really just comes down to this: What’s your roadmap? As long as you’re following what you feel like your own personal roadmap is, then good for you. Me? I personally want to build generational wealth in my communities. So you tell me when that hustle’s gonna end. Never.


To view John Henry’s entire brunchwork interview, check out his YouTube channel.


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This interview was conducted by Aastha Jain and condensed by Abby Wolfe.

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