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How I’m Crushing It

John Lee Dumas, Entrepreneurs on Fire

IG: @johnleedumas

“I was dying a slow death in the cubicle.”

Sound familiar?

If you’re still young or in school, is it something you are trying like hell to avoid?

“I had this whole world of creativity inside of me, but I wasn’t able to use any of it. I felt like I was almost choking on my own creativity because I had to be in a suit and tie and very formal. Everything was black and white, and I needed some color in my life.”

Until he turned thirty-two, John Lee Dumas’s life had been as traditional as apple pie. The grandson of two military veterans and the son of a JAG officer, service to his country was in his blood. He left his small town in Maine in 1998 on an Army ROTC scholarship to major in American Studies at Providence College in Rhode Island. A member of the first round of officers commissioned after 9/11, a year to the day after graduating college, he started a thirteen-month tour of duty in Iraq. He spent four years on active duty before returning to the civilian world. He was at the start of a four-year stint as a captain in the reserves, but otherwise he had no idea what to do with himself.

He tried law school but dropped out six months later. He then worked in corporate finance for a few years, but when he’d look at the people working in the positions above him, he knew he didn’t want their jobs. He had a feeling that he was destined for entrepreneurship, but he didn’t know what it really entailed or how to even begin. So he started reading self-help and business books. In 2009, one month after its publication, he read Crush It! That was the book that inspired him to quit the finance job, move to San Diego (where he’d never been), and become a real estate agent.

He kept at it for three years, but the job still didn’t feel like a perfect fit. He kept rereading Crush It! every year, though, and in 2012, something new struck him. I emphasized that, no matter what industry you worked in, you had to build a personal brand. He realized that he wasn’t doing that at all. He had a personal Facebook page, but he wasn’t even on LinkedIn or Twitter in any professional capacity. So he knew that needed to change right away.

The other thing that caught his attention was the idea of podcasting. He wasn’t really sure what a podcast was, so he decided to research it. He discovered that they were free and offered focused, targeted content. All those self-help books and audiobooks were getting expensive, and now he had to listen to even more if he was going to build a personal brand. Podcasts sounded like they were right up his alley.

“And that’s when I fell in love with the medium. I became a super-consumer. For eight months, I listened to as many podcasts as I could. And it struck me that, jeez, I’m driving to work every single day, I’m hitting the gym multiple times per week—I need to find that seven-day-a-week show that interviews an entrepreneur and talks about their failures, lessons learned, aha moments. So I went to iTunes to find that show. It didn’t exist! And I thought, I can’t believe this. Why not be the person to create that show?” So what if he had no experience in production or interviewing people? “I thought, Well, if I do a daily show, I’ll get better quicker. Because all these people, they’re doing four episodes a month with their weekly shows. I’m going to be doing thirty episodes a month. I just need to step into this void and do it, and I’m going to be bad. I’m going to do a hack job for a decent amount of time. And you can listen to today’s podcast and go back to episode 15, and you can see, this guy isn’t the same person. I was so bad. I was nervous, I was naïve. I was just hacking my way through it. But I kept doing it every single day.” He didn’t just turn on a mic and start talking. Instead, he researched, diving into YouTube, absorbing all the free content and advice made available by other podcasters, and he found two mentors. Unnervingly, both strongly advised against doing a daily show, explaining that they made all their money doing other things beside podcasting. A daily show would preclude all those other activities. It was the only piece of advice Dumas rejected.

“I was like, ‘You don’t understand. I’m so bad that if I did do what everybody else is doing, nobody’s going to listen. It’s just not going to be good. So I have to do something different. I have to be unique. I have to do something that’s going to raise people’s eyebrows.’”

Those two mentors, with their large virtual Rolodexes, were invaluable to helping Dumas land his first interviews. They weren’t going to introduce him to A players, but they were willing to introduce him to the B, C, and D players who were still building an audience, publishing books, and eager to share their stories with a neophyte in exchange for additional exposure.

It might sound as though Dumas has more confidence than the average human. Yet despite his conviction that podcasting every day—learning by doing—would be the best way to create a quality product, and despite many of his early guests’ relatively low profiles and the public’s almost immediate positive response, Dumas found himself almost paralyzed by imposter syndrome. Who was he to reach out to anyone for a one-on-one conversation? But he soldiered on and worked through his doubts and fears.

I started my entrepreneurial journey with one strength, and that was discipline, and I can tie that directly back to the army. But discipline alone is not going to get you anywhere. The two biggest areas I had to develop to go along with discipline were productivity and focus. People who are “just disciplined” can do something all day long, but what if they’re producing the wrong content? That’s where productivity has to come in. And you’re not going to be able to consistently produce the right content unless you’re able to block out what I call the weapons of mass distraction.

He launched his podcast, Entrepreneurs on Fire, in September 2012. As his guests shared their interviews with their sizable audiences, the podcast started ranking on the iTunes New and Noteworthy list. The dual effect meant that within two-and-a-half months the podcast drew over a hundred thousand unique downloads. He started receiving invitations to conferences, which gave him greater credibility and, along with his rapidly growing numbers, the opening to approach bigger names, such as Seth Godin and Tim Ferriss, who had both just released new books, Barbara Corcoran, and yes, Gary Vaynerchuk.

Now he was ready to explore ways to monetize. He turned to his audience and asked them what they wanted, and he listened.

What I found very clearly was, if you are willing to commit to delivering free, valuable, and consistent content, you are going to build an audience from that. Then, if you are willing to engage that audience one-on-one and ask them, “What are you struggling with?” and then just listen, they will tell you what their pain points are, their obstacles, their challenges, their struggles. And then you, the person that they know, like, and trust, who’s been delivering that free, valuable, and consistent content for a significant amount of time, can provide the solution in the form of a product, or a service, or a community.

And he did. Like Pat Flynn, each month he publishes a breakdown of what the business earns from his various revenue streams, which all add up to anywhere from around $200K to $300K per month. He also analyzes the company’s successes, so other people can emulate them, and all the mistakes they’ve made, including money lost, so people can avoid making them.

Despite being a millionaire several times over, Dumas still reads Crush It! every year.

The thing that keeps coming back to me is the landgrab. That’s what I think so many people miss. All the time, people say, “John, you’re so lucky that you started podcasting when it was nothing and now it’s the golden age of podcasting. You had the landgrab.” And they’re completely right. My timing was perfect. It was super amounts of luck and great timing, but what they miss is that there’s always that next thing. They’re not focusing on the next thing; they’re looking at the past and there’s the next Snapchat, then there’s Instagram Stories, now there’s Facebook Live. There’s always that next opportunity to landgrab and to become that person. Yes, I’m considered the “king of podcasting” in a lot of niches because I’ve been able to build a seven-figure business around just podcasting. But since I’ve launched my podcast, there have been people that have become the king of Periscope, and then the king of Snapchat, and the king of Instagram. Things that didn’t even exist when I launched my podcast. And while people were saying, “John, I just missed the boat with podcasting,” I’m like, “Yeah, but you’ve also missed the boat with all these other things.” So what I learned from Crush It! and continues to be relevant to me is, always keep your eyes on that horizon.