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What I Learned Interviewing Millionaires, Best-Selling Authors, and Wild Digital Nomads

The past year I’ve had the amazing opportunity to interview wildly successful people.

Recently I interviewed Chris Brogan (NY Times Best-Selling Author), Michelle Schroeder — a millionaire blogger — and Rob Edwards, who wrote Disney’s Princess And The Frog.

While they all were great, my favorite interview ever was with Stephen Warley (Creator of the “UnStuckable” podcast) — which happened a few weeks ago.

We didn’t even mean to do the interview, but we really hit it off after 5 minutes of chatting and decided to record the call.

I really think we’re going to be good friends.

To be honest with you, I was scared shitless before many of these interviews. I’m a 24-year-old who’s largely done absolutely nothing with his life yet, so how the hell could I get all these successful people on the phone?

And how can you?

Well, I’ll talk about all that, and what you can learn from my experiences moving forward.

People Legitimately Want To Help You

Chris Brogan was probably the coolest guy I’ve ever interviewed. After the call I told him I felt like he was the kind of guy I’d want to get a beer with (or ten).

He thanked me, and told me he agreed to the call because I seemed like a good, hard-working kid with good intentions.

He was extremely generous with his time.

To be honest with you, I did NOT expect Chris to hop on the phone with me. In fact, when I send out detailed, personalized messages to people I want to interview, I just assume 70 percent of them won’t respond.

It’s just how it goes.

Gary Vee says he siphons off 20–25 percent of his time for things that won’t give him a big return. He always gets on podcast shows that have little-to-no followings because

  1. He’s a nice guy
  2. He believes karma is practical.

The reality is a good portion of people you reach out to won’t get back to you, but I’ve found the uber successful people — the ones who have really done something incredible — seem to get back at a much higher rate (weirdly enough).

The ones who aren’t super famous, but have made a lot of money, seem to not give much of a damn about you.

The point here isn’t that people suck — it’s that really, really big names WILL respond to you. They aren’t untouchable. Some people are very, very generous, and they’re going to make you feel like a million dollars on your call with them.

All it takes is the guts to email them.

These People Are Actually A Lot Like You

When I see someone’s name attached to Disney movies or the NY Times best-seller list or any of that jazz, it’s easy to think of them like they’re a billion lightyears ahead of me.

Like I don’t deserve their attention or something.

Because of this, I also start believing they won’t be able to relate to me either.

Guys, for me to interview someone who had a house in Beverly Hills was absolutely nuts. For me to interview a millionaire who travels aimlessly across the country in her RV was nuts.

How can they possibly relate to me?

But the more I talked with these people, the more I realized how genuine they actually were.

As you settle into the conversation, you realize the thing that actually makes these people special is the fact that they’ve seen massive success and still decided to hop on a call with a nobody.

And that was so cool to me.

They’re On Top Of Their Sh*t

When you talk to friends, the conversation can get pretty aimless, right?

When you talk to somebody who’s super successful, the conversation intensifies. They’re either going to spout off about a billion different things or they’re going to answer your question with one sentence because it sucked.

They don’t waste time. They’re focused. They hear every word you’re saying.

They’ll blow you away with a perspective you never could’ve thought about, and then you as the interviewer need to snap back to reality, try not to fanboy out, and ask them the next question.

It’s intimidating as hell to interview somebody with 1.7 million Twitter followers.

It’s even more intimidating when they’re blowing your mind and you feel like you’re not worthy.

The Internet Is Smaller Than You Think

I aimed pretty high trying to find people for my virtual summit.

As I went further down the internet rabbit hole emailing people like Nicolas Cole, Tim Denning, and Chris Brogan, I started to realize all these big names know each other.

My friend Stephen Warley also interviewed Dorie Clark and Chris Brogan. Chris Brogan knows Gary Vee. The list goes on and on.

Josh Steimle recently published an article detailing the top 50 marketing influencers of 2018 (I’m paraphrasing the article title), and two of my 30 summit speakers were part of that list.

I read his article and pretty much knew everybody he highlighted.

This gave me a huge window into how the internet actually works.

All the biggest influencers help each other. There’s legitimate trust between them. They are friends.

This is really why the internet is dominated by a couple big names in my opinion..

It’s sort of a monopoly except it’s not because everybody is helping one another.

When you have one person with an audience of 20,000 shouting out another person with an audience of 30,000 (and vice-versa), word spreads pretty quick.

And it pays to do this because you’re essentially trading audiences. That’s the real reason why influencers come on big podcast shows/why podcasters want influencers with big audiences, too.

That’s why you see such amazing growth among certain influencers.

Who wants to have a beginning blogger on their podcast who has 4 people reading them?

After you do get that initial audience, however, things move full-steam forward because other people want to get in front of your audience, too.

It’s sort of crazy to think about — why it’s actually happening like this — but then again that’s what’s happening.

The content that’s brought to you isn’t necessarily brought to you because it’s good, it’s brought to you because the people involved have a gigantic audience.

You Can Be An Influencer, Too

The greatest lesson I learned from all this interviewing?

You can be an influencer too.

I’m serious.

It’s really easy to divorce ourselves from the people we read, listen to, and watch because they have such a big audience and so many people talking to them.

It’s easy to look at them like these amazing figures.

But the truth is once you actually sit down and talk with these people, you realize there’s a lot that’s special about them, but there’s also a lot that’s not.

I don’t mean to say the people I interviewed aren’t amazing — they are — I just mean to say that there’s no real “thing” they have that you don’t have.

They’re not necessarily smarter than you — they were just willing to face their fears more.

I watched Chris Brogan give a talk at some conference on YouTube before I interviewed him, and my interpretation of the footage was that he was nervous at the start of the talk.

Then he got good.

Like, insanely good.

He had the whole room laughing like he was a stand-up comedian.

Like, Kevin Hart needs to watch out.

Chris may or may not have been a little nervous, but my interpretation was he wasn’t scared to face the common fear of speaking on-stage.

It’s incredibly nerve-racking to publish words for the world to see. It’s incredibly nerve-racking to interview someone who wrote a movie that made a major impact on you.

It’s incredibly nerve-racking to do a lot of things in life, but the fact of the matter is you have to do them if you want to be great.

Tim Ferris once said:

“A person’s success in life can usually be measured by the number of uncomfortable conversations he or she is willing to have.”

I just had 30 for my virtual summit because I was so nervous.

I’d even amend that quote to say:

“A person’s success in life can usually be measured by the number of uncomfortable situations he or she is willing to put themselves in.”

That’s seriously it.

I’m scared to death of vlogging. The idea of holding a camera in front of my face and speaking into it in front of people is nerve-wracking.

But I know that if I do it once and get over the awkwardness, vlogging will lead to bigger and better things. I just need to get over it already.

There is no REAL thing separating you from being an influencer — just your fears. Most people give in to that. I could NEVER see myself speaking on-stage, but I know if I got over my fear of doing that I could level-up my business in a HUGE way.

But I don’t know if I could ever get over that.

Most don’t, which is why most aren’t Chris Brogan.

I’m scared like the rest of you. I’m a 24-year-old who has Crohn’s disease and isn’t sure when my symptoms are going to act up again. Once they do, the whole traveling thing will basically go out the window.

I try to face my fears as much as I can — and you should too. You’ll find that once you do, you’ll be on the fast track to being who you want to be.

Want to get started writing online? I actually have a free 5-day email course called “Your First 1,000 Medium Followers” that will teach you how to build an audience here on Medium! Sign up for it right here. I’d love to teach you a couple things.



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