The Worst Interview EVER. What I Learned From It.

I gave the worst interview of my life yesterday. I’m humiliated and feeling awkward and embarrassed.

But since I like to learn from my mistakes, Aaron and I listened to the interview and recorded a blow by blow during the interview of everything I did wrong. So you can listen to me interview Biz plus my analysis of what I was doing wrong.

It’s up on iTunes so people can listen. Here’s the link on itunes.

People will listen and think, “Ewww, that was just awkward.” Or even worse, “Did James just say something racist?”

This isn’t the worst problem I could have in life. I’ve had a lot worse. But when you are trying to get good at something I just want it to be non-stop good.

But “getting good” implies by definition you are often bad. That’s how we learn.

I felt so awkward in the interview but learning to be comfortable in awkwardness is a valuable skill to have.

Even the engineers after the interview said afterwards, “what. the hell. was that?”

Unfortunately, I was interviewing rap LEGEND Biz Markie, my hero. And I kind of wanted to be his best friend.

I’ve been obsessed with him for 25 years. He was a legend when I was a kid and I wanted to talk to a living legend.

People sometimes ask me, “how can I start a podcast/business/whatever without your connections?”

I have no connections. I had to reach out. A friend’s lawyer’s son is friends with Biz Markie’s manager. They all reached out for me.

Then no less than 20 emails and phone calls later I got the news: he MIGHT call in at 2pm. So I waited and he called.

I’ve had plenty of times like this where the person didn’t call and no interview happened.

I know his whole career inside out. I wanted to find out what happened. Was he a one-hit guy? Did he resent the hundreds of millions that rappers made later on? How did he reinvent himself to succeed in other careers.

I was so excited. I took a nap beforehand. I watched every interview I could find with him. I danced to all his videos. I even watched him on “Men in Black” and “Sponge Bob Square Pants” and I listened to his segments on various albums dating from 1985 to the Beastie Boys in the 90s.

My ex-wife kept saying, “Can we please stop listening over and over to ‘Just a Friend’?” And I had an excuse, “but I have to prepare.”

When it happened I felt like the most unprepared schoolboy trying to interview the President of the United States and saying things like “did you always want to be President?”

But I did learn some things that were fascinating.


He told me he wanted to be a rapper in 1977 but no group would have him. “I had to get good first.”

I asked him what that meant. “Practice.” How much practice? “Six to ten hours A DAY!”

Six to ten hours a day of practice a day. A DAY. To be a good rapper.


In 1977 he started. “By 1983 I made the first dollar by rapping at a party but it wasn’t until I had an album out a few years later I was making real money.”

He then did some beatboxing on the interview to describe what it was. I wanted to know how much money he made when he said he made “real wealth” but he wouldn’t tell me.

I said what was it like when everyone knew who he was after “Just a Friend” but he said he had big hits before that. I asked how he met the Beastie Boys, he said they were playing basketball together and it was “a lot of laughs”. He did three albums with the Beastie Boys.

He told me he invested in gold in 1990 and he still has it.


“Because it never goes down,” he said. I said, but it went down from 1980 to 1990. He said, “I bought in 1990.” And that was that. Good investors hold forever.


He ended up never really going in a group. His major hits were off of his solo albums. “I wanted to be in control of my own career.” I think this is the key thing for every artist. To always think how to get through the gatekeepers.

Too often artists and entrepreneurs feel the need to partner. To outsource the most important aspects of their life.

It relieves part of the burden. It makes it seem like things will be easier. This could be true. I’ve had many good partners. But ultimately, I view my full business as just me. And Me, inc. makes occasional partnerships with others but it’s clearly specified and the ultimate focus for me is back to “Me, Inc”.

He didn’t have all the methods of distribution that artists have today but he could still control his career. He told me he owns all the rights to “Just a Friend” so every time that song is played he makes money.

The other key thing he did to choose himself was by having multiple sources of income. He was a rapper, a DJ, an actor, a manager, a performer, a cartoon character, a show producer, and so on.


He told me the key: “Master only one thing at a time”

And when you get bored with one (“I was bored making albums”) master the next thing you love doing. And that’s how you keep young. If you look at his photos, he’s 50 now but looks almost the same as when he was 20.

Biz Markie never made a huge amount of money. But that doesn’t matter. Money is a side effect of doing what you love to do.

“I always just have fun,” he said. “I never stopped having fun.”

The other thing is, once you get good at mastering one thing (rapping, which took 7 or 8 years and 6-10 hours a day) it’s easy to master the next things. You learn the language of mastery. “Mastering a new thing was easy for me.”


“I lost 150 pounds in the past year,” he told me. How did you do that? “I drank a lot of water and didn’t eat a lot of food,” he said. And that was that. “Paleo?” I asked. “Nah,” he said, “just drink a lot of water and don’t eat a lot of food.”

We talked about other stuff. I’m making the interview seem better than it was. I was feeling really awkward throughout. We never really connected.

I asked him if he had any regrets. Like switching out of rap right before the deals got into the tens or hundreds of millions. “I never regret anything,” he said. “I’m blessed all the time.”


We talked about the battles that rappers have with each other. I asked him if he had battles when he was younger. “I still do battles!” he said.

“Would you battle me?” I said.

“I’d battle you on a pogo stick right now if you want.”

“How about we play chess,” I said. I had this fantasy that we could be friends. That we’d be playing games and laughing and talking about the good ol days.

And then he hung up and that was the end of the interview.

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