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Failing My Podcast Interview with James Altucher

I had just wrapped up eight in-person interviews over three days with Toronto entrepreneurs and I’m now headed to the Big Apple for an interview with James Altucher.

Let’s back up a couple months.

I email James about being interviewed on my show. He replies to that initial email within five minutes and says, “Sounds good. I’m tired right now, but let’s talk soon.”

I don’t get a reply from my next eight emails. And I get it. The dude is busy. And yes, I sent eight emails without a reply. Persistence.

So, I change tactics.

I know that I have to make it insanely easy for him to say yes, otherwise it will be a no. So, I tell him that I am going to be in New York this weekend and will come to him to record. It can be as short as he needs it to be.

I have absolutely zero intention of being in New York. If I can get James to agree, I will cancel my flight home from Toronto to San Diego and fly to NYC instead.

I notice that Pamela Sisson, James’s lady friend, seems to be working closely with James and helping out with his social media and communication. So, I decide to email Pamela on Tuesday.
Still nada. Now it’s Thursday and I’m supposed to fly home to San Diego on Saturday.

Suddenly, James adds me as a friend on Facebook. Before being friends on Facebook, I knew that I couldn’t message him and get a response because it would go to his inbox from unknown senders and get buried.

But, now we are friends. He can’t escape my FB messages.

Why he added me as a friend that day, I still don’t know.

I shoot him a FB message and he replies right away. “Sorry I haven’t been able to keep up with my inbox, but sure, we can meet up on Saturday afternoon at my new Airbnb since we’re moving on Saturday. Just confirm with Pamela.”
No sweat. I email Pamela again and she replies right away, “Sure, 4pm Saturday.”

Game on.

I’ve read Choose Yourself and Reinvent Yourself months earlier, arguably his two most well-known books. I start listening to all of his podcasts. I listen to him being interviewed by Tim Ferriss and Lewis Howes. I also listen to James interviewing folks on his show like AJ Jacobs and Sara Blakely.

I build up the interview in my head to be larger than life.

I’m interviewing one of my favorite writers in the world. He bleeds on the page like no one else can. And I’m not sure he even does it on purpose. I don’t think he knows any other way to write.

I’m interviewing a guy that embodies the Fail On movement like no one else. He has seen the bottom of the barrel. He has made millions of dollars. He has lost millions of dollars. He knows how to Fail On.

This could be the moment for my brand new podcast to take off and explode (trust me, it wasn’t).

I told Philip McKernan in the Bahamas I don’t get nervous with in-person interviews.
Up until now, I truly believed that.

Walking to the interview from my hotel on 30th and Madison, I start to feel anxiety envelop me. My heart’s beating fast, hands sweating and I’m trying my best to tell myself to lean into the fear.

Easier said than done.

As I’m building James up in my head, I’m subconsciously tearing myself down and feeling a huge bout of imposter syndrome. “Why the hell should James care about what I have to ask or say? I bet I’m just a task in his day that he really doesn’t want to do, but he’s just too nice to say no.”

I can’t get these thoughts out of my head.

These thoughts are now running rampant before entering the beautiful glass foyer off 29th St and Park, the new Airbnb James and Pamela had moved into just five minutes earlier.

I take the elevator to the 34th floor penthouse to an absolutely stunning space. Floor to ceiling windows facing north to the Chrysler building and Empire State Building. The fear starts to consume me.

Pamela greets me with an ear to ear welcoming smile telling me to come in and that James is in the kitchen. James greets me and asks if it’s okay if he finishes his online chess match before recording.

Who am I to say no? I shouldn’t even be here.

With all of these negative thoughts building, I fail to realize that my energy level and enthusiasm are completely void. I don’t fully realize how low my energy is until I get back to my hotel and play the audio back to myself. I sound like I’m giving a eulogy. It might as well be my eulogy. Shit.

I had crammed in so much research that it was almost counter-productive. I had scripted a bunch of questions that I wanted to ask and, man, did they come out sounding scripted. This might be the worst interview I have done to date (Since the time of writing this, I have done worse. Much worse.) and it was the one that I so desperately wanted to make great. Shit. Again.

I’m not enunciating words and stutter often.

My confidence destroyed, James is now calling me Ron over and over in the interview.

Shit. Shit. Shit.

It’s not his fault. If I can’t make a strong enough impression for him to remember my name, that’s on me.
So, James, if you are reading this, please do not feel bad.

I don’t care what you call me. That’s what editing is for. And you’re my favorite writer.

I hung out with James and Pamela for over two hours. We recorded for about an hour.
Our offline chat may have been better than our recorded chat. Funny how that works, right?
We talked about break dancing, stand up comedy, gender battles in tennis and mutual friends.

James and Pamela offered advice and a critique of the interview.

I learned to toss out my boilerplate questions, or at least deliver them so they don’t sound like boilerplate questions.

  • I learned to push boundaries and ask hard questions.
  • I learned that I want the audience to feel the tension and drama that is created when I ask hard questions.
  • I learned how to break patterns with guests to get unique, uncanned answers.
  • I learned that if Coolio mentions cocaine, you damn well better ASK Coolio about said cocaine.
  • I learned to be an active listener and engage in extreme curiosity.

I learned that interviewing well is one of the most challenging projects I have ever taken on.

While completely discarding the article intially, I now appreciate Ryan Holiday’s take on why you should NOT start a podcast. And it made me appreciate @Jordan Harbinger’s roundtable on the same subject at MastermindTalks.

Unless you want to be world class and master the craft, don’t bother. It’s deceivingly difficult.

Anyone can pick up the required equipment and ask questions. To do it really well, to pull out deeply rooted emotion in oftentimes the first and only conversation with someone…That’s an art.

While this interview was a fail, I’m taking away priceless feedback, a new friendship and an insatiable hunger to suck less next time.

Thank you James. Thank you Pamela. Fail On.

Your friend,

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