A Conversation with James Altucher and A.J. Jacobs


I have to admit that this episode is one that I favour for selfish reasons. I mean, interviewing A.J. Jacobs and James Altucher gave me a chance to ask two of the greatest interviewers of our time anything that I wanted. Which, I have to admit, is particularly timely for me since I’m conducting so many interviews myself these days…

Just to give you a little context, these two are total pros when it comes to the art of the interview. In his seventeen years at Esquire Magazine, A.J. has interviewed big celebrities including George Clooney, Scarlett Johansson, and the George H.W. Bush. Whereas in just three short years James has interviewed over 200 people as host of his top-rated podcast The James Altucher Show including folks like Tim Ferriss, Seth Godin and Arianna Huffington.

So yes… I capitalized on the opportunity to get some advice about what makes a great interview and I am not ashamed. Here’s what I learned from James Altucher and A.J. Jacobs about The Art of the Interview in this episode of the Community Made Podcast…

How to Get Great Guests…

The key to a great interview is a great guest. Sounds simple, but you would be amazed at how complicated it can be. When it comes to looking for interesting people to interview on his show, James looks for two things: Peak Performance and Reinvention.

What does that mean? Well, James looks for someone with a kind of “rock bottom” story; they experienced hardships, maybe even lost everything, got through it and ended up wildly successful despite it all. For him, that makes for an interesting guest, someone with a great story and strong character. Personally, I can’t argue with that.

Now, finding someone with an interesting story to tell is one thing, but booking them for an interview is another. It can be hard to nail guests for interviews, particularly if you’re shooting for big names. To this day, James still finds it to be a challenge, “I mean, every guest has been kind of difficult in the long run” he says.

The key? Be patient! Many of James’ guests took a long time to finally confirm. I’m talking years, not weeks or months. So be persistent, continue to follow up, and don’t give up.

“You have to give people a why… why they should go on your show. And if there’s no why that will entice them then they’re just not going on any show.”

Don’t worry though, it will get easier. Over time you’ll build a relationship with publicists and that will make it easier to confirm guests for your show, and as you do more and more interviews you’ll build social proof that will make it much easier to confirm relevant guests.

How to Prepare for an Interview

This is actually widely debated. Marc Maron is famous for not preparing at all to interview guests on his podcast. Larry King prepares the first question or two and lets the conversation flow from there. A.J. Jacobs sits firmly in the over-preparing camp (along with myself and James). And actually, he likes to go deep. One of A.J.’s favourite moves is to find something obscure and buried on the internet and ask his guest about it to get a reaction.

So if you’re preparing to interview someone for an article or on your show, read everything and do your research online. It’s important not only to prepare yourself to ask compelling questions, but it will also help you build instant rapport with your guests.

“People like it when you bring up things that not everybody knows. They appreciate it when you do your research.”

Don’t miss a minute of this masterclass on interview greatness with James Altucher and A.J. Jacobs: