Interviewing the Wolf of Wall Street, Jordan Belfort: My Experience

It was a Saturday morning in Mid-October when I got the email., “Jordan can do the interview for your podcast at 3pm this afternoon.” After a solid six weeks of missing each other we were finally getting the chance to have a conversation with the original Wolf of Wall Street Jordan Belfort, the man whose life was the basis for the famed movie The Wolf of Wall Street, one of the most popular movies for my generation. [Here is the interview with the Wolf.]

I called Tom (co-host of the podcast), and we agreed to meet at the office to start our pre podcast preparations.

Preparing for a podcast can be a tricky thing because you have to balance being conversational and naturally curious but also have enough information to know where you want to dive deep. Joe Rogan likely doesn’t have a list of questions for his guests and in turn his podcasts are incredibly conversational, whereas Tim Ferris is very detailed in his questions and preparation.

Typically we have a week to prepare for an interview, but with the Wolf we had 3 hours.

Tom and I got into the office around 10, had our coffee, and started calling our friends, family and die-hard listeners to source questions and ensure we had a beat as to what our listeners wanted to learn from the Wolf. After a solid few hours of research we split for lunch at Irish Times.

Over a couple Bud Lights, burgers and fries, we kept coming back to the same point — we couldn’t believe that we were about to talk with the Wolf of Wall Street!


You have to understand that our fascination with Jordan had more to do with his confidence, self-belief and insane ability to seemingly manifest whatever he wants, than his sales tactics and legal issues. He also has a unique ability to interpret events different from how most folks would. For example, after dropping out of dental school because his professor said that the golden age of dentistry was over, Jordan broke the single day record for selling meat and seafood door to door. Rather than staying on as a salesman, Jordan started his own meat and seafood business, recruiting a couple dozen able bodies to sell with him. That business ultimately got overextended and went bankrupt when Jordan was 23. Rather than look at the meat and seafood collapse as failure or convince himself that he was just a salesperson and couldn’t run a business, Jordan’s interpretation of the event was different. It motivated him to learn about finance and continue his path to riches.

How we interpret events and respond to situations in our life is something I’ve been working on a lot lately. The majority of past guests from the podcast talk about their ability to see the positive in a given event, and also know when to forget a loss and move on. Their self belief never wavers and they know deep-down that they will get the job done. Jordan is no exception which you can clearly see in Part 1 of our interview with the Wolf.

After closing out our tab we headed back to the office for the interview. As we nervously sat in the studio waiting for the interview to begin we received an email from Jordan’s assistant, “can we push the interview back two hours? We had a scheduling conflict.” No problem we said, we had waited long enough and weren’t going to let a few hours deter us.

Over the next two hours we did anything but think about the interview. We updated the podcast website, prospected guests for upcoming podcast episodes and checked the college football scores.

Finally, we were back in the studio ready to interview one of the most controversial figures on Wall Street. Right at 5pm, the interview began with a heavy Long Island accent saying, “Alright guys, ask me anything you want.”

Part of 1 of our podcast with Jordan can be found here, and Part 2 is here.

Enjoy and please let us know who you’d like to see on future TR Talk Podcasts.

About the Author:

Ryan Warner is the co-host of TR Talk Podcast, where hosts Tom Alaimo and Ryan interview leaders in their fields to learn how millennials can fast-track their personal development. Past guests include CEO’s, Olympic gold medalists, former NBA and NFL players, New York Times bestsellers, and famed podcasts hosts. You can connect with Ryan on his social channels:

RyanWarner.Net | LinkedIn | Medium | Twitter