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

The 10 Day Prospecting Playbook

[This blog was originally published on Salesforce's Blog which can be found here.]

This is the environment that today’s account executive lives in:

  • Our buyers receive 100+ emails a day
  • Our voicemails have a less than a 5% chance of being returned
  • We “engage” a prospective client 2 attempts or less before giving up
  • We use email & phone as the primary means of outreach

Oh yeah, if you rely solely on marketing created pipeline, you will have a tough time differentiating yourself from the pack.

The good news is that there is hope! There are more mediums than ever before to reach your prospects, and when those mediums are employed consistently, meeting rates can exceed 80% (see below for Day 1). I mention meeting rates because pipeline can only be created during a meeting — meetings = pipeline.

If your outbound prospecting game is flawless, stop reading now. But if you want a 10-day playbook for prospecting net new clients, have a look below.


  • You have a list of target, tier one accounts, and have the accounts CEO / COO/ CMO/ CIOs’ email, LinkedIn and address handy.
  • You are not following up solely on marketing generated leads. This is for the account executive who is responsible for generating new logos.
  • Your goal with this campaign is getting a meeting, which then creates the opportunity to generate pipeline.

Without further ado, here is the 10-day plan.

Day 1: Thursday - High Impact Direct Mail

  • Send a tailored piece of mail to your targets, such as a relevant book (bonus tip – write a short note in the book sleeve), a congratulatory note.
  • Or, take a play from sales thought leader Gabe Larsen's Coffee Play, which registered a 37 meeting hit rate (out of 42 recipients) and one of the mediums used to engage prospects was a direct mail piece.
  • For details on how to run your own Coffee Play, skip to 24:35 of this interview with Gabe.

Day 2: Friday – Follow Prospects on Social & Send LinkedIn Message

  • 8-9am: LinkedIn message prospects
  • 12-1pm: Follow all prospects on Twitter and LinkedIn and then engage: re-share, comment, or like their content. This is a theme that should be practiced everyday of this plan. I like to use 7:30 – 8am to scan LinkedIn and Twitter for relevant news for my prospects.

Day 5: Monday - Send Tailored Email

  • When: 4-5pm
  • What to write? See Tucker Max’s Guide to Cold Emailing.
  • What’s worked for me?
    • Subject line should reference the title of a recently published press release.
    • The first sentence should focus on the prospect, e.g., congrats on the new funding round.
    • Avoid leading with a sentence about yourself or your firm.
  • Did my email hit their inbox? I’m a big fan of using Salesforce’s Inbox to see who opened the emails, if any links were clicked, and to automatically set a task if the receipt doesn’t get back to me by Thursday.

Day 6: Tuesday - First Round of Calling

Day 7: Wednesday - Calling & LinkedIn Message Round Two

  • 8-9am: Call prospects and leave a voicemail round two. This is the second best time to call, according to the same MIT study.
  • 4-5pm: LinkedIn message round two.

Day 8: Thursday – Email Take Two & More Calling

  • 8-9am: Thanks to Salesforce Inbox, I know who received my initial email and who didn’t. For those who received it, do a take two email. For those who didn’t, change the subject and re-send original email.
  • 4-5pm: calling round 3 and voicemail

Day 9: Friday – Finish Strong

  • 8-9am: Email take three
  • 2 – 3pm: Call but no voicemail

Day 10: Saturday – Reap the Rewards

  • Take a minute to acknowledge the number of meetings you just created and the resulting pipeline.
  • For those contacts that didn’t get back to you, didn’t open your emails, and didn’t accept your LinkedIn message, there is still hope but I’d advise swapping in a new contact.

I hope this approach helps you in your outbound prospecting efforts. If it does work, feel free to share with your colleagues. If it doesn’t, please email, or reach out on social media and we can revise together

About the Author

Ryan Warner is an account executive on Salesforce’s Financial Services team. Ryan also co-hosts the TR Talk Podcast, where co-host Tom Alaimo and Ryan interview leaders in their fields to learn how millennials can make an impact in today’s workforce.
Twitter: @Ryan_N_Warner