"Habits and Hustle" – Episode 512: The Best of Habits & Hustle: Jordan Belfort (Wolf Of Wall Street)

Host: Jen Cohen
Guest: Jordan Belfort
Release date: December 19, 2025

Episode Overview

In this vibrant and unfiltered "Best of" episode, Jen Cohen sits down with Jordan Belfort, the notorious "Wolf of Wall Street," for a candid conversation about reinvention, the real story behind his rise and fall, the power of specialized skill, habits that drive sustained success, and his celebrated Straight Line sales system. They also dive deep into the behind-the-scenes truths of the film "The Wolf of Wall Street," sales psychology, the financial industry, and the mindset required for bouncing back and thriving after public failure.

Key Discussion Points & Insights

1. Aging, Health, and Staying Energetic

• Belfort at 61: Jen immediately remarks on how youthful Jordan appears, jokingly calling him "Benjamin Button" ([00:27]).
• Physical Health: Belfort credits his activity (sports, wrestling, tennis) for keeping him fit, despite injuries.
• Stem Cell Treatments: Jordan shares that he’s done stem cell therapy both for injuries and subtle facial rejuvenation—opting for natural over surgical approaches ([01:43]).
• Quote:

  “I’ve done stem cells. That’s the only thing I’ve done… in my neck and my hands, and my face, too. It’s supposed to enrich the collagen, very subtle, but it works.”
  — Jordan Belfort ([01:43]–[02:21])

2. The Real Story Behind "The Wolf of Wall Street"

• Timing: The events depicted occurred over 30 years ago, not recently as many assume ([04:24]).
• Personal Downfall:

  “You’re dying in slow motion, literally. Jail wasn’t even the bad part…it was waiting, while your possessions are stripped away one by one.”
  — Jordan Belfort ([05:13])

• Turning Point in Jail: Cellmate Tommy Chong encouraged Jordan to write a book; the absurdity of Belfort’s stories finally hit home ([05:47]).
• Learning to Write: In jail, he rigorously self-taught writing, using "Bonfire of the Vanities" as a textbook, meticulously dissecting Tom Wolfe’s style ([06:11]).
• Personal Writing: Jordan affirms he writes every word of his books and despises the act itself for its difficulty—but stresses the importance of acquiring specialized skills to achieve big goals ([07:03]).
• Quote:

  “So much of success is getting yourself to do the shit you don’t like doing every single day, even when you don’t feel like it. That’s what I think I’m really good at.”
  — Jordan Belfort ([07:58])

3. The ‘Why’ and the Power of Belief

• Formative Experience: At 16, selling ice cream at Jones Beach, he made more in one day than his parents made in a week. This early win gave him the belief that relentless hard work leads to outsized rewards ([09:41]).
• Rebuilding After Rock Bottom: In jail, thinking of his children became his driving ‘why,’ allowing him to push through despair and continue writing ([12:29]).
• The Real ‘Why’:

  “If you really know your ‘why’ at the deepest level, it is freaking powerful. The secret? It’s never about you—it’s about someone you love unconditionally or a cause you believe in.”
  — Jordan Belfort ([13:55])

4. Financial Health and Investing Wisdom

• Book Motivation: Frustrated by predatory practices in the financial sector, Jordan wrote "The Wolf of Investing" as an accessible guide to protect regular people from Wall Street traps ([17:11]).
• Beating The Market? Not Likely:

  “Human beings are the worst stock pickers ever. There’s like five people in the world who can beat the S&P 500, and guess what? They’re not taking your money.”
  — Jordan Belfort ([18:35])

• Sensible Advice: Go for low-cost index funds, a mix of bonds, some cash, and a small portion (under 10%) for speculation—most people shouldn’t do more ([19:13]).
• On Financial Planners: Useful for tax and retirement planning, but buyers should avoid complex investment products—stick to simple, low-fee funds ([20:51]).
• Quote:

  “Wall Street is a fee machine complex to basically rob you blind. But you don't have to play in their corrupt casino. You can extract all the value they create by buying certain types of funds that have no expenses, no fees.”
  — Jordan Belfort ([20:39])

• Crypto: Bullish on Bitcoin as a long-term hold, skeptical about the rest of crypto ([87:00]–[88:11]).

5. Behind the Film: How “Wolf of Wall Street” Came to Be

• Factual Accuracy: The movie was about 90% accurate but actually downplayed the insanity of real events. Some bachelor party antics were too depraved for the page or screen ([25:59]–[34:38]).
• Selecting Leo & Marty: Jordan hand-picked Leonardo DiCaprio and Martin Scorsese ([35:27]). Leo read the manuscript before the book was published, fought Brad Pitt in a bidding war for rights, and got Scorsese onboard ([36:54]–[38:08]).
• Late Changes: The film’s ending was revamped to reflect Jordan’s comeback, inspired by his post-prison speaking career ([68:10]).
• Quote:

  “I rewrote my own life story while it was being made into a movie. I changed my own ending through hard work, perseverance, and some luck too. But mostly hard work and perseverance.”
  — Jordan Belfort ([69:45]–[70:12])

• Movie’s Impact: The popularity endures with every generation. Young fans become business leaders who invite him to consult or speak—his influence grows over time ([71:18]–[72:04]).

6. The Straight Line Sales System: Distilling Sales to Science

• Jordan’s System: Focuses on moving a prospect’s emotional certainty about three things—the product, the salesperson, and the company—to a ‘10’ on a 1-10 scale ([45:30]–[47:45]).
• The Failures of Average Salespeople: Most stumble over objections, assume every sale is different, and can't control the interaction ([51:53]–[52:01]).
• Core Realization: Every sale is fundamentally the same—control the encounter, build massive certainty, and align three beliefs ([52:01]–[56:51]).
• You Have to Sound Like an Expert:

  “You have four seconds to establish three crucial things: sharp as a tack, enthusiastic as hell, and most important—an expert in your field. People judge books by their covers.”
  — Jordan Belfort ([53:56]–[56:51])

• Transformative Outcomes: Using the Straight Line, even novices became seven-figure earners in 90 days ([58:27]).
• Notable Example: He outperformed 50 other professionals in a staged sales test simply because he studied, prepared, and presented like an expert ([60:45]–[63:02]).

7. Mindset, Redemption, and Reputation

• True Redemption: Prison returned Jordan to his core values—delivering real value, never just chasing profit ([83:07]).
• On Bouncing Back:

  "I didn’t have to become a good person from a bad person—I had to change back into the person I was originally. Ambition turned into greed. Jail was the reset."
  — Jordan Belfort ([83:08])

• Financial Industry Ironies: Points out that his offenses, while real, pale in scale to the crimes that crashed the world in 2008—public perception softened as Wall Street’s broader excesses became known ([85:35]).
• Living Example: Jordan is not banned from trading or managing assets (except for owning a brokerage); today, he’s a successful investor, consultant, and educator ([85:22]–[86:23]).

8. Modern Success and Influence

• Speaking & Consulting: Built a large international business as a speaker, earning six figures per talk; consults for top companies and quietly owns stakes in multiple ventures ([67:38]–[90:57]).
• Selective Branding: Not every big corporation will hire him due to his brash style, language, and controversial history—but his programs are widely used by sales teams globally ([91:05]).
• Cultural Commentary: Voices strong opinions on “woke” culture and victim mentality ([91:48]–[92:29]).
• Final Advice:

  “If you're an entrepreneur or someone starting a business, sales is 101—you have to be good at it.”
  — Jordan Belfort ([93:14])

• Find Jordan:
  jordanbelfort.com, Wolf of Wall Street on Instagram, TikTok, Twitter ([93:40])

Notable Quotes & Moments

• "So much of success is getting yourself to do the shit you don’t like doing every single day, even when you don’t feel like it." — Jordan Belfort [07:58]
• On his bachelor party:

  “Sodom and Gomorrah on the 22nd floor of Mirage… we rated them like stocks: blue chip hookers, NASDAQ hookers, and pink sheets—the bottom of the barrel.”
  — Jordan Belfort [27:49]

• On building belief:

  “If you really know your ‘why’ at the deepest level, it is freaking powerful… it’s not about you.”
  — Jordan Belfort [13:55]

• On selling:

  “Sales at the highest level is the transference of emotion. The emotion you’re transferring is certainty.”
  — Jordan Belfort [45:30]

• On Straight Line success:

  “You have four seconds to establish three crucial things: sharp as a tack, enthusiastic as hell, and expert in your field.”
  — Jordan Belfort [53:56]

• On his redemption:

  “I didn’t have to become a good person from a bad person—I had to change back into the person I was originally.”
  — Jordan Belfort [83:08]

Segment Timestamps

• [00:27] Youthfulness and health routines
• [01:43] Stem cells, facial treatments, and sobriety
• [05:47] Jail, Tommy Chong, and learning to write
• [07:03] The value of specialized skill and doing what you hate for success
• [09:41] Early hustle: selling ice cream at Jones Beach
• [12:29] Finding a "why"—family, comeback after prison
• [17:11] Motivation for “Wolf of Investing” and market pitfalls
• [18:35] The myth of beating the market—why most don’t
• [20:39] Wall Street’s “fee machine” and sticking to index funds
• [25:59] The real bachelor party and film’s understatements
• [35:27] Selecting DiCaprio and Scorsese for the film
• [45:30] The Straight Line system: sales as transference of certainty
• [52:01] Control in sales and the myth of endless objections
• [58:27] Straight Line’s transformative power at Stratton Oakmont
• [67:38] Pre-movie speaking career and business resurgence
• [83:08] What jail taught Jordan about himself and business
• [85:35] Wall Street before and after the 2008 financial crisis
• [87:00] Thoughts on Bitcoin and crypto
• [91:05] Who hires Jordan, who doesn’t, and opinions on “woke” culture
• [93:14] Closing thoughts: selling as a non-negotiable skill

Tone & Takeaways

Jordan Belfort’s candid, direct, self-deprecating, and often profane style fills the episode with energy and practical wisdom. Both he and Jen keep the conversation moving with humor, curiosity, and pointed insights on personal growth, business resilience, and the non-negotiables of high performance in sales and life. Belfort’s journey from excess and ruin to a hard-won redemption and global influence stands as both warning and inspiration—rooted in relentless work, hard-acquired skill, and serving a cause bigger than oneself.

For those who haven’t listened:
Expect a masterclass in both the art of selling and the science of seizing second chances, delivered with the raw storytelling only the real Wolf of Wall Street can provide.