Jordan Belfort Trained an AI to Sell Like Him 🤖 E161
2/23/20261 hr 5 min
On this episode of The Money Mondays Podcast, Dan Fleyshman sits down with Jordan Belfort (The Wolf of Wall Street) and Hollywood super-connector Gavin Navarro for a rapid-fire masterclass on the three Money Mondays pillars: how to make money, how to invest it, and how to give it away.
Jordan breaks down what really holds people back from earning more: it’s not just “mindset”—it’s missing skills, missing mentorship, and not putting in the reps. He shares why sales is the ultimate life skill, how to treat rejection as a numbers game, and why top performers don’t waste time trying to “convert” hard no’s.
Then Gavin pulls back the curtain on turning relationships into real opportunities—without becoming the person who pitches everyone every day. He explains how to bring deals to high-profile people the right way, how to filter constant incoming pitches, and how he built a career by being the guy who can connect the right people in the right cities at the right time.
On the investing side, Jordan shares his long-term approach (including S&P 500 and Bitcoin), while Dan lays out his 40/40/20 framework for balancing low-risk stability, medium-risk growth, and high-risk “shots at glory.” They also explain why businesses like beverages can require serious capital even when demand is booming.
Finally, they talk about why charity matters—not just for optics, but for trust, culture, and legacy—and Dan closes with his signature question that always gets a different answer: what percentage of your net worth should go to your family?
Clips
Transcript preview
First 90 secondsDan Fleyshman· Host0:00
[upbeat music] Ladies and gentlemen, welcome to a very special edition of the Money Mondays podcast, where we cover three core topics: how to make money, how to invest money, how to give it away to charity. As you guys know, these podcasts run under 40 minutes for your listening pleasure, because the average workout is 45 minutes, the average commute to work is 45 minutes. This episode will be between 34, 38 minutes, so it's nice and easy for you. Keep in mind, these podcasts are not just for you. It might be for a friend, family, or a follower. It also might be for someone from your past, present, or future. It might be four months from now, [snaps fingers] and you remember something that you heard on this episode, and you share it with your friend that might change their life. So without further ado, we're gonna dive right in. I'm gonna have my dear friend, who I actually was on podcast number one of his podcast years and years ago. [laughing] Very excited to have him here, Mr. Jordan Belfort, the Wolf of Wall Street. Give us the quick two-minute bio so we can get straight to the money.
Jordan Belfort· Guest0:54
A bio?
Dan Fleyshman· Host0:55
Two-minute bio.
Jordan Belfort· Guest0:56
Wow, that- It's- ... you know, I think everyone knows my story- Yes -really well, right? So- Number, number one grossing movie of all time. [chuckles] Yeah, so, um, yeah, I mean, sh- I, I guess, you know, everyone knows what happened. I built a massive firm, uh, in my 20s, so a long time ago. Uh, and, uh, and, and behind all that success was really one thing, was I invented a system of sales and persuasion, and it allowed me to train a bunch of kids who were, you know, you know, you know, barely acquainted with a razor blade, you know, not overly intelligent, so to speak, right? Not the dumbest people in the world, but let's say they weren't rocket scientists, and they didn't have a lot of natural sales ability, and